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Top Holiday Rentals in Long Island

Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (71)
"We loved this property. It’s open floor plan made it a great gathering place. Great location, clean and comfortable. Highly recommend"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (24)
"Had a wonderful time with friends in this lovely home. We had everything we needed. Excellent communication with our host. Perfect location. Thank you, Michelle 💕"
Beautiful Family Home Nestled In The Heart Of Sagaponack
Pool
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
10.0 out of 10, Exceptional, (5)
"We loved our stay here! The hosts were very helpful and communicative leading up to and during our short stay. The house was perfect for our family - the pool area is fantastic and being able to grill food at the outdoor kitchen is such a bonus. No back and forth to the house for snacks or drinks! We spent the evening around the fire pit and the extended deck meant that there was plenty of room for us to relax and our kids to play. We also explored the local area and nearby beaches. The property...
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
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Smart TV
LUX, ALL NEW-4BR/2FUL BATH, 5 MIN TO F TRAIN, 35 MIN TO CITY. 20 MIN TO- JFK/LGA
10.0 out of 10, Exceptional, (2)
"It was the perfect fit for us in terms of location and functionality. We enjoyed staying very much; it was like being on vacation in a hotel, but local. KK, who was in charge of the apt., was available at any time, responsive, and very helpful."
LUX, ALL NEW-4BR/2FUL BATH, 5 MIN TO F TRAIN, 35 MIN TO CITY. 20 MIN TO- JFK/LGA
Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is £784
per night
20 May - 21 May
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Fridge, microwave, oven, stovetop
Cozy Beach Getaway - 1000' from Ocean/Boardwalk; 6 blocks from LIRR
10.0 out of 10, Exceptional, (12)
Cozy Beach Getaway - 1000' from Ocean/Boardwalk; 6 blocks from LIRR
Interior
Airstream Art Studio Sculpture/Nature Preserve
10.0 out of 10, Exceptional, (1)
"I found it cozy, comfortable and very peaceful. Bonus wildlife visits of deer, geese and turkeys, Most people will understand this accommodation as quality “clamping”."
The price is £193
per night
19 May - 20 May
Airstream Art Studio Sculpture/Nature Preserve
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Beach nearby, sun-loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (60)
"Perfect spot in Montauk, close to the beach and town. We walked to town with a 3 year old and infant in the stroller and very doable nice walk. The condo is clean and equipped with basic necessities so bring anything you might need cooking wise. Kept the baby in the bedroom and our 3 year old in the living room but we made it work. Kelly is extremely responsive and a pleasure to rent from."
Newly Renovated Montauk Condo with Ocean Views!
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (27)
The price is £483
per night
13 Jun - 14 Jun
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1021)
"Best affordable hotel in Montauk"
The price is £167
per night
22 May - 23 May
Montauk Manor
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
Deluxe Studio Suite | Private kitchen
Starlight Hotel
2.0 star property
9.0 out of 10, Wonderful, (125)
"We liked the size of the room and how it had everything we would have needed it we forgot something. Would have been nice to change the thermostat, got a little humid in there in the evening "
The price is £144
per night
29 May - 30 May
Starlight Hotel
Superior Apartment, 2 Bedrooms, City View | Living area | Flat-screen TV
Sonder Court Square
3.5 star property
9.0 out of 10, Wonderful, (66)
"Too much auto email. I was trying to contact before i arrived but was never able to get through. However, once we arrived,.there was a staff person 24/7 to assist us. All the lobby staff were grest."
The price is £294
per night
13 Jun - 14 Jun
Sonder Court Square
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is £202
per night
29 May - 30 May
Cliffside Resort Condominiums
Rooftop terrace
Sonder The Dutch
3.5 star property
8.8 out of 10, Excellent, (60)
"The hotel itself was amazing, clean, staff were friendly and helpful, the views from the hotel were breathtaking - it was located quite close to three different subway stations. Sonder is 10/10. "
The price is £204
per night
11 Jun - 12 Jun
Sonder The Dutch
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (236)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is £155
per night
19 May - 20 May
Windward Shores Ocean Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (185)
"Every room in the hotel has a little garden in the backyard which is linked with the park, it’s super natural and quiet and definitely worth to stay"
The price is £163
per night
2 Jun - 3 Jun
Driftwood Resort
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is £199
per night
29 May - 30 May
The Surf Club
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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.

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

Lobby
Four Points by Sheraton Flushing
3.0 star property
9.0 out of 10, Wonderful, (1549)
"Clean"
The price is £173
per night
27 May - 28 May
Four Points by Sheraton Flushing
Lobby
Pod Brooklyn
3.0 star property
8.8 out of 10, Excellent, (1003)
"Had a very nice stay at this hotel! Room was smaller than expected, but we were there just for one night so it didn’t matter. "
The price is £126
per night
27 May - 28 May
Pod Brooklyn
Bar (on property)
Hampton Inn NY-JFK
2.5 star property
8.0 out of 10, Very good, (1653)
"Staff was very nice, helpful, and welcoming"
The price is £209
per night
16 Jun - 17 Jun
Hampton Inn NY-JFK
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.

Everything you need to know about Long Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Long Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Long Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Long Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Long Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Long Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Long Island holiday rentals we have selected for you start as low as £90 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Long Island rentals

At Expedia, we put the best Long Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Long Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Long Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Long Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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