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, 200 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Oct 13 – 20
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
Aug 7 – 14
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Feb 24 – Mar 3
Home in Southampton
4.87 out of 5 average rating, 237 reviewsSecluded Southampton Luxury Estate with tennis 288
Dec 24 – 31
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Dec 19 – 26
Home in Norwich
4.82 out of 5 average rating, 183 reviewsGrand 9 BR Near Casinos
Mar 8 – 15
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Dec 2 – 9
Condo rentals with a pool
Condo in Greenport
4.83 out of 5 average rating, 145 reviewsSound front condominium
Apr 28 – May 5
Condo in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Oct 20 – 27
Condo in Greenport
4.92 out of 5 average rating, 125 reviewsBeautiful Waterview Condo on the North Fork of LI
May 21 – 28
Condo in Norwich
5.0 out of 5 average rating, 39 reviewsVillla, king bed, Spa, casinos, hot tub, pool
Nov 17 – 24
Condo in New Britain
4.87 out of 5 average rating, 39 reviewsBeautiful Space All For You!
Aug 25 – Sep 1
Condo in Norwich
4.98 out of 5 average rating, 57 reviewsSpa-KING bed-Casino-HotTub-Pools-Massage chair
Oct 31 – Nov 7
Condo in Norwich
4.94 out of 5 average rating, 52 reviewsSpa Creek - Chic Modern Villa near Spa & Casinos
Apr 2 – 9
Condo in Norwich
4.82 out of 5 average rating, 45 reviewsLighthouse Villa! Your own relaxing getaway!
Jul 19 – 26
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
Dec 30 – Jan 6
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Feb 17 – 24
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Apr 2 – 9
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 30 – Jun 6
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Jan 12 – 19
Destinations to explore
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