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, 173 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)

Guest favorite

Guest suite in Westport

4.98 out of 5 average rating, 60 reviews

Westport Paradise! Every Amenity Right Here.

1,000 Sq Ft of private air conditioned and heated space. Fresh, bright and cheerful space with 14 ft. ceilings, 1 bedroom with a large closet, a full bath, kitchen, laundry, and a 75" TV. Enjoy full access to a resort-like property that is among the most beautiful in Westport. There is a large heated pool with chaises and plenty of shade. Other amenities include, tennis, pickleball, basketball, hot tub, BBQ, fire pit, & biking. A park, a farm, and a country store are all a short walk away.

Guest favorite

Home in Hamden

4.92 out of 5 average rating, 103 reviews

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Looking for privacy, seclusion, and direct access to Sleeping Giant State Park right from your back yard? Then look no further! Entire Mid Century home centrally located to many great attractions and colleges. Featuring an open floor plan characterized by large glass windows and open space featuring simplicity and an integration with nature. Access to I-91 or Rt15 are both about 1 mile away, with Yale University and Downtown New Haven about a 20 minute drive. Farmington Canal bike trail-.5 miles

Guest favorite

Home in Branford

5 out of 5 average rating, 7 reviews

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot curved custom-built, direct-waterfront, home. Amazing location with water on three sides, two small private beaches, boulders by the water, large pool, hot-tub, outdoor bar, pier, kayaks, boat house, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor rooftop. Open floor plan, sweeping staircase, 5 bedrooms plus loft. So much to do and enjoy in this waterfront oasis! (Pool not heated; pool closed after mid Oct.)

Guest favorite

Guesthouse in Southbury

4.94 out of 5 average rating, 309 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

Villa in Killingworth

5 out of 5 average rating, 14 reviews

1-of-a-kind Estate w/ Pool, Spa, Tennis & Pond

Nestled in nature, this luxurious property is situated on 3.5 park-like acres with two streams that wrap around the house. This one-of-a-kind estate has breathtaking views, deluxe amenities, & comes fully stocked for all your vacation needs. Relax in the comforts of the home or enjoy the blue stone patios, heated gunite pool & spa, private tennis court, or kayaking on the pond. Secluded yet conveniently located, the property is a mere 15 minutes away from shops, restaurants, and the shoreline.

Guest favorite

Home in Monroe

4.96 out of 5 average rating, 199 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 Fairfield

5 out of 5 average rating, 16 reviews

4BR/2.5BA Refuge Near University, Downtown & Beach

Forget your worries in this spacious and serene 4BR, 2.5BA home with backyard oasis, including heated in-ground saltwater pool, outdoor kitchen and firepit! Located in Fairfield's University District, 1 mile from historic downtown Fairfield, and within 2 miles of several beaches along Long Island Sound. Ideal for family college visits, girls' trips, or family vacations! Entire house and backyard are yours privately - no shared spaces. Attached apartment with separate entrance is on property.

Guest favorite

Rental unit in Milford

4.99 out of 5 average rating, 84 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Guest favorite

Home in Fairfield

4.95 out of 5 average rating, 20 reviews

Old Post Road w/Pool and Cottage, walk to Beach

Location, Location, Location. Renovated Spring 2023. Covered in ivy, this 6 bed/4 bath English Tudor on Fairfield's street of historic homes is downtown w/restaurants, theatres, shopping and Metro North. Walk 4 blocks to Penfield Beach with pavilion, lockers/showers/concessions. The grounds feature a heated pool and Cottage with kitchenette, leather sectional, 65" TV, Queen bedroom and full bath. Enjoy both indoor and outdoor dining in this beautiful setting. Premium Cable/Fiber (1G).

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

Home in Roxbury

5 out of 5 average rating, 13 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

Mid-Century Modern, newly renovated 3 bedroom, 2.5 bath located on a secluded road. Inground heated pool & mature landscaping. Enjoy Sonos inside and out. Light shines into the living room, vaulted ceiling, wall of windows and sliders to a wooden deck overlooking the pool. Dining room with floor-to-ceiling windows and skylights. 2 bedrooms and 2 full baths on the main level; a 3rd bedroom with balcony, and a half bath. Electric charging station. Pool is currently close for the season.