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Holiday Rentals with Pools in Gary

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    R 5 836 Average
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    Don't let other travellers get your favourite Gary area holiday rental. You're so close to securing your perfect getaway. Book today.
    15 Matching Rentals in the Gary AreaView all 78 rentals
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    The following rentals are within 40 kilometres of Gary.
    Mint Julep1 / 18
    (5)Very good
    Michigan City
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Blueberry Cottage1 / 11
    (4)Excellent
    Michigan City
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Southern Belle1 / 14
    (5)Very good
    Michigan City
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    My Blue Heaven1 / 22
    (2)Very good
    Michigan City
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    Beautiful house, perfect location, awesome time! This is a great family-friendly town with tons of things to do!
    Reviewed 14 July 2017
    We found the home very accommodating as far as the long eating table, the open concept of the living area and kitchen and all the bathrooms!!!!!! We used the pool most days and...
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    About this property
    New luxury lake house available in the beautiful Beachwalk Resort community in Michigan City, Indiana. Home can accommodate up to 16 adults with beds and dining. This home has two master bedrooms – both with king beds and private bathroom. One is on the second floor and the other on the first...
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    Location Information
    46360, Michigan City, Indiana
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    Guest House in Private Gated Nudist Community1 / 2
    (2)Excellent
    Valparaiso
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Grill
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2017
    Let me start off by saying this is a great place to come if you're a first timer. The wife was a little apprehensive about being nude around other people ,but she warmed up...
    Reviewed 22 June 2017
    I have visited numerous other nudist communities but Lake of the Woods Club was by far the best. The guest house we stayed in had everything we could have wanted, and the hosts...
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    About this property
    This guest house is located on private property inside Lake O the Woods Club. The oldest continually operating Nudist Club in the United States. You will have access to 203 private acres with hiking paths, a 27 acre lake, heated pool, 12 person hot tub and sauna. Very private, this is the perfect...
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    Location Information
    46383, Valparaiso, Indiana
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sun King--Brand New 6th Full Bathroom!--Huge Beautiful Home1 / 39
    (16)Excellent
    Michigan City
    7 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    Amenities & Details
    • Children's Pool
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 2017
    This place was amazing! Everything is set up so nicely and it's roomier than I ever could have imagined. My family and I, along with some friends, went up here after I got...
    Reviewed 13 March 2017
    This colorful beach house with wonderful wrap-around porch had a happy feel, and was so inviting and comfortable for our large group. An open spacious kitchen with all the...
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    About this property
    Beachwalk Resort is an award winning beach community located in the Indiana Dunes on one of Lake Michigan's most beautiful stretches of beach. Sun King, and the included coach house The Jester, combine to create one of Beachwalk’s largest properties, complete with 7 bedrooms and 6 full bathrooms....
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    Location Information
    46360, Michigan City, Indiana
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 24
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    Moondance--Open Concept Beachwalk Favorite; Spring Weekends Will Go Fast1 / 36
    (11)Excellent
    Michigan City
    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Children's Pool
    • Wi-Fi
    • DVD Player
    • Washer
    • Housekeeping Included
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    We recently spent one week at Moondance and had a very nice time. The house is very spacious and has comfortable seating for everyone, plus three bathrooms. Adam is very...
    Reviewed 10 July 2017
    Great rental house. Large, clean and well-stocked. Very comfortable for our group of 12. Great resort community. The location of this house is perfect, very close to pool, kayak...
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    About this property
    Located in the acclaimed Beachwalk resort community in the Indiana Dunes on Lake Michigan, just one hour from Chicago, this house ('Moondance') and its perfect central location is a Beachwalk favorite. Unique among Beachwalk homes, Moondance has an open floor plan with a stunning cathedral ceiling...
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    Location Information
    46360, Michigan City, Indiana
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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    5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool1 / 16
    (1)Excellent
    Chesterton
    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2015
    We spent a incredible week at the Lake Michigan Compound to celebrate our mother's 80th birthday. The house is stunning and the view from both houses are breathtaking especially...
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    About this property
    THE PERFECT BEACH VACATION RETREAT FOR A FAMILY - 2 HOUSES, THE BEACH, A POOL, PANORAMIC LAKE MICHIGAN VIEWS, JUST STEPS TO THE BEACH, LOTS OF SPACE FOR EATING, SLEEPING ,OR GATHERING INDOORS OR OUT AND JUST AN HOUR FROM CHICAGO. We call it our secret hideaway! The Main House: An all glass...
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    Location Information
    46304, Chesterton, Indiana
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 20
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    Highland
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully furnished home offers everything you need for a week or two of self-indulgence. Located in the prestigious Highlands Reserve Golf Community, this wonderful 4 bedroom 2 bathroom home comprises of two queen bedrooms and two twin bedrooms capable of sleeping up to 9 people...
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    Location Information
    46322, Highland, Indiana
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    The Queen Bee--Reserve Spring Weekends While You Can1 / 42
    (9)Excellent
    Michigan City
    7 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Patio
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2017
    We have rented before from the same owners(Sun King) and this property too surmounted our expectations! The owners are very easy to work with and very accommodating! Amazing...
    Reviewed 27 October 2016
    Wonderful place for a large group. The kitchen table was awesome to gather around for games and meals. Had everything we need and more. Would definitely return.
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    About this property
    The Queen Bee, along with its included coach house, Buzz Inn, are not to be missed. This massive property is perhaps Beachwalk’s largest and, under new ownership for 2016, has been transformed into its nicest. Seven bedrooms and eight bathrooms spread across six separate floors of living, with...
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    Location Information
    46360, Michigan City, Indiana
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 24
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    Michigan City
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A spacious main floor with open kitchen, dining area and living room with access to the screened porch to extend your space even further. Dining table seats 6 with an additional 4 stools at the kitchen island extending your dining seating to 10. The second floor hosts 3 of the 5 total bedrooms....
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    Location Information
    46360, Michigan City, Indiana
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    Crete, IL
    4 Bedrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates: In-Season weeks of June 23 - August 18: $13,100 per week~~ 8/25-9/7: $9,500 per week. Off-Season Rates: 11/1/2017 - 4/27/2018: $6000/week 4/28-5/25: $7,200/week ~~ 5/26-6/22: $8,700/week ~~ 9/8-10/31: $7,900/week All Rates Include Cleaning and Linens! Brand new, upscale, double...
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    Location Information
    02633, Crete, Illinois
    Holiday Rental House - 4 Bedrooms, Sleeps 12
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    Michigan City
    9 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Patio
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Restored in 2018, this impressive home is the ideal space to have some rest and relaxation with friends and family. With a quick 3 minute walk to Sheridan beach and a private in ground pool, you'll never want to leave! This home includes 4 queen beds, 3 full size beds, 6 twin beds. Maximum of 20...
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    Location Information
    46360, Michigan City, Indiana
    Holiday Rental House - 9 Bedrooms, 5 Bathrooms, Sleeps 20
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    Michigan City
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Washer
    • Hot Tub
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable accommodations for 12-14. Walk into a bright full size kitchen and dinning room with a large dining table and counter bar top seating for all to gather. The living room has another table for 4 with plenty more cozy seating to relax and watch TV on the flat screen located in this...
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    Location Information
    46360, Michigan City, Indiana
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    Michigan City
    8 Bedrooms, 6 Bathrooms, Sleeps 27 Quick View
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    Amenities & Details
    • Children's Pool
    • Air Conditioning
    • Private Garden
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Poseidon is a brand new Beachwalk listing and it is Beachwalk's largest home. The new owners poured their money and energy into turning this home into Beachwalk’s premier property. This listing continues to be updated with new photos as work is completed. Poseidon and Trident, the included coach...
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    Location Information
    46360, Michigan City, Indiana
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 27
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