Essex which includes a marina

Middlesex County rentals with pool

We found 95 rentals with pool — enter your dates for availability

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Dates

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Flexible dates

September 2025

14

October 2025

Explore Middlesex County rentals with pools

Exterior

AIR-CONDITIONED Gorgeous Newly Renovated Home with an Oceanview and Beach Access

Sleeps 6 · 2 bedrooms · 1 bathroom

Find spaces that suit your style

Rentals with Pool in Middlesex County

Rentals with Pool in Ivoryton

Rentals with Pool in Killingworth

Rentals with Pool in Haddam

Rentals with Pool in Westbrook

Rentals with Pool in Middletown

Rentals with Pool in Portland

Rentals with Pool in East Haddam

Rentals with Pool in Deep River

Rentals with Pool in East Hampton

Rentals with Pool in Centerbrook

Rentals with Pool in Moodus

Rentals with Pool in Higganum

Rentals with Pool in Essex

Rentals with Pool in Clinton

Rentals with Pool in Chester

Rentals with Pool in Durham

Rentals with Pool in Cromwell

Rentals with Pool in Old Saybrook

Holiday Rental options in Middlesex County

Monthly rentals in Middlesex County

Pet-friendly holiday rentals in Middlesex County

Family-friendly holiday rentals in Middlesex County

Lake holiday rentals in Middlesex County

Ski holiday rentals in Middlesex County

Mountain holiday rentals in Middlesex County

Beach holiday rentals in Middlesex County

Holiday rentals with spa pool in Middlesex County

Oceanfront holiday rentals in Middlesex County

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