Vacation rentals with a pool in Shelter Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Shelter Island

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

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Guest favorite

Bungalow in East Hampton

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 favorite

Home in Sag Harbor

5 out of 5 average rating, 34 reviews

Sag Harbor Modern Oasis

Luxury 5 bedroom, 3 1/2 bathroom home designed around a central courtyard/non heated pool area (5300sqft) Grill & contemporary seating area with fire pit; perfect entertainment area against a backdrop of arboreal gardens. Split across 3 levels; light filled main living, dining and eat in kitchen; two entertainment rooms with built in wet bars. Lower level has 5th bedroom with en-suite and dedicated office.Quiet neighborhood; walkways, bike paths. 5mins by car to Sag town beach. 12mins to village

Guest favorite

Home in Hampton Bays

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

Guest favorite

Home in Sag Harbor

4.9 out of 5 average rating, 182 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence and gates around pool. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Superhost

Home in East Hampton

4.87 out of 5 average rating, 203 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.

Guest favorite

Home in North Fork

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, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic 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

4.94 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

Superhost

Home in East Quogue

4.92 out of 5 average rating, 12 reviews

Private Hamptons Escape with Large Pool & Hot Tub

NEW listing from experienced 5 STAR HOST. Nestled in East Quouge, a stunning Victorian sitting on over 1.5 private acres with a 20x40 inground pool & 6 person hot tub in the spacious backyard. This 4 bedroom, 4 full bath is over 4000 Sq Ft, has addtional sleeping spaces, and play area for your younger ones. Gorgeous fully stocked kitchen and a 10 person dining space, as well as 8 person outdoor teak dining set, make this house great for gathering and entertaining your close friends and family.

Guest favorite

Guesthouse 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.

Guest favorite

Home in Mastic Beach

4.93 out of 5 average rating, 118 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

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 favorite

Home in East Hampton

5 out of 5 average rating, 33 reviews

Stunning Central E. Hampton Home w/ gunite pool.

EH Registry #24-65. This 2800 sq foot home boasts 10' ceilings & has been re-vamped from top to bottom. Beautiful landscaping, 44' x20' deck & a 6' privacy fence Outdoor lounge furniture & dining set. The indoor dining room seats 10. Upstairs: 4 bedrooms: All mattresses are new! Baths fully stocked. Pool closes in mid Oct. and opens mid May. Pool heat is a separate fee! NO PETS. Significant pet fee required for your non shedding well behaved dog.