Vacation rentals with a pool in Middlesex County
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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 Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Sep 9 – 16
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Oct 8 – 15
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Jan 22 – 29
Home in Southampton
4.95 out of 5 average rating, 131 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
Nov 29 – Dec 6
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Nov 4 – 11
Home in Norwich
4.82 out of 5 average rating, 183 reviewsGrand 9 BR Near Casinos
Mar 7 – 14
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Nov 11 – 18
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
Oct 23 – 30
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
Sep 22 – 29
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!
Sep 2 – 9
Condo in Norwich
4.98 out of 5 average rating, 57 reviewsSpa-KING bed-Casino-HotTub-Pools-Massage chair
Aug 17 – 24
Condo in Norwich
4.99 out of 5 average rating, 100 reviewsJacuzzi/Sauna/Pool, On-site Spa, 3-mins to Mohegan
Jan 31 – Feb 7
Condo in Norwich
4.94 out of 5 average rating, 52 reviewsSpa Creek - Chic Modern Villa near Spa & Casinos
Feb 24 – Mar 3
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 13 – 20
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Mar 25 – Apr 1
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 29 – Jun 5
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Apr 1 – 8
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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