Vacation rentals with a pool in New Haven

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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
A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.
Cottage in Guilford
4.95 out of 5 average rating, 187 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
A serene view of the Long Island Sound is captured at sunset, featuring soft pastel hues in the sky. A few clouds are present, and the gentle water surface reflects the vibrant colors. A flagpole with an American flag stands prominently in the foreground.
Home in Milford
4.83 out of 5 average rating, 104 reviews

Spacious 4 bedroom, oasis with ocean views galore

Scio by the sound is a home that is steps from the water, overlooking the Long Island Sound. Whether you want to lounge by the in ground pool or walk to the beach, you will find your happy place here. The home sleeps up to eleven guests in beautiful Milford, CT with a great location to local beaches and downtown Milford. It is also the perfect place with a large private backyard great for families for vacations or a friends get together or for a local wedding. The possibilities are endless!

Superhost
A stone patio is presented, featuring wooden lounge chairs and a table, all framed by expansive glass doors. Beyond the patio, lush greenery stretches across the property, creating a serene and private outdoor space, ideal for relaxation or entertaining.
Home in Redding
4.89 out of 5 average rating, 19 reviews

Meeker Hill House - Country Escape w/ Heated Pool

Meeker Hill House is a spacious and chic escape nestled in the heart of Fairfield County, located 90 minutes from NYC and minutes from the hamlet of Redding. Set on a quiet road, this 3 bedrooms and 3.5 baths house is riddled with old world charm. Amenities include a heated pool, fireplaces, fire pit, outdoor dining, screened in porch and a luxury chef's kitchen. Kick back and relax in this calm, stylish space as if in the English Countryside, all under two hours from NYC & under 3 hours fro

Superhost
A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.
Home in Hamden
4.91 out of 5 average rating, 118 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

Top guest favorite
A white Dutch door is framed by rustic wooden walls, showcasing a combination of horizontal and vertical planks. A small lantern hangs nearby, and a woven basket adorns the wall beside the door. A simple bench with a patterned cushion sits on the side.
Guesthouse in Southbury
4.93 out of 5 average rating, 353 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
A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.
Guest suite in Monroe
4.97 out of 5 average rating, 209 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!

Top guest favorite
A spacious loft area features high ceilings with exposed beams and warm wooden accents. Two comfortable leather sofas face a central ottoman, surrounded by artwork and decor. Natural light floods in through large windows, highlighting the rich wooden floors and a decorative rug.
Cottage in Black Rock
4.98 out of 5 average rating, 103 reviews

Spacious Cottage Loft

Welcome to the Spacious Cottage Loft! Please enjoy a nice quiet relaxed atmosphere in this unique space. Its a little bit rustic with its shiplap pine and exposed beams. Its a little bit rock and roll with its little music space along with some favorite framed albums hanging on the walls. Very comfy queen size bed. 2 smart TVs (65" up & 55" down) for your entertainment pleasure. Roomy kitchen with brand new appliances. Bath-walk in shower. THIS SPACE IS DESIGNED TO ACCOMMODATE 1-2 GUESTS.

Top guest favorite
Apartment in Milford
4.98 out of 5 average rating, 126 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.

Top guest favorite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in North Fork
4.93 out of 5 average rating, 101 reviews

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Guest favorite
The exterior of the guest house features a stone facade complemented by a sloped roof. Lush greenery surrounds the property, and the driveway is lined with gravel. Two white planters with flowers are positioned in front of the entrance, while the sky displays a mix of clouds and blue.
Guesthouse in Easton
4.85 out of 5 average rating, 108 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.

Top guest favorite
A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.
Home in North Fork
4.98 out of 5 average rating, 180 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

Guest favorite
An outdoor swimming pool is surrounded by lounge chairs and umbrellas. The pool's clear blue water reflects the evening lights from surrounding windows. Cozy seating areas with striped cabana curtains are visible in the background, creating a welcoming outdoor space.
Apartment in New Haven
4.99 out of 5 average rating, 117 reviews

King 1BR Apt with Cozy Den and Luxury Amenities

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 • 24/7 fitness center • Rooftop sun terrace + grills • Entertainment lounge w/ bowling alley

Popular amenities for New Haven rentals with a pool

Quick stats about vacation rentals with a pool in New Haven

  • Total rentals

    10 properties

  • Nightly prices starting at

    € 51 before taxes and fees

  • Total number of reviews

    840 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

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