A marina with various boats docked, a house with an American flag, and a clear sky.

Long Island Holiday Rentals

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Our top choices for Long Island holiday rentals

1. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,415 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is NZ$344
includes taxes & fees
2 Nov - 3 Nov
Montauk Manor

2. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (326 reviews)
"The room was nice but the bed was horrible. They need to replace the bed ASAP. It is so old that the middle of the bed is touching the floor due to it being worn out. Our backs are still hurting. Otherwise it was a nice room."
United States
William
The price is NZ$334
includes taxes & fees
18 Oct - 19 Oct
Windward Shores Ocean Resort

3. Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder
3.5 star property
Queens
7.2 out of 10, Good, (529 reviews)
"Everything was as advertised - smooth check in, clean room, transparent process overall."
United States
Leon
The price is NZ$329
includes taxes & fees
25 Oct - 26 Oct
Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

4. Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Brentwood
9.4 out of 10, Exceptional, (56 reviews)
"This stay was very clean and easy. The check-in process was efficient. Thank you, I would definitely book again for a short stay!"
United States
Jaelyn
The price is NZ$295
includes taxes & fees
18 Oct - 19 Oct
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

5. Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
8.8 out of 10, Excellent, (13 reviews)
The price is NZ$318
includes taxes & fees
28 Oct - 29 Oct
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

6. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (456 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is NZ$308
includes taxes & fees
22 Oct - 23 Oct
Montauk Oceanside Suites

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is NZ$544
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums

8. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (9 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is NZ$598
includes taxes & fees
26 Oct - 27 Oct
The Royal Suite - Ronkonkoma

9. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is NZ$496
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort

10. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is NZ$300
includes taxes & fees
14 Oct - 15 Oct
Driftwood Resort

11. Tremendous 1-bedroom apartment with AC in Hempstead

Tremendous 1-bedroom apartment with AC in Hempstead
Hempstead
The price is NZ$210
includes taxes & fees
14 Oct - 15 Oct
Tremendous 1-bedroom apartment with AC in Hempstead

12. Cozy Studio by Hofstra University

Cozy Studio by Hofstra University
Uniondale
9.6 out of 10, Exceptional, (48 reviews)
"Great stay "
United States
Tyshieka R.
The price is NZ$312
includes taxes & fees
19 Oct - 20 Oct
Cozy Studio by Hofstra University

13. 1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (25 reviews)
"Exactly as advertised, comfortable bed easy entry, overall great experience."
United States
Monte P.
The price is NZ$313
includes taxes & fees
14 Oct - 15 Oct
1 bedroom 1 bath private entrance

14. Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
The price is NZ$869
includes taxes & fees
22 Oct - 23 Oct
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

15. Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is NZ$534
includes taxes & fees
25 Oct - 26 Oct
Sundown Escape-South Shore Long Island

16. 2 Pvt bed Rm 1bathroom no kitchen attic

2 Pvt bed Rm 1bathroom no kitchen attic
Uniondale
9.2 out of 10, Wonderful, (10 reviews)
"Parking on the street was always available."
United States
William
The price is NZ$277
includes taxes & fees
19 Oct - 20 Oct
2 Pvt bed Rm 1bathroom no kitchen attic

17. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is NZ$530
includes taxes & fees
19 Oct - 20 Oct
Spacious 3BR Family Home Near Everything

18. Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
9.6 out of 10, Exceptional, (31 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is NZ$322
includes taxes & fees
14 Oct - 15 Oct
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

19. East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
East Meadow
8.8 out of 10, Excellent, (24 reviews)
"Everything was good"
United States
Elena
The price is NZ$343
includes taxes & fees
14 Oct - 15 Oct
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

20. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (303 reviews)
"Staff are nice"
United States
na
The price is NZ$526
includes taxes & fees
27 Oct - 28 Oct
The Surf Club
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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Top Long Island Hotel Reviews

Find out more about Long Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Long Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Long Island. 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 Long Island. 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 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 holiday 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 Long Island short-term rentals, that won’t be hard to do.

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