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Holiday Rentals in Sarasota

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    Travellers to Sarasota are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 325 Rentals in Sarasota
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    Pet Friendly Pool Home Close to Beaches & Town1 / 28
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Siesta Beach Cottage1 / 13
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oceanfront home w/sunset views of Sarasota Bay1 / 37
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Walk to Crescent Beach, Upgraded Sea Winds Condo1 / 19
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • DVD Player
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2016
    This condo is an end unit, so one less neighbor to worry about, noise wise, and nice and bright - 3 walls with plantation shuttered windows. The location is perfect, only a...
    Reviewed 3 August 2015
    The condo was a walking distance to the private beach (belonged to other resorts, but no one cared if you accessed it as well.) it was clean and exactly how you see it on the...
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    About this property
    Siesta Key located on the Gulf of Mexico. Tropical beauty with white powder sand, gorgeous sunsets, pristine waters and expansive wide beaches. Beach shops, restaurants, ice cream shops and nightlife all can be found on the palm tree paradise, Siesta Key. The city of Sarasota is just over the...
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    34242, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Fido Friendly w/Fenced Yard, Spa/Swimming Pool,  Wifi, Large Ranch Home, Large L1 / 31
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 April 2018
    We stayed here as an extended family: grandparents, parents, and a 2 year old.The property is located near to the north end of Sarasota–Bradenton Airport just off the I-41...
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    About this property
    This is a beautiful, large 3 bedroom, 2 bath ranch home on the Northside of Sarasota with a heated (optional) swimming pool and jetted spa. (See below for more details) With a two car garage, it's conveniently close to the Sarasota/Bradenton airport and just 10 minutes to downtown Sarasota. Walk...
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    34243, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Canal Pool Home with Free Golf Aug - Nov '18  (15 mins to Siesta Key Beach)1 / 44
    (24)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2018
    My family and I spent 7 days at this beautiful and spacious home. There was ample space for five of us and the pool was used on a daily basis. We had many night swims! The...
    Reviewed 26 June 2018
    This home is located in a nice quiet neighborhood and is conveniently located to shopping, downtown, and of course the beaches of Siesta Key, Lido Key & Longboat Key. Mark...
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    About this property
    Our 4 bedroom, 3 bath house is located in a family friendly neighbourhood on the side of a tidal canal. Have your morning coffee on the covered pool side lanai as you enjoy the wildlife that calls the canal home. 2 sets of sliding doors lead out to the lanai and pool (30x16). It's a great place to...
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    34239, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lovely Lido Key Villa - away from it all but close to the BEACH -1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2017
    Lido Key is a perfect getaway for locals and visitors from distant locations alike. This rental comfortably sleeps 5, with all of the amenities for a perfect vacation at an...
    Reviewed 18 February 2017
    My husband and I stayed at this fantastic villa in July 2016. We were pleasantly surprised at how beautifully decorated and conveniently located this little gem is. The...
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    About this property
    This newly remodeled villa will delight you with it's contemporary charm and pristine interior. Featuring a master bedroom with king-sized bed and a loft bedroom with queen bed, it has two full baths, a deluxe kitchen and high-end furnishings throughout. Among Lido Key’s premier vacation rentals...
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    34236, Lido Key, Sarasota
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Private Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3.5 miles to Siesta Key, North Bridge Dawson House is closely located within a few miles to Siesta Key and close to downtown Sarasota. This home offers an open kitchen that is truly 'The Heart of the Home.' Completely remodeled with custom wood cabinets, a cast Iron farm sink, Granite Counter tops,...
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    34239, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Location Location Location,The 'NEST' west of Tamiami Trl close to everything.1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2018
    This a very clean two-bedroom second-floor apartment with all the amenities of home. Great location, close to a fabulous gourmet market, excellent restaurants, shopping, and...
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    About this property
    THE SARASOTA 'NEST', West Of Tamiami Trail This vacation getaway is an immaculate, 2 bed room upstairs apartment, located in the heart and soul of old Sarasota. Walk to Sarasota's most desired locations, including Shelby Gardens, Bay Front Park, Southside Village (has everything, best restaurants,...
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    34239, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine combining privacy of staying in a private home with the resort amenities of a fine hotel matched with a fantastic location, just 5 minutes from the beach and very easy access to Sarasota sporting cultural amenities and an array of dining options. Enjoy all that Sarasota has to offer while...
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    Location Information
    34231, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Lovely 2 BR Beach Cottage at Lido Key Villas across from Lido Beach1 / 21
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2018
    Nice house in a good location if you have rented a car. Very close to beautiful beach. The bedrooms and kitchen/sitting area are quite small but very comfortable and nice garden...
    Reviewed 26 October 2017
    just want to say this 2 bedroom home was cozy and very clean loved the private back yard that had a cool breeze everyday there they also have everything there that you need the...
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    About this property
    Our spacious fully furnished two-bedroom cottage is directly across the street from the beach (600 ft, a 2 min walk). It offers everything you need to enjoy a memorable beach vacation. It features all the conveniences – full kitchen, full bath and a lovely tree-shaded back yard. There is also a...
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    Location Information
    34236, Lido Key, Sarasota
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach1 / 30
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2016
    We just spent a delightful 4 days in the heart of historic Burns Court. This renovated apartment was so wonderfully located in it's proximity to historic Sarasota. Everything is...
    Reviewed 19 August 2015
    We had a great stay here, the apartment was right downtown, it was very comfortable, and we hope to return soon!Denise was very helpful.
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    About this property
    Historic 1920's Mediterranean & 1950’s Historic mixed-use building in Burns Square, downtown Sarasota, safely nestled between high-end residential neighborhoods of Palm Avenue, Laurel Park and Hudson Bayou. Apartment is private and secure, located on the second floor (stairs) with original hardwood...
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    34236, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Balcony
    • Patio
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Embrace the tropical climate and active outdoor lifestyle of Siesta Key in this nearly 2,000 sq.ft., home! This is a 3 bedroom, 2.5 bath light and bright, modern, town home and just a short bike ride to our beloved Crescent Beach! With the patios, there is more than 2,500 sq. feet of living...
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    34231, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2 bath Pet Friendly renovated and fenced 1900 sq. ft BEACH COTTAGE has an iconic Sarasota feel upon pulling up and entering the home. This cozy home is newly renovated and is a short five minute drive or 20 minute bike ride to the #1 beach in the US or the incredible restaurants and...
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    34239, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key Voted #1 Beach, Lovely Home 10 min away1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Patio
    • Cable/satellite TV
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2018
    Our family had a wonderful vacation,Yvonne ' s house was lovely, clean and just perfect. Thanks for making our trip memorable! !
    Reviewed 13 July 2018
    This place had it all! Great location, numerous amenities, lovely home with almost everything we could have wanted. The owner was very nice.Our only negative feedback would be...
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    About this property
    This home is in walking distance to all facilities, 2 car drive/ car port, lanai. Manured garden and trees. Area for BBQ and out door eating. Located ideally for easy access to Sarasota's famous 'Siesta Beach' Downtown and St. Armands Circle have many restaurants to suit all eclectic tastes....
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    34233, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay at this beautiful 2 bedroom, condo minutes (by car less than 1 minute) from Crescent Beach and Siesta Key. Looking for a perfect getaway? This is the place for you. This unit is located in a very quiet, quaint, tight-knit community. Perfect for couples who are looking to get away but not be...
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    34231, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedroom Family friendly Coastal Manor of Sarasota1 / 22
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Balcony
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2018
    Stayed all over Florida in many rentals,this one is amazing the house its self felt more like a home,so much room inside and out all the rooms were very nice decor different...
    Reviewed 22 March 2017
    Perfect stay in an amazing Southern State style house. Lovely apartment, well equipped and a lot of space. Wonderful surrounding with pool at Phillipi creek. Best place for...
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    34231, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stoneybrook in Palmer Ranch is a condo in a gated community of upscale homes. Surrounded by lush vegetation, a golf course, lighted 'har tru' tennis courts, clubhouse with restaurant and activities and a beautiful community pool, there is plenty of open space as well as peace, quiet and...
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    34238, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Condo on Private Golf Course - Close to Siesta Key1 / 17
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Air Conditioning
    • Washer
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 2 bedroom 2 bath, 1st floor condo in a gated community with private 18 hole golf course. Amenities include 5 swimming pools, tennis courts, fitness center, clubhouse, and nature trails. Transfer membership privileges allow use of all facilities including clubhouse restaurants and...
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    34241, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Calm: King Room, Yoga, Spa1 / 22
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
    • Air Conditioning
    • Housekeeping Included
    • Washer
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 2018
    This location has become one of our favorite spots to stay. It is extremely well kept and the perfect weekend getaway for yoga doers and people looking to just relax alike.
    Reviewed 23 March 2016
    We spent 5 days at this yoga retreat. We don't usually do yoga but other reviewers mentioned how relaxing this place was even if you do not do the included yoga sessions so we...
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    About this property
    Red Tide Update: Casa Calm is located 20 miles inland from the Gulf Coast. Therefore, our lake is not affected by the current algae blooms. The water is clear and the wildlife it supports is healthy and thriving. Plenty of tranquil water views to be had here without venturing to the beach. And...
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    Location Information
    34251, Sarasota, Southwest Gulf Coast
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    bring A Boat, 12 Minutes To Sarasota Bay1 / 11
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2018
    We (2) were guests at Jim‘s house for 6 days and we liked the place very much. The house is very clean and good equipped. Jim is a very kind host and gives good recommendations...
    Reviewed 7 April 2018
    A very clean and updated home. We enjoyed our stay here. We spent a week, family of four with two teens. We all enjoyed the pool and hot tub. The home is very convenient and...
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    About this property
    Clean and spacious, 3/4 of the house is yours, kitchen and laundry, 2 bedroom with 1 and 1/2 bath, pool and spa, on the canal that leads to Sarasota bay, offering morning coffee, light breakfast and an occasional visit from the manatees off the dock. Bedroom 1, has a double bed, bedroom 2, has a...
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    34243, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Family friendly house with pool/spa1 / 29
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2016
    The owners are great, very friendly and helpful. The house was clean and almost everything needed was supplied. The rooms are nice and clean. The pool was the main focus of the...
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    About this property
    We want you to enjoy, staying here this year & be back with your friends/family. Beautiful house on 1 acre lot, close to everything located in one of the best and desirable area in south Sarasota. This property offers easy access to all local attractions and beaches. Only a short drive to the...
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    34233, Lido Key, Sarasota
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Charming 'Old Florida' one bed apartment, Sarasota1 / 24
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Balcony
    • Hot Tub
    • Parking
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 April 2018
    We enjoyed our stay at this Sarasota apartment. The outside is very enjoyable in the evening. The hot tub was pleasant and private. We used Uber for our trip to Siesta Key...
    Reviewed 7 October 2017
    We had a great time on our first visit to Sarasota. Our stay was amazing, it had all the comforts of home. We were minutes from the best beach I have ever been too and very...
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    About this property
    This property is attached to the main house but has a private entrance with a private patio and back yard which is fully fenced in. A 10 minute drive to either Siesta Key or Lido Beach and minutes from downtown Sarasota, this charming 'Old Florida' one bedroom apartment is available for weekends,...
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    Location Information
    34239, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Waterfront 2BR 2 Bath Suite at the Sara Bay Marina1 / 16
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2015
    My wife and I stayed here for 5 nights - friends joined us for 3 nights. Lots of room, well appointed through out with a view out over the water. Great location for travelling...
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    About this property
    PLEASE EMAIL ME FOR A LINK TO PREFERRED LISTING ADDRESS, VACATION RENTAL BY OWNER LISTING: 442427 THIS IS A PRIVATELY OWNED CONDOMINIUM AT THE RAMADA INN, 7150 N Tamiami Trail, SARASOTA, Directly on the Sara Bay Marina with direct access to the Gulf of Mexico. Yacht rentals are available on...
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    Location Information
    34243, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simply paradise. We're located in the highly desirable Kingston Arms complex in one of the few coveted end units on Lido Key just steps from St. Armand's Circle. Lido Key is surrounded by the beautiful gentle, clear waters of the Gulf of Mexico. The complex sits on a prime location just a few...
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    Location Information
    34236, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is a 1000 square foot two bedroom apartment with 1 car garage, offers a...
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    Location Information
    34236, Lido Key, Sarasota
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Superb Village Des Pins Sarasota vacation villa near Siesta Key1 / 24
    (10)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2014
    We had a wonderful week in this villa. I am sorely tempted to go live there. It's enormous! There were only the 2 of us, but even for a family there was loads of room. The...
    Reviewed 16 June 2014
    My wife and I stayed here on our recent honeymoon and absolutely loved it. It's a really lovely villa with large rooms, very modern furniture, and plenty of useful appliances...
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    About this property
    Thanks for considering our property. If you have stayed with us before, let us know for a loyalty discount! We would be happy to answer any questions on any aspect of the rental. This top quality spacious modern corner villa is set in an award winning, safe, semi gated community, and are the...
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    Location Information
    34238, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Walk to Everything Downtown, Bring Fido, Wifi, Huge Screened Lanai, Extensive Ou1 / 24
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2018
    This location is within walking distance of downtown. My family used to live a few blocks away so I was very familiar with the area. This is a beautiful place to stay. Very...
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    About this property
    Bring Fido to this dog friendly 2 bedroom, 1 bath duplex in downtown Sarasota near Gillespie Park. Downtown Sarasota and all it has to offer is just blocks away from this adorable cottage like duplex! Feel free to leave your car under your covered carport because you can walk to many downtown...
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    Location Information
    34236, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    St.Armands Circle condo ( Kingston Arms )1 / 9
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Terrace
    • Balcony
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    We stayed in this condo at Kingston Arms for a week! It is beautiful! I cannot say enough great things about it! It is a short blocks walk to St. Armand’s Circle and 3 blocks...
    Reviewed 10 July 2017
    This is a very nice unit in an older condo facility. We loved how close to the shops and restaurants we were. The walk to the beach is also not bad at all. We never used the...
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    About this property
    2 bedroom,2 bathrooms,modern updated condo.Walking distance to Lido Beach. Fully furnished,microwave,A/C,cable,local phone only,dishwasher, 3 new LCD TV's ,Stereo,Laundry (common area) Beautiful heated pool ,hot tub, all in common area Great shopping,excellent restaurants,great entertainment in St....
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    Location Information
    34232, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck1 / 58
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Grill
    • Balcony
    • Air Conditioning
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2018
    Beautiful condo overlooking the pool. Able to see the ocean from the sliding doors. We enjoyed wonderful weather. Just a few steps from the washer and dryer and elevator...
    Reviewed 22 May 2017
    Perfect location & beautiful condo many amenities. Would highly recommend staying at this condo. Steps away from the beach & stunning pool. We will vist again.
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    About this property
    Hi, I have several weeks available this April. I’ve reduced the rate to $1,395 with the only additional fee being sales tax and the resort booking fee, $100. Let me know if you would like to set up a reservation. Thank You. WE ARE HAVING A LAST MINUTE SALE FOR THE REMAINING OPEN WEEKS OF APRIL...
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    Location Information
    34242, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are in the heart of historic Burns Square in downtown Sarasota, nestled between high end residential neighborhoods S. Palm Avenue, Laurel Park and Hudson Bayou. The property is a mixed-use historic property with residential on the second floor with stairs. You do not need a car as we are in...
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    Location Information
    34236, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Executive 2 Bed 3 Bath Pool Home near Siesta Key1 / 45
    (25)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Outdoor Dining Area
    • Grill
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2018
    We just came back from one of our top beach-vacation experiences, considering location and lodging. This is a beautiful home, with a very responsive and flexible owner, just a...
    Reviewed 30 November 2017
    We have recently returned from a wonderful stay in this beautiful home which is equipped with everything you could need and looks exactly like it does in the photographs. It is...
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    About this property
    Desirable Gulf Gate - Large 2 bedroom 3 bathrooms home near Siesta Key Beaches. Tile and laminate wood flooring thruout. Fully equipped kitchen Stainless Steel Appliances. Gas BBQ Grill. Perfect home for entertaining or just enjoy the scenery and the tranquil view overlooking the large screened in...
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    Location Information
    34231, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Downtown Apartment in Historic Burns Square downtown Sarasota1 / 21
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed 24 January 2017
    My husband and I stayed here for a long weekend in January and really enjoyed. The place is very cozy! Very clean! The bed was extremely comfortable! I loved the fact there...
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    About this property
    My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publix, fabulous restaurants, diverse shopping options, performance theaters, movie theaters, nightlife, public transport, boat/water activity rentals, parks, spas, and a short...
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    Location Information
    34236, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Elegant 4 Bedroom 3 bath Executive Home - HEATED POOL near Siesta Key Beaches!!!1 / 34
    (11)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Internet Access
    • Hot Tub
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    • Private Outdoor Pool (Heated)
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    We booked this villa from trip advisor But it didn’t show floor plan we assumed it would have had on suite bathrooms to at least 2 bedrooms it only had one bed room with onsuite...
    Reviewed 10 June 2018
    We rented this house for the last seven days with a very large group. This house is perfect for multiple families staying together. The house had an abundance of everything from...
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    About this property
    Heated Pool with therapy jets. You will Love this Large 4 bedrooms Home situated within minutes to #1 Siesta Key Beaches, Downtown, Live Entertainment, Fine Dinning, Shopping, etc.... The home has a oversized covered Lanai, A screened in Pool and a 2 Car Attached Garage. #1 -'Master Bedroom Suite'...
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    Location Information
    34231, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Walk to beach & St Armand's Circle !!!1 / 10
    (30)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Balcony
    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Had a great time! All accommodations were awesome. The property is gorgeous, and we love how walkable St. Armand’s is.
    Reviewed 2 August 2018
    Best vacation ever! Beyond lovely apartment/pool/yard/neighborhood. So peaceful. Minutes to great beach. Gracious hostess. Absolutely everything we needed was in that apartment...
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    About this property
    Be swept away to luxurious Spain in this beautiful one bedroom guesthouse overlooking a lovely pool. Relax and sip your morning coffee as you take in the peaceful surroundings and bay breezes, with a private entrance, spacious outdoor dining room in tropical paradise. Features include:Mexican...
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    Location Information
    34236, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Five star Downtown Sarasota tropical garden Cottage1 / 44
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Secure Parking
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2017
    Maureen, our host, was super helpful and her place was a peaceful sanctuary, close to everything downtown. We have a toddler and it was great for him too.
    Reviewed 25 February 2017
    We have rented more than 20 homes and apartments in lieu of staying in hotels. My husband and I were very comfortable at this cottage and look forward to renting it again next...
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    About this property
    This location is central to everything and everywhere in Downtown Sarasota, near all area Beaches, Marinas, Golf courses, YMCA and Sarasota Bayfront. Only 7.5 miles to the 2017 World Rowing Championships at Benderson Park. This Charming Florida style home has been totally updated and stylishly...
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    Location Information
    34237, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love our beautifully maintained and clean Villa Youppie in Sarasota. It is located at the corner of a lake which provides lots of privacy and thanks to a southern exposure you have sun in the pool and on the patio all day long. New travertine tiles on the patio, granite counter tops in the...
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    Location Information
    34238, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Stunning Beach Front Pool Home (Sand Castle Unit)1 / 27
    (7)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly overlooking breathtaking views of privately owned beach on North end of Siesta Key. Just renovated everything brand new. Four bedrooms, 2 baths, sleeps 11, living room, dining room, full kitchen and game room. Flat screen TVs in living room, game room, and each bedroom with DVD players,...
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    Location Information
    34242, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    Newly Updated 3 Bedroom Pool Home - Close to Beach1 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2017
    We were in Florida for my nieces wedding. The location was perfect for us. Nice quite neighborhood, close to grocery stores and shopping. We really enjoyed the back yard and pool.
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    About this property
    Enjoy your time in Sarasota in this newly renovated 3 bedroom 2 bathroom pool home. Located in a quiet family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach...
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    Location Information
    34232, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is a 1000 square foot two bedroom apartment with 1 car garage, offers a...
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    Location Information
    34236, Lido Key, Sarasota
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Amazing  Location-Short Walk to Beach!!!1 / 61
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Balcony
    • Cable/satellite TV
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    Awesome get away. Everything was found to be as described. Perfect weather, close enough to the trolley and the beach for us. Safe neighborhood, too!
    Reviewed 16 October 2016
    It was a nice stay in a very well equipped appartment.You can really walk to the beach, wonderful!We enjoyed very much our stay and contact to the owner, nice people!
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    About this property
    Discount for 3 months or more!!! Walk less than 10 minutes to the white sands of Siesta beach (Gulf of Mexico) just over the bridge, or to many island restaurants, marina and shops where you can rent absolutely anything for your outdoor activities and adventures. Walk to the opposite direction and...
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    Location Information
    34231 3847, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your well-behaved dog along with you and stay just off Siesta Key in the Southgate area. Here you can walk to the Westfield Southgate Mall, complete with restaurants, shopping and the brand new CinéBistro movie & dining venue or walk to the many other restaurant choices close by. Completely...
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    Location Information
    34239, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    The Bedroom Cottage with an Old Florida feel.The unit has full kitchen, and Queen size bed plus queen size sleeper sofa. The beach is a 6 minute walk and St. Armands 14 minutes, according to Google Maps. The unit has private patio and separate screen porch. The complex has a heated pool. The unit...
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    Location Information
    34236, Lido Key, Sarasota
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fantastic Sarasota location close to everything... 4 minutes to the Ed Smith Oriole's stadium, 5 minutes to Marina Jacks, 4 minutes to the Hillview section of Sarasota by Sarasota Memorial Hospital, 12 minutes to St. Armands Circle on Lido Key and 15 minutes to Siesta Key Beach. Nicely...
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    Location Information
    34237, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Charming Lido Key Beach House 5 min Walk to Beach!1 / 33
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Balcony
    • Outdoor Dining Area
    • Wi-Fi
    • Patio
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    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 October 2015
    I had been staying in Sarasota for springtime vacations for about ten years before renting this house on Lido Key. The house is charming and spacious with all the extras you...
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    About this property
    This beautifully decorated Beach House of about 1400 sq ft includes a living room, dining room, KitchenAid equipped newly renovated kitchen, laundry room, 2 bedrooms, and 2 bathrooms. The living room has a large and comfortable couch, a coffee table, and cable TV. The dining room includes a...
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    Location Information
    34236, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beautiful Main Street Loft Apartment1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 25 August 2018
    This location was just what I looking for. The loft was very cozy and neat. I loved the jazz artwork on the walls which fits right into the locale setting of art galleries...
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    About this property
    The front door of our 1920 vintage loft apartment opens directly onto Main Street... You will be surrounded with all the world-class attractions Sarasota, Florida has to offer - from beaches and boating to arts and culture. When you stay here, each day dawns with endless possibilities, many of the...
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    Location Information
    34236, Lido Key, Sarasota
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
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    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 February 2016
    Must admit that I was nervous before my arrival, there was no reviews for that location, usually I take them in consideration. Was very pleased, answers were given fast, easy to...
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    About this property
    Great private cozy apartment with a nice outdoor terrace / bbq area Located in a quiet family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is...
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    Location Information
    34232, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beautiful 3 bedms/2 bathms with pool close to Downtown1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2018
    Great place conveniently located at 15 minutes to Siesta Key,Lido Key.The only thing that would have been better was for Alberto storm to choose a different path,but we were...
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    About this property
    This is spacious house, located in Novus Place, close to downtown and beaches. With 3 bedrooms, 2 bathrooms, a private swimming pool, equipped kitchen and TV equipped living room, it can perfectly accommodate a family or group of friends of 6 guests. The house is located in a residential area,...
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    Location Information
    34237, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Late SALE Sep/Oct only -Lakeside villa Uni. Park,golf,cycles,pool, beach1 / 33
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2018
    I just completed a 3 week stay at this home in University Park, Bradenton Florida. The home exceeds its representation. It was very clean, well appointed and a very comfortable...
    Reviewed 20 May 2011
    My husband and I and 2 other couples stayed here for a week...really comfortable, clean home. Excellent friendly communication with the owner who made it easy for us to get the...
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    About this property
    SALE LAST AVAILABILITY - $999/week (was $1250). Please note we only have 2-18 September dates and 29 Sep - 9 October left. We may be able to offer a further reduction for 2 week stays in early September (if dates available). Please inquire for rate. Enjoy the ultimate vacation in our luxury...
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    Location Information
    34201, Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    1920's mixed-use building in historic area that is nestled between high-end residential neighborhoods. The studio apartment is super nice, safe and secure in a quaint shopping/theater area and walking distance to marina, fishing, supermarkets, transportation, theaters, opera, library, parks and...
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    Location Information
    34236, Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    1
    Sarasota Holiday Rentals

    Encompassing some of the state’s most impressive cultural attractions, world-class beaches and a slew of eco-tourism activities, Sarasota and its surrounding islands, is the perfect destination to unwind in style. If you want to luxuriate in style, you should consider a holiday rental. From roomy, beachside homes to sophisticated high-rise condos, quaint cottages and classy villas and town homes, the selection in the Sarasota area is appealing to a range of tastes and desires. Amenities like fully equipped kitchens and spacious indoor and outdoor dining areas make holiday rentals perfect for families seeking to prepare their own meals and save money.

    Sarasota attractions and activities

    You’ll have access to one of the world’s great beaches. Siesta Key Beach, which was included in Dr. Beaches’ Top 10 “Best Beaches in America” in 2007 & 2008, is a don’t miss experience. While beach activities like parasailing, snorkelling and sailing are popular pastimes, away from the sands, cultural attractions are big draws in Sarasota. A great family outing is the John and Mable Ringling Estate, a Venetian-inspired mansion along Sarasota Bay featuring an art museum, circus museum, a Circus Ring of Fame and the Flying Trapeze and The Flying Fantasy Circus. When it’s time to shop and dine, head to St. Armands Circle on Lido Key, a classy area with a European charm featuring bistros with outdoor dining and a plethora of boutiques, art galleries, speciality shops and restaurants. Popular outdoor activities in the Sarasota area include kayaking at Myakka River State Park, playing golf at top-notch layouts like the Arnold Palmer designed Legacy Golf Club at Lakewood Ranch and the Scottish links-style Tatum Ridge Golf Links and hiking the newly opened Legacy Trail, which stretches more than 12 miles from Sarasota to Venice.

    Family holiday rentals in Sarasota

    From beachfront bungalows to golf course villas and everything in between, the Sarasota area has holiday rentals in a variety of settings. Sarasota is a great destination for kids. It boasts attractions like the Mote Aquarium, Marie Selby Botanical Gardens and Sarasota Jungle Gardens. After a long day of sunbathing, shopping, playing golf or visiting attractions, you can return to a holiday rental that gives your family room to spread out instead of a cramped, mundane hotel room.

    Saving money on Sarasota holiday rentals

    We have a long list of money saving holiday rental options. Regardless of your price range and budget, we have special deals and discounts on all types of properties in different settings in the Sarasota area.

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