Top 20 Vacation Rentals in Long Island

Westhampton Waterfront 6 Bedroom Secluded 3 Acre E

Westhampton House

6 bedrooms 6
4 bathrooms
sleeps 16 16
2 nights min

Beach/lakeside relaxation
Swimming pool
Child friendly

“Brian was very accommodating and he has a beautiful home. My family stayed here for a weekend getaway and to attend my wedding in East Islip. He was very responsive throughout the entire process. I would love to stay here again...”

- Review left on 11/22/2016

$1,145.00

Excellent (1 reviews)

Book

from $1,145.00 / night

Book

North Fork 5 bed room home with forever farm view

Aquebogue House

5 bedrooms 5
2 bathrooms
sleeps 10 10
1 night min

Child friendly
Air conditioning
Private garden

“Great accommodations for my family and myself. I would rent again if I find myself in the NY area in the future”

- Review left on 08/03/2017

$458.00

Excellent (10 reviews)

Book

from $458.00 / night

Book

Luxury Hamptons Vacation Home w/NEW Pool, Tennis Court, Hot Tub

Quogue House

6 bedrooms 6
5 bathrooms
sleeps 14 14
min stay varies

Nearest beach 4 mi
Swimming pool
Child friendly

Responds fast! Avg. 1 hour 2 minutes

“Great house! Gorgeous cedar deck and professional looking tennis court, not to mention the nice hot tub. Perfect location for enjoying all that the Hamptons has to offer. Plentry of room for a big group to relax and get away from the city...”

- Review left on 02/08/2017

$1,031.00

Excellent (1 reviews)

Book

from $1,031.00 / night

Book

Stately Waterfront 7 Bedroom Home in Westhampton Beach!

Westhampton Beach House

7 bedrooms 7
5 bathrooms
sleeps 20 20
min stay varies

Beach/lakeside relaxation
Swimming pool
Ask about children

$2,863.00

Book

from $2,863.00 / night

Book

North Fork Long Island Wine Country Cottage, Water Views

Cutchogue House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Child friendly
Air conditioning
Pet friendly

$315.00

Book

from $315.00 / night

Book

Breathtaking 2 Bedroom Westhampton Beach House

Westhampton Beach House

2 bedrooms 2
4 bathrooms
sleeps 8 8
2 nights min

Beach/lakeside relaxation
Ask about children
Air conditioning

$2,290.00

Book

from $2,290.00 / night

Book

Private Waterfront W Beach, New Renovation

Southold House

3 bedrooms 3
3 bathrooms
sleeps 8 8
7 nights min

Beach/lakeside relaxation
Nearest beach 0.25 mi
Ask about children

$602.00

Book

from $602.00 / night

Book

LUXURY HAMPTON ESTATE 4 prvate heated pool,TENNIS, basketball, beach vollleyball

Westhampton House

8 bedrooms 8
6 bathrooms
sleeps 20 20
min stay varies

Nearest beach 2 mi
Swimming pool
Child friendly

“For the second time in four years my friends and I stayed at Mark's beautiful house for three nights during New Years weekend. The house is very spacious, tenchnologically modern, and feels like a home. With a basketball court, tennis court, volley...”

- Review left on 01/12/2016

$287.00

Excellent (7 reviews)

Book

from $287.00 / night

Book

WATERFRONT BEACH HOUSE - SOUND BEACH

Sound Beach House

3 bedrooms 3
2 bathrooms
sleeps 10 10
3 nights min

Beach/lakeside relaxation
Child friendly
Air conditioning

“Our extended family went back to Sound Beach after 40+ years and picked this house for the views and location. It didn't disappoint! We had most of our meals on the deck table, saw some stunning sunsets and had an easy walk down to the beach. The...”

- Review left on 07/01/2013

$539.00

Excellent (10 reviews)

Book

from $539.00 / night

Book

Hamptons Retreat Pool & Spa

East Quogue House

3 bedrooms 3
2 bathrooms
sleeps 7 7
7 nights min

Swimming pool
Child friendly
Car not necessary

“After spending a few days in New York this was the perfect place to relax for a couple of weeks. Pictures don't do house justice. Felt more like a home than a rental. Pool much bigger than we thought and was used every day. Was a little concerned at...”

- Review left on 08/25/2016

$655.00

Excellent (1 reviews)

Book

from $655.00 / night

Book