Beachfront holiday rental in Shelter Island Heights

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Popular amenities for Shelter Island Heights beachfront rentals

Pet-friendly beachfront home rentals

Guest favourite
Home in Westbrook
4.96 out of 5 average rating, 26 reviews

Barnacle Bay Beach House

AshlynRating, 5 stars1 week ago
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!
Guest favourite
Home in Old Lyme
4.94 out of 5 average rating, 17 reviews

Old Lyme Shores Beach house! Walk to water!

CarolineRating, 5 stars1 day ago
Beautiful house, amazing location. Super close to the beach! The house is beautiful and spacious, we were 8 people and did not feel crowded at all. The amenities are great and we felt right at home. Totally recommend it! We already want to come back. Thank you so much.
Guest favourite
Apartment in Branford
4.97 out of 5 average rating, 107 reviews

Ridgeview Suite at Stony Creek Depot

EmilyRating, 5 stars2 weeks ago
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!
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
Guest favourite
Bungalow in Montauk
4.91 out of 5 average rating, 619 reviews

Montauk Oceanview with Fireplace (2)

AdrienneRating, 5 stars3 weeks ago
Loved the stay! Exactly what we thought it was - extremely convenient and cozy. Plenty of beaches to walk to and the food options were plentiful. Would definitely stay again.
Guest favourite
Cottage in Milford
4.95 out of 5 average rating, 325 reviews

Spring Sale|CozyCottage|Pet-friendly|Walk to Beach

LeaRating, 5 stars1 day ago
This house was perfect for my anniversary getaway. It was a short 4/5 min walk to the beach. The house itself was great. The neighborhood was super peaceful and the surrounding restaurants were good as well. Definitely would make this a yearly visit. Thank you so much for the amazing stay
Guest favourite
Guest suite in Montauk
4.96 out of 5 average rating, 108 reviews

Twin Pond Ocean View Studio 3

MollyRating, 5 stars4 days ago
We had a great time at Twin Ponds! The studio was spotless and had everything we needed for two nights. It was a easy walk across the street to the beach and close to town. Would definitely come back.
Guest favourite
Home in New London
4.9 out of 5 average rating, 134 reviews

Beauty and the Beach!

Elizabeth H.Rating, 5 stars2 weeks ago
This house was PERFECT for us - four women returning to their college for their 45th reunion. The beds were comfortable and the neighborhood was quiet. The house was extremely comfortable. Carlos was responsive and helpful. We would definitely return to this house.

Beachfront home rentals with a pool

Superhost
Home in Hampton Bays
4.86 out of 5 average rating, 35 reviews

Close to Beach | With Pool | Hampton Bays

HunterRating, 5 stars2 weeks ago
We loved the location and the place was beautiful. Its was nice and clean. Definitely will be booking again
Top Guest favourite
Home in Lordship
5 out of 5 average rating, 8 reviews

Akasa Ocean Front Oasis- Seasonal Pool, Grill

JcRating, 5 stars3 weeks ago
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.
Superhost
Apartment in Amagansett
5 out of 5 average rating, 3 reviews

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

AlexisRating, 5 stars11 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 North Fork
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 Hampton Bays
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!
Superhost
Home in Woodmont
4.83 out of 5 average rating, 90 reviews

Spacious 4 bedroom, oasis with ocean views galore

ChrissyRating, 5 stars5 days ago
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!
Guest favourite
Apartment in Montauk
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
Villa in Guilford
4.91 out of 5 average rating, 11 reviews

Private Luxury Waterfront Home

VirginiaRating, 5 stars23 months ago
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.

Private beachfront home rentals

Guest favourite
Cottage in Westbrook
4.9 out of 5 average rating, 87 reviews

A Beach House Gem

JaimeRating, 5 stars7 months ago
We continue to visit Rose’s house for our yearly weekend girls getaway. It’s the perfect cozy beautiful place to catch up with friends and relax. Rose is an amazing host!
Guest favourite
Home in Branford
4.97 out of 5 average rating, 36 reviews

Adorable Beach House on LI Sound

LisaRating, 5 stars1 day ago
There’s so much to love about this charming open plan beach cottage! We especially enjoyed the water views, hearing the birds, and eating on the breezy porch. It was sparkling clean and stocked with everything you’d need, from comfortable beds and towels to many thoughtful essentials like hand and dish soaps, tea and coffee pods, paper towels/toilet paper, and shampoo/conditioner. Eileen is a gracious and responsive host — she was particularly understanding when we had to reschedule our visit. Thank you for a wonderful stay, Eileen, and we hope to return!
Guest favourite
Cottage in Lordship
5 out of 5 average rating, 33 reviews

Waterfront Beach Cottage in Connecticut

ErikaRating, 5 stars1 week ago
Eglantine’s place was an absolute DREAM! The pictures do not do it justice, it is much bigger than expected! It really feels like you are on your own private beach. It is so private and calm and peaceful. Both indoor and outdoors are absolute perfection and no matter where you sit, it’s the best seat in the house. Eglantine is also extremely friendly and always responsive. We most certainly would recommend her place to anyone looking for a peaceful and beautiful getaway and would love to book again sometime soon!!
Guest favourite
Home in Old Saybrook
5 out of 5 average rating, 40 reviews

Romantic Couples Retreat with Private Sandy Beach

RajRating, 5 stars3 weeks ago
Fantastic cute spot in Old Saybrook. Key things for future guests to know - there is no A/C in the winter months so the air can get a bit stale / stuffy in the house. Plus there is no washing machine / dryer in the house, so defo bring enough clothes!
Top Guest favourite
Holiday home in Guilford
4.99 out of 5 average rating, 97 reviews

Spacious Oceanfront Getaway with Spectacular Views

RachelRating, 5 stars2 weeks ago
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!
Superhost
Home in Hampton Bays
4.83 out of 5 average rating, 70 reviews

Hamptons Oceanfront Oasis

MonicaRating, 5 stars4 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!
Guest favourite
Home in North Fork
5 out of 5 average rating, 17 reviews

Hang by the (Chel)SEA

JillRating, 5 stars2 weeks ago
Spent to my birthday here with my husband, dogs and toddler. Had my gender reveal birthday cake, outback under the sunset. Truly magical.✨ The backyard was ideal. Was able to tie the dogs to the deck with a 20 foot leash. It kept them contained to the backyard & away from beach goers on foot and other dogs. The dunes kept the backyard private you’re not staring at your neighbors. Felt so secluded. I also have some mobility issues and you couldn’t ask for an easier way to enjoy the beach & get your toes in the sand. The house & deck are spacious and easy to navigate with a walker. Was able to add extra days to our stay. Would 100% stay here again.
Guest favourite
Home in North Fork
4.85 out of 5 average rating, 34 reviews

North Fork True Beachfront Home

RickRating, 5 stars1 week ago
We have had several family vacations on the North Shore now, but this was beyond our expectations. Pretty much a private beach on LI Sound in your backyard. Amazing layout with a wrap around deck with three daybeds for lounging outside among the tall hardwood trees and listening to the waves. Hammocks, hot tub and sauna below with a private gym and knocked out theater setup for streaming movies. There were 5 adults and two three year olds on this trip so the 3 full baths were great. The house felt like home for 7 great days and nights. Rainy days were filled with train museums, an aquarium and butterfly gardens and a fabulous library. And the North Atlantic waves are a 25 minute drive. Oh , and everyone said the beds were super comfortable.

Quick stats about beachfront rentals in Shelter Island Heights

  • Total rentals

    30 properties

  • Nightly prices starting at

    $186 AUD 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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