50 Best Long Island Apartments on Holiday Lettings - Condos

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14 properties
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12 properties
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6 properties

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520 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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from $900 / 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

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

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

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

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 $400 / night

$2800 - $5110 / week

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from $400 / 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

28

Vacation home in Hampton Bays

Hamptons / Hampton Bays

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Updated recently , professionally painted, this home has a cozy feel,open plan available indoors. First floor has for guests : 2 Queen size bedrooms, 2 full marble bathrooms, formal blue dining room,fully equipped and renovated marble kitchen,(stainless steel appliances …see more

from $400 / night

$2800 / week

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from $400 / night

15

Vacation condo in Long Beach

Long Island / Long Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Car not necessary
Beautiful 1BR Condo across the street from the beach and new boardwalk. Centrally located to the Long Island Railroad, Shopping, and Restaurants. New York City is a 40 minute train ride away. Come see for yourself! Beach Passes Included! Beach Volleyball Tournaments, Mo …see more

from $250 / night

$1200 - $1651 / week

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from $250 / 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 $250 / night

$1750 - $4000 / week

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from $250 / 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 - $6601 / week

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from $350 / night

(1) Excellent 

16

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
A grand historical Beach Estate in Long Beach NY it is one of the original homes on the barrier island and was built in 1907. Located on the historical block in Long Beach, the home is an Italianate Villa style home restored to its original glamour. The home is 1 bloc …see more

from $159 / night

$1113 / week

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from $159 / night

18

Vacation home in Long Island

Hamptons / Montauk

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
WE OFFER ONLY MONTHLY RENTALS IN JULY AND AUGUST. Our Montauk Home is a 2 bedroom, 2 bathroom beautiful remodeled and refurbished villa. There is a queen size bed and closet in each room, the master bedroom has its on bath-toilet and shower. The living room and dining …see more

from $600 / night

$4000 - $6000 / week

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from $600 / 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 $191 / night

$975 - $3500 / week

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from $191 / 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

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

7

Vacation home rental

Hamptons / East Quogue

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Air conditioning
Hello, I am a Supper Host on other sites, want to make your stay pleasurable. (`ROOM RENTAL ONLY') ...In a 3 bedroom Ranch Home...Cozy Zen Artist quite home ,Get away from all the noise or hectic life style want to try country living ...Romantic Nite sitting by the fire …see more

from $75 / night

$400 - $550 / week

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from $75 / 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 / week

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from $2143 / night

30

Home rental in Long Island

Long Island / Baiting Hollow

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Monthly Rentals Available! East End Retreat is your quintessential North Fork summer getaway! This house has expansive water views, a huge deck for entertaining, and its own private stairs leading down towards beach!! Located in a private beachfront community and mi …see more

from $250 / night

$2500 - $5639 / week

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from $250 / 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

37

Long Island Vacation apartment rental

Long Island / Valley Stream

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
Large Bright and freshly remodeled. The property is equipped with anything you can possibly imagine. A warm cozy feeling will make you feel at home. Super quite/cool/safe residential location surrounded by park. Steps to Valley Stream train station (Long Island Rail Ro …see more

from $75 / night

$500 - $1021 / week

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from $75 / 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 $375 / night

$2500 - $3500 / week

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from $375 / night

(4) Excellent 

16

Long Island Vacation home rental

Long Island / Long Beach

5 11 4 nights min

  • 5 bedrooms
  • Sleeps 11
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Large luxury air conditioned home located on Reynolds channel. Fish off the dock ,bring your boat and moor it in the yard or just enjoy the heated pool, short walk to town and beach. Take the train into NYC in less than an hour. Indoor and outdoor fireplace. 4 bedro …see more

from $1100 / night

$7700 / week

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from $1100 / night

11

Vacation hotel apartment in Montauk

Hamptons / Montauk

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Situated on Montauk's most pristine stretch of oceanfront real estate, Gurney's Montauk Resort & Seawater Spa is a Hampton's icon and the only four-season resort in Montauk. With five unique dining and cocktail venues, guests can enjoy a wide range of dining options, fr …see more

from $715 / night

$4999 / week

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from $715 / 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 $230 / night

$1450 / week

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from $230 / night

23

Vacation home in Long Island

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
Great Hamptons style in Amagansett's Bell Estate. Less than two miles to ocean beaches and one mile from the bay, close to town, has every amenity and plenty of style. Overlooks a 60-foot heated gunite pool. Details include marble baths, wide plank Walnut flooring, cath …see more

from $750 / night

$4200 - $4900 / week

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from $750 / 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 $191 / night

$975 - $2895 / week

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from $191 / night

(3) 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 $250 / night

$1500 - $2550 / week

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from $250 / night

12

Aquebogue Vacation home rental

Riverhead / Aquebogue

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
Updated North Fork home located in the beautiful wine country of Long Island. Gourmet kitchen, perfect for entertaining. Luxurious master Suite with spa-like shower. Living room and each bedroom has its own TV. Rec-room located on separate level, great for kids & privac …see more

from $400 / night

$1500 - $2700 / week

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from $400 / night

(1) Excellent 

14

Long Island Vacation home rental

Hamptons / Shelter Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
Beautifully renovated waterfront cottage from early 1800s. Marble baths, two master suites. Sweeping waterfront lawn. 100 foot dock. Swimming, boating, grill on back deck. Beaches easy bike ride or walk. All amenities. Flat screen TVs in all bedrooms, wood burning …see more

from $267 / night

$1295 - $4999 / week

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from $267 / 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 

16

Vacation home in Long Island

Fire Island / Fair Harbor

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly
Fair Harbor is on Fire Island in Suffolk county ny.. Imagine a barefoot community with wooden walkways great sandy beaches, great sunsets, wooden walkways... no cars... Sounds like paradise.. less than 2 hours from New york.. so close yet so far away. Our house is 1 …see more

from $750 / night

$3800 / week

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from $750 / 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

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! This immaculate Southampton vacation rental house is sure to provide the perfect vacation spot for your next family getaway. Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this gorgeous …see more

from $750 / night

$5099 - $8750 / week

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from $750 / night

(3) Excellent 

71

Vacation home in Long Island

Hamptons / Hampton Bays

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool
Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Large deck with BBQ. Fully equipped kitchen. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for …see more

from $800 / night

$5500 - $6201 / week

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from $800 / night

(1) Very Good 

16

Vacation home in Long Island

Hamptons / Hampton Bays

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Swimming, beach fun, and the finest sunsets are a 5 minute stroll away at Penonic bay down the private beach access path. This charming cottage is 650 sq/ft with two bedrooms, living room, kitchen and bathroom with shower. The house sleeps four comfortably (two twin bed …see more

from $285 / night

$1995 / week

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from $285 / night

18

Vacation home in Long Island

Long Island / Long Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Beach house 45 minutes to NYC. Close to Train. 3 bedroom, 2.5 bath. Ocean view deck. Stainless Steel appliances. Dining Area. Washer /Dryer. Parking Spot. (The lower level den is available for an extra fee.. includes the additional sleeping space with bathroom separate …see more

from $195 / night

$900 - $1600 / week

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from $195 / night

(5) Good 

14

Vacation home with golf nearby in Long Island

Long Island / Baiting Hollow

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Charming cottage in the woods just steps from the peaceful Long Island Sound. This cottage has two bedrooms and sleeps 4. One of the twin beds is on a our porch in a common area but it is indoors. See photo. New Kitchen counters and cabinets. Built in 1950, this cottage …see more

from $175 / night

$1050 / week

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from $175 / night

1