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Holiday Rentals with Pools in Hampton Bays

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    12 Matching Rentals in Hampton BaysView all 25 rentals
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    Travellers to Hampton Bays are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    3 Reviews
    4 Bedrooms, Sleeps 10Quick View
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    2 Bedrooms, Sleeps 4Quick View
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    3 Reviews
    4 Bedrooms, Sleeps 9Quick View
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    3 Bedrooms, Sleeps 12Quick View
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    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Hampton Bay Home Getaway -- 2500sqft, 3br (sleeps 12) - 3 full bths & 1 half bth (HUGE Master Suite), sitting rm w/fp, living rm, dining rm, eat in kitchen, billiard room & game room -- Large Backyard w LARGE in-ground heated pool, wood burning fire pit, barbecue grill, sand volleyball...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Reviews
    7 Bedrooms, Sleeps 16Quick View
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    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 4 January 2016
    Our family had a lovely time during our stay at this house, the amenities were great and we had a warm welcome when we got there. the pool, hot tub, and game room were all above...
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    About this property
    Only 600 feet from one of the most beautiful (private) Hampton's beach. Enjoy poolside living in this stunning contemporary home complete with lots of skylights and cathedral ceiling. Bike along the Peconic Bay or enjoy miles of sandy beach just steps away. This spacious home has a large heated...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    1 Review
    4 Bedrooms, Sleeps 8Quick View
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    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For family or group adults over 28 years old please up to max.8 guests inquire with your specific details for availability I'm on several sites.Not a party house noise ordinance in effect in all Hamptons from 10pm and 11pm on holiday. Quiet relaxing time outdoors especially after these...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Review
    5 Bedrooms, Sleeps 12Quick View
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    • Ocean Views
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly refurnished and upgraded Hamptons Beach House. Amazing bay views from every room. Heated pool and private sandy beach. Ideal for large families. Swim in the bay or your own pool. This home is on the border of Shinnecock Hills and Hampton Bays making it very desirable due to its...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, Sleeps 12Quick View
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    • DVD Player
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your own private summer resort. This house has it alll, you won't want to leave! Waterfront dock, jacuzzi, sparkling pool, multiple patios, 2 outdoor grills, and multiple balconies are key outdoor features. State of the art kitchen, large country dining room table, 2 fireplaces, 2 open airy...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    8 Bedrooms, Sleeps 20Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Washer
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Inspired by Walden, Thoreau and Emerson, Shell House is the quintessential luxury rental in the Hamptons. Dock in the nearby marina or rent a boat for the day. Shell House is your gateway to world class fishing, sprawling vineyards and quaint villages bustling with charming shops. With a resort...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    4 Bedrooms, Sleeps 10Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Patio
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large swimming pool (43' x 22' free form) with changing colors LED lights and water fall, a 10 people outdoor spa jacuzzi tub. Complete and well equipped outdoor kitchen, walking distance to the bay and 5 minutes drive to town or the OCEAN. Big and clean house in the woods. The house indulge...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    7 Bedrooms, Sleeps 18Quick View
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    • DVD Player
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Patio
    • Internet Access
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Huge 7 bedroom contemporary with 4 1/2 baths, huge deck, in-ground pool, outdoor bar, 7 person hot tub, gas BBQ. Spectacular recreation room, wonderful for entertaining. Fully loaded kitchen, 10 minute drive to ocean beach, near restaurants, clubs and all. This luxury home is available for...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
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    4 Bedrooms, Sleeps 8Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nicely renovated 4 BR, 3 BA home offers fine amenities, including marble baths, an upscale industrial-style kitchen, a spacious dining room, wood floors and wood-burning fireplace in a sun-filled living room. Its exterior features include a heated pool surrounded by a spacious mahogany deck in full...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    9 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    • Washer
    • Outdoor Dining Area
    • Satellite TV
    • Parking
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 16 September 2016
    Doug and Susan were wonderful hosts! We were a group of 9 friends and this house was perfect to reconnect, bond and relax. The house was neat , clean and cosy! Doug and Susan...
    Excellent of 5 bubbles
    Reviewed 9 August 2016
    We never did FRBO since we had heard of people having trouble being stung by rental fee and no access to the rental. But this was a wonderful experience.....the home met our...
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    About this property
    Completely renovated 4 bedroom home on quiet street in Hampton Bays. In town location. Walk to shops and dining. 3.5 miles to Atlantic Ocean and 1.0 miles to Shinnecock Bay. Large property with lovely deck and furniture. Handicap accessible with bedroom and wet room on first floor. Deck...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    • Satellite TV
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed 18 August 2016
    Booking last minute we were worried about what type of choices we would have left in Long Island. We were happy to find this home still available. We received a prompt response...
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    About this property
    Swimming, beach fun, and the finest sunsets are a 5 minute stroll away at Penonic bay down the private beach access path. This charming cottage is 650 sq/ft with two bedrooms, living room, kitchen and bathroom with shower. The house sleeps four comfortably (two twin beds in kids room and a king in...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    • Washer
    • Wi-Fi
    • Grill
    • Ocean Views
    • DVD Player
    • Patio
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterview Hampton home located in sought after Shinnecock Hills. 900 ft from Shinnecock bay with mooring rights. Which means you can basically keep your boat in your backyard of Shinnecock bay. 5min from Southampton village and ocean beaches. 5 star restaurants within walking distance. 1mile to...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 8Quick View
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    • Central Heating
    • Washer
    • Grill
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunny & Peaceful home within walking distance to the bay and a 15 min bicycle ride to the ocean. With an outdoor fireplace, outdoor shower and spacious backyard the day doesn't have to end. Master bedroom has a queen bed, daybed, and en-suite bathroom. The second bedroom has two full beds. The...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    8 Bedrooms, Sleeps 20Quick View
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    • Hot Tub
    • Grill
    • DVD Player
    • Washer
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunsets on the Beach, Walk in the Woods Inspired by Walden, Thoreau and Emerson, Shell House is the quintessential luxury rental in the Hamptons. Dock in the nearby marina or rent a boat for the day. Shell House is your gateway to world class fishing, sprawling vineyards and quaint villages...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    4 Bedrooms, Sleeps 8Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a lovely older home with modern amenities. Great for a family reunion, get together with friends and for visiting the North Fork and South Fork of Eastern Long Island. This spacious home is ideally located. Five minutes to Ocean beaches, Shinnecock Bay restaurants and shops, 15 min to...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    • Air Conditioning
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Home on Shinnecock Bay, on one of the nicest private streets in Hampton Bays, you will have use of the 2 kayaks on the bay, beautiful sunsets, and a mile away from the ocean beaches on Dune Road. We are about 2 miles from town. Great little cafe/market walking distance (1 1/2 blocks...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    • Washer
    • Waterfront
    • Hot Tub
    • Wi-Fi
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    • Patio
    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WaterFront Walkout is the Ground Floor of Stunning Private Legal 2 Family with 1500 Sq. Feet, Roomy Open Floor Plan, Laundry Room, AC, Heat & Water Views Galore. The Upper Unit is never Rented and for Owner's Exclusive Use Only. It is Available For Short Stays Year Round. Property Has Approx 200...
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    Hampton Bays, Hamptons 11946
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My wife and I have a quaint country/beach house with new furniture and a fresh coat of paint. We have furnished our home with our love for the ocean and the country. Terra cotta tiles and farm style kitchen table with bench and chairs in the kitchen. Living room with brand new Pottery Barn...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Completely renovated historic farmhouse on 7 acres, with its own 3 acre pond, pool, and tennis will make this summer an affair to remember. Experience a serene summer in this perfect setting. The home dates back to 1740 but has been completely renovated and designer furnished in a Tuscan/Provencal...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    This three bedroom home with a beautiful one bedroom guest house and heated pool is perfect for your summer getaway. Close to the ocean, shopping and Southampton village this home is centrally...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 2Quick View
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    About this property
    This newly constructed beautiful Beach cottage is in a private Red Creek Community, with one bedroom with a king size bed. The cottage has one full bath with a tub, New appliances, Granite countertops, French doors, New Cabinets, wood floors, New Washer/Dryer, Shingle Exterior, Fujistsu HVAC Wall...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, Sleeps 8Quick View
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    This great four bedroom offers everything you could want in a summer rental. The property has an amazing backyard that has a tremendous pool. No better place...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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