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

Private completely fenced in property. Near beach.

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

Modern East Hampton Home w/ Heated Saltwater Pool

Pool House

Stunning Central E. Hampton Home w/ gunite pool.

Long Island home w/ large pool

Private East Hampton Estate

Southampton Getaway, Heated Pool, Hot Tub, 3 Bed
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

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.
Enchanting Home with Large Decks and Heated Pool
East Hampton Ranch with Access to Clearwater Private Beach

Perfect Getaway at Sunny Modern Shampton Lake House
Destinations to explore
- Private suite rentals Middlesex County
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Rentals with a hot tub Middlesex County
- Family-friendly rentals Middlesex County
- Rentals with breakfast Middlesex County
- House rentals Middlesex County
- Rentals with an EV charger Middlesex County
- Bed and breakfasts Middlesex County
- Kid-friendly rentals Middlesex County
- Beachfront rentals Middlesex County
- Rentals with a patio Middlesex County
- Rentals with outdoor seating Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with a washer and dryer Middlesex County
- Rentals with a fireplace Middlesex County
- Guesthouse rentals Middlesex County
- Apartment rentals Middlesex County
- Rentals with beach access Middlesex County
- Rentals with lake access Middlesex County
- Rentals with a fire pit Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with pools Connecticut
- Rentals with pools United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes