Vacation rentals with a pool in New Haven

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in New Haven

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

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Guest favorite

Cottage in Guilford

4.95 out of 5 average rating, 177 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Superhost

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!

Top guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 319 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).

Top guest favorite

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 Monroe

4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

Guest favorite

Home in New Milford

4.95 out of 5 average rating, 21 reviews

Spacious and relaxing New Milford 5br home w pool!

Pool is closed for winter September 15-May 15th thank you Take it easy and relax at our unique and comfy getaway! With amazing outdoor spaces, plus pool and spa hot tub! Across the street is the lovely town reservoir. Close by are Lovers Leap State Park, Candlewood Lake, and amazing antiquing including New Englands largest flea market, Elephants Trunk! Wonderful farmers markets, and the quaint town of New Milford is also a short drive, has great shops, restaurants, and a cute movie theater.

Guest favorite

Guesthouse in Easton

4.84 out of 5 average rating, 101 reviews

Entire Guest House at Fox Pond Farm.

Recently renovated private guest house with access to swimming pool offers sleeping for eleven in four bedrooms. Tastefully decorated with all amenities. Close to Merritt Parkway and train to Manhattan. This is a natural refuge on eleven very private acres. Large private terrace faces westerly for amazing sunsets and offers a "Plein Air" environment for alfresco meals, cocktails and relaxation. An attached vegetable and flower garden with fountain offer a quiet space to relax and reflect.

Guest favorite

Apartment in Glastonbury

4.9 out of 5 average rating, 433 reviews

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

Guest favorite

Home in North Fork

4.92 out of 5 average rating, 36 reviews

Gorgeous home with saltwater pool. Steps to beach!

Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

Guest favorite

Home in North Fork

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.

Guest favorite

Home in North Fork

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

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