Holiday rentals with a pool in Wainscott

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Top-rated rentals with a pool in Wainscott

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

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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 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

Cozy fireplace, yard4pup, walk to beach, 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 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 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 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.

Guest favourite

Home in East Quogue

5 out of 5 average rating, 33 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 in Mastic Beach

4.93 out of 5 average rating, 119 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 Southampton

4.94 out of 5 average rating, 31 reviews

Newly Renovated SH Village 5bd with pool

Sol Cottage is a charming five bedroom four bathroom home with a separate guest house on the property. The house is a 5 minute drive to town and the beach. A Jeep Wrangler is available for rent through turo (inquire for details). The house has a beautiful HEATED saltwater Gunite pool and a large fenced in yard. The house has brand new wide plank floors, HVAC system, and furniture. There is a wood burning fire place in the main living space, which sets a cozy welcoming vibe.

Superhost

Home in Montauk

4.85 out of 5 average rating, 41 reviews

Amazing Spacious Waterfront Property Infinity Pool

**PLEASE MESSAGE US BEFORE SUBMITTING A BOOKING REQUEST** *We do not allow weddings or events at the home** **Outdoor pools do not remain open in Winter - pool is open Memorial Day Weekend to Oct 15 ****** **Families only**No share houses or groups - strictly enforced* Sparkling water views from this amazing home. Located directly on Lake Montauk, for paddleboarding and kayaking. The infinity pool gives way to a huge lush lawn, perfect for kids to enjoy.

Guest favourite

Home in East Hampton

5 out of 5 average rating, 35 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.