50 Best Long Island Apartments on Holiday Lettings - Condos

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33 properties
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13 properties
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8 properties
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6 properties

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355 Vacation rentals

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

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

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

21

Home rental in Long Island

Hamptons / East Hampton

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Lovely cedar shingled home with immaculate gardens. A short walk or bike to Gardiner's Bay and Clearwater Beach. Enjoy the heated swimming pool, fire pit or hot tub. The house is in excellent condition with 4 brs, 3.5 baths and additional bedroom space in the finished b …see more

from $858 / night

$6000 / week

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from $858 / 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 $7143 / night

$50000 / week

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from $7143 / 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

9

Long Island Vacation home rental

Fire Island / Ocean Beach

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Pet friendly
Beautiful beach house located on wooden pathway, steps from the ocean. Inside the home you will find 4 bedrooms and 2 bathrooms. The two story open living and dining rooms have vaulted ceilings. This space is very bright and airy with two sets of sliding doors leading o …see more

from $551 / night

$3851 / week

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from $551 / 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 - $5111 / week

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from $400 / 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

11

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

from $215 / night

$1500 - $4000 / week

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from $215 / night

28

Hamptons / Hampton Bays

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $400 / night

$2800 / week

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from $400 / night

6

Long Island / Kings Point

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

from $252 / night

$1412 - $3528 / week

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from $252 / night

(2) Excellent 

6

North Fork / East Marion

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from $400 / night

$2200 / week

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from $400 / night

9

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

from $145 / night

$876 / week

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from $145 / night

25

North Fork / Greenport

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from $225 / night

$3000 - $5500 / week

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from $225 / night

6

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

from $251 / night

$1500 / week

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from $251 / night

(3) Excellent 

16

Long Island / Huntington

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $85 / night

$551 - $900 / week

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from $85 / night

30

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

from $400 / night

$2793 - $4893 / week

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from $400 / night

(1) Excellent 

10

North Fork / East Marion

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from $400 / night

$2200 / week

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from $400 / night

23

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly

from $751 / night

$4200 - $4900 / week

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from $751 / night

(16) Excellent 

25

North Fork / Southold

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

from $296 / night

$1751 - $3325 / week

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from $296 / night

(9) Excellent 

28

Hamptons / Hampton Bays

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly

from $400 / night

$3000 / week

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from $400 / night

(4) Excellent 

16

Long Island / Long Beach

5 11 4 nights min

  • 5 bedrooms
  • Sleeps 11
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $1100 / night

$7700 / week

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from $1100 / night

(4) Excellent 

14

North Fork / East Marion

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from $202 / night

$1412 - $3085 / week

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from $202 / night

24

Hamptons / Sag Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning

from $449 / night

$3000 - $6293 / week

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from $449 / night

(7) Excellent 

30

Fire Island / Kismet

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly

from $500 / night

$3500 / week

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from $500 / night

(1) Excellent 

28

Hamptons / East Hampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly

from $280 / night

$1960 - $4400 / week

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from $280 / night

15

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

from $300 / night

$1200 - $2200 / week

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from $300 / night

41

Hamptons / Montauk

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly

from $600 / night

$4200 / week

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from $600 / night

(1) Excellent 

16

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

from $125 / night

$875 / week

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from $125 / night

(13) Excellent 

24

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

from $286 / night

$2000 - $5000 / week

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from $286 / night

(2) Excellent 

17

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

from $376 / night

$2500 / week

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from $376 / night

(3) Excellent 

71

Hamptons / Hampton Bays

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool

from $800 / night

$5500 - $6200 / week

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from $800 / night

18

Long Island / Long Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $196 / night

$900 - $1600 / week

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from $196 / night

19

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $351 / night

$1500 - $6600 / week

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from $351 / night

(4) Excellent 

28

Hamptons / Sag Harbor

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

from $2143 / night

$15000 / week

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from $2143 / night

28

Hamptons / Southampton

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from $749 / night

$4120 - $8751 / week

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from $749 / night

(6) Excellent 

20

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

from $229 / night

$1451 / week

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from $229 / night

(1) Very Good 

16

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

from $751 / night

$3800 / week

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from $751 / night

(4) Excellent 

10

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly

from $500 / night

$3500 / week

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from $500 / night

1