Vacation rentals with beach access in Shelter Island Heights

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Popular amenities for Shelter Island Heights beach access rentals

Apartment rentals with beach access

Guest favorite
A single-story white house is set against a clear blue sky. The structure is surrounded by manicured grass and ornamental grasses, with a gravel driveway leading up to it. The entrance features a small stone path and decorative boulders, creating a welcoming approach.
Apartment in Montauk
4.9 out of 5 average rating, 217 reviews

Montauk Beach Bungalow West

LaurenRating, 5 stars6 months ago
I had an amazing stay at Krae’s beach house in Montauk! The location is perfect, just a short walk to the beach and close to Montauk town, making it easy to explore the area. The house itself is beautiful—tastefully decorated, clean, and well-maintained. The kitchen was fully stocked with all the amenities we needed, which was great for cooking meals. Krae was incredibly responsive and accommodating, even allowing flexibility with check-in and check-out times. Overall, it was a fantastic experience, and I can’t recommend this place enough!
Guest favorite
A wide sandy beach stretches towards the horizon, where soft waves gently lap at the shore. Tall lifeguard stands are positioned along the beach, with a few distant figures walking. The sky features a gradient of muted colors as the sun sets, creating a serene atmosphere.
Apartment in Southampton
4.96 out of 5 average rating, 203 reviews

Sunny Southampton Studio

Marianthi-AnnaRating, 5 stars1 month ago
great place for a weekend getaway from the city! Zoi was very communicative and helpful!
Guest favorite
A modern living space features a dark sectional sofa with light throw pillows, complemented by two accent chairs. A wooden coffee table and a round area rug are arranged on the floor. A dining table with two chairs is visible, alongside large windows providing ample natural light.
Apartment in East Lyme
4.96 out of 5 average rating, 113 reviews

Lakefront Luxury on Pattagansett

CarrieRating, 5 stars4 days ago
This was a lovely and quiet place that felt more like a vacation spot than I had expected! It was perfectly quiet and peaceful, just what we needed! I would definitely recommend.
Top guest favorite
A bright living room features large windows allowing natural light to flood the space. A comfortable gray sofa is positioned alongside a rustic coffee table. A small television is mounted on a wooden console, and an accent chair provides additional seating. Soft area rugs add warmth to the hardwood floor.
Apartment in Sayville
4.97 out of 5 average rating, 156 reviews

1 bedroom apt In the beautiful town of Sayville

ScottRating, 5 stars3 weeks ago
“Jamie’s Airbnb was incredible—just a short walk from Main St., couldn’t have dreamed of a better spot or host. Perfect location, cozy vibes, and top-notch hospitality made the stay unforgettable!
Guest favorite
A cozy living area features a plush couch adorned with decorative throw pillows in teal and cream. A rectangular coffee table with a wicker design is complemented by a patterned ottoman, enhancing the inviting space. Natural light is filtered through the partially covered window.
Apartment in Shirley
4.94 out of 5 average rating, 102 reviews

Boho Beach Vibez Retreat! Private entrance

MicahRating, 5 stars1 week ago
Great place with lovely accommodation
Guest favorite
A spacious living room area features a dark sectional couch adorned with light throw pillows. A wooden coffee table sits nearby, complemented by decorative greenery. The room is illuminated by three floor lamps, with natural light entering through multiple windows.
Apartment in New Haven
4.92 out of 5 average rating, 179 reviews

Tranquil Apartment with Waterview, Walk to Beach!

KhanhRating, 5 stars1 month ago
We enjoyed our stay at Samantha and Robert’s place. Convenient location, close to downtown and the beach. The place is spacious and cozy. Samantha and Robert provided us with everything we needed.
Top guest favorite
An elevated deck features a rectangular pool surrounded by lounge chairs and shaded by bright umbrellas. A wooden dining table with ample seating offers a space for meals outdoors. Lush greenery is visible nearby, complementing the modern architecture in the background.
Apartment in Fire Island Pines
5 out of 5 average rating, 101 reviews

"NORTH APT." Renovated 1 Br Apt. In Great Location

MitchRating, 5 stars7 months ago
Had an absolutely wonderful stay! Location is perfect and Jaime was incredibly friendly throughout!! He let me know that they had everything we would need.. but as a self-described obsessive packer I didnt listen. He wasn't kiding! They had beach chairs, umbrellas, and everything else you need for the perfect beach day. I brought an entire wagon of stuff and used one bag. It really is an awesome little find!!
Guest favorite
A vibrant sunset is captured over calm water, displaying shades of orange, pink, and purple in the sky. The reflection of these colors dances across the water's surface, creating a serene and picturesque view.
Apartment in Montauk
4.94 out of 5 average rating, 204 reviews

Private paradise 3 min from town ice skating pond!

Verena & MoritzRating, 5 stars3 weeks ago
Clare was a fantastic host. She helped us with getting around which was super helpful because we didn’t have a car. Her food recommendations were great. All in all, she created a warm and welcoming atmosphere which made our stay in Montauk a beautiful experience. Thanks for everything!

House rentals with beach access

Guest favorite
A view from the second-level deck features houses arranged closely together under a cloudy sky. The rooftops display various architectural styles, with gray shingles predominating. A distant beach area is visible at the end of the road, bordered by trees and power lines.
Home in Milford
5 out of 5 average rating, 23 reviews

Modern 3 Bedroom Home with Beach Views

TipyaRating, 5 stars7 months ago
Thank you Rachel for another great stay! The house is so close to a private beach. Well equipped and high end. This is our 2nd year renting Rachel’s place - thank you for being so accommodating!
Guest favorite
A sunlit view of a sandy beach stretches towards the horizon, with gentle waves lapping at the shore. Colorful umbrellas dot the sandy area, and a wooden walkway runs parallel to the beachfront. In the distance, sailboats can be seen on the calm water.
Home in New London
4.93 out of 5 average rating, 353 reviews

Amazing Beach House

TinaRating, 5 stars5 days ago
We loved staying here, it was so close to the beach and everything was so nice and easy! Very clean, well kept, great shower pressure, would recommend to anyone!!
Guest favorite
A balcony view overlooks Long Island Sound, featuring a small table and two red chairs. The serene water is framed by distant homes and greenery, creating a peaceful seaside atmosphere. The clear sky enhances the inviting outdoor space.
Home in New London
4.89 out of 5 average rating, 9 reviews

Paradise on Pequot

GarrettRating, 5 stars8 months ago
Excellent stay. The Private beach is perfect for families and is an extremely short distance from the house which is convenient. Great view of the ships right from the windows. Stay was perfect
Guest favorite
A serene beach scene captures a sandy shoreline meeting calm waters, with a beautiful beach home in the background. Green trees frame the property, while soft waves lap gently at the shore, creating a tranquil atmosphere.
Home in Madison
5 out of 5 average rating, 16 reviews

Beach Home & Garden Paradise

NicoleRating, 5 stars3 weeks ago
We had a wonderful stay in Brian's charming home. The house is even more luxurious than in the photos--everything is first-class from the beds and linens; to the spacious kitchen with every new appliance you could need; to the comfy living room area with huge flat-screen TV. We had more than enough room for our family of four and our kids loved how close the private beach was, literally out the door. They kayaked and enjoyed walks on the beach. The area is in a very quiet, private neighborhood with close access to the shops and restaurants on Madison's main street. A perfect retreat any time of year, we hope to come back soon.
Guest favorite
The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars2 weeks ago
It was wonderful stay and I’d go back anytime
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 cottage, 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
Home in Old Saybrook
4.97 out of 5 average rating, 121 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

SueRating, 5 stars5 days ago
Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.
Superhost
A bright living room features light-colored hardwood floors and original wood wainscoting. Soft seating includes a pink armchair and a light sofa, complemented by a round coffee table. A Smart TV is mounted on the wall. Large doors lead to another room filled with natural light.
Home in Milford
4.93 out of 5 average rating, 84 reviews

Chic Beach Bungalow - Amazing Sunsets!

LauraRating, 5 stars1 week ago
I am 68 & I have traveled pretty extensively and have to say, this was the coziest, cleanest & well-stocked Airbnb I’ve ever stayed at - absolutely has everything you could want/need. My cousins & I kept on saying, “If we could just win the lottery and buy this place! 😀 Thank you Cail, Jayne & Dylan for sharing this little piece of Paradise! 🤗

Condo rentals with beach access

Superhost
A private balcony is featured, overlooking the ocean with a clear blue sky. A small, round table is accompanied by four chairs in a light blue hue, creating a comfortable setting for outdoor relaxation.
Condo in Montauk
5 out of 5 average rating, 12 reviews

Second Floor Corner Unit Overlooking the Ocean

VishnuRating, 5 stars6 months ago
A brief stay but a great stay. It was offseason but we got lucky with sunny October weather. The stay was less than a 5 minute drive from the main village with tons of shops, cafes, etc.. the room itself had a beautiful ocean view and was very clean and comfy. Nice shower, comfy beds, plenty of linens and towels provided. Parking included. Overall a very nice stay.
Superhost
A sandy beach stretches along the Long Island Sound, bordered by greenery. A wooden boardwalk leads to the shore, with lounge chairs positioned for sunbathing. In the background, several buildings are nestled among the trees, completing the tranquil seaside scene.
Condo in North Fork
4.84 out of 5 average rating, 128 reviews

Oceanfront Condo – Incredible Spring Rates!

DanielleRating, 5 stars2 weeks ago
We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!
Superhost
Condo in Montauk
4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

StephenRating, 5 stars20 months ago
We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.
Superhost
A cozy living area is furnished with a beige sofa, a round wooden coffee table, and stylish light blue armchairs. A large window allows natural light to fill the space. Potted plants add a touch of greenery, creating a relaxed atmosphere.
Condo in Old Saybrook Center
4.89 out of 5 average rating, 72 reviews

Seashore getaway - CT shoreline

JulieRating, 5 stars3 months ago
Thanks Lauren! We enjoyed your lovely place!
Guest favorite
Condo in North Fork
4.92 out of 5 average rating, 138 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

RoxanaRating, 5 stars6 months ago
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.
Superhost
The image captures a serene shoreline intersection at sunset, with pastel colors spreading across the horizon. The road leads towards the water, framed by residential buildings and utility poles, creating a welcoming coastal vibe.
Condo in Old Lyme
4.9 out of 5 average rating, 29 reviews

Forecastle at Soundview · Beach+OceanView+Sunrise

BrittonRating, 5 stars5 months ago
Very nice stay. Appreciated the bedside chargers. Kitchen was smartly stocked, was able to prepare a Thanksgiving meal with amenities provided. Very clean. Stunning views of the ocean. Downside, small bathroom/shower, limited bathroom shelf space/counter.
Top guest favorite
The exterior of a historic Tudor-style building is framed by large, blooming cherry blossom trees. The soft pink flowers create a vibrant contrast against the architecture. A paved pathway leads to the entrance, where benches are positioned for seating.
Condo in Montauk
4.95 out of 5 average rating, 119 reviews

Deluxe Studio Apt@The Montauk Manor

ChristinRating, 5 stars6 months ago
Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!
Superhost
A spacious green lawn extends towards the ocean, with gentle waves visible in the distance. A multi-story building with defined balconies is situated to the left, surrounded by well-maintained bushes and trees, contributing to a serene coastal atmosphere.
Condo in Montauk
4.82 out of 5 average rating, 94 reviews

Beautiful Condo on the Ocean Bluffs

AdrianeRating, 5 stars8 months ago
You can not beat this location - quiet private beach right across the street, nice pool and about a 20 minute walk to town or super short car ride. The place is clean, as pictured and John was great to deal with. Will definitely be back!

Quick stats about vacation rentals with beach access in Shelter Island Heights

  • Total rentals

    200 properties

  • Nightly prices starting at

    $120 before taxes and fees

  • Total number of reviews

    8.3K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    70 properties have a pool

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