Holiday rentals with a pool in Shelter Island Heights
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Shelter Island Heights
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 Shelter Island Heights rentals with a pool
House rentals with a pool
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
Home in Shelter Island
5.0 out of 5 average rating, 51 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Home in Greenport
5.0 out of 5 average rating, 3 reviewsQuaint Chalet w/Salt-heated Pool
Home in Southold
5.0 out of 5 average rating, 13 reviewsGorgeous home with heated gunnite pool!
Home in Cutchogue
5.0 out of 5 average rating, 26 reviewsNorth Fork paradise between beaches and vineyards
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Apartment rentals with a pool
Apartment in Montauk
4.99 out of 5 average rating, 184 reviewsMontauk Waterfront Condo w/ Sunset Views
Apartment in Montauk
4.94 out of 5 average rating, 109 reviewsDeluxe Studio Apt@The Montauk Manor
Apartment in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
Apartment in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Apartment in Greenport
4.83 out of 5 average rating, 100 reviewsSeaside Escape w Pool, Private Beach + Patio
Apartment in Greenport
5.0 out of 5 average rating, 91 reviews"Breathtaking Waterfront Water's Edge view"
Apartment in Bridgehampton
4.92 out of 5 average rating, 13 reviewsBridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Apartment in Montauk
5.0 out of 5 average rating, 3 reviewsMontauk Retreat - Steps from Beach and Town
Home rentals with a private pool
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Quick stats about holiday rentals with a pool in Shelter Island Heights
Total rentals
100 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
€ 120 before taxes and fees
Destinations to explore
- New City Holiday rentals
- Long Island Holiday rentals
- Martha's Vineyard Holiday rentals
- Newark Holiday rentals
- Montauk Holiday rentals
- Hoboken Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Rentals with pools New York
- Rentals with pools United States
- Rentals with pools Manhattan
- Rentals with pools Brooklyn
- Rentals with pools New York
- Rentals with pools Suffolk County
- Rentals with breakfast Shelter Island Heights
- Rentals with beach access Shelter Island Heights
- Rentals with a patio Shelter Island Heights
- Waterfront rentals Shelter Island Heights
- Rentals with a firepit Shelter Island Heights
- Beachfront rentals Shelter Island Heights
- Fitness-friendly rentals Shelter Island Heights
- Rentals with outdoor seating Shelter Island Heights
- Rentals with a kayak Shelter Island Heights
- House rentals Shelter Island Heights
- Family-friendly rentals Shelter Island Heights
- Rentals with a washing machine and dryer Shelter Island Heights
- Monthly Rentals Shelter Island Heights
- Family-friendly rentals Shelter Island Heights
- Rentals with a fireplace Shelter Island Heights
- Pet-friendly rentals Shelter Island Heights
- Rentals with a hot tub Shelter Island Heights
- 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