Vacation rentals with a pool in Greenwich

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Greenwich

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

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Superhost

A spacious pool area is surrounded by lush greenery and autumn foliage. The inviting swimming pool reflects the clear sky, with lounge chairs placed around its perimeter. A charming house with a covered porch in the background adds to the serene setting.

Home in Roxbury

5 out of 5 average rating, 22 reviews

Zoom Map 5* Town Roxbury! "Tophet Pool" PoshPadsCT

PoshPadsCT - 1-BR Large Open Pool House with Rec Room/Office/Sleeper Queen Sofa. Luxury Down Feather Beds, Comforters, Pillows, Frette Pressed Cotton Sheets, towels, Bathrobes. Roxbury and Washington are the best country escapes under 2 hours to NYC with the best homes, restaurants and activities. It is the country escape of choice to actors, writers, artists, Wall Street execs and more. A rural farm area of the best homes and estates in historic Litchfield County. Best country destination!

Guest favorite

A stone pathway leads to a sparkling pool surrounded by lush greenery. Flowering plants in pots frame the pool area, while lounge chairs and a shaded umbrella provide seating options. Tall trees offer privacy, creating a serene outdoor retreat.

Guesthouse in Southbury

4.93 out of 5 average rating, 318 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest favorite

A spacious, circular pool is surrounded by a wooden deck, featuring two reclining chairs and a small table set nearby. Lush greenery creates a natural backdrop, enhancing the serene outdoor space, which is equipped with safety rails for easy access.

Home in West Milford

4.98 out of 5 average rating, 149 reviews

On The Rocks In The Hot Tub

Unique home featuring a large deck with an enclosed hot tub, indoor/outdoor bars, game room and seasonal pool (pool is not heated) Fall-Winter:Minutes away from the town of Warwick. Pennings, Heaven Hill Farm for apple-pumpkin picking, Peter Mountain, Mountain Creek for skiing. Many vineyards/cideries Summer: Boating on Greenwood Lake, kayak rentals, hiking (Appalachian Trail), drive-in theater, family activities at Wawanique State Park, Crystal Springs Golf and ice cream at Bellvale Creamery

Guest favorite

An aerial view captures a two-story colonial home surrounded by lush greenery. A fenced-in pool is centrally located in the yard, complemented by a brick patio and lounge chairs. The expansive landscape features manicured lawns and trees, enhancing the serene outdoor environment.

Home in Monroe

4.96 out of 5 average rating, 114 reviews

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

Guest favorite

An indoor heated pool spans 37 feet, surrounded by large glass windows that illuminate the space. The serene water reflects light from stylish wall sconces, while outdoor seating is visible beyond the glass, offering a view of the surrounding greenery and water.

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.

Top guest favorite

An indoor pool area features a sleek, stone-tiled floor and a wooden beamed ceiling. Large windows provide ample natural light, while potted plants add greenery. The pool stretches invitingly, reflecting the warm tones of the surrounding architecture.

Place to stay in Saint James

5 out of 5 average rating, 23 reviews

1 bedroom w/ private cold plunge indoor lap pool

Exclusive private use of entire indoor pool and pool room, private driveway, 1 bedroom, 1 private bathroom. 5 minute walk to a picnic beach area. Your space includes a mini fridge, microwave, bar, keurig coffee maker, chaise lounges for chilling in all seasons. The pool is used as a wellness cold plunge in the winter months and lap training pool. It is not heated but the entire pool space is exclusive and private. Private side yard with Adirondack chairs, string lights and fire pit.

Guest favorite

A well-maintained saltwater pool glistens in the sunlight, surrounded by a spacious patio. Comfortable loungers are situated nearby, and lush greenery creates a serene atmosphere, with a partially shaded area provided by an umbrella.

Home in Walden

4.87 out of 5 average rating, 61 reviews

Stunning Hudson Valley Getaway with Pool

Stunning 4 bedroom property with a saltwater pool open until mid-October, outdoor dining, grill and firepit. Situated close to the Catskill mountains and the Hudson River, this spacious property is the perfect getaway for both families and groups of friends alike. Whether it's hiking in the mountains, cycling the many local trails, visiting the many wineries and breweries, playing golf, fishing, taking in the local towns or simply chilling in the pool there is something for everyone.

Top guest favorite

A large outdoor saltwater pool is visible, surrounded by a paved area. Lush greenery and trees are present in the background, complemented by a blue sky. A fence encloses the pool area, providing privacy and safety.

Vacation home in Holmes

5 out of 5 average rating, 23 reviews

The Dahlia Villa within Westerhall Gardens

Reconnect with nature at this unforgettable escape. A gorgeous mature garden in a park like setting. Two queen bedrooms, great room, 75 inch TV. Radiant bathroom floor. Outdoor 45,000 gallon salt pool…that’s shared with other property (summer months - POOL IS FOR REGISTERED GUESTS ONLY - NO EXCEPTIONS) Decompress in our sauna. This a no smoking/vaping property. A sprawling 17plus acre estate. Dahlia Villa is a beautiful two bedroom completely independent unit on the estate.

Top guest favorite

A private pool is situated at the back of the property, featuring a deep end and a diving board. The pool is surrounded by lush greenery and landscaped vegetation, creating a tranquil outdoor space. The area includes a paved deck for relaxation.

Apartment in Chester

4.98 out of 5 average rating, 96 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 10 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Guest favorite

A modern kitchen features light grey cabinetry and a spacious countertop, complemented by stainless steel appliances, including a refrigerator and stove. A cozy living area with a beige sofa and coffee table is visible, along with a soft area rug enhancing the warmth of the space.

Apartment 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 favorite

A spacious outdoor area features a rectangular pool bordered by vibrant greenery. A hot tub is situated adjacent to the pool, surrounded by potted plants. Comfortable seating is provided under a gazebo, contributing to a serene environment for relaxation.

Apartment in Suffern

4.94 out of 5 average rating, 128 reviews

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

Guest favorite

A spacious outdoor area is visible, featuring a winding path that leads through a grassy landscape. Trees of varying heights frame the view, capturing seasonal colors with a backdrop of rolling hills under a clear blue sky.

Home in New Milford

4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

THIS IS A PRIVATE HOME🏡 THE BOTTOM FLR 2 car garage and a double bedroom with a full bathroom attached. THE MIDDLE FLR KITCHEN, LIVING, DINING 1/2 bath, wrap-around decks w/ a fire pit THE TOP FLR 1 K rm w/ a fireplace & a private deck 1 Q rm 1 ba w/ jet tub & standing shower 6 acres Foothills of the Berkshires May-Sept We provide day passes for access to tennis, pickle ball, pool, yoga, swim, water aerobics