
Vacation rentals with a pool in Shelter Island
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Shelter Island

Total vacation rentals
Explore 60 vacation rentals in Shelter Island

Nightly prices starting at
Shelter Island vacation rentals start at G$35,552 GYD per night before taxes and fees

Verified guest reviews
Over 1,070 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Shelter Island vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Shelter Island rentals

4.9 Average rating
Shelter Island stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Shelter Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)
Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

Swimming pool w/Hot tub Fire Pit Coffee Bar
Relax in this cozy loft filled with amenities that will create lasting memories. Recently renovated so fresh and clean. Located on a wooded lot. Large fenced in landscaped yard with hammocks and firepit. Heated pool seasonal. We are just minutes from the beach. Spend time in our 6 person jacuzzi. 10 min to Southampton village. 15 min to Sag Harbor. Centrally located. Fresh farm (home of Tate’s Cookies) around the corner with fresh meats and produce. A tasty restaurant near by and a deli too.

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

The Quail’s Nest
A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

Family Retreat with Heated Pool, Hot Tub, Sauna.
🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Brand new house with an all year round hot tub.
Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

East Hampton Oasis - Pool and Hot Tub
Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through October 5. The hot tub remains open year round.

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR
Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

Private Oasis W/Stunning Vinyard and Pool Views
Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong
Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Pool Central Private Bridgehampton Home
Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. NOTE* Rest assured, as always, even more so now, our housekeeper is aware to put in the extra tedious clean needed for a happy healthy stay! 7 minute drive to Hampton classic or less 20 min bike ride. Restaurants, studio 89 gym, on same rd. Ocean+bay 5-10 min drive. Bike to 1 ocean Yoga/winery. Halfway to Sag Harbor+Bridgehampton. There is pet fee.

Private Cozy Cottage with Pool / Private Beach
**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway
Popular amenities for Shelter Island rentals with a pool
House rentals with a pool

3 BR/Pool. Walk to Beach & Town!

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Newly Renovated w/ Pool, Hot tub & Fireplace

Designer home in Sag Harbor : 5BR walk to beach

Chic Southampton Home. Mins to Village and Beach!

Surf Scoter Cottage Shelter Island

Dream Home with a wonderful heated pool in SH

Secluded and Sheltered
Condo rentals with a pool

Greenport Getaway at Cliffside Condos

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Beautiful condo on Long Islands Northfork

Montauk Royal Atlantic Beach Resort North

Montauk Waterfront Condo w/ Sunset Views

Beautiful Waterview Condo on the North Fork of LI

Beachside Waterview 2Br Condo w/ Pool in Greenport

Beautiful Condo on the Ocean Bluffs
Other vacation rentals with a pool

Modern Oasis in Southampton

4 Bedroom Sag Harbor Home w/ Pool & Tennis Access

Luxe|Pool|BeachCar|Games|Movie|HotTub|Firepit

Hamptons Elegant and Comfortable Apartment

Luxury Southampton Home/outdoor Sauna/hottub

Wainscott Vacation Home

Southampton Stunner: Pool, Beach & more!

Head of Pond House - Waterfront Cottage
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- Pet-friendly rentals Shelter Island
- Rentals with a hot tub Shelter Island
- Family-friendly rentals Shelter Island
- Rentals with a fire pit Shelter Island
- Rentals with outdoor seating Shelter Island
- Rentals with beach access Shelter Island
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- Rentals with a patio Shelter Island
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- East Matunuck State Beach
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Seaport Museum
- Southampton Beach
- Mystic Aquarium
- Point Judith Lighthouse
- Sunken Meadow State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Yale University Art Gallery
- Soundview Beach
- Wölffer Estate Vineyard
- Ocean Beach
- Long Island Aquarium
- Orient Beach State Park
- Blue Shutters Beach
- Meschutt Beach





