Vacation rentals with a pool in Sag Harbor

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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 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 Hampton Bays

4.89 out of 5 average rating, 85 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 in East Hampton

4.87 out of 5 average rating, 203 reviews

EastHampton-Fireplace-Walk2Beach-Yard4Pup-HSWPool

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community. Ask about kayaks.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

Guest favorite

Home in North Fork

5 out of 5 average rating, 9 reviews

Luxury Escape - Saltwater Pool

Welcome to our fully renovated sanctuary, on a sprawling 1.5-acre property just one block away from the beach. Indulge in the luxury of our 4-bedroom, 2.5-bathroom home, where tranquility meets elegance. Unwind in the expansive back yard, enveloped in lush greenery, and discover the centerpiece of our oasis—a magnificent, 20x50 saltwater heated pool with an in water tanning ledge. Bask in the sun on one of the two generously-sized decks, perfect for relaxation and taking in the surroundings.

Guest favorite

Home in Hampton Bays

5 out of 5 average rating, 36 reviews

Scenic Stay in Sparkling Summer Home

Unwind in a Charming, Sparkling Clean Open Layout House w/King Primary, Stocked Kitchen, Antique Accents, Hardwood Floors. Scenic Yard w/Heated 5’ Pool, Cedar Outdoor Shower, Gated Mahogany Decks, Fire Table, Deck Heater, BBQ, so you can Enjoy Nature. 5 Smart TV's, Bonus Family Room. 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

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.

Guest favorite

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 favorite

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 favorite

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.

Guest favorite

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)!