
Holiday rentals with a pool in The Hamptons
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in The Hamptons
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Modern Southampton Cottage | Heated Pool & Peloton
Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

Detached bungalow w/ private bath
Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

Amazing Home close to Everything -
Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)
Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Stylish+Cozy Hamptons Winter Getaway-5min to Beach
Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully fenced tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

Montauk Waterfront Condo w/ Sunset Views
Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

3 BR/Pool. Walk to Beach & Town!
Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Luxury modern farmhouse with heated pool & hot tub
*pool closed November to end of April This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

Luxury Hamptons Home with Heated Saltwater Pool
Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

Peaceful Retreat in Immaculate Architect’s House
This "like new" contemporary home features 4 bedrooms, 3.5 baths, open living spaces, soaring ceilings, abundant natural light, and a modern kitchen. Nestled in tranquil West Tiana Shores, minutes from bay & ocean beaches, and charming Hampton villages (Southampton, Westhampton, Quogue). The living room directly faces your private pool, cedar deck, and lush garden—a perfect getaway for vibrant summers and relaxing winters
Popular amenities for The Hamptons rentals with a pool
House rentals with a pool

Splendid private cottage

Spectacular Village Home: Close to Town and Ocean

Stunning Farmhouse in NoFo I Heated Pool, Wineries

East Hampton Secluded Escape with Gunite Pool

Delightful Sag Harbor Home w Pool

Chic & Spacious Designer Home, Heated Pool/Spa

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Renovated Southampton Home+Pool
Condo rentals with a pool

Second Floor Corner Unit Overlooking the Ocean

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Beautiful condo on Long Islands Northfork

Montauk Royal Atlantic Beach Resort North

Endless Summer Studio Condo w Balcony Bayview

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

Waterfront Summer Escape in Wine Country: 2BR
Other holiday rentals with a pool

Sag Harbor Hamptons hideaway

Sunny, walk to beach, large pool

5BR/4BA: Sag Harbor, Pool, Fireplace, Near to town

Remarkable Montauk Views: 4 Bedroom, Pool

Chic, Modern, & a Walk to Beach!

Civilian Surf Club: a family-friendly beach house

Southampton Stunner: Pool, Beach & more!

Head of Pond House - Waterfront Cottage
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Hotel rooms The Hamptons
- Bed and breakfasts The Hamptons
- Luxury rentals The Hamptons
- Rentals with a fire pit The Hamptons
- Holiday home rentals The Hamptons
- Rentals with lake access The Hamptons
- Rentals with outdoor seating The Hamptons
- Beach house rentals The Hamptons
- Fitness-friendly rentals The Hamptons
- Mansion rentals The Hamptons
- Farmstay rentals The Hamptons
- Apartment rentals The Hamptons
- Villa rentals The Hamptons
- Pet-friendly rentals The Hamptons
- House rentals The Hamptons
- Rentals with a patio The Hamptons
- Bungalow rentals The Hamptons
- Cottage rentals The Hamptons
- Condo rentals The Hamptons
- Rentals with beach access The Hamptons
- Rentals with an EV charger The Hamptons
- Guesthouse rentals The Hamptons
- Family-friendly rentals The Hamptons
- Rentals with a fireplace The Hamptons
- Boutique hotels The Hamptons
- Waterfront rentals The Hamptons
- Rentals with a hot tub The Hamptons
- Rentals with a kayak The Hamptons
- Beachfront rentals The Hamptons
- Rentals with breakfast The Hamptons
- Private suite rentals The Hamptons
- Rentals with a washing machine and dryer The Hamptons
- Rentals with pools Suffolk County
- Rentals with pools New York
- Rentals with pools United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Sunken Meadow State Park
- Mohegan Sun
- Hammonasset Beach State Park
- Long Island Aquarium
- Powder Ridge Mountain Park & Resort
- Mystic Seaport Museum
- Yale University Art Gallery
- Burlingame State Park
- Sleeping Giant State Park
- Dunewood
- Orient Beach State Park
- East Hampton Main Beach
- Meschutt Beach
- Wölffer Estate Vineyard
- Ditch Plains Beach
- Bluff Point State Park
- Napatree Point Conservation Area




