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
4.97 out of 5 average rating, 201 reviewsPrivate Oasis W/Stunning Vinyard and Pool Views
Home in East Lyme
5 out of 5 average rating, 15 reviewsPerfect Holiday Getaway w/ Spa and Activities
Home in Clinton
4.9 out of 5 average rating, 10 reviewsClinton Beach House & Cottage w/ Pool, Near Shore
Home in Mattituck
4.94 out of 5 average rating, 66 reviewsModern farmhouse w/ pool, beach, horses and winery
Home in Southampton
4.95 out of 5 average rating, 151 reviewsWaterview, DogsStayFree! Kayaks, Ping-Pong
Home in Madison
5 out of 5 average rating, 24 reviewsWaterfront Beach House with pool
Home in Old Saybrook
5 out of 5 average rating, 44 reviews3BR Updated Cottage w/ Pool in Old Saybrook
Home in Branford
5 out of 5 average rating, 7 reviewsBreathtaking Panoramic Waterfront
Condo rentals with a pool
Condo in Norwich
5 out of 5 average rating, 18 reviewsModern Loft Villa, 1 mile to Mohegan Sun
Condo in Norwich
5 out of 5 average rating, 72 reviewsKING bed! Hot tub! Pool! Spa! Casinos! Hot tub!
Condo in Norwich
4.93 out of 5 average rating, 28 reviewsCozy Vacation Villa 5 minutes from Mohegan
Condo in Greenport
4.88 out of 5 average rating, 147 reviewsBeautiful Waterview Condo on the North Fork of LI
Condo in Norwich
4.98 out of 5 average rating, 155 reviewsPeaceful Oasis steps from Mohegan Sun
Condo in Norwich
4.97 out of 5 average rating, 117 reviewsThe Vacay Villa
Condo in Greenport
5 out of 5 average rating, 107 reviews"Breathtaking Waterfront Water's Edge view"
Condo in Greenport
4.9 out of 5 average rating, 112 reviewsSeaside Escape w Pool, Private Beach & Patio
Home rentals with a private pool
Bungalow in East Hampton
4.93 out of 5 average rating, 107 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
Home in Water Mill
4.92 out of 5 average rating, 120 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Home in East Hampton
4.82 out of 5 average rating, 45 reviewsEnchanting Home with Large Decks and Heated Pool
Home in Southampton
4.93 out of 5 average rating, 61 reviewsSouthampton Quiet Private Home/Pool 6min to Villag
Home in East Hampton
5 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Home in East Hampton
4.94 out of 5 average rating, 16 reviewsWalk to Water. Stunning Home with Gorgeous Pool & Grounds.
Home in East Hampton
4.98 out of 5 average rating, 128 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in Southampton
5 out of 5 average rating, 81 reviewsBest of Country and Beach Living
Destinations to explore
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