
Beachfront holiday rental in Shelter Island Heights
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Top-rated beachfront accommodation in Shelter Island Heights
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Popular amenities for Shelter Island Heights beachfront rentals
Pet-friendly beachfront home rentals

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Look no further! The Beach Cottage is beautiful, immaculate, private, and all things one would hope a vacation getaway would entail. This location feels “off the grid” albeit close to modern amenities/stores. Hope to be back soon!

Cozy Beach - Direct Waterfront!
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!

Barnacle Bay Beach House
My husband, dog, and I LOVED our stay here- so much that Danielle accommodated for us to stay an additional day! It was the perfect location. Private enough where we felt secluded, but yet right off of a main road with so many great restaurants to walk to! The beach was about a 5 minute walk, and left us with the perfect spot and feeling like we had the beach completely to ourselves the days we were there. We are already talking about going back, and can’t wait to plan our next trip. Thanks so much!

Walk to town, Marina Views, Greenport Village
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.

Ridgeview Suite at Stony Creek Depot
Barbara’s place reminded me of the way airbnbs used to be. It felt like home-away-from-home. The accommodations were high quality and clean, and there were even some tasty snacks! We loved our stay. Everything was as pictured. Stony Creek was wonderful, and we look forward to visiting again next year!

Beach Waterview, 3 KING Beds, Golf Putting Green
Completely great place! Looked like the photos but even better! Super responsive! Great stay

Beach Haven - waterfront, near Yale, sunsets
I had the most amazing stay at this Airbnb beach house. The views were absolutely immaculate, turning every moment into a picture perfect scene. The property was not only impeccably clean but also radiated a sense of peacefulness that immediately helped me disconnect from the hustle of daily life. Every detail was thoughtfully curated from the comfortable bedding that guaranteed a night of uninterrupted sleep to the high quality toiletries that added a touch of luxury to my routine. The well-equipped kitchen made it easy to prepare meals whenever I wished, and the fast WiFi ensured that I could seamlessly blend work and leisure as needed. A true highlight was the friendly welcome with a customized snack basket that set a warm, personal tone right from the start. Additional amenities, such as a cozy fireplace perfect for evening gatherings, stylish decor that elevated the overall ambiance, and easy access to local attractions, truly made my stay unforgettable. I will be returning.

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly
Loved our stay at Cameron’s in Milford! Location is within walking distance to the ocean and there were bigger beaches+parks near by (driving distance). Not much other than the beach to do in Milford but we managed to have fun plenty of fun and made lots of memories with our dogs!
Beachfront home rentals with a pool

Close to Beach | With Pool | Hampton Bays
We loved the location and the place was beautiful. Its was nice and clean. Definitely will be booking again

Akasa Ocean Front Oasis- Seasonal Pool, Grill
Amazing time front of the ocean, enjoying time with kids and familly. The pool seems great but was too cold for us in this early time of the year.

Gorgeous home with saltwater pool. Steps to beach!
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!

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

Spacious 4 bedroom, oasis with ocean views galore
We had a wonderful girls weekend at Allana’s house by the sea! When we had a small incident with the keypad, Allana was quick to answer my call and resolve the issue no problem. Everything was clean and beautiful! We especially enjoyed the screened in porch in the back to enjoy our meals. The view from the master bedroom and deck is incredible! We highly recommend and will be back!

Oceanfront Corner Studio Bungalow on the beach
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.

Private Luxury Waterfront Home
We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

Recharge at our Renovated ocean front unit
Great place ideally located next to town and the view is amazing. highly recommend in particular for short term stay.
Private beachfront home rentals

Adorable Beach House on LI Sound
We had a wonderful stay at Eileen’s place. Many great restaurants close by…Lenny’s, Dockside and Rosso Vino we enjoyed. Delicious ice cream spots..Bishop’s Orchard Creamery and Ashley’s.

Waterfront beach cottage
I can't say enough good things about this place. This place was so beautiful, quiet and exactly as described. Rachel was responsive, flexible with check in and provided everything you would need to feel right at home. The place was spotless, bed and linen were extremely comfortable, bathroom had all necessities. We absolutely loved the location- less than 10 minutes from town and RIGHT on the beach. Private walk out and lounge area, we can't wait to come back!

Designer Beach Retreat on Exclusive Cedar Beach
We had a great stay! Incredible one-of-a-kind view over the marsh. We saw so many different beautiful sea birds and an incredible sunset. Very short walk from the beach. Great place to stay with young kids. Well stocked kitchen with supplies and basic seasonings. Would return! Very cozy great family getaway! There are extensive requirements for clean up upon check out.

The Sandy Shack - Coastal Escape
As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

Hamptons Oceanfront Oasis
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!

Coastal Cottage on the Water
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!

Spacious Oceanfront Getaway with Spectacular Views
I had an amazing stay at Linda’s home! The view is absolutely beautiful and the spacious house made for great relaxation. Amenities made it easy to feel right at home along with games to play and enjoy the space even more. Loved that there were 3 bathrooms as well! Perfect for our group of 6 and we will definitely be back!

Sterling Harbor 2 Bedroom Apt
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 :)
Quick stats about beachfront rentals in Shelter Island Heights
Total rentals
30 properties
Nightly prices starting at
$199 NZD before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Quotonset Beach
- Heckscher State Park
- Ninigret Beach
- Sunken Meadow State Park
- Outer Beach at Smith Point County Park