Holiday rentals with a pool in New Haven County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in New Haven County

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

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Guest favourite

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 favourite

Loft in Branford

5 out of 5 average rating, 64 reviews

Shoreline Carriage House

Overlooking acres of salt marsh and distant views of Long Island Sound, this cozy one-bedroom carriage house is perfect for a weekend (or week!) away. The Carriage House boasts access to the pool, a quick 3-5 minute walk to gorgeous beaches, a short drive or bike to restaurants and breweries, and a charming historic downtown. If you are in the mood to stay in (we totally get it), the space includes a brand new queen-sized bed, comfy couch, smart TV and a deck to enjoy the view and sea breeze.

Guest favourite

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 favourite

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 favourite

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 favourite

Rental unit in New Haven

4.97 out of 5 average rating, 63 reviews

King 1BR W/ Parking, Pool & Gym

This gorgeous apt, located in a brand-new luxury building at the center of New Haven’s historic downtown, offers unparalleled comfort, service, and amenities. You can watch a movie on a 65" HDTV, work in one of 5 co-working spaces, or relax at the pool w/ grills and cabanas. Highlights: - Walkable access to Yale - Deep-clean prior to every guest - Coffee, fresh linens, and bathroom essentials provided - 24/7 fitness center - Sun terrace + pool and grills - Entertainment lounge w/ bowling alley

Guest favourite

Place to stay in Middletown

4.96 out of 5 average rating, 46 reviews

Luxury Estate Elegant & Private~White Lion Manor

Escape the frenzy of the world in this family friendly rental, every detail is taken care of, From the garden, saltwater pool, and courtyard views. With over 7,500 sq ft of opulent living space, White Lion Manor is more than a stay it’s a unique experience tailored for those seeking the extraordinary.The 6 person hot tub, sauna, massage chair, and endless amenities will help you Indulge in the opulence of our meticulously curated mansion and immerse yourself in the lavish lifestyle you deserve.

Guest favourite

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 favourite

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 favourite

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 favourite

Rental unit in Glastonbury

4.9 out of 5 average rating, 423 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 favourite

Home in Wallingford

4.93 out of 5 average rating, 45 reviews

Family Oasis 4bd/2ba Private Home & Yard

Just minutes from Quinnipiac University, Choate Rosemary Hall, & Oakdale Theater. This 4- Bedroom, 2-Full Baths home includes 1-master suite, 3-bedrooms, full kitchen, & lots of room for the whole family to spread out. Located on the edge of the wood line, find yourself immersed in the peaceful surroundings with a book on the patio, or go on an adventure in minutes to local attractions. This property has an inground swimming pool (open during season Mid May/June- mid/late Sept)