50 Best Long Island Apartments on Holiday Lettings - Condos

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17 properties
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12 properties

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372 Vacation rentals

8

Villa rental in Long Island

Long Island / Bayville

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
This is a luxury, modern, waterfront house with 4500 square ft. There are 10 large rooms. All rooms have wall to wall glass windows overlooking the bay. Brand new house with all brand new appliances. KItchen, 2 living areas, 2 fire place 2, dining room, family room, rec …see more

from $950 / night

$6650 / week

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from $950 / night

17

Cottage rental in Long Island

Hamptons / Sag Harbor

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Wonderful Sag Harbor VillageWaterfront Cottage for Rent 3 bedrooms, 4 queen size beds , 1 1/2 baths, A/C, Screaming Water views, multi level Decks, Private Sand beach, with Kayaks and fire pit. All inclusive utilities, Maid service (weekly) and wonderful clear Water …see more

from $900 / night

$6000 / week

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Responds fast!
avg. 3 hours 55 minutes

from $900 / night

14

Long Island Vacation cottage rental

Long Island / Fire Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
Fire Island is a 35mile long barrier island located just off the South Shore of New York's Long Island. It is an island of many diverse communities. The house is located in a community called Lonelyville, one of the oldest on Fire Island. There are no cars permitted on …see more

from $658 / night

$4600 / week

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from $658 / night

20

Vacation home in Long Island

Hamptons / Southampton

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Pet friendly
Located in Southampton, this 6 bedroom home is 8 km from Agawam Park. Southampton 6 Bed with Pool features a grand entrance, kitchen area with marble counters, stainless steel appliances and French doors with an outside seating area. The living room offers an archway w …see more

from $1515 / night

$10605 / week

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Responds fast!
avg. 3 hours 34 minutes

from $1515 / night

11

Vacation home in Long Island

Hamptons / East Hampton

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A new construction estate in the exclusive Georgica Pond section of East Hampton brings the fabled tradition of Long Island country houses into the here and now. This gracefully proportioned gambrel home continues the proud lineage of East Hampton estates for the New co …see more

from $5715 / night

$40000 / week

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from $5715 / night

18

Vacation cottage in Long Island

Hamptons / Montauk

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Two bedroom cottage with vaulted ceilings set on a double lot, last house on a dead end quiet road with a pond and a nature preserve across the road. Lots of outdoor living/dining space. Outdoor shower, gas grill, herb/flower gardens, washer/dryer. 5 minute walk to priv …see more

from $300 / night

$2100 / week

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from $300 / night

15

East Marion Vacation home rental

North Fork / East Marion

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
Renovated Waterfront Cottage with private beach and spectacular views! The house sits on the edge of the bluff with views of a secluded cove on the sound and has access to an infinity deck where you can relax and enjoy the water views, the sunsets, the landscaped garden …see more

from $470 / night

$3290 - $5110 / week

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from $470 / night

21

Home rental in East Hampton

Hamptons / East Hampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Green Rock is located in the Northwest Wood section of East Hampton. The property is so well situated you will probably not want to leave it. The moon rises over the water, the sun sets in the back. Turn on the landscape lighting, open a great bottle of wine and enjoy …see more

from $900 / night

$6300 / week

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from $900 / night

13

Vacation home in Long Island

Hamptons / East Hampton

5 12 30 nights min

  • 5 bedrooms
  • Sleeps 12
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Furnished 5 bedroom 4 bathroom home on a quiet cul de sac. In-law/nanny suite with private bathroom and living room. Viking/subzero appliances with granite countertops. Spacious deck and Porch on one acre piece of property. Great house for entertaining. Air conditioning …see more

from $1000 / night

$7000 / week

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from $1000 / night

4

Apartment rental in Long Island

Long Island / Hicksville

1 1 2 nights min

  • 1 bedroom
  • Sleeps 1
  • 2 nights min
  • Air conditioning
Single room in an dorm style setting with a shared bathroom. Room is equipped with free WiFi, basic cable, mini fridge and microwave, heat and A/C. Location is in the center of Hicksville with walking distance to LIRR, shopping, and restaurants. Close proximity to LIE. …see more

from $45 / night

$315 / week

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from $45 / night

24

Vacation home in Long Island

Hamptons / East Hampton

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Immerse yourself in all that East Hampton has to offer at this stunning 4-bedroom, 3-bathroom vacation rental house that comfortably sleeps 10. Situated on 2 acres of fenced land with a playground, lush grass, and 50-foot pool with 10 chaise lounge chairs, you'll feel a …see more

from $560 / night

$3920 - $22400 / week

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Responds fast!
avg. 28 minutes

from $560 / night

(1) Excellent 

6

Vacation home in Long Island

Hamptons / Westhampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Located on the bayside of Dune Road, this property is a beach lovers paradise. Walk across the street to one of the top 15 beaches in the country; fish, swim or boat on the bay just footsteps away; or just lounge on the large deck and enjoy a . sunset. The property fe …see more

from $190 / night

$975 - $2895 / week

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from $190 / night

24

East Hampton Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Let this stunning 3-bedroom, 2-bathroom vacation rental home jump start your East Hampton retreat! Offering fantastic amenities, accommodations for 6 and an unbeatable location near East Harbor, this unit leaves little to be desired! THE PROPERTY From the moment you a …see more

from $275 / night

$1650 - $3900 / week

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Responds fast!
avg. 37 minutes

from $275 / night

21

Vacation home in East Marion

North Fork / East Marion

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
This is a one-bedroom efficiency apartment with a kitchen and bistro dining area, located in the heart of East Marion on the beautiful North Fork. It is part of the main farmhouse that dates to the late 1800's with a separate entrance that once belonged to the Stars fa …see more

from $175 / night

$950 - $1000 / week

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Responds fast!
avg. 31 minutes

from $175 / night

(1) Good 

11

Orient Vacation home rental

North Fork / Orient

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Pernchief Cottage Located In The Village Of Orient Is The Perfect Place To Summer With Family And Friends. Front Porch Offers Lovely Views Of The Bay. Wide Pine Floorboards, Great Architectural Detils Abound. Property Is Beautifully Set On 1/2 Acre With Lovely Gardens A …see more

from $500 / night

$3000 / week

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from $500 / night

13

Vacation apartment in Long Island

Long Island / Snyder Square

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
Fully furnished two bedrooms, central HVAC, back porch, back yard, . Accessible to public transportation. Families & Professionals welcome. Definitely a home away from home. Plenty closet space One Queen bed. Two twin beds, convertible to a King bed. …see more

from $200 / night

$1400 / week

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from $200 / night

(1) Excellent 

19

Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIALS: July 21-31 (=2 weekends!) at only 10k plus cleaning and pool heat (=10.75k Total) Peace and quiet awaits in this modern house on the village fringe, featuring a first floor master with walk in closet, wonderfull spa-style master bath, flatscreen TV and direct …see more

from $350 / night

$1500 - $6600 / week

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from $350 / night

19

Vacation home in Long Island

Long Island / Westhampton Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Located on the bay side of Dune Road on a scenic peninsula and surrounded by water, this contemporary is a beach lovers paradise. It's a short walk to the great Westhampton Beach, one of the top 15 ocean beaches in the country; a 5 minute drive to the village; or you ca …see more

from $190 / night

$975 - $3500 / week

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from $190 / night

67

Vacation home in Long Island

Long Island / Brookhaven

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay. The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the …see more

from $350 / night

$2450 / week

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from $350 / night

24

Home rental in Long Island

Long Island / Rocky Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Take in the crisp salty air from this beautiful vacation rental house, situated just steps from the Long Island Sound. This 3-bedroom, 2-bathroom home, called 'McFords on the Sound,' accommodates up to 8 and features bright and homey decor, an open floor plan, and large …see more

from $275 / night

$1925 - $3326 / week

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Responds fast!
avg. 1 hour 28 minutes

from $275 / night

(2) Excellent 

17

Home rental in Long Island with tennis court

Hamptons / Quogue

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Will your mom have to sit on the end of your futon with a plate of turkey and stuffing balanced on her knee? Will your mother in-law fill your entire kitchen.... with herself... only to find out the Turkey she bought doesn't fit in your oven? Well it is time to escape …see more

from $400 / night

$2500 / week

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from $400 / night

28

Southampton Vacation home rental

Hamptons / Southampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
***PLEASE INQUIRE FIRST (EMAIL OWNER) BEFORE INSTANT BOOKING!!.. 631 - 365 - 3828 Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft …see more

from $3800 / night

$26600 / week

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Responds fast!
avg. 1 hour 0 minutes

from $3800 / night

(7) Excellent 

33

Vacation home in Rocky Point

Long Island / Rocky Point

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Quaint 3 bedroom, 1 bath home, with beautiful views of the long island sound, and Connecticut, from the kitchen, dining area, bedroom, and back yard.Heat and Central air conditioning, cable, internet, Netflix,phone. electric stove/oven, toaster, coffee maker,microwave,c …see more

from $275 / night

$1925 / week

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from $275 / night

(13) Excellent 

24

Long Island Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Minimum two-week stay. This well-designed contemporary beach house with three bedrooms and two baths sits on an acre of blissful privacy. This vacation rental is located in East Hampton NW woods, 4 miles from East Hampton Village and 1.5 miles from Sammy's Beach. Close …see more

from $286 / night

$2000 - $5000 / week

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Responds fast!
avg. 3 hours 22 minutes

from $286 / night

(9) Excellent 

18

Vacation cottage in Cutchogue

North Fork / Cutchogue

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Cozy Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fi …see more

from $150 / night

$950 - $2030 / week

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from $150 / night

11

Vacation home in Long Island

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets
Perfect get away in the heart of the village. Newly renovated carriage house in the historic district. 2 bedrooms, kitchen, dining room, living room, full bathroom, private yard. Located in the Historic District of Sag Harbor Village. Only 10 minutes walk to the cente …see more

from $600 / night

$3000 / week

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from $600 / night

12

Vacation hotel apartment in Westhampton

Hamptons / Westhampton

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
Our SeaBreeze Suite sleeps up to 4 guests in two rooms - one queen bed in private bedroom and two twin sized beds in living room - as well as a small kitchen w/ refrigerator, microwave, stove top oven and coffee maker. This suite also has free wifi, premium cable and p …see more

from $130 / night

$600 - $1300 / week

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Responds fast!
avg. 3 hours 22 minutes

from $130 / night

25

Vacation home in Long Island

Long Island / Westhampton Beach

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Visit one of the most desirable places in the world at this private 5-bedroom, 3-bathroom vacation rental home on Moriches Bay, Westhampton. This 3,200-square-foot castle on the bay comfortably accommodates 10 guests and is located at the end of a private cul-de-sac, of …see more

from $858 / night

$6000 - $16500 / week

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Responds fast!
avg. 38 minutes

from $858 / night

21

Vacation home with swimming pool, golf nearby in Long Island

Long Island / Bellport

3 10 4 nights min

  • 3 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This house has it all! 3 bedrooms with plenty of space for addition guests to sleep in the den. 2 bathrooms. Big living room, dining room, eat in kitchen. The den boasts a large screen TV with surround sound. Patio with furniture and gas grill. Heated pool! Dish washer …see more

from $400 / night

$3000 / week

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from $400 / night

16

Vacation cottage in Long Island

Long Island / Baiting Hollow

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Seasonal rental within a 5 minute walk to private beach, ten minute walk to Giorgio's. 5 minute drive to local horse riding farm and ten minutes drive to local north fork wineries. 10 minute drive to downtown Riverhead, Long Island rail road, outlets and restaurants. …see more

from $150 / night

$800 - $1325 / week

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from $150 / night

28

Vacation home in Long Island

Hamptons / Southampton

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Welcome to your private Hamptons escape! Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this immaculate Southampton vacation rental house is sure to provide the perfect spot for families or a close group of friends traveling tog …see more

from $849 / night

$5944 - $10500 / week

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Responds fast!
avg. 52 minutes

from $849 / night

(4) Excellent 

21

Vacation apartment rental

Hamptons / Sag Harbor

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
From its commanding position on Main Street in the heart of Sag Harbor village, this spectacular vintage Victorian is an authentic testament to the history of Sag Harbor. With distinctive architecture and classic styling, the impressive house features the Upstairs Apart …see more

from $495 / night

$2600 - $2950 / week

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Responds fast!
avg. 1 hour 41 minutes

from $495 / night

(2) Excellent 

6

East Marion Vacation cottage rental

North Fork / East Marion

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Welcome to the Victorian Seasons guest cottages, nestled between wildlife preserves and protected land. Victorian Seasons is a significantly important historic site that dates back to 1855. It is on the historic corridor in the heart of East Marion on the beautiful Nort …see more

from $400 / night

$2200 / week

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from $400 / night

(2) Excellent 

15

Vacation home in Long Island

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spend your summer relaxing by the heated pool or enjoying the close beautiful bay beaches of the North West Woods or just a quick car ride to a sandy ocean beach of the Hamptons. This charming air-conditioned home is sited on a privately landscaped half acre property. …see more

from $715 / night

$5000 - $7000 / week

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from $715 / night

(5) Excellent 

14

Home rental in East Marion

North Fork / East Marion

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Contemporary 4 bedroom 3 bath house with private Long Island Sound beach access and community tennis and bocce courts in East Marion. Secluded lot with swing set. 2 adult bikes and 2 kids bikes, beach chairs and toys included. Cook's kitchen, large deck. 10 rooms total, …see more

from $299 / night

$2200 - $2760 / week

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from $299 / night

(2) Excellent 

7

Vacation home in Long Island

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Enjoy this sophisticated, newly renovated, three-bedroom, three-bath contemporary on one of the premier lanes near Jackson Pollack's house in East Hampton. Twenty-four-hundred square feet with oak flooring throughout. Great light in the beautifully designer decorated d …see more

from $370 / night

$2600 - $5900 / week

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from $370 / night

18

Home rental in Montauk

Hamptons / Montauk

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The professionally styled, newly renovated/furnished upside down house is on a private wooded acre with ocean views from the living areas and is one block to ocean beach and Gurney’s. The open living/dining/kitchen and master bedroom suite are on the top floor. An add …see more

from $2000 / night

$10000 - $18000 / week

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Responds fast!
avg. 1 hour 16 minutes

from $2000 / night

(6) Excellent 

20

Vacation cottage in Long Island

Long Island / Baiting Hollow

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Adorable 2 bedroom cottage sleeps 4 1000 ft to private beach! All new paint Full kitchen. New bathroom Master BR w/ queen bed , a/c,ceiling fan ,flat screen TV . 2nd BR w/ 2 twin beds. Living room with a/c, flat screen TV with netflix. Wireless Internet. Living room op …see more

from $239 / night

$1450 / week

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from $239 / night

(2) Excellent 

13

Long Island Vacation villa rental

Long Island / Long Beach

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 0.5 mi
  • Car not necessary
  • Air conditioning
Step Back In Time in this old world Historical Mini Mansion in Long Beach NY. The Home is one of the original homes on the barrier island and was built in 1909 . Its Located on the Historical block in Long Beach, on a Brick street with other Historical Homes. as we …see more

from $179 / night

$1253 / week

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Responds fast!
avg. 2 hours 27 minutes

from $179 / night

(2) Very Good 

9

Vacation apartment in Bellmore

Long Island / Bellmore

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Ask about children
Enjoy Long Island's pristine beaches, listen to an outdoor waterfront concert at Nikon theater venue,or relax in the back yard of this decorator furnished one bedroom/one full bath apartment situated on a canal. Spectacular sunsets. 45 min by train to NYC and 30 min fro …see more

from $100 / night

$600 - $875 / week

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Responds fast!
avg. 2 hours 39 minutes

from $100 / night