
Waterfront vacation rentals in Shelter Island
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Shelter Island
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Shelter Island waterfront rentals
Waterfront apartment rentals

Stony Crk Studio ideal for trvl nurses…
Great stay in Stony Creek Village with a view of Long Island Sound and short walk to the pier, Stony Creek Market (breakfast & lunch). I used the Library and went to services at the Stony Creek Congregational Church. Overall, a nice experience.

Sugarloaf Annex
Really cute and clean place, so happy we stayed here! It was perfect little place for a getaway to relax, even in the winter months. Everything inside was up to date and it had everything we needed. It even looked better in real life than the photos. Highly recommend!

Fresh&Crisp 1BR w/Loft, Corner Unit + Amazing View
Great stay!! Beautiful ocean view and the complex itself is recently renovated, much more modern and luxe than expected!

Bayside Boho Retreat
This is our first AirBnB experience. Communication with KC in advance was great. The place is very nicely decorated, so we felt very comfortable right away. Our children liked the children's room very much and I liked the veranda. Our kids are very bright and loud and that's certainly a challenge for hosts. We are therefore glad that there were no complaints. The area is very nice and quiet. We will be happy to come back.

Private waterside retreat- Vineyards/Outlets
What a beautiful home. It is located in a park like setting, so peaceful and quiet. We were visiting family and the location was perfect for us. We would highly recommend this property and we will use it again ourselves.

Amazing Greenport Village Apartment in CENTER!
Just as expected. Our second time staying there. Recommend for an affordable stay in a great location!

Oceanfront Corner Studio Bungalow on the beach
My stay here was a perfect respite away from the hustle and bustle of everyday life. Tucked away in the dunes, very short walk to access the beach, quick ride into downtown Montauk, and private. Very beautiful place and I will definitely be back. Thank you again!

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Amazing views! Beach. Glamping. Camp store and great pizza place.
Waterfront house rentals

Direct Waterfront Home Located on Private Beach
Great location with amazing views. I can only imagine how lovely it would be in summer for a little getaway. .

Waterfront Retreat at Goose Creek
We try and rent this place every time we come to the area. It is immaculate, well appointed and the hosts are very responsive. The property is also beautiful - with a swing set, giant yard and fire pit and it’s a great set-up for families with dogs and kids. I should mention for non kid and dog people that the level of cleanliness is incredible and the place is beautiful so don’t shy away if you don’t have kids or pets!!

Mastic Beach Surf House
The place was absolutely beautiful, clean and had great amenities. The host was also very responsive and attentive to any questions we had to ask. Would come back in a heartbeat!

Luxurious Waterfront Beach House On The Bay
We had a wonderful stay at Steve and Dorry’s place! The living room and kitchen is surprisingly spacious and feels so open & inviting because of the outdoor deck space and view of water. We hope to be back again!

Private beach, fully updated house, on 2 acres.
This home is beautiful and so spacious! Proximity to East Hampton and Springs, yet very private and peaceful. Couldn’t recommend enough!

Private Waterfront home with Dock!
We had a lovely fall weekend stay at Paul’s place. The house and the water views are just as pictured. Convenient location allowed us a good home base to explore the north fork wine trail and local businesses. We did have one small plumbing issue during our stay however Paul was extremely responsive to ensure it did not affect our stay at all. It was a nice experience having such a responsive host. Overall our friend group had a great time and would return again.

Beach Haven - waterfront, near Yale, sunsets
It is a charming place back into the water. Love listening to the sound of the ocean and watching the sunset and the noght light on the other side of the water.

Sunset Cottage - Waterfront Getaway
John and his wife are excellent hosts. Their home is pristine with an abundance of amenities. The sunset on the bay is spectacular. I highly recommend. Thank you. Keith and Donna W.
Waterfront condo rentals

Beautiful 2 Bedroom 2 Bathroom Waterfront Condominium Getaway
Very clean and nicely decorated condo for our enjoyable weekend getaway. Would love to stay here again!

Waterfront Condo C-204 at The Cliffside Resort
lovely 2 bedroom with gorgeous water views from two roomy terraces , nice to wake up to the breeze of the water and the unspoilt natural surroundings of the wild sound. Thomas was a great host and very responsive

Water front, sunsets, sail boats, Wi-fi, birds
John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!

Beautiful condo on Long Islands Northfolk
We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

Beautiful Waterview Condo on the North Fork of LI
Such a beautiful condo by the water! Too bad we stayed in November, we would have enjoyed the terrace way more! Mia was so responsive and helpful with my questions prior to the weekend at her place.

Seaside Summer Escape –2BR Waterfront Condo w/Pool
My stay at Julie’s was wonderful, I was always able to message and get a quick response she was very accommodating. The view was beautiful and felt comfy like home. I will definitely be returning in the summer once it’s warmer !
Quick stats about waterfront rentals in Shelter Island
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ1,102 before taxes and fees
Total number of reviews
130 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Shinnecock Hills Golf Club
- Giants Neck Beach
- Woodmont Beach
- Walnut Public Beach
- TPC River Highlands
- Clinton Town Beach
- Seaside Beach
- Jennings Beach
- Amagansett Beach
- Blue Shutters Beach
- Attawan Beach
- Shennecossett Beach
- Sunken Meadow State Park
- Connetquot River State Park Preserve
- Outer Beach at Smith Point County Park
- Anchor Beach
- Long Island Aquarium
- Clinton Beach