Holiday Homes in Long Island

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Featured Holiday Homes in Long Island and around

LA MAISON DES SIRENES 1, Bohemian and charm,ing 20mn away from city.

9.6 out of 10, Exceptional, (103)
"The perfect stay. Cute places close by and overall safe feeling. Subway is near and easy to access. The place is absolutely adorable and has such a cozy vintage vibe. Beds were comfy and WiFi was good. Host was so catering and super quick with responses. I have zero complaints and would visit again!"
LA MAISON DES SIRENES 1, Bohemian and charm,ing 20mn away from city.

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (16)
"Our group of friends stayed at this house for a long weekend in October 2024. The house is just as good or better than the pictures in the listing. Very clean and updated inside and out. Most importantly, the bathrooms and kitchen are clean and updated. And the huge backyard with pool, hot tub, and outdoor shower takes this house to the next level. The backyard space is great for families, small groups, or anyone looking for a quiet private space to relax. The owner/manager was very...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

10.0 out of 10, Exceptional, (34)
"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

10.0 out of 10, Exceptional, (47)
"We thoroughly enjoyed staying here, short walk to town, beautiful scenery, quiet and clean. "
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Northfork Townhouse- walk to all/ newly renovated

9.4 out of 10, Exceptional, (3)
"The place was as advertised and in great walking distance to everything in town! "
Northfork Townhouse- walk to all/ newly renovated

Charming 2-bedroom Apartment with WiFi, AC in fabulous Brooklyn NYC

2.0 star property
Charming 2-bedroom Apartment with WiFi, AC in fabulous Brooklyn NYC

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

10.0 out of 10, Exceptional, (11)
"The house is very nice. Very updated and clean. Best bathrooms in any house we have stayed in. The kitchen was large and very nice. Backyard is nice and private with plenty of room. My only issue is that there are so many trees that it blocks a lot of the sun. The pool is in the shade most of the time. In the hot summer it might be great to get some shade but our week was in the low 70's and we could have used a little more sun on the pool. House is in a good location, close to town and the...
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

Welcome to the J Luxury Southampton Estate w/Pool

9.8 out of 10, Exceptional, (30)
"Joe was an amazing host - always responsive from the moment of booking throughout the entire stay. The kitchen was a chef's dream - spacious and stocked with every appliance, seasoning, etc you can think of. We were a group of 8 and cooked family dinners each night. The highlight of the property was most definitely the deck, which was beautifully decorated and with a perfect amount of seating. Neighborhood was very walkable and it was a very short drive to the beach! I would note that there are...
Welcome to the J Luxury Southampton Estate w/Pool

Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!

10.0 out of 10, Exceptional, (12)
"Very nice house in very conditions. Thank you for everything."
Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!

Spacious Sanctuary 1 block to train!

Spacious Sanctuary 1 block to train!

🌊☀️🌲Vibrant Stay with Free Wine🌲🌊☀️

9.8 out of 10, Exceptional, (6)
"The reservation was great. Clean , convenient & very organized. Looking forward to another stay !"
🌊☀️🌲Vibrant Stay with Free Wine🌲🌊☀️

Cozy queen-size room with private bathroom in BedStuy

10.0 out of 10, Exceptional, (2)
"We had a very good time. Emanuele and Francesco were very welcoming and gave us good tips to discover the city. Yuki and Lenu are lovely cats <3. The location is in a quiet neighborhood and close to the subway, making it very easy to go to Manhattan. I recommend this place and would stay again."
Cozy queen-size room with private bathroom in BedStuy

Autumn in the Hamptons! Pumpkin picking, apple picking, wine tasting and more!

10.0 out of 10, Exceptional, (80)
"The property was exactly as explained and all in our group loved the place. The house was clean and spacious with plenty of space to rekax."
Autumn in the Hamptons! Pumpkin picking, apple picking, wine tasting and more!

Private and Immaculate East Hampton Home With Heated Pool

10.0 out of 10, Exceptional, (85)
"We enjoyed the visit. The space was clean and the beds were very comfortable. Kitchen was well appointed. We visited in the offseason but the deck and pool space is beautiful. We would definitely rent this property again."
Private and Immaculate East Hampton Home With Heated Pool

Perfectly Located, Newly Renovated Montauk Beach House with Plunge Pool/Hot Tub

9.8 out of 10, Exceptional, (6)
"We really enjoyed our stay, it was what we were expecting and the host was very quick to respond on all communications!"
Perfectly Located, Newly Renovated Montauk Beach House with Plunge Pool/Hot Tub

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (2)
"We had a fantastic time at this rental on the East end of Long Island. The place was clean, spacious, and perfect for our family getaway. Highly recommend!"
The price is €959
includes taxes & fees
26 Nov - 27 Nov
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Private access Ocean beach, steps away...Perfect home for family vacations!

10.0 out of 10, Exceptional, (60)
"This property was a dream and so was working with Paul! The location is absolutely perfect (so close to downtown and the shops) and a stunning property. The house is gorgeous and Paul was incredibly accommodating with my last minute trip. I could not recommend a place more! "
Private access Ocean beach, steps away...Perfect home for family vacations!

Unique Modern Barn House in Sag Harbor

10.0 out of 10, Exceptional, (15)
"We had a great week at george and iris’s lovely home in sag. The proximity of the home to sag harbor shopping and restaurant district as well as haven beach (block away) was great! House was clean, organized and uncluttered. There was space for everyone and my family particularly enjoyed the back porch area which was completely shaded with options lighting and fans and plenty of seating. George was very pleasant and quick to respond. "
Unique Modern Barn House in Sag Harbor

Walk to town, Bike to beach. Private pool oasis

10.0 out of 10, Exceptional, (18)
"Cozy upper floor of duplex with private pool and nice landscaping. Car noise is significant when outside because it’s at a busy intersection. Tight for 4; perfect for 2-3. Very convenient to East Hampton "
Walk to town, Bike to beach. Private pool oasis

Beautiful Southampton Village home, new reno, Heated pool!

10.0 out of 10, Exceptional, (32)
"Stayed with my elderly parents and teenage kids. Great Southampton location, well stocked house from kitchen to beach needs. Loved the bikes! "
Beautiful Southampton Village home, new reno, Heated pool!
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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Other property types in Long Island

Starlight Hotel

2.5 star property
8.2 out of 10, Very good, (355)
"Es un buen lugar. "
The price is €161
includes taxes & fees
21 Dec - 22 Dec
Starlight Hotel

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1069)
"Property was beautiful, view overlooking the area was great! Parking was convenient and there were charging spots for electric cars! "
The price is €179
includes taxes & fees
25 Nov - 26 Nov
Montauk Manor

Condor Brooklyn

3.5 star property
8.2 out of 10, Very good, (1033)
"The room was super comfortable and well designed for the limited space available - also quiet, so we slept great. The only elevator broke down while we were there, and we had to climb 4 flights of stairs a few times to reach our 5th floor room. (We saw others who had to carry very heavy luggage down the stairs). The surrounding area feels quite safe but is a bit dark and dingy. The hotel no longer offers parking, and the nearby options are sketchy, so we don’t recommend it if you’re driving...
The price is €139
includes taxes & fees
15 Dec - 16 Dec
Condor Brooklyn
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.