
Vacation rentals with a pool in Watermill
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Watermill
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 Watermill rentals with a pool
House rentals with a pool

Sag Harbor Hamptons hideaway

New Modern Minimalist Zen Den (New Pool)

Breathtaking Sag Harbor 5 bed 6 bath-Heated Pool

Modern East Hampton Home w/ Heated Saltwater Pool

Perfect Beach Home in Sag Harbor

Monthly Specials - 5 Bed Village Cottage Retreat

A Fall/Winter Escape from the City

Curated Artist Home with New Pool
Condo rentals with a pool

Montauk Waterfront Condo w/ Sunset Views

Endless Summer Studio Condo w Balcony Bayview

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

Waterfront Autumn Escape in Wine Country: 2BR

Beachside Waterview 2Br Condo w/ Pool in Greenport

Deluxe Studio Apt@The Montauk Manor

Montauk Oceanfront Condo
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach

Explore the Water & Woods at a Relaxing Retreat
Enchanting Home with Large Decks and Heated Pool
Perfect Holiday Getaway with Gourmet Kitchen
Saltbox with Separate Poolhouse in Northwest Woods
Quick stats about vacation rentals with a pool in Watermill
Total rentals
220 properties
Nightly prices starting at
$279 CAD before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Destinations to explore
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- Rentals with pools Suffolk County
- Rentals with pools New York
- Rentals with pools United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Blue Shutters Beach
- Shinnecock Hills Golf Club
- Napeague Beach
- Cedar Beach
- Groton Long Point Main Beach
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Sandy Beach
- Jennings Beach
- Wildemere Beach
- Ninigret Beach
- Mystic Seaport Museum
- Outer Beach at Smith Point County Park
- Seaside Beach