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Waterfront vacation rentals in Shelter Island

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Shelter Island waterfront rentals

Waterfront apartment rentals

Top guest favorite
The studio features a bed dressed in neutral bedding, complemented by decorative pillows. Natural light filters through two windows, illuminating a soft area rug. A small side table holds a plant, while a cozy seating area is arranged with a white couch and tabletop.
Apartment in Branford
4.95 out of 5 average rating, 20 reviews

Stony Crk Studio ideal for trvl nurses…

CarolRating, 5 stars2 months ago
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.
Top guest favorite
A cozy living area features wood-paneled walls and abundant natural light from four windows. A circular dining table accompanied by four chairs is positioned near the entrance, while a gray sofa and a side table provide additional seating options. A decorative wall art piece enhances the space.
Apartment in Southampton
5 out of 5 average rating, 8 reviews

Sugarloaf Annex

DianaRating, 5 stars3 months ago
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!
Superhost
Aerial view showcases a community setting surrounded by lush greenery and pathways, leading to the ocean's edge. Multiple buildings can be seen with varying architectural styles, while the calm sea stretches across the horizon under a clear sky.
Apartment in Amagansett
4.67 out of 5 average rating, 3 reviews

Fresh&Crisp 1BR w/Loft, Corner Unit + Amazing View

AmyRating, 5 stars8 months ago
Great stay!! Beautiful ocean view and the complex itself is recently renovated, much more modern and luxe than expected!
Guest favorite
A wooden dock extends over a serene waterway, framed by tall grass and greenery. The calm water reflects the sky, with distant homes visible along the shoreline. Clouds drift overhead, creating a tranquil atmosphere in the natural landscape.
Apartment in East Quogue
5 out of 5 average rating, 8 reviews

Bayside Boho Retreat

KatjaRating, 5 stars6 months ago
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.
Apartment in Center Moriches
4.83 out of 5 average rating, 36 reviews

Private waterside retreat- Vineyards/Outlets

WalterRating, 5 stars7 months ago
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.
Apartment in North Fork
4.78 out of 5 average rating, 318 reviews

Amazing Greenport Village Apartment in CENTER!

MariaRating, 5 stars5 months ago
Just as expected. Our second time staying there. Recommend for an affordable stay in a great location!
Top guest favorite
An inviting outdoor space features a large patio area with an outdoor dining table and umbrellas providing shade. A grill sits ready for use, complemented by beach lounge chairs arranged for relaxation. The building's exterior showcases a mix of natural stone and vibrant accents.
Apartment in Montauk
5 out of 5 average rating, 8 reviews

Oceanfront Corner Studio Bungalow on the beach

ZackRating, 5 stars6 months ago
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!
Superhost
A single-story, wooden structure is shown, featuring a brown exterior with a sign that reads 'General Store Cedar Point.' A wooden ramp leads to the entrance, surrounded by a grassy area and trees in the background.
Apartment in East Hampton
4.77 out of 5 average rating, 31 reviews

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

NateRating, 5 stars6 months ago
Amazing views! Beach. Glamping. Camp store and great pizza place.

Waterfront house rentals

Guest favorite
A private deck is shown, featuring a wooden dining table surrounded by multiple chairs. Two lounge chairs are positioned for sunbathing, with a view of a sandy beach and calm waters extending toward the horizon.
Home in East Haven
5 out of 5 average rating, 56 reviews

Direct Waterfront Home Located on Private Beach

MilenaRating, 5 stars4 months ago
Great location with amazing views. I can only imagine how lovely it would be in summer for a little getaway. .
Top guest favorite
The front entrance of the home is framed by well-maintained shrubs on either side. A welcome mat lies in front of the door. A lantern is mounted beside the entryway, and the staircase leading to the upper level is visible through the doorway.
Home in North Fork
5 out of 5 average rating, 25 reviews

Waterfront Retreat at Goose Creek

StephRating, 5 stars1 week ago
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!!
Guest favorite
An inviting living space is presented, featuring a plush sectional sofa paired with a wooden coffee table. Large glass doors allow natural light to fill the room, offering expansive views of the surrounding landscape. A modern chandelier hangs elegantly from the ceiling.
Home in Mastic Beach
4.97 out of 5 average rating, 36 reviews

Mastic Beach Surf House

AshRating, 5 stars4 months ago
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!
Guest favorite
An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.
Home in Shirley
4.98 out of 5 average rating, 198 reviews

Luxurious Waterfront Beach House On The Bay

ShrutiRating, 5 stars2 weeks ago
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!
Top guest favorite
A charming cottage is set against a backdrop of lush greenery, featuring a welcoming front porch with a white railing. Natural light illuminates the exterior, showcasing the textured shingle siding and a gabled roof. The grassy area extends toward the tree line, creating a serene atmosphere.
Home in East Hampton
4.95 out of 5 average rating, 230 reviews

Private beach, fully updated house, on 2 acres.

CaitlynRating, 5 stars2 months ago
This home is beautiful and so spacious! Proximity to East Hampton and Springs, yet very private and peaceful. Couldn’t recommend enough!
Top guest favorite
A serene view of a wooden dock extending over calm waters, surrounded by lush greenery and marshland. The distant shoreline is punctuated by trees and several homes, offering a glimpse of the peaceful coastal environment.
Home in North Fork
5 out of 5 average rating, 11 reviews

Private Waterfront home with Dock!

MeganRating, 5 stars6 months ago
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.
Guest favorite
A bright sunroom features a comfortable white sofa adorned with colorful pillows. Large glass sliding doors provide unobstructed views of the water, while natural light floods the space. A small outdoor seating area is visible, enhancing the connection to the beach outside.
Home in New Haven
4.95 out of 5 average rating, 108 reviews

Beach Haven - waterfront, near Yale, sunsets

CathyRating, 5 stars1 month ago
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.
Guest favorite
An interior view captures a dining table set with a vase of colorful flowers, framed by a large sliding door. Outside, a spacious deck overlooks Bellport Bay, featuring a set of stairs leading down to the water and a single lounge chair positioned against the serene backdrop.
Home in Shirley
4.96 out of 5 average rating, 28 reviews

Sunset Cottage - Waterfront Getaway

DonnaRating, 5 stars1 month ago
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

A sandy beach is viewed from above, with a wooden boardwalk leading down to the shoreline. Rows of white lounge chairs are positioned on the sand, facing the ocean. A grassy area borders the beach, alongside a multi-story building in the background.
Condo in North Fork
4.75 out of 5 average rating, 4 reviews

Beautiful 2 Bedroom 2 Bathroom Waterfront Condominium Getaway

MicheleRating, 5 stars9 months ago
Very clean and nicely decorated condo for our enjoyable weekend getaway. Would love to stay here again!
Top guest favorite
A well-maintained lawn is visible, extending towards the water's edge. The grassy area is framed by gentle landscaping, with a distant view of the ocean creating a serene backdrop. The exterior of the condominium building can be seen to the left.
Condo in North Fork
4.88 out of 5 average rating, 97 reviews

Waterfront Condo C-204 at The Cliffside Resort

RafaelaRating, 5 stars8 months ago
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
A serene waterfront view showcases a calm blue waterway, with boats docked at a wooden pier. Lush green grass leads towards the shoreline, and a clear sky adds to the tranquil ambiance of the setting.
Condo in North Fork
5 out of 5 average rating, 6 reviews

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

CharlesRating, 5 stars8 months ago
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!
Guest favorite
Four white Adirondack chairs are arranged on a lush green lawn, facing the Long Island Sound. The calm water stretches into the distance, framed by clear blue skies with a few scattered clouds.
Condo in North Fork
4.84 out of 5 average rating, 106 reviews

Beautiful condo on Long Islands Northfolk

LauraRating, 5 stars3 days ago
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!
Guest favorite
A spacious outdoor dining area features a rectangular table surrounded by six chairs. The setting provides a clear view of the ocean, with a grassy area and parking visible in the background, offering a serene space for meals or relaxation.
Condo in North Fork
4.89 out of 5 average rating, 149 reviews

Beautiful Waterview Condo on the North Fork of LI

AnnaRating, 5 stars5 months ago
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.
Superhost
A private beach stretches along the coastline, with soft sand and patches of greenery. A wooden pathway leads from the grassy area to the water, while several beach loungers are positioned facing the shore. The gentle waves of Long Island Sound meet the sandy beach under a clear sky.
Condo in North Fork
4.9 out of 5 average rating, 119 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

CynthiaRating, 5 stars3 weeks ago
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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