
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.

Beachfront W/ HotTub, Sauna, Pool & Panoramic view
Welcome to the Heart of Somerset! Nestled at the very tip of Somerset on a private dead-end road, this coastal waterfront home is the perfect place for a family retreat, romantic getaway or friends seeking adventure Marvel at the panoramic views and dramatic colors from Sunrise to Sunset of the Braga Bridge, Mt. Hope Bridge & Bay, Bristol, Tiverton Rhode Island & the Fall River cityscape on the horizon. Grab a kayak or relax, soak up the sun & let the gentle sea breeze wash your worries away!

Rustic Farmette Studio w/yearround Hot Tub
Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

Artist studio in the woods
Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quite, tranquil, relax. As of 1/1/26 booking rate will be $120 per day. Pool $20 seasonal.

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 grouds are smoke-free.

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)

East Hampton Village Fringe, Renovated with Pool
This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf
Spa Resort | Casinos | Heated Seasonal Pool and Hot Tub | Sauna | Fitness Room | Clubhouse | Golf | Restaurants | Heated Massage Chair | Warm Robes and Blankets | Electric Fireplace with Remote| New Serra topper Whether you’re looking to get away or jump in, enjoy this relaxing retreat surrounded by upscale amenities! We’ve done our very best to ensure your stay is comfortable and tranquil, full of necessities and extras, and that there are many nearby options for adventure and fun.

Perfect New England Getaway has a pool/ hot tub
traditional New England style that is not just a great home, but a great vacation compound with lots of amenities and outdoor living spaces. Enjoy recreational activities on land and sea that abound locally. Mystic, Stonington Borough, Westerly, and Watch Hill are all close IMPORTANT INFORMATION: Please be advised Stonington, CT has a STRICT OUTSIDE Noise ordinance after 10pm that is enforced by the Police. If a report is generated for any reason , you will forfeit your deposit.

Get comfy in the country!
This special place is close to everything, making it easy to plan your visit. Just 10 minutes away from town. Secluded cabin on a 57-acre farm outlooking a large paddock with 4 highland cows. This beautiful property has a neighboring golf course and trails connecting to Heritage Park. Pool. Fireplace. Amazing sunsets! Who wouldn’t want to live like Yellowstone for a little? Home of Welcome Pastures, a Nonprofit 501(c)3 organization. Portion of proceeds go towards the foundation.

Casino Stay & Play House w/Hot Tub, Game Room
Come have an unforgettable vacation at our fun-packed home! The house is loaded with of games and conveniently located close to Mohegan Sun, Foxwoods, Mystic, Vineyards, Navel Submarine Base, Ct College and several beaches. Enjoy our game room where you can sing karaoke, play over 3,000 classic games and draw on our giant chalk board wall. Outside enjoy swimming in your own private pool, take dip in the hot tub, play a game of corn hole and watch tv by the fire pit on the deck

Spacious East Hampton Getaway with Pool
This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

FREE Private Indoor Heated Pool - Mystic Home
Experience Mystic in style at this spacious retreat with a private year-round heated indoor pool. Sleeps up to 11 with 4 king beds + bunk, 3 full baths, and open living spaces perfect for groups. Relax poolside, cook in the gourmet kitchen, or gather on the patio by evening. Walk to downtown Mystic’s shops, restaurants, and attractions. Designed for comfort and convenience, this home is your perfect coastal escape! Min age 25. Govt ID required..
Popular amenities for Block Island rentals with a pool
House rentals with a pool

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Modern East Hampton Home w/ Heated Saltwater Pool

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

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Condo rentals with a pool

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Montauk Oceanfront Condo
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach

Explore the Water & Woods at a Relaxing Retreat

5br / 5ba; Bike to town and beach; Heated Pool
Enchanting Home with Large Decks and Heated Pool

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Saltbox with Separate Poolhouse in Northwest Woods
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- Foxwoods Resort Casino
- Brown University
- Charlestown Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Point Judith Country Club
- Ocean Beach Park
- Easton Beach
- Shinnecock Hills Golf Club
- Blue Shutters Beach
- Groton Long Point Main Beach
- Oakland Beach
- Roger Williams Park Zoo
- Horseneck Beach State Reservation
- Napeague Beach
- Second Beach
- Amagansett Beach
- Sandy Beach
- The Breakers
- Ninigret Beach
- Island Park Beach
- Groton Long Point South Beach
- Clinton Beach
- Goddard Memorial State Park




