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Shelter Island Vacation Rentals

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Check prices for these dates

Tonight
Jun 19 - Jun 20
Tomorrow
Jun 20 - Jun 21
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Shelter Island

Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (43)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
Work and Play Special! Extended Stay Discount
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1195)
"The property was gorgeous, and the staff were very friendly and eager to assist. Also, the restaurant was very good!"
The price is ￥52,853
￥63,225 total
includes taxes & fees
Jun 22 - Jun 23
Montauk Manor
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (285)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is ￥39,099
￥47,826 total
includes taxes & fees
Jun 22 - Jun 23
Windward Shores Ocean Resort
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (382)
"great place to stay"
The price is ￥27,131
￥32,575 total
includes taxes & fees
Jun 23 - Jun 24
Montauk Oceanside Suites
Offshore Montauk
1 bedroom, laptop workspace, blackout drapes, free WiFi

Offshore Montauk

4.0 star property
The price is ￥32,350
￥53,526 total
includes taxes & fees
Jun 26 - Jun 27
Offshore Montauk
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (223)
"The staff was very friendly I will definitely be back again 👍"
The price is ￥46,757
￥58,145 total
includes taxes & fees
Jun 22 - Jun 23
Driftwood Resort
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (256)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is ￥32,546
￥45,090 total
includes taxes & fees
Jul 1 - Jul 2
The Surf Club
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (221)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is ￥36,653
￥48,194 total
includes taxes & fees
Jun 26 - Jun 27
Cliffside Resort Condominiums
3-bedroom Montauk Coastal Getaway
Microwave, oven, stovetop, dishwasher

3-bedroom Montauk Coastal Getaway

3-bedroom Montauk Coastal Getaway
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
TV, fireplace, video games, DVD player

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.6 out of 10, Excellent, (25)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
The price is ￥248,776
￥301,280 total
includes taxes & fees
Jun 29 - Jun 30
Canoe Place Waterfront Residences
Fairy Tale Guest Cottage in Magic Garden by Pool
Outdoor pool

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (66)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool
Charming Montauk Getaway centrally located
Beach nearby

Charming Montauk Getaway centrally located

9.6 out of 10, Exceptional, (43)
"Quiet, private, well-appointed spot with everything you need for a getaway. Conveniently located within walking distance to town, it has its own outdoor area perfect for lounging and cooking out. We loved it!"
Charming Montauk Getaway centrally located
Shoreline Oasis
Exterior

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is ￥25,955
￥37,787 total
includes taxes & fees
Jun 25 - Jun 26
Shoreline Oasis
Freeboard at Soundview · Beach+Ocean+Sunrise
On the beach

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is ￥14,201
￥32,254 total
includes taxes & fees
Jul 2 - Jul 3
Freeboard at Soundview · Beach+Ocean+Sunrise
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Smart TV, fireplace, stereo

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (85)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach
A heated pool

Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

10.0 out of 10, Exceptional, (83)
"Great time"
Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10
Sun loungers, beach towels

Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

10.0 out of 10, Exceptional, (7)
"We thoroughly enjoyed the home, and Carter was extremely helpful throughout our stay. The private parking access to the beach was awesome!"
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage
Pool

Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

9.4 out of 10, Exceptional, (10)
"I stayed here with family recently and loved the house. The location was private and convenient. The management company was available to answer our questions. It was perfect for an off season get away. "
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage
The Mast at Soundview · Beach+Ocean+Sunrise
On the beach

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect spot for my stay! I loved being able to walk down to the beach and enjoyed the quiet neighborhood. Check in directions were straightforward and I had no issues getting into my room or finding the place. Host was very responsive! "
The price is ￥18,549
￥38,001 total
includes taxes & fees
Jun 22 - Jun 23
The Mast at Soundview · Beach+Ocean+Sunrise
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.

What are some of the best vacation home rentals that Shelter Island has to offer?

3-bedroom Montauk Coastal Getaway: This vacation home rental near Shelter Island offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals are there in Shelter Island?

Choose from 87 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. Gardiner's Bay Country Club and Shelter Island Historical Society 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.