Holiday 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.
Holiday rentals for every style
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Popular amenities for Middlesex County rentals with a pool
House rentals with a pool
Home in Old Saybrook
5 out of 5 average rating, 13 reviewsBeautiful Shoreline home in parklike setting
Home in Old Lyme
4.7 out of 5 average rating, 10 reviewsGorgeous 1700s Home Sleeps 10, 3 bath, Pool
Home in Guilford
5 out of 5 average rating, 5 reviewsPeaceful private home with pool and pond
Home in East Hampton
5 out of 5 average rating, 4 reviewsDirect riverfront luxury home!
Home in Clinton
4.96 out of 5 average rating, 28 reviewsNEW! 5-bedroom historic cottage, near beach
Home in Killingworth
4.75 out of 5 average rating, 4 reviewsQuiet Connecticut Retreat w/ Pool, Deck & Fire Pit
Home in Westbrook
4.73 out of 5 average rating, 132 reviewsSecluded Family escape w/ pool & jacuzzi
Home in Madison
4.79 out of 5 average rating, 38 reviewsBeautiful 1820 Colonial, Madison, CT
Apartment rentals with a pool
Apartment in Greenport
4.83 out of 5 average rating, 125 reviewsSeaside Escape w Pool, Private Beach + Patio
Apartment in Greenport
4.89 out of 5 average rating, 148 reviewsBeautiful Waterview Condo on the North Fork of LI
Apartment in Norwich
4.98 out of 5 average rating, 159 reviewsPeaceful Oasis steps from Mohegan Sun
Apartment in Norwich
4.97 out of 5 average rating, 118 reviewsThe Vacay Villa
Apartment in Norwich
4.93 out of 5 average rating, 70 reviewsSpa Creek - Chic Modern Villa near Spa & Casinos
Apartment in Greenport
5 out of 5 average rating, 107 reviews"Breathtaking Waterfront Water's Edge view"
Apartment in Greenport
4.92 out of 5 average rating, 137 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Apartment in Norwich
4.88 out of 5 average rating, 229 reviewsThe N-V ...The Spa at the Norwich Inn.
Home rentals with a private pool
Home in East Hampton
4.73 out of 5 average rating, 15 reviewsHistorical Estate Home with Backyard 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 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
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