Beachfront holiday rental in Shelter Island

Find and book unique beachfront homes on Airbnb

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Popular amenities for Shelter Island beachfront rentals

Pet-friendly beachfront home rentals

Top Guest favourite
Home in The Hamptons
5 out of 5 average rating, 7 reviews

Southampton hidden gem! Beach cottage, water views

BrandonRating, 5 stars5 days ago
Great location between Hampton Bays and Southampton. Place appears exactly as shown in photos; perfect for 2 people looking to enjoy the beach along the south fork.
Guest favourite
Home in The Hamptons
4.98 out of 5 average rating, 50 reviews

Best View + Private Beach + Putting Green

CharlesRating, 5 stars3 days ago
I had a fantastic stay! The property was exactly as described—clean, comfortable, and located in a great neighborhood. Check-in was smooth, and the host was communicative and welcoming throughout my stay. The space had everything I needed, from thoughtful touches to all the essentials. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a great experience!
Superhost
Home in East Haven
4.96 out of 5 average rating, 100 reviews

Cozy Beach - Direct Waterfront!

SarahRating, 5 stars6 months ago
This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!
Guest favourite
Cottage in North Fork
5 out of 5 average rating, 16 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

BridgetRating, 5 stars3 days ago
The place was exactly as described! Meredith was very accommodating and quick to respond. She was even able to let us check in a little early. The home is beautiful and cozy.
Guest favourite
Holiday home in North Fork
4.89 out of 5 average rating, 37 reviews

Walk to town, Marina Views, Greenport Village

LisaRating, 5 stars2 days ago
This home is just as advertised. The home had lots of extra amenities and the kitchen is very well stocked. The home is beautiful inside and has plenty of space for 4 people. The home has been remodel and they did an excellent job of incorporating the old with new modern conveniences. We would recommend this home to anyone and would love to stay there again if we are ever back to Greenport.
Guest favourite
Home in The Hamptons
4.96 out of 5 average rating, 23 reviews

Magnificent Bayfront Retreat

ErinRating, 5 stars1 month ago
Ashley’s house is the perfect get away. I booked this house for my family to stay for my wedding weekend. My mom had never stayed in an Airbnb before and I’ve never seen her so happy and relaxed. She truly enjoyed her first Airbnb experience at Ashley’s place. It was exactly as described and the view is beautiful. Ashley was very responsive and made sure to answer any questions I had.
Guest favourite
Home in Shirley
4.95 out of 5 average rating, 128 reviews

Beach Waterview, 3 KING Beds, Golf Putting Green

IsabelRating, 5 stars1 week ago
Completely great place! Looked like the photos but even better! Super responsive! Great stay
Superhost
Home in The Hamptons
4.84 out of 5 average rating, 69 reviews

Hamptons Oceanfront Oasis

MonicaRating, 5 stars2 days ago
Had a lovely time in the Hamptons! Tasha was an amazing host- easiest check in/out, very responsive, and gave great recommendations for places in the area. Would love to stay here again!

Beachfront home rentals with a pool

Superhost
Home in The Hamptons
4.86 out of 5 average rating, 35 reviews

Close to Beach | With Pool | Hampton Bays

HunterRating, 5 stars1 week ago
We loved the location and the place was beautiful. Its was nice and clean. Definitely will be booking again
Superhost
Apartment in The Hamptons
5 out of 5 average rating, 3 reviews

Ocean theme Balcony-View Studio Apt w/ 1 BTH & Tub

AlexisRating, 5 stars10 months ago
Fantastic location! We were literally a two minute walk from the beach. The studio apartment was as advertised and we would stay there again. We highly recommend!
Guest favourite
Home in South End
4.9 out of 5 average rating, 41 reviews

Gorgeous home with saltwater pool. Steps to beach!

michelleRating, 5 stars3 weeks ago
An amazing stay overall. It was comfortable for 6 adults. Spencer was extremely helpful throughout our stay — I had lots of questions and Spencer was quickly responsive. The house itself is beautiful and has that eastern Long Island charm. The backyard had lots of space and is well maintained alongside the pool. We also enjoyed a sunset evening at the beach which is just a few steps away. It was a wonderful weekend and I am certainly looking forward to staying here in the future!
Guest favourite
Home in The Hamptons
4.97 out of 5 average rating, 60 reviews

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access

MatthewRating, 5 stars1 month ago
Gorgeous house and property that is even better than the photos. Like other reviews have mentioned, the highway noise in the backyard is definitely present, but easy enough to ignore. Really enjoyed our stay and communication was great!
Top Guest favourite
Guest suite in The Hamptons
5 out of 5 average rating, 27 reviews

Hamptons Waterfront Romantic King Suite

BarbaraRating, 5 stars7 months ago
Dan is the most responsive host we've ever had. Usually we got a reply within minutes or even seconds. He happily got the hot tub heated up for us when we needed it and replenished our towels within an hour of our request. That hospitality made our stay so much better. The home is beautiful! It's right on the water, and features lots of luxurious tile, a huge patio, a little dock and lots of windows and open space from which to see it all. We especially loved the hot tub. I wouldn't hesitate to stay again if I'm ever on Long Island again.
Guest favourite
Apartment in The Hamptons
4.9 out of 5 average rating, 10 reviews

Oceanfront Corner Studio Bungalow on the beach

EdRating, 5 stars1 month ago
Loved Samy’s corner unit, which gave us a bit more privacy and quiet than other parts of the property. The studio was as described, with great light and well-cleaned prior to our arrival. Enjoyed use of the tennis courts every day. Only minor disappointment was that we were not yet allowed to use the pool, which we were told would be ready by Memorial Day (we were there one week prior). Still, a worthwhile stay and I’d come back and recommend it to others.
Superhost
Apartment in The Hamptons
4.87 out of 5 average rating, 45 reviews

Montauk Ocean View One Bedroom

ScottRating, 5 stars1 week ago
Great spot for a few days in Montauk. Really close drive to town only about 15 walk into town. Great food cart on property open when the weather is good. Amazing ocean views from most rooms hard to find in the Hamptons.
Top Guest favourite
Home in Bellport
5 out of 5 average rating, 17 reviews

Private oasis with pool steps away from the bay

JustinRating, 5 stars1 week ago
Great and responsive host. Home was lovely and we felt welcome. Host responded quickly to questions and requests. The home was very peaceful and relaxing. We really enjoyed the outdoor patio and pool area. I would recommend for a peaceful time away from the city.

Private beachfront home rentals

Top Guest favourite
Home in The Hamptons
5 out of 5 average rating, 34 reviews

Tranquility at the Water’s Edge

JenniferRating, 5 stars3 months ago
A beautiful, relaxing and peaceful setting and a quick and easy trip to town. Great views and house was perfect with tons of amenities and perfect to bring our dog. Host was fantastic and so responsive. An amazing stay!
Guest favourite
Apartment in East Shore
4.95 out of 5 average rating, 37 reviews

Walk to Beach, Wedding Venues. 15m to Yale.

LaraRating, 5 stars3 months ago
The place is lovely and as expected from the ad. Everything went smoothly. Highly recommend
Superhost
Home in East Haven
4.94 out of 5 average rating, 47 reviews

Oceanfront Getaway - Quiet, Firepit + Pvt Beach

MayurRating, 5 stars3 days ago
Lovely gem, right in new haven, You get a beach built into the house, lovely sand. You get the peaceful surrounding and a great house with great amenities to enjoy like a firepit, a kids slide & swing and a barbeque. You get the ability to order in food from any variety of restaurant from new haven. You get a nice host that helps you all along the way All in all great choice for a relaxing walkaway.
Guest favourite
Home in East Haven
4.95 out of 5 average rating, 40 reviews

Direct Beachfront Modern Cottage on Private Beach

MacKenzieRating, 5 stars3 weeks ago
We had a great stay at the Airbnb. One thing I haven’t seen mentioned in the reviews or descriptions is that this beach had tons of sea glass! In our short stay we found over 100 pieces and my 4 year old was absolutely delighted scouring the beach for it. There are also tide pools less than a five minute walk from the house. These two things made the stay quite magical for my kids. Otherwise the location is great and the house was very clean. I appreciated the bed on the first level having a trundle as well as a door at the top of the stairs for safety. The house is minimally decorated which is honestly a plus when you don’t have to worry about your kid breaking nicknacks on coffee tables. A few nice throw blankets and nicer glassware would have added to the stay though. Overall we were very happy with this property.
Guest favourite
Home in Shirley
4.94 out of 5 average rating, 31 reviews

Sunset Cottage - Waterfront Getaway

KarlyRating, 5 stars3 weeks ago
John’s place is absolutely stunning! The deck and the dock made for beautiful mornings with coffee and evenings with wine. It’s a short drive from a few beaches or to the ferry to fire island. Overall would definitely stay again!
Guest favourite
Home in South End
4.92 out of 5 average rating, 25 reviews

Coastal Cottage on the Water

MeghanRating, 5 stars3 weeks ago
Loved our girls’ getaway on the North Fork! Mae’s house is the perfect spot with a quick walk to the beach and gorgeous views right from her backyard - even close drives to beautiful Southold, Mattituck, and Greenport. I will absolutely stay again!
Guest favourite
Apartment in North Fork
5 out of 5 average rating, 17 reviews

Sterling Harbor 2 Bedroom Apt

AlizaRating, 5 stars1 week ago
Perfect place to unwind after a long day of exploring the North Fork 😍 Steps away from downtown Greenport and its charming restaurants, shops and bars. Not to mention we could find everything we needed and felt right at home in the beautifully appointed apartment :)
Guest favourite
Home in Shirley
4.98 out of 5 average rating, 66 reviews

Stunning sunset charming waterfront home 4 seasons

AllisonRating, 5 stars5 months ago
Absolutely stunning! This house has an amazing view from gigantic glass doors in the main room. Details in the house are well thought out and of great quality, including a high end coffee maker and other appliances. The place has lots of premium touches that make this experience a cut above the rest. Steven is an amazing, friendly, and communicative host. Incredible experience all around, I would definitely book here again.

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