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 Sag Harbor
4.81 out of 5 average rating, 133 reviewsHalloween / Autumn special - Sag Harbor Gem
Home in Southold
4.9 out of 5 average rating, 30 reviewsGorgeous home with saltwater pool and fireplace!
Home in Waterford
5 out of 5 average rating, 76 reviewsBeach Front w/ Amazing Views, Pool, Hot Tub, Dock
Home in East Hampton
4.94 out of 5 average rating, 155 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in Mattituck
4.94 out of 5 average rating, 63 reviewsModern farmhouse w/ pool, beach, horses and winery
Home in Southampton
4.95 out of 5 average rating, 148 reviewsWaterview, Dogs StayFree! Kayaks, Ping-Pong
Home in East Hampton
4.93 out of 5 average rating, 139 reviewsHeated pool, games room, near beach, kid-friendly
Home in East Lyme
5 out of 5 average rating, 13 reviewsThe Atrium at Seven Acres - Pool, Retreat, Privacy
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
4.95 out of 5 average rating, 19 reviewsNear Casino-KING Bed-Heated Pool/Jacuzzi/Sauna-Spa
Condo in Norwich
5 out of 5 average rating, 69 reviewsKING bed! Hot tub! Pool! Spa! Casinos! Hot tub!
Condo in Norwich
4.94 out of 5 average rating, 16 reviewsCozy French style Villa-3 Bed-Casino-Pools-Jacuzzi
Condo in Greenport
4.89 out of 5 average rating, 145 reviewsBeautiful Waterview Condo on the North Fork of LI
Condo in Norwich
4.97 out of 5 average rating, 113 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, 109 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
4.98 out of 5 average rating, 128 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in East Hampton
4.88 out of 5 average rating, 33 reviewsChic Poolside Hideaway in East Hampton
Home in Southampton
5 out of 5 average rating, 81 reviewsBest of Country and Beach Living
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