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 Manorville
4.99 out of 5 average rating, 201 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Oct 18 – 25
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
Sep 24 – Oct 1
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Jul 18 – 25
Home in Sag Harbor
4.94 out of 5 average rating, 102 reviewsSag Harbor Village Cottage with Pool
Jun 11 – 18
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Nov 15 – 22
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Dec 8 – 15
Home in Southampton
4.95 out of 5 average rating, 132 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
May 26 – Jun 2
Home in New London
4.89 out of 5 average rating, 132 reviewsOASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS
Sep 30 – Oct 7
Condo rentals with a pool
Condo in Greenport
4.92 out of 5 average rating, 125 reviewsBeautiful Waterview Condo on the North Fork of LI
Apr 19 – 26
Condo in Greenport
4.83 out of 5 average rating, 145 reviewsSound front condominium
Jun 5 – 12
Condo in Greenport
4.9 out of 5 average rating, 108 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Oct 20 – 27
Condo in Norwich
5.0 out of 5 average rating, 39 reviewsKING bed, Spa, casinos, hot tub, pool, balcony
Nov 17 – 24
Condo in New Britain
4.85 out of 5 average rating, 40 reviewsBeautiful Space All For You!
Sep 18 – 25
Condo in Norwich
4.98 out of 5 average rating, 60 reviewsSpa-KING bed-Casino-HotTub-Pools-Massage chair
Sep 12 – 19
Condo in Norwich
4.94 out of 5 average rating, 52 reviewsSpa Creek - Chic Modern Villa near Spa & Casinos
Apr 8 – 15
Condo in Norwich
4.98 out of 5 average rating, 90 reviewsThe Vacay Villa
Aug 10 – 17
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
Nov 16 – 23
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Jan 1 – 8
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 7 – 14
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Apr 7 – 14
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Jan 1 – 8
Destinations to explore
- Rentals with pools New York
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