
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
Get the amount of space that is right for you
Popular amenities for Middlesex County rentals with a pool
House rentals with a pool

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Modern East Hampton Home w/ Heated Saltwater Pool

Pool House

Southampton Escape, Heated Pool, hot tub, 3 bed,

Stunning Central E. Hampton Home w/ gunite pool.

Long Island home w/ large pool

POOL in APRIL! Waterview, Free For Dogs! Kayaks

Private East Hampton Estate
Condo rentals with a pool

Villa Flora @ Norwich Inn & Spa

CASiNO, Spa, Hot Tub, Pool, Private Villa, Kingbed

Oceanfront Condo – Incredible Spring Rates!

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi

Peaceful Oasis steps from Mohegan Sun

The Vacay Villa

Beachside Waterview 2Br Condo w/ Pool in Greenport

The N-V ...The Spa at the Norwich Inn.
Home rentals with a private pool
Enchanting Home with Large Decks and Heated Pool

Explore the Water & Woods at a Relaxing Retreat
East Hampton Ranch with Access to Clearwater Private Beach

Perfect Getaway at Sunny Modern Shampton Lake House
Destinations to explore
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Six Flags New England
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Bushnell Park
- The Connecticut Golf Club
- Burwells Beach