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Holiday Rentals near Rain Barrel Village

86700 Overseas Hwy, Mile Marker 86.7, Bayside, Islamorada, Florida 33036-3138
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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Islamorada
    Newly refinished  condo open water views very nice1 / 16
    (6)Excellent
    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!1 / 39
    (5)Excellent
    5.4 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Modern Executive Bay Club Townhouse with Pool & Beach1 / 28
    (3)Very good
    0.7 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    5.4 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2018
    Wow! This property is just perfect for a quick getaway! The backyard was so fun, for our entire family. My kids loved the hot tub, my wife loved the waterfront view and I loved...
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    About this property
    The moment you step in the back yard, you'll know vacation has begun. . . time stands still as the laid-back island lifestyle takes over...Totally remodeled, canal-front home, quiet and in the nicest of neighborhoods (Plantation Key Colony). The 2 bed/2 bath stilted (upper unit) island retreat is...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    THIS IS IT! Magnificent Oceanfront Paradise!  WE ARE OPEN!!1 / 17
    (5)Excellent
    5.4 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2018
    Great vacation. Received the much needed peace/quiet for rest that was well overdue. Room clean and relaxing. Visited Key West for a day trip while here and had a great time...
    Reviewed 2 June 2018
    The condo was fantastic, clean and with great facilities. The pool was excellent and fellow guest very friendly. The owner was in touch throughout our stay and could not have...
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    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 2-5 people. , large pool on the ocean, . many water-front restaurants and bars nearby. Oceanfront mm 90, Plantation Key. Books up very quickly. Reserve early! Note: We are licensed in Islamorada:...
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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony1 / 14
    (8)Very good
    5.4 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 November 2018
    This was our first visit to the Keys. Although the area has mostly recovered from the hurricane, there were still a number of construction projects in progress. The condo was...
    Reviewed 20 October 2018
    Beautiful view from the 3rd floor. Located away from US1 traffic so very quiet. Centrally located between Islamorada and Key Largo.
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    About this property
    Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door pool, plenty of parking, and elevator.. My condo is kept meticulously with attention to detail. Linens, towels and pool towels are included in the rental price. The balcony is...
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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.1 / 18
    (7)Excellent
    0.6 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2016
    This was our first trip to Florida, it was agreed that we would leave Orlando and the parks for a few years as our children are still quite young (4 and 1). We did extensive...
    Reviewed 18 January 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5.1 kilometres from Rain Barrel Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage....
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2.2 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    107 San Remo Drive1 / 36
    (2)Excellent
    1.3 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2019
    This house is perfect if you want to be close to everything. Tons of great restaurants within 5 minutes. Dock for your boat and lots of seating outside and on the screened porch...
    Reviewed 29 January 2018
    What a fabulous area and home, Nancy and Norm were (the owners) told us places for dining out, Island times grill, Craigs seafood ( Mahi Mahi sandwich is to die for) Mrs Mac...
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    About this property
    Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs. The downstairs apartment has a complete kitchen and living room and separate bedroom. There is a screened in porch of the living room upstairs. The home has awesome...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Bayside Condo, marina, pool and beach1 / 70
    (17)Very good
    2.4 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Balcony
    • Terrace
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2018
    We recently rented this condo unit for a week for our family of six. It accommodated us great, 3 bedrooms plus a pull out couch. Outside was beautiful, very clean and well...
    Reviewed 13 March 2018
    Love staying in this condo was our second year hoping to return next winter if available. already made request.. I would never leave if it were up to me but the location and the...
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    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for...
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    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.4 kilometres from Rain Barrel Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for an amazing home in Venetian Shores? This home has everything - 4 bedroom, 4 bath home that has been updated. The kitchen is amazing, suited for any type of entertaining. The 3rd floor floor is a lofted master bedroom suite with a walk-in closet. Two guest bedrooms are located on the...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    0.7 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relaxation at its best awaits you in our beautiful, Keys townhome on mile marker 87. Executive Bay Club is located in Islamorada, the Sports Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a heated swimming pool, a clubhouse, a private beach...
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    THE PERFECT GETAWAY1 / 14
    (6)Very good
    1.3 kilometres from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2016
    My husband and I searched for six weeks to find the perfect house for our vacation with another couple, and kept coming back to this one. All four of us were looking for a...
    Reviewed 9 April 2016
    We thoroughly enjoyed staying at the Perfect Getaway. My family and I had enough space to sleep, relax and enjoy meals together. The pool was a great addition to the property...
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    About this property
    This four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. It is situated in a clean, upscale neighborhood of all waterfront homes. The house is equipped with all the comforts of home. It is modernly furnished. Upstairs there are...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    5.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Washer
    • Patio
    • Grill
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peaceful and Scenic Keys Home, Newly Remodeled; Centrally Located on Plantation Key, near grocery stores, Old Tavernier Restaurant, Marinas, Founder's Park, and much more! The peaceful, secluded surroundings make this home the Ultimate Keys Getaway! Plenty of spacious accommodation on patios for...
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    Tavernier, Key Largo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Family Friendly Executive Bay Townhome with Beach & Pool1 / 28
    (10)Excellent
    0.7 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2015
    We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple.Due...
    Reviewed 13 September 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.7 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Grill
    • Balcony
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Executive Bay Club at mile marker 87 is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a heated pool, a clubhouse, a private beach area and a fishing dock. The waters are filled with plant and marine life,...
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Spacious Condo in Futura Yacht Club w/Heated Pool, Tennis, Marina; Bring your Bo1 / 25
    (1)Excellent
    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Grill
    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    My husband and I love the Florida Keys and this condo made our stay very enjoyable. Everything was very clean, organized and modern. It has the perfect feel of a Florida Keys...
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Futura Yacht Club is located in the Upper...
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    Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5.3 kilometres from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise!! Come and relax in our Bayside home and enjoy the coastal breeze and rustling palms in your own private oasis. Sure to become your favorite Keys home-away-from-home, this waterfront villa boasts elegance at every level with its spacious layout, modern decor and luxurious...
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    Tavernier, Key Largo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    0.7 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • DVD Player
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach area and a...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    0.7 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This 2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.7 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5.4 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Waterfront
    • Balcony
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tavernier Waterfront Retreat Treat yourself to a sun-filled vacation in this cute oceanfront condo with breathtaking ocean views and shared amenities that include a pool and barbecues. Here in the Sea Gull Condos complex, you'll be less than one mile off Old Highway 1 in the upper Florida Keys, and...
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    Tavernier, Key Largo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.4 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE KING MASTER BEDROOM IS DRESSED IN ISLAND FINERY WITH PRIVATE BATHROOM, COMBINATION SHOWER/TUB, AND FLAT SCREEN TV MAKES FOR THE PERFECT RETREAT. THE SECOND BEDROOM OFFERS A QUEEN SIZE BED, A FLAT SCREEN TV, AND AN ATTACHED BATHROOM. YOU CAN “COOK YOUR CATCH” IN THE FULLY EQUIPPED KITCHEN WITH...
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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    2.0 kilometres from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    Everything was perfect. Weather was great, the unit was clean and fully furnished with everything we needed. The other vacationers and full-time residents were friendly and...
    Reviewed 5 May 2016
    This condo was to die for. The decor was fabulous and the location was perfect and close to many restaurants. The sunset from the balcony was breathtaking. The owner was a...
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    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also...
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    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    5.4 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated and remodeled 2 Bedroom Condo is only about an hour and fifteen minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale in the Village of Islamorada, the 'Fishing Capital of the World.' This unit is comfortably and stylishly furnished, it has(2)...
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    Location Information
    Tavernier, Key Largo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Balcony
    • Ocean Views
    • Terrace
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dock of the Bay The condo is located in the Futura Yacht Club and boasts a plethora of amazing amenities that you'll be able to enjoy during your stay including a heated pool, two lighted tennis courts, basketball and sand volleyball courts, and great areas to grill and picnic! You won't want to...
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    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.7 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and relax at our beautiful townhome on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sports Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach area and a...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    2.2 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Wi-Fi
    • Grill
    • Washer
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Kid friendly
    Smoking allowed
    About this property
    Coral Harbour Condo Enjoy excellent ocean and lagoon views from your furnished patio! This top-floor condo is located in the Coral Harbour Club, which is one of Islamorada's best-kept complexes. This community is located right on the water and offers marina access and use of a slip capable of...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
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    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard terrace with barbecue, front porch seating, balcony, and dock....
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1.6 kilometres from Rain Barrel Village
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    This is a beautiful Venetian Shores home... It truly is a must see! The interior is clean and nicely decorated. The large porch on the back allows you to see the famous Florida Keys sunsets from your own home! Located a few houses down from Snake Creek, you'll have quick ocean and bay access. Deep...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (4)Very good
    1.5 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    I was having trouble booking my reservation online (technicality), and had to call in for help. One of the girls there was able to help me quickly, booked me & took my payment...
    Reviewed 19 January 2018
    Yes there was..DO NOT RENT FROM ITRIP/PHOENIX RENTALS.They were totally dishonest with me. They did not tell me that there was major construction going on in the building I...
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    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.4 kilometres from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This lovely 1 Bedroom 1 Bath Condo is only about an hour and fifteen minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale in the Village of Islamorada, the 'Fishing Capital of the World.' The unit offers sea breezes and ocean views. Seagulls condo offers a...
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    Location Information
    Tavernier, Key Largo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    SANCTUARY IN PARADISE1 / 21
    (5)Excellent
    3.2 kilometres from Rain Barrel Village
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2017
    We booked Sanctuary in Paradise as there were three families (9 people) traveling together. It was perfect as each family had separate sleeping quarters. We were able to...
    Reviewed 23 October 2014
    My family/extended family stayed here in June 2012 for two weeks and it was beyond wonderful. The owner ALWAYS was quick to respond to emails even if it was to say "you're...
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    About this property
    This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. We love The Lord and look forward to sharing our home with you. Whether your vacation ideal is relaxing in a hammock in view of the ocean with a good book or...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Luxurious Anglers Reef with Boat Slip, Pool, Ocean1 / 29
    (26)Excellent
    2.6 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    We stayed at Angler's Reef and had an amazing time. Jo was very helpful with the booking and very easy to work with. We felt like we were at home in her rental. She has...
    Reviewed 10 July 2017
    The island is beautiful. The condo is so clean and high quality. The area is located on the water. Nice boat docks.
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    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    3.6 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    ISLAMORADA Waterfront GREEN IVIS PARADISE Min 28 Ngts. Max 10 ppl. 26% Disc >1mo1 / 17
    (1)Excellent
    1.4 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
    • Ocean Views
    • Grill
    • Washer
    • Waterfront
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    We had. Great time. Can't wait to come back. The house was impeccable and the host gave us great customer service. Amazing time in the water. Great canal!
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    About this property
    Relax in this peaceful keys home with wide canal with easy access to ocean & bay. Located in one of the best neighborhoods in the keys!! You will enjoy a morning stroll, jogging or a bike ride around this picturesque neighborhood. We have plenty of room for your boat and all your toys. Bring or...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Islamorada Luxury Home Ocean & Bay Access1 / 14
    (9)Excellent
    2.0 kilometres from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Waterfront
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5.4 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Charming 3 bedroom, 1.5 bath canalfront home in great neighborhood. This home has everything you need for a perfect vacation! Open living, kitchen, and dining room with sliding glass doors to the screened in back porch, absolutely perfect for entertaining. With 50 ft. of dockage and great fish...
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    Location Information
    Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This tropically decorated 2 bedroom 2 bath unit, has a King bed and (2) Twins beds is approximately 1 hour and 20 minutes from Miami International Airport and 90 Minutes from Ft. Lauderdale airport.  Futura Yacht Club is located in the Village of Islamorada in the Upper Florida Keys. Located...
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    Tavernier, Key Largo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3.3 kilometres from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dubbed Aguazul, the home has four bedrooms and three bathrooms.  Two separate kitchens, one on each of the home's two levels, are another unique feature. Cool off in the home's oceanfront swimming pool, fish or swim from its dock, play in the sand of its private beach or merely sip a...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    5.4 kilometres from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Sauna
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unwind in our beautifully remodeled condo beside the turquoise waters of the Atlantic Ocean in Idyllic Islamorada. A charming 1 bedroom 1 bath suite with sleeper sofa in Sea Gulls Condominium; a quiet community nestled on the Atlantic's Edge. Located on the fifth floor, featuring beautiful ocean...
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    Location Information
    Tavernier, Key Largo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool1 / 34
    (2)Excellent
    1.3 kilometres from Rain Barrel Village
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2019
    The location, the amenities, the house, and the pool area was perfect. Everything needed to spend a weeks vacation with your family is within this home. I bring my 3 grown...
    Reviewed 17 April 2019
    We are three families that vacation together, everyone was just amazed at the expansive ocean views and the size of the property and home. The pictures do not do justice to it...
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    About this property
    Beautiful Gated Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding Staircase, Expansive Ocean Views, Over 4000 Sq. Ft. of Living Space. Heated Pool, Sandy Back Yard, Gated Entrance Lined With Palm Trees. Enjoy the Ocean Views and...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    3.2 kilometres from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Secure Parking
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    Kid friendly
    Smoking allowed
    About this property
    Rental amount includes all fees except boat dock fee. This newly renovated modern 3rd floor condo in Futura Yacht Club unit 302 is in a private gated community and has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened...
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    Location Information
    Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.4 kilometres from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Terrace
    • DVD Player
    • Grill
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ****Recently updated paint, furniture and a Beauty Rest Mattress!!**** Looking to escape reality? Look no further! Spacious 1 bedroom/1 bathroom condo located in the newly renovated Summer Seas Condominiums. Sit back and relax at the pool, go swimming at the private beach. Feeling adventurous?...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    2.6 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2016
    Everything we expected and more!! Condo very well maintained. Very adequately supplied with everything you need during your stay. Wonderful!! Thank you Susie and Matt for...
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    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Oceanfront Anglers Reef Islamorada Florida Keys1 / 14
    (3)Very good
    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2018
    This home is in a gated community in the heart of Islamorada. The site is beautiful, and seemed to have suffered no damage from Hurricane Irma. There are two artificial...
    Reviewed 25 August 2017
    Very well appointed and comfortable house, conveniently located to local amenities in Islamorada. It was like a home from home with easy to use washing machine, dryer and...
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    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,1 / 20
    (1)Excellent
    4.8 kilometres from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2019
    We loved our stay in Islamorada. The property is spacious and gated offering lots of quiet privacy in a prime location close to everything, shopping and dining. We enjoyed...
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    About this property
    San Roc is a private home with 150 feet of oceanfront and spectacular views of open water with heated pool and spa. Beautiful 4 Bedroom 3 Bath Home situated on over 2.5 acre secluded wooded lot. Landscaped grounds in a premier area of Islamorada, Florida known as 'Millionaires Row' Enjoy...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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