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Long Island Vacation Rentals

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Vacation Rentals in Long Island

Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
The price is CA $148 per night from Nov 8 to Nov 9

Situated near the beach, this condominium resort is within 1 mile (2 km) of Shadmoor State Park, Fort Pond and Fort Pond Bay Beach. South Edison Beach and Montauk ...

4.5/5Wonderful! (329 reviews)

"Gorgeous property. Lovely furnishings. Great service"…"

Reviewed on Oct. 26, 2020

Montauk Manor
Breakers Montauk

Breakers Montauk

3 out of 5
769 Old Montauk Highway, Montauk, NY

Situated in Montauk, this beach condo is within a 10-minute walk of Second House Museum, Kirk Park Beach, and Fort Pond. South Edison Beach and Fort Pond Bay ...

3.9/5Good! (37 reviews)

"Really enjoyed our stay at breakers! It was very clean and comfortable with a nice view of the ocean! Also loved having easy access to the beach. Self check in and check out was very easy."…"

Reviewed on Oct. 26, 2020

Breakers Montauk
The Montauk Soundview

The Montauk Soundview

3 out of 5
6 Soundview Drive, Montauk, NY

Nestled on the beach, this Culloden Shores condo is within a 15-minute walk of Montauk Marine Basin and Gin Beach. Fort Pond Bay Beach and Ditch Plains Beach ...

4.2/5Excellent! (50 reviews)

"Very quaint and clean rooms. View of the beach is absolutely beautiful. Make sure to walk down to the ocean for the sunset"…"

Reviewed on Oct. 19, 2020

The Montauk Soundview

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The Surf Club

The Surf Club

3.5 out of 5
20 Surfside Avenue, Montauk, NY
The price is CA $284 per night from Oct 28 to Oct 29

Nestled on the beach, this Montauk condo is within a 15-minute walk of South Edison Beach, Kirk Park Beach and Fort Pond. Shadmoor State Park and Second House ...

4.2/5Very Good! (156 reviews)

"We have 2 kids that were able to stay in 1 room while we used the pull out couch."…"

Reviewed on Oct. 13, 2020

The Surf Club
Driftwood Resort

Driftwood Resort

3.5 out of 5
2178 Montauk Highway, Montauk, NY

Nestled on the beach, this Montauk condo is within 1 mi (2 km) of Napeague State Park and Walking Dunes Trailhead. Hither Woods Preserve is 1.8 mi (3 km) ...

4.2/5Excellent! (113 reviews)

"Beautiful place! Booked a studio unit and it what was expected! Room clean with full usable kitchen and beautiful terrace! Pool and beach absolutely beautiful! Front desk staff so nice and helpful for anything you need !! Overall would definitely recommend this place to stay if you are looking for ..."…"

Reviewed on Jul. 17, 2020

Driftwood Resort
The Ocean Colony Beach & Tennis Club

The Ocean Colony Beach & Tennis Club

3 out of 5
2004 Montauk Highway, Amagansett, NY
The price is CA $256 per night from Oct 29 to Oct 30

Situated in Amagansett, this apartment building is 0.1 mi (0.1 km) from Napeague State Park and within 3 miles (5 km) of Walking Dunes Trailhead and Hither Woods ...

4.1/5Very Good! (71 reviews)

"Booked two rooms, one room was great and the other was dated."…"

Reviewed on Sep. 22, 2020

The Ocean Colony Beach & Tennis Club
Beach Plum Resort

Beach Plum Resort

3 out of 5
779 Old Montauk Highway, Montauk, NY

With direct access to the beach, this Montauk condo is within a 10-minute walk of Second House Museum, Kirk Park Beach and Fort Pond. South Edison Beach and ...

4.3/5Excellent! (93 reviews)

"Room was very clean and contactless check in was super simple. Great location - about a 10-15 min walk into the village or the beach. Staff was super helpful when needed, and would highly recommend a stay here."…"

Reviewed on Oct. 21, 2020

Beach Plum Resort
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway, PO Box 7031, Amagansett, NY
The price is CA $182 per night from Nov 1 to Nov 2

Nestled on the beach, this Amagansett apartment building is within 1 mi (2 km) of Napeague State Park and Walking Dunes Trailhead. Amagansett Beach and Atlantic ...

4.2/5Excellent! (111 reviews)

"Excellent location, well-maintained, seem less check-in and check-out."…"

Reviewed on Jun. 20, 2020

Windward Shores Ocean Resort
Born Free Suites by the Sea

Born Free Suites by the Sea

3 out of 5
115 South Emerson Avenue, Montauk, NY
The price is CA $177 per night from Nov 7 to Nov 8

Situated near the beach, this condo is within a 5-minute walk of South Edison Beach and Kirk Park Beach. Fort Pond and Second House Museum are also within 15 ...

4.2/5Excellent! (117 reviews)

"Great location across the street from the beach. Studio with full kitchenette, dining area, and sofa. A coffee table, nightstand, and more accessible electric plugs would have been good."…"

Reviewed on Oct. 24, 2020

Born Free Suites by the Sea
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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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Long Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Other types of properties in Long Island you may be interested in

Ravel Hotel Trademark Collection by Wyndham

Ravel Hotel Trademark Collection by Wyndham

4 out of 5
8-08 Queens Plaza South, Long Island City, NY
Free cancellationReserve now, pay when you stay
The price is CA $135 per night from Nov 24 to Nov 25
Ravel Hotel Trademark Collection by Wyndham
Gurney’s Star Island Resort & Marina

Gurney’s Star Island Resort & Marina

3.5 out of 5
32 Star Island Rd, Montauk, NY
Gurney’s Star Island Resort & Marina
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.