50 Best Long Island Apartments on Holiday Lettings - Condos

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638 Vacation rentals

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

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

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 $1500 / night

$10000 - $12000 / week

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from $1500 / 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

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

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

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

27

Long Island Vacation home rental

Long Island / Hempstead

4 6 4 nights min

  • 4 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
Located within walking distance of The Garden City Hotel. The property is 15 Miles from Manhattan & just 25 Minutes from LaGuardia & JFK Whether you're in town for business or pleasure, This house allows you to enjoy our upscale accommodations at an exceptional value. …see more

from $448 / night

$3136 / week

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from $448 / night

6

Home rental in Long Island with shared pool

Long Island / Kings Point

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Beautiful house with an independent studio close to railroad station Beautiful water view. Fishing and paddle boat. Kitchen facilities neat people only We can offer extra bedroom. Shower and pool spa also. Near shopping and restaurants. Internet Wifi and TV room. Deck a …see more

from $250 / night

$1400 - $3500 / week

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from $250 / night

(4) Excellent 

11

Vacation b&b in Long Island

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Suitable for children age 5+
This whaling captain's house has been in my family six generations. We offer the original wing of house for weekend rental May through October. Each bedroom has a water view, and they share a dressing room/office. Enjoy the spacious porch, that includes an eating ar …see more

from $275 / night

$1701 - $2750 / week

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from $275 / 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

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

(7) Excellent 

30

Vacation home in Kismet

Fire Island / Kismet

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly
Our wonderful cottage comes with all the expected amenities for the total vacation experience. It has two decks, a large private rear deck and fun smaller front deck for people watchers . Fire Island boasts no private cars in the summer until Sept 15 so the kids have fr …see more

from $380 / night

$2500 - $3500 / week

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Responds fast!
avg. 1 hour 53 minutes

from $380 / night

24

Home rental in Long Island

Long Island / Rocky Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • 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 - $3325 / week

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from $275 / night

(6) Excellent 

24

Vacation home rental

Hamptons / Montauk

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
East Hampton Rental Registry #16185 *** Please see Summer 2017 (May - October) availability, minimum stay requirements and pricing information at the end of this listing before contacting *** Thinking of spending time in Montauk? Great idea! Enjoy all the East End has …see more

from $575 / night

$3500 - $9000 / week

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from $575 / 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

(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 34 minutes

from $286 / night

(4) 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 - $3060 / week

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from $299 / night

(7) Excellent 

14

Vacation apartment in Greenport

North Fork / Greenport

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Overview: Waterfront Water's Edge suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes …see more

from $300 / night

$2100 - $2600 / week

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from $300 / night

(16) Excellent 

25

Vacation home in Southold

North Fork / Southold

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Bright private sunny renovated three bedroom waterfront house on private street adjoining Arshamamague Pond. The sun is out and all we need is you to complete the picture. Join us at our three bedroom one bath renovated house. Private waterfront. Central AC. Hardw …see more

from $295 / night

$1750 - $3325 / week

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from $295 / night

(1) 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 45 minutes

from $100 / night

8

Greenport Vacation farmhouse accommodation

North Fork / Greenport

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Historic Greenport Village has been recently renovated and is in walking distance to all. This is a 2 family home that can be rented separately or together. Pricing here is for house 2. One bedroom has a queen and the other can be configured as a king or two twins. Park …see more

from $400 / night

$2800 / week

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from $400 / night

(1) Excellent 

10

Vacation cottage in East Marion

North Fork / East Marion

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
. North Fork- East Marion- Charming unique twin cottages with cedar roof and historical significance. Each cottage is new and elegantly appointed. Wide plank flooring and knotty pine doors. Complete kitchen with granite counters and dishwasher. New bath with Itali …see more

from $400 / night

$2200 / week

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from $400 / night

(1) Excellent 

28

East Hampton Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Very stylishly renovated on .60 acre, this East Hampton property features central air, 3 bedrooms and 2 baths. Great room with fireplace and lots of sunlight. Skylights in kitchen and living room. Top of the line Sub-zero refrigerator and wine storage. A chef's dream ki …see more

from $280 / night

$1960 - $4200 / week

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from $280 / night

(2) Very Good 

9

Vacation apartment in Jamesport

North Fork / Jamesport

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 2 mi
  • Car not necessary
  • Air conditioning
Spend a relaxing few days at our romantic vineyard and winery in our newly finished 650 sq. ft. luxury apartment situated on beautiful Manor Lane in Jamesport. Our one bedroom (queen size bed), bath w/shower, large open living room, kitchenette, cathedral ceiling, flat …see more

from $250 / night

$1750 / week

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from $250 / night

(1) Very Good 

10

Vacation home in Greenport

North Fork / Greenport

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Renovated and tastefully furnished, The Farmhouse features one of the largest wrap around porches in the village and it is enviably located steps away from the town's best restaurants and bars, as well as just 3 short blocks to the beach. The space Just steps away fro …see more

from $600 / night

$4000 - $10625 / week

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Responds fast!
avg. 2 hours 25 minutes

from $600 / 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

(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

(1) 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

6

Vacation log cabin with shared pool in Long Island

Fire Island / Fire Island Pines

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Just 90 minutes from Manhattan, but worlds away from NYC! In the Fire Island Pines, an idyllic gay community (but friendly to all) on the beach with no cars, just the deer roaming wild. The cabana is small but very self contained. BBQ on the deck overlooking the ocean …see more

from $250 / night

$1500 / week

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Responds fast!
avg. 2 hours 27 minutes

from $250 / night

(4) Excellent 

28

Long Island Vacation home rental

Hamptons / Sag Harbor

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is 2 weeks during High Season unless you see an availability between rentals. During the off season 1 week rentals may be possible. This elegan …see more

from $2143 / night

$15000 - $19000 / week

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Responds fast!
avg. 2 hours 44 minutes

from $2143 / 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

6

Home rental in Long Island

Hamptons / Sag Harbor

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
This beach vibes cottage is located in Sag Harbor village, you can walk to town, bike or walk to the beach. The house is located in the only private beach community in Sag Harbor. The cottage comes fully furnished with everything you need to have a memorable stay in Sag …see more

from $350 / night

$2450 / week

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from $350 / night

11

Vacation cottage rental

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Our home is right on the sand, just a block away from a beautiful, uncrowded ocean beach in one of the world's most famous resort communities. Clean and comfortable, there is an upstairs deck off the living room and a downstairs patio off the eat-in kitchen, three bedro …see more

from $286 / night

$2000 - $4000 / week

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from $286 / night

(2) Excellent 

17

Vacation home rental

North Fork / Southold

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly
3 bedrooms, 2 1/2 baths, sleeps 6 private Pristine, year round, vacation getaway, within 5 minute walk to two white, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, …see more

from $375 / night

$2500 / week

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from $375 / night

14

Southampton Vacation home rental

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Ask about children
  • Ask about pets
The Space Located in Southampton less then a half a mile from the quite beaches of Peconic Bay, this house is also just a 10 minute drive to Sag Harbor or Southampton Villages. Close to ArtHampton (5 mi), Art Market (5 mi) and Hampton Classic Showgrounds (6.5 mi)! Th …see more

from $434 / night

$3034 / week

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from $434 / night

15

Vacation home in Amagansett

Hamptons / Amagansett

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Beach house right on the sand, just a block away from a beautiful, uncrowded Atlantic Ocean beach. Clean and comfortable. Upstairs deck and downstairs patio off eat-in kitchen. Big living room, three bedrooms, two full bathrooms, washer and dryer, outdoor shower, gas gr …see more

from $500 / night

$1000 - $4250 / week

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from $500 / 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 …see more

from $229 / night

$1450 / week

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from $229 / night

30

Vacation home in Wading River

Long Island / Wading River

4 8 21 nights min

  • 4 bedrooms
  • Sleeps 8
  • 21 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
Immerse yourself in the tranquility of New York’s Long Island area when you stay at this wonderful Wading River vacation rental home, called 'The Stella House,' ideally situated just steps from a spectacular private beach! With 4 bedrooms, 2 bathrooms and enough sleepi …see more

from $649 / night

$4543 - $4893 / week

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from $649 / night

1