A wooden pier with tires and crates, overlooking a sunset over the water.

Fair Harbor Holiday Rentals

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Our top choices for Fair Harbor holiday rentals

1. 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
15 Oct - 16 Oct
1 bedroom 1 bath private entrance

2. 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, (55 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$294
includes taxes & fees
18 Oct - 19 Oct
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

3. 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
12 Oct - 13 Oct
Sundown Escape-South Shore Long Island

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

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
Deer Park
10.0 out of 10, Exceptional, (3 reviews)
"My family and I really enjoyed this property! The host was welcoming, the property was clean and well-cared for, and it’s in a very nice area. We would stay again next time we’re in Long Island!"
United States
Danielle M.
The price is NZ$883
includes taxes & fees
22 Oct - 23 Oct
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

5. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is NZ$594
includes taxes & fees
8 Nov - 9 Nov
Sundown Escape Near SouthShore University Hospital

6. Charming Secluded Waterfront retreat

Charming Secluded Waterfront retreat
Oakdale
The price is NZ$483
includes taxes & fees
4 Nov - 5 Nov
Charming Secluded Waterfront retreat

7. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (16 reviews)
"Great place to stay. Clean room."
United States
melissa a.
The price is NZ$430
includes taxes & fees
15 Oct - 16 Oct
Your Perfect Getaway Between Farmingdale & Amityville

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$610
includes taxes & fees
12 Oct - 13 Oct
The Royal Suite - Ronkonkoma

9. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is NZ$527
includes taxes & fees
19 Oct - 20 Oct
Spacious 3BR Family Home Near Everything

10. Private Apartment on River Ave. close to main st

Private Apartment on River Ave. close to main st
Patchogue
9.6 out of 10, Exceptional, (8 reviews)
"Nice little property. Perfect for what we needed. Host was great."
United States
A H.
The price is NZ$547
includes taxes & fees
20 Oct - 21 Oct
Private Apartment on River Ave. close to main st

11. 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)
"Ample on street parking - a smooth self check in - a comfortable bed and a clean bathroom in a quiet and safe walkable neighborhood. I did not know NYC could be so user friendly!"
United States
Susan O.
The price is NZ$304
includes taxes & fees
12 Oct - 13 Oct
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
9.4 out of 10, Exceptional, (30 reviews)
"The property was very easy to find, clean, and comfortable. The hosts were very communicative and accommodating. Highly recommend!"
United States
Karen D.
The price is NZ$321
includes taxes & fees
12 Oct - 13 Oct
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

13. Modern 2BR Retreat w/ Full Kitchen & Living

Modern 2BR Retreat w/ Full Kitchen & Living
Deer Park
6.0 out of 10, (2 reviews)
"Needs lots of repairs and cleaning.Didn’t understand how one room had two AC and two TV while the other room had none. I would liked to hang out on the porch but also not clean and there was no table but a couple dirty chairs."
United States
marlene D.
The price is NZ$613
includes taxes & fees
9 Nov - 10 Nov
Modern 2BR Retreat w/ Full Kitchen & Living

14. Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
8.8 out of 10, Excellent, (3 reviews)
"My stay was amazing! The place was bigger in person than i expected, which was such a pleasant surprise. The house was spotless and very clean, making me feel comfortable from the moment I arrived. The host was incredibly helpful, responsive, and made the entire experience smooth and stress-free. I enjoyed my stay and would absolutely book this home again. Highly recommend to anyone looking for a clean, spacious, and welcoming place to stay!"
United States
Tatiana J.
The price is NZ$910
includes taxes & fees
19 Oct - 20 Oct
Bright & Comfortable Home in the Heart of It All

15. Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
8.2 out of 10, Very good, (12 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is NZ$603
includes taxes & fees
11 Oct - 12 Oct
Spacious one Bedroom Apt with private entrance

16. 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$870
includes taxes & fees
22 Oct - 23 Oct
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

17. Private 1 bedroom apt in a quiet neighborhood, close to all!

Private 1 bedroom apt in a quiet neighborhood, close to all!
Centereach
9.6 out of 10, Exceptional, (29 reviews)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is NZ$444
includes taxes & fees
12 Oct - 13 Oct
Private 1 bedroom apt in a quiet neighborhood, close to all!

18. Cozy 1-bedroom apartment in charming Centereach with AC

Cozy 1-bedroom apartment in charming Centereach with AC
Centereach
The price is NZ$334
includes taxes & fees
25 Oct - 26 Oct
Cozy 1-bedroom apartment in charming Centereach with AC

19. Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
8.8 out of 10, Excellent, (8 reviews)
"He’s an excellent hosts and his place is well worth it."
United States
Rowena V.
The price is NZ$503
includes taxes & fees
1 Nov - 2 Nov
Peaceful private 2-bedroom house in Bayport. Amazing location!

20. 3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (24 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is NZ$1,070
includes taxes & fees
3 Nov - 4 Nov
3 Story Beach Waterview, 3 KING bed, golf putting green!
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 Fair Harbor Hotel Reviews

Find out more about Fair Harbor

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 Fair Harbor 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 Fair Harbor. 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 Fair Harbor. Seeing all the best attractions is bound to make you fall in love with Fair Harbor. 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 Fair Harbor short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Fair Harbor?

Yes, there are holiday rentals close to the most popular sights in Fair Harbor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Fair Harbor has to offer?

Large Beach House Steps From Town and Ocean: This holiday home rental outside of Fair Harbor has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Fair Harbor?

Choose from 20 Expedia holiday rentals in Fair Harbor for a memorable holiday.

What’s there to see and do in Fair Harbor?

While exploring the area, visit family-friendly sights like Adventureland, or get outside and enjoy nature at Atlantique Beach. Ocean Beach and Fire Island Lighthouse are a couple of places you'll find in the wider area.

What’s a holiday rental in Fair Harbor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Fair Harbor. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for small groups.