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 East Hampton
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Home in Sag Harbor
4.94 out of 5 average rating, 101 reviewsSag Harbor Village Cottage with Pool
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Home in Southampton
4.96 out of 5 average rating, 130 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
Home in Norwich
4.82 out of 5 average rating, 183 reviewsGrand 9 BR Near Casinos
Condo rentals with a pool
Condo in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Condo in Greenport
4.83 out of 5 average rating, 145 reviewsSound front condominium
Condo in Greenport
4.93 out of 5 average rating, 124 reviewsBeautiful Waterview Condo on the North Fork of LI
Condo in New Britain
4.87 out of 5 average rating, 39 reviewsBeautiful Space All For You!
Condo in Norwich
5.0 out of 5 average rating, 38 reviewsVillla, king bed, Spa, casinos, hot tub, pool
Condo in Norwich
4.99 out of 5 average rating, 99 reviewsBeautiful Villa- Fully stocked, jacuzzi/sauna/pool
Condo in Norwich
4.98 out of 5 average rating, 56 reviewsSpa-KING bed-Casino-HotTub-Pools-Massage chair
Condo in Norwich
4.94 out of 5 average rating, 52 reviewsSpa Creek - Chic Modern Villa near Spa & Casinos
Home rentals with a private pool
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in East Hampton
4.79 out of 5 average rating, 39 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
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
Destinations to explore
- Rentals with pools New York
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