Holiday rentals with a pool in Shirley

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Shirley

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.

Superhost

Cabin 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 w/ Heated pool (optional in summer) and lots of sunlight. Located on a quiet cul-de-sac very close to Ocean Beach and the Village! Includes Pool (Summer) w/ outdoor shower and changing room. Relax in teak furniture or hammock after a swim in the large pool. Peaceful setting. All amenities one would expect. High speed wireless internet, 3 Smart TVs. Late Checkout Fee $175. inc pet Rental Registration # 20-1005.

Superhost

Home in East Hampton

4.87 out of 5 average rating, 203 reviews

Clean&EasyHome-PrivateBeach-HeatedPool-Fenced Yard

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.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.Registry 23-625

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.

Guest favourite

Home in Mastic Beach

4.93 out of 5 average rating, 121 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

Flat in Deer Park

4.87 out of 5 average rating, 15 reviews

Serene one bedroom retreat w/ backyard oasis

**Welcome to Your Private Oasis!** Enjoy a serene escape at our cozy one-bedroom retreat. Highlights include: - **Above-Ground Pool**: Perfect for refreshing dips. - **Outdoor Patio with Gazebo**: Ideal for relaxing and unwinding. - **Private Daybed**: Your perfect spot for lounging in peace. Experience the tranquility and privacy of our oasis while being close to local attractions. Book your stay today for a relaxing getaway! Pool is seasonal until October 1st.

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 Westhampton Beach

4.92 out of 5 average rating, 144 reviews

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

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.

Guest favourite

Home in Westhampton

5 out of 5 average rating, 13 reviews

1940’s Westhampton renovated bungalow

Come stay at this centrally located hamptons chic property. The whole group will enjoy easy access to many beaches, downtown Westhampton Beach and many NoFo wineries. Westhampton Beach is 6 minutes from the house and filled with many amazing restaurants and shops to explore. Explore all of the Hamptons and Northfork from this beautiful 4 bed and 3.5 bath home with inground pool. Pool open MDW- LDW *** No smoking or drugs on property. ***No pets