Shelter Island Holiday Rentals - Holiday Homes in Shelter Island

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Vacation Rentals in Shelter Island

Stunning multi-story building with a traditional design, featuring balconies and a beautifully manicured lawn.

"Beautiful property and spacious rooms "

P31,018 total

includes taxes & fees

Jul 15 - Jul 16

Relax on the beach with comfortable lounge chairs and umbrellas, surrounded by serene ocean views.

"Quiet, relaxing place to stay, great access to the beach and town!"

P24,780 total

includes taxes & fees

Jul 16 - Jul 17

Cozy living space with a dining table, sofa, and kitchenette, complete with a stove and refrigerator.

"great place to stay"

P18,544 total

includes taxes & fees

Jul 22 - Jul 23

Enjoy a panoramic ocean view from the comfort of this room, featuring a dining table, seating area, and sliding glass doors to the outdoor patio.

"Easy checking in and out Easy access few steps to beach from first floor unit "

P26,738 total

includes taxes & fees

Jul 16 - Jul 17

Stunning beachfront residential area with multi-story buildings and a central park.

"Very nice, clean and cosy place! Highly recommend!"

P37,123 total

includes taxes & fees

Jul 28 - Jul 29

Enjoy cooking in this well-equipped kitchen with a tiled backsplash and black refrigerator.

"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."

P25,864 total

includes taxes & fees

Jul 20 - Jul 21

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Find out more about Shelter Island

Search for holiday rentals in Shelter Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island using one of the methods below:

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Look no further and take a look at our great range of rental properties in Shelter Island!

Recent reviews of Shelter Island properties

5/5 Excellent

"Great experience! Very clean felt upscale ! Staff was great! "

A verified traveler stayed at Offshore Montauk

Posted 2 days ago

5/5 Excellent

"Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery.. "

A verified traveler stayed at Sound View Greenport

Posted 4 days ago

5/5 Excellent

Excellent Place to Stay!!!...5 Stars & More!!

"We stayed 5 days! Customer service was great ;) Housekeeping was great, the cafe in the morning was excellent! Lounge area if you wanted to go out in the evening they had Pool, Darts, & Karaoke If you didn't want to go to the Beach, they had a Pool/Gym Right near the Highway & Route 1 We had a wonderful Stay!!...Will definitely go back!!! Gave them 5 Stars ;)"

A verified traveler stayed at Quality Inn Old Saybrook - Westbrook

Posted 4 days ago

5/5 Excellent

"We loved our stay at Marram! The property is a little slice of beach magic. The location was absolutely perfect, and the private beach was exactly what we were hoping for. Tranquil and beautiful, they have effortlessly blended luxury into the unpretentious surf town vibes that Montauk is known for. The staff is attentive, friendly, and helpful. The common areas were family friendly and we loved the fire pits, covered patio deck, and lounge area. Our beds were insanely comfortable and the room decor simple and elegant. A few things could have improved our stay: Our room had very limited storage, so with no closet to stow things away the minimalist aesthetic quickly went out the window. Our room had the sink/vanity area outside the bathroom, and only the shower and toilet inside. This was awkward for us to navigate as a family. We loved the smell of the Le Labo bath products, but I am always hesitant to use communal products in hotels as you never know if it has been tampered with. I would have preferred individually sized recyclable bottles to enjoy that amenity. Overall, we adored it and would recommend it 10/10! "

A verified traveler stayed at Marram

Posted 4 days ago

Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

How many vacation rentals are there in Shelter Island?

Choose from 85 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Mashomack Preserve and Shell Beach are other places to visit while you're in town.

What are vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.

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Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Montauk Manor

The Surf Club

Montauk Oceanside Suites

Windward Shores Ocean Resort

Cliffside Resort Condominiums

Driftwood Resort

Canoe Place Waterfront Residences

Find out more about Shelter Island

Recent reviews of Shelter Island properties

Offshore Montauk

Beachcomber Resort at Montauk

Sound View Greenport

Quality Inn Old Saybrook - Westbrook

Kenny's Tipperary Inn

Marram

Montauk Yacht Club

Hyatt Place Long Island East End

Aqualina Inn Montauk

Frequently asked questions