Vacation rentals with a pool in Block Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Block Island

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

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Guest favorite

The exterior of a modern wooden house features a sloping roof and a welcoming front porch. Lush green grass surrounds the structure, complemented by small shrubbery thoughtfully arranged near the entrance. Three large windows provide natural light to the interior.

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

A heated pool is surrounded by a spacious wooden deck, providing ample room for relaxation. Sun loungers are positioned neatly nearby, offering comfortable seating options. A colorful inflatable float is visible on the water's surface, with lush greenery framing the tranquil setting.

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

A serene outdoor scene showcases a heated saltwater pool surrounded by vibrant flowers. Sun loungers are positioned beside the pool, offering a place to relax. The background features a two-story house, framed by tall trees that create a sense of privacy.

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 favorite

A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.

Home in Southold

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.

Guest favorite

A large pool is surrounded by a wooden deck and fencing, featuring colorful floats floating on the clear water. Lounge chairs are positioned along one side of the pool, with a staircase leading to an upper deck visible in the background.

Home in Middletown

4.93 out of 5 average rating, 122 reviews

Modern Home w/ Pool & Game Room | Mins to Newport

Escape to our stunning, upscale, renovated home in Middletown, RI! This property boasts a prime location with the beach & downtown Newport just minutes away! With sleeping space for 10 adults + kids, our home offers a private getaway for groups in town for a wedding or seeking a memorable vacation. Lounge by the pool, grill up some food, or snuggle up and watch a movie inside, this home has it all! Make memories that will keep you coming back year after year. Follow us on Insta: Searenity.House

Top guest favorite

The expansive patio area features a large pool with a unique shape, surrounded by sun loungers and shaded seating options. A hot tub is positioned nearby, and additional amenities include a fire pit and a shaded cabana. The enclosed space is accentuated by landscaped elements.

Home in East Haddam

4.98 out of 5 average rating, 51 reviews

Spacious 5 bdrm, 6 bth, 30 min to beach & casinos

Spacious 5 bedroom 6 bath sleeps 14 -WHAT YOU’LL LOVE- • Private resort style patio, including STUNNING POOL, HOT TUB, fireplace and firepit, bar and grill, 65" TV, outdoor bathroom and shower. • Open concept floor plan that is great for groups and families. • Authentic New England experience. • Fun game room for adults and kids with wet bar and mini fridge • Quiet street and neighborhood. NY times listed East Haddam in their “52 places to love” in 2021 1 mile to East Haddam Center

Top guest favorite

Home in Oak Bluffs

4.94 out of 5 average rating, 194 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Superhost

A large, heated swimming pool is surrounded by paved stone. The clear blue water reflects sunlight, while a nearby hammock and wooden seating area are visible, contributing to a relaxing outdoor space. The pool's shallow entry is designed for easy access.

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 favorite

A well-maintained outdoor space features a large swimming pool surrounded by a wooden deck. Lounge chairs are placed around the pool, with red umbrellas providing shade. Adjacently, a patio area includes a dining table. Lush greenery frames the area, contributing to a serene ambiance.

Guesthouse 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.

Guest favorite

A clear view of a gunite pool reveals crystal blue water, surrounded by a spacious lawn. Four lounge chairs are positioned nearby, and the house is seen in the background, framed by lush hedges and trees, with a deck that offers steps leading up to the entrance.

Home in Cutchogue

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 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 Cutchogue

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.