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

Home in Shelter Island

4.97 out of 5 average rating, 197 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

Dec 5 – 12

G$187,798 GYD per night

Guest favorite

Apartment in Norwich

4.9 out of 5 average rating, 231 reviews

Cozy Stay w Pool 4 mi to Mohegan, 7 mi to Foxwoods

THE POOL IS OPEN AS OF MAY 1st! Welcome to our charming 2-bedroom apartment. This centrally located spot is the perfect getaway to escape the hustle and bustle of the big city and enjoy a more relaxed pace of life. The unit comes in at a spacious 950 sq ft - ideally suited for couples, solo travelers, families and can comfortably accommodate up to 4 people. Feel free to use the grill of course, but you may have to fill the propane tank. You can do so at the Walmart which is 12 minutes away!

Oct 2 – 9

G$21,256 GYD per night

Guest favorite

Apartment in Bristol

4.96 out of 5 average rating, 135 reviews

Cozy, Peaceful One Bedroom Apartment in Bristol

Cozy peaceful one bedroom apartment centrally located in picturesque Bristol. Located on a dead end street. Just a 20 minute walk to downtown, Colt State Park and waterfront. Centrally located between Providence and Newport and Boston and the Cape. Enjoy amenities such as; pool, private deck, espresso and tea bar, and Netflix . Enjoy all Bristol has to offer: museums, Saturday market, fantastic restaurants, boating, beach, quaint shops and of course the oldest continuous 4th of July Parade!

Jan 10 – 17

G$24,549 GYD per night

Guest favorite

Condo in Montauk

4.99 out of 5 average rating, 181 reviews

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 area only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy fishing and 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)

Feb 4 – 11

G$79,877 GYD per night

Guest favorite

Condo in Norwich

4.99 out of 5 average rating, 112 reviews

Peaceful Oasis steps from Mohegan Sun

Feel at home at our contemporary yet cozy villa. A private and quiet space in the heart of the area's local attractions (walkable to Mohegan Sun/short drive to Foxwoods). Perfect for a fun-filled weekend or a simple and quiet getaway. Enjoy the scenic views of the surrounding golf course or indulge at the on-site renowned spa. Other noteworthy amenities include a year round opened clubhouse, sauna, and hot tub as well as two beautiful seasonally opened pools. This unit comfortably sleeps 4.

Oct 6 – 13

G$31,059 GYD per night

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 164 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Jan 21 – 28

G$73,983 GYD per night

Guest favorite

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence for pool area. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

May 7 – 14

G$110,717 GYD per night

Guest favorite

Farm stay in Thompson

4.99 out of 5 average rating, 133 reviews

Rustic Farmette Studio w/ Hot Tub & seasonal pool

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, a small family. Please include all individuals (&pets) in your booking.

Sep 19 – 26

G$39,907 GYD per night

Guest favorite

Home in Stonington

4.97 out of 5 average rating, 185 reviews

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.

Mar 20 – 27

G$107,910 GYD per night

Guest favorite

Home in Middleborough

4.94 out of 5 average rating, 296 reviews

Private retreat setting on 4 acres 1

Gatherings, parties, events, reunions, etc. with 8 or more total sleepers /non sleepers MUST be discussed prior to booking. A 5 minutes from Rte. 495, secluded, 2 bedroom 1200 sq.ft. apartment. Amenities include -- in-ground pool, horseshoe pits, tennis/basketball court, fully lit for night time use. Central air, full bath, eat in kitchen, Juliet balcony, private drive & entrances, 2 HD flat screen TV"s, Netflix, On Demand WIFI. Very comfortable for two or a couple with children.

Apr 14 – 21

G$21,063 GYD per night

Guest favorite

Guest suite in North Kingstown

4.83 out of 5 average rating, 610 reviews

Morgan Cottage

We Know it's Winter and it's cold outside but you will love our cozy, relaxing, self contained one bedroom apartment, with its private access. Get away for a day or two or more for an invigorating forest or beach walk or explore the scenic south county or hang out in one of the funky bars and restaurants that are found from East Greenwich to Newport. And we are just a 10 minute stroll to the historic village of Wickford with its quaint shops and 18th Century seaside charm.

Nov 3 – 10

G$33,913 GYD per night

Guest favorite

Guest suite in Brooklyn

4.92 out of 5 average rating, 153 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Oct 2 – 9

G$15,393 GYD per night