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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.

Guest favorite
Cottage in Guilford
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)
Dec 12 – 19
$293 per night
Guest favorite
Guesthouse in Southbury
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).
Jul 25 – Aug 1
$135 per night
Guest favorite
Apartment in New Haven
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 - Rooftop sun terrace + grills - Entertainment lounge w/ bowling alley
Sep 28 – Oct 5
$241 per night

Popular amenities for New Haven rentals with a pool

House rentals with a pool

Guest favorite
Home in Hamden
Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
Nov 6 – 13
$594 per night
Home in Redding
Meeker Hill House - Charm & Pool
Mar 15 – 22
$376 per night
Guest favorite
Home in Milford
Spacious 4 bedroom, oasis with ocean views galore
Aug 15 – 22
$700 per night
Guest favorite
Home in Stratford
Lordship Beach House - Pool & Beach (seasonal)
Oct 15 – 22
$580 per night
Home in Wallingford
Classic 4Bd/2Ba Entire Family Friendly Home.
Aug 26 – Sep 2
$398 per night
Guest favorite
Home in Fairfield
Fairfield! 5 bedroom, 3.5 bath on cul-de-sac
Mar 4 – 11
$763 per night
Guest favorite
Home in Fairfield
Old Post Road w/Pool and Cottage, walk to Beach
Mar 22 – 29
$900 per night
Home in West Haven
Cozy 3 bedroom minutes from Yale and the beach
Mar 26 – Apr 2
$145 per night
Home in New Haven
Secluded Retreat with Private Pool -7 mins to YALE
Sep 10 – 17
$728 per night
Guest favorite
Home in Fairfield
Fairfield Beach - Walk to Town & Private Beach
Aug 18 – 25
$575 per night
Guest favorite
Home in Redding
Lovely Country Retreat:
Apr 5 – 12
$550 per night
Guest favorite
Home in Fairfield
Bright Zen Studio
Dec 22 – 29
$140 per night

Quick stats about vacation rentals with a pool in New Haven

Total rentals

20 properties

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

980 reviews

Nightly prices starting at

$40 before taxes and fees

Destinations to explore