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

Sunny Saltbox in Wainscott

Sag Harbor Hamptons hideaway

Perfect Beach Home in Sag Harbor

East Hampton Rental w/ Pool, Moments to Amenities

Serene Hamptons oasis. Minutes to Main St. + beach

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

2025! Immaculate Beach Chic Retreat Pool & Hot Tub

Spacious Village Fringe East Hampton Home W/ Pool
Condo rentals with a pool

One Bedroom Apartment Nestled in the Dunes

Water front, sunsets, sail boats, Wi-fi, birds

Beautiful condo on Long Islands Northfolk

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

A Unique Piece of Paradise, Water Front pool

Seaside Summer Escape –2BR Waterfront Condo w/Pool
Home rentals with a private pool

Explore the Water & Woods at a Relaxing Retreat
East Hampton Ranch with Access to Clearwater Private Beach
Enchanting Home with Large Decks and Heated Pool

Southampton Quiet Private Home/Pool 6min to Villag
Perfect Getaway at Sunny Modern Shampton Lake House
Saltbox with Separate Poolhouse in Northwest Woods
Quick stats about vacation rentals with a pool in Sag Harbor
Total rentals
120 properties
Nightly prices starting at
$122 CAD before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Destinations to explore
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- Beach
- Charlestown Beach
- Yale University
- Southampton Beach
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Ocean Beach Park
- Napeague Beach
- TPC River Highlands
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Woodmont Beach
- Blue Shutters Beach
- Amagansett Beach
- Ninigret Beach
- Silver Sands Beach
- Sandy Beach
- Groton Long Point Main Beach
- Brownstone Adventure Sports Park
- Cedar Beach
- Seaside Beach
- South Jamesport Beach
- Mautucket by the Sea
- Connetquot River State Park Preserve