Holiday rentals with a pool in Sag Harbor

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sag Harbor

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Bungalow

4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

Dive into the saltwater pool, set amid professionally landscaped grounds. Later, head for the multiple outside entertaining areas for a meal from the built-in outdoor grill. Round off the day with a soak in the claw foot tub in the marbled bathroom. The pool is available from May to September, and the temperature is regulated at 87 degrees. Check with the host for additional requirements. Walk to the Clearwater Beach Association's private beach, just a few blocks from the house, with a local grocery store also close. East Hamptons village is 12 minutes away, with recommended restaurants including Roudy Hall and Citta Nova.

Guest favourite

Home

5 out of 5 average rating, 36 reviews

Scenic Stay by Beaches, Farms, Wineries, Breweries

Unwind this Fall in Charming, Sparkling Clean House w/Mahogany Decks, Fire pit Table, Deck Heater, BBQ, Pool, Hot OD Shower, large Landscape Lite Yard to enjoy nature & Cornhole. 5 Smart TV's, Arcade Machine, PS4.Bonus family room w/double bed. On private road, w/king primary, antique accents. Visit wineries, farms, breweries, aquarium, mini-golf, golf, beach, restaurants, shop antiques, boutiques & outlets. Hardwood floors, stocked kitchen. desk, WIFI, Sleeps 8, 2 full Baths+.. 1.5 hr to NYC

Guest favourite

Home

4.89 out of 5 average rating, 84 reviews

Perfect Hamptons Summer Rental with Pool

Self check in to Private Entrance of this beautiful home. Long driveway and plenty of space for parking at the home. Use of pool and amenities. Host will be staying on the property with in a separate apartment. Will be around if needed, friendly and accommodating but not intrusive! Other things to note: • Pool heating: $100 per day • House is ONLY for guests on the reservation. No exceptions. • Don’t reserve the house under one guest UNLESS you are one guest. Reservation won’t get approved

Superhost

Home

4.87 out of 5 average rating, 202 reviews

Heated SW Pool, Walk2Beach, 5*Yard4Pup, Spotless

Meticulously cleaned home. Tranquil family neighborhood in historic artist's beach community. Wood burning fireplace. Private fenced-in backyard . Heated saltwater pool in summer. Half mile to private bay beach, bike great trails & savor delicious meals prepared in fully equipped kitchen. Don’t miss Clearwater Beach's stunning sunset. Easy living home.Welcoming to all respectful families & guests.East Hampton's best restaurants are nearby. Smoke free.Small dogs permitted.Rental Registry 23-625.

Superhost

Home

4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

Relax in Adirondack chairs on the expansive front porch of a custom-built traditional with cedar shakes. Inside too, find classic style with this stunning Cape Cod's lovely decor. Prepare family meals in a kitchen with state-of-the-art appliances & dine at a country-style table. Stroll 2 blocks to a marina to view glorious sunsets over the harbor. Luxuriate by the pool in total privacy, surrounded by the lush backdrop of mature pine trees & hydrangea. Pool is closed during the winter. #24-1026

Guest favourite

Guest house in Southampton

4.96 out of 5 average rating, 160 reviews

Wonderful Private Spacious Pool House

Light, open, spacious and private pool house less than 1/2 mile from the bay beach and 4 miles to ocean beaches. Close to Southampton, Sag Harbor, and Water Mill. Families love it as do our many girl getaways. Pool and deck and BBQ and umbrellas and pool toys and lounge chairs are for your exclusive enjoyment too. Enough beds to sleep 6, but we allow up to 3 additional guests for a total of 9 with an additional fee. Portable beds and linens will be provided. Can’t book just 1 weekend night.

Superhost

Home

4.87 out of 5 average rating, 23 reviews

Beautiful Hilltop Property on Shinnecock Hills

Beautiful Hilltop 5 Bedrooms and 3 baths Property on Shinnecock Hills. Amenities including a beautiful kitchen with new cabinets, granite countertops, and stainless appliances. Five bedrooms, two on the first floor sharing a bath, with queen size beds in both. A master bedrooms suite with en-suite bathroom on the second floor, and two additional bedrooms with queen-size beds. Hampton style house, lots of windows allowing for plenty of sunlight. This house is built for outdoor entertainment.

Guest favourite

Home

5 out of 5 average rating, 32 reviews

Estate-Indoor & Outdoor Pools- 5k SF + Amenities

Welcome to this modern luxurious new home boasting over 5,000 sf w/ 5 BRs and 4.5 BA, situated at the end of a private cul-de-sac. This spacious home was masterfully finished and boasts an open concept with gorgeous interiors, featuring year-round heated indoor pool & hot tub, outdoor pool, chef’s kitchen, two ground floor en-suite primary bedrooms, private en suite studio apt. Basketball, ping pong, fire tables, outdoor heaters, outdoor kitchen, private fenced in yard, high end furniture

Guest favourite

Home

5 out of 5 average rating, 9 reviews

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby farms & wineries. Bedrooms include luxury linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Superhost

Home in East Hampton

4.83 out of 5 average rating, 6 reviews

Peaceful, Summer Pool, Close to Ocean & Village

Village fringe. Great location. Close to all. 4 Bedrooms/2 Bath. Log home with Heated pool (summer) and lots of sunlight. Located on a quiet cul-de-sac very close to Ocean Beach and the Village! Includes Pool with outdoor shower and changing room. Relax in the teak furniture or the hammock after a swim in the large pool. Peaceful setting. All the amenities one would expect and high speed wireless internet, 3 Smart LCD TVs. Rental Registration # 20-1005.

Guest favourite

Home

4.97 out of 5 average rating, 200 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Superhost

Home in East Hampton

4.8 out of 5 average rating, 10 reviews

East Hampton Cheerful 3 bedroom home with pool.

Peaceful home set back from the road. Light-filled, clean, with updated kitchen and marble bathrooms. Upstairs primary bedroom and bath, with comfortable family room with big screen TV and work space. Downstairs has two additional bedrooms and bath, as well as living room and kitchen. Fully finished basement. Private pool area with professional landscaping and grill. Near beaches and close to town.