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.

0 of 0 items showing

1 of 3 pages

Guest favourite

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 favourite

Home in Hampton Bays

5 out of 5 average rating, 36 reviews

Scenic Stay in Sparkling Home, Heated Pool 6bds

Unwind in a Charming, Sparkling Clean Open Layout House w/King Primary, Stocked Kitchen, Antique Accents, Hardwood Floors. Scenic Yard w/Heated 5’ d inground Pool, Outdoor Shower, Gated Mahogany Decks, Fire Table, Deck Heater, BBQ, so you can Enjoy Nature. 5 Smart TV's, Bonus Family Rm. St Fighter Arcade Machine, PS4, WIFI. Eat at the best Restaurants, Visit Wineries, Farms, Breweries, Mini-Golf, Golf, Beaches, Shop Antiques & Boutiques. Sleeps 8, 2+ full Baths. On private road, 1.5 hr to NYC

Top guest favourite

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 Southampton

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.

Top guest favourite

Home in East Quogue

5 out of 5 average rating, 36 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

Superhost

Home in East Hampton

4.87 out of 5 average rating, 203 reviews

Walk2Beach-HeatedPool-FencedYard4Dog-Fireplace

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset.Easy living home.Welcoming to all respectful families & guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Ask about kayaks&EVcharger.Registry 23-625.

Top guest favourite

Guest house in East Hampton

5 out of 5 average rating, 90 reviews

The Quail’s Nest

A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

Top guest favourite

Home in Mastic Beach

4.93 out of 5 average rating, 120 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.

Guest favourite

Home in North Fork

4.92 out of 5 average rating, 24 reviews

North Fork Farmhouse with Saltwater Pool

Enjoy spectacular sunsets from the great room and deck overviewing your secluded hedged yard and saltwater pool. Located in the heart of the North Fork this 1820s farmhouse with modern amenities is nestled amongst vineyards and farmland with dramatic views in every direction. Quaint villages, premier restaurants, wineries, farms and beaches surround you. A truly magical, peaceful paradise for you and your group. Note pool is open May through mid October.

Top guest favourite

Home in East Hampton

5 out of 5 average rating, 36 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.

Guest favourite

Home in North Fork

4.97 out of 5 average rating, 203 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.

Top guest favourite

Home in Remsenburg-Speonk

5 out of 5 average rating, 40 reviews

5-Star Listing: Hamptons Oasis, Easy from NYC

Welcome to our coastal retreat. Minutes away from Westhampton Beach and a super-easy commute from NYC. Perfect for families or a group of close friends to get away from it all. A bright, spacious, recently renovated home with light-filled rooms, new floors, coastal decor. Ultrafast Wifi, Alexas, and a new kitchen with the latest appliances. Beautifully landscaped gardens, heated pool, 6-person salt water hot tub (in winter or summer)!