Vacation rentals with a pool in Middlesex County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Middlesex County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Middlesex County rentals with a pool
House rentals with a pool
Home in Cutchogue
4.96 out of 5 average rating, 192 reviewsPrivate Oasis Stunning Views 7/6 - 7/20 Available
Home in East Hampton
4.93 out of 5 average rating, 149 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in Hampton Bays
4.98 out of 5 average rating, 117 reviewsBeach House Feel - newly renovated backyard Oasis
Home in East Hampton
4.92 out of 5 average rating, 131 reviewsHeated pool, games room, near beach, kid-friendly
Home in East Hampton
4.87 out of 5 average rating, 190 reviewsHeated Salt Water Pool, Walk 2 Beach, Fence 4 Pup
Home in Watermill
4.88 out of 5 average rating, 130 reviewsModern House close to the beach
Home in New London
4.89 out of 5 average rating, 137 reviewsOASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS
Home in Middletown
4.96 out of 5 average rating, 23 reviewsHot Tub and pool Home away from home
Condo rentals with a pool
Condo in Greenport
4.84 out of 5 average rating, 155 reviewsSound front condominium
Condo in Greenport
4.91 out of 5 average rating, 129 reviewsBeautiful Waterview Condo on the North Fork of LI
Condo in Greenport
4.9 out of 5 average rating, 115 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Condo in Norwich
4.96 out of 5 average rating, 84 reviewsKINGbed-Casino-HotTub-SaltwaterPools-Massage chair
Condo in Norwich
5 out of 5 average rating, 47 reviewsKING bed, Heated Pool, Spa, casinos, hot tub
Condo in Norwich
4.95 out of 5 average rating, 55 reviewsSpa Creek - Chic Modern Villa near Spa & Casinos
Condo in Norwich
4.96 out of 5 average rating, 57 reviewsKing Bed - hot tub - saunas - 1 mile Mohegan Sun
Condo in Norwich
4.98 out of 5 average rating, 94 reviewsThe Vacay Villa
Home rentals with a private pool
Home in East Hampton
4.97 out of 5 average rating, 119 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in East Hampton
4.76 out of 5 average rating, 75 reviewsBike to Town and Beach; Saltwater Pool + Cinema
Home in East Hampton
4.77 out of 5 average rating, 13 reviewsHistorical Estate Home with Backyard Pool
Home in East Hampton
4.81 out of 5 average rating, 43 reviewsEnchanting Home with Large Decks and Heated Pool
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Home in East Hampton
5 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Bungalow in East Hampton
4.93 out of 5 average rating, 100 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
Destinations to explore
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