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Accommodations in Shelter Island

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Popular amenities for Shelter Island accommodations

Other great vacation rentals in Shelter Island

A shaded seating area is presented under an orange canopy, featuring a wooden table surrounded by six deep blue cushioned chairs. It is set on a wooden deck, with the serene in-ground saltwater pool visible in the background, complemented by verdant gardens and vibrant plants.
Home in Shelter Island
4.89 out of 5 average rating, 9 reviews

Serenity on Shelter Island with a Pool & Hot tub

ChrisRating, 5 stars9 months ago
Mary Ann was a great host. Super responsive and provide excellent details and very helpful information. Her house is beautiful with a wonderful oasis in the back with pool, hot tub, and fire pit with plenty of space to lounge. Our family felt right at home and very comfortable. We hope to come back again.
Guest favorite
An outdoor mahogany deck features a circular dining table surrounded by four wicker chairs, with additional seating in the form of a loveseat. Two large umbrellas provide shade, and a gas grill is covered and positioned nearby. Lush greenery is visible in the background.
Home in Shelter Island Heights
5 out of 5 average rating, 10 reviews

Laid Back Relaxation

SallieRating, 5 stars3 weeks ago
We really enjoyed Jared’s property. The light-filled living and dining room were spacious and comfortable, and the kitchen was modern and well-equipped. We would stay here again!
Guest favorite
A serene waterfront scene captures gentle waves lapping against smooth rocks. The sky displays a captivating sunset with hues of orange, pink, and purple reflecting on the water's surface, creating a peaceful atmosphere at the day's end.
Home in Shelter Island
4.93 out of 5 average rating, 80 reviews

Family Friendly Island Home

LelandRating, 5 stars9 months ago
Bruno’s place was really quaint and nice. Bruno was easy to communicate with. Would recommend it again for sure!
A newly built house features a light-colored exterior with large, dark-framed windows. The entrance is highlighted by a small covered porch. Surrounding the home is a well-maintained lawn with neatly trimmed bushes lining the pathway, leading to a white gate on one side.
Home in Shelter Island
5 out of 5 average rating, 3 reviews

New vacation house on the island(new pool)

JamesRating, 5 stars9 months ago
Iwona was a terrific host. The home is immaculately maintained, with high ceilings and large windows looking over beautiful green space. It is a calming environment, both indoors and out. The location is convenient to the town center, a nature preserve, beaches, restaurants, and the north and south ferries. Based on our experience, we recommend highly!
Top guest favorite
A spacious estate is set against a twilight sky, with two separate dwellings visible amid well-manicured lawns. Large trees provide shade, while warm light glows from the windows, indicating a welcoming atmosphere. The serene surroundings emphasize the property's privacy and seclusion.
Home in Shelter Island
5 out of 5 average rating, 7 reviews

6-acre Hidden Estate for 10 w/FP, Pool, Chef's Kit

JaneRating, 5 stars2 weeks ago
Several of my family members stayed at Christine's house while on Shelter Island for a family wedding. The main house and cottage were both so beautiful and so comfortable and cozy. The grounds were positiviely idyllic including the tucked away, inviting pool. It truly felt like it could be our family's house. We all fell in love. The beds were comfortable with crisp white linens. When we weren't outside, the kitchen was a constant gathering place as was the sunroom and the dining room. I can't say anything about the TVs since we didn't turn one on once. Didn't even think about it - were having too much fun being together. Internet was great! Before arrival, Christian was a constant source of communication, making sure we were all set. Pay attention to his succinct instructions of how to get to the house. They are spot on. Kim, the manager, was there to greet us and let us in and answer any questions. She was so helpful. Going to SI? Stay at Christine's! You'll be glad you did!
Guest favorite
A spacious outdoor seating area with a low, sectional sofa and a circular coffee table is set on a wooden dock. Two large umbrellas provide shade over the seating area, while the surrounding greenery reflects in the calm water of Menantic Creek.
Guesthouse in Shelter Island
4.89 out of 5 average rating, 9 reviews

Stylish Studio Suite on Shelter Island

AnnaRating, 5 stars10 months ago
Kate’s place was perfect—down a quiet and private road but close to everything Shelter Island has to offer. The apartment was cozy and comfortable with all the necessities. Kate was very responsive when needed but you also have privacy. Lovely stay—I hope to come again!
The living area features large glass doors that open to a view of trees and distant water. A light grey rug anchors two chairs and a sectional sofa, while a small circular coffee table holds a chess set. A television is mounted on the wall.
Apartment in Shelter Island
5 out of 5 average rating, 15 reviews

Modern Waterview Apartment in Silver Beach

MarkRating, 5 stars3 weeks ago
We really enjoyed our stay at Ena and Robs well appointed quiet apartment on shelter Island. It was in a great location close to beaches and in a perfect spot to bike around the island. Everything in the apartment was of a high quality, spotlessly clean including the comfortable bed and the linens, the kitchen was well equipped, the shower very nice and there was a lovely little balcony to sit and have your coffee in the morning. The host were very friendly and open. We would definitely go back!
Guest favorite
A life-sized chess set occupies the vibrant green lawn, with large white and black pieces arranged strategically on a stone pathway. The modern wooden house features dark siding and a bright yellow door, offering a welcoming contrast. A cozy chair and a sculptural element add to the inviting outdoor space.
Home in Shelter Island
4.92 out of 5 average rating, 13 reviews

Moonlit Manor | Shelter Island Escape w/ NEW Sauna

CarolynRating, 5 stars5 days ago
We loved our stay! The house had everything we needed to relax and unwind. The kitchen was fully stocked with a great selection of spices and condiments. The grocery store was just a 4-minute drive away. Having bikes made exploring Shelter Island so much fun without the hassle of parking. We also took our dogs to the nearby dog-friendly beach and had the best time. The host was incredibly friendly and responsive, making sure we had everything we needed throughout our stay.

Quick stats about vacation rentals in Shelter Island

  • Total rentals

    150 properties

  • Nightly prices starting at

    G$2,093 GYD before taxes and fees

  • Total number of reviews

    3.1K reviews

  • Family-friendly rentals

    110 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    50 properties have a pool

Frequently Asked Questions

  • How much does it cost to stay in house rentals in Shelter Island?

    Experience the best of Shelter Island with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Shelter Island?

    Yes! Work meets play with ease at over 60 house rentals in Shelter Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly house rentals in Shelter Island?

    Four-legged friends are welcome in Shelter Island. Choose from more than 40 house rentals for guests traveling with pets.

  • Do house rentals in Shelter Island have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Shelter Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Shelter Island have a bbq area?

    Absolutely! We offer over 60 house rentals with a bbq area in Shelter Island. Enjoy a tailored experience with all the comforts you desire.

  • Are there Shelter Island house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Shelter Island, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Shelter Island have wifi?

    Absolutely! We offer over 110 house rentals with wifi in Shelter Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Shelter Island have self check-in?

    Absolutely! We offer over 20 house rentals with self check-in in Shelter Island. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Shelter Island?

    Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a bbq area, over 20 homes with self check-in, over 110 homes with wifi, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly house rentals in Shelter Island?

    Shelter Island has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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