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 Bdr /2 Bath. Log home w/ Heated pool (optional heat in summer) & lots of sunlight. Located on quiet cul-de-sac very close to Ocean Beaches & the Village! Includes Pool (Summer Memorial Day Wknd) w/ outdoor shower & 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 $175 Ask Rental Registration # 20-1005.

Superhost

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

Home in East Hampton

4.86 out of 5 average rating, 206 reviews

HeatedPool-Walk2Beach-Yard4Pup-Peaceful-Clean-Easy

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, 11 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

A clear, inviting pool is set within a wooden deck area surrounded by lush mature pine trees. Comfortable lounge chairs are positioned nearby, offering a relaxing space beside the water. A sun umbrella provides shade for those seeking respite from the sun.

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

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, 52 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

Guest favorite

An expansive saltwater pool is surrounded by a spacious patio with lounge chairs. The area is bordered by lush greenery and colorful flowering bushes, enhancing the serene setting. Pebbled landscaping delineates the pool area, creating a calm and inviting atmosphere.

Home in Orient

5 out of 5 average rating, 10 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 Oak Bluffs

4.93 out of 5 average rating, 195 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!

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, 37 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.

Guest favorite

An inviting in-ground pool is framed by a patio of grey stone tiles. Lush greenery surrounds the pool area, providing a private and serene environment. A wooden fence creates an additional sense of seclusion, enhancing the feeling of relaxation and tranquility.

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