50 Best Long Island Apartments on Holiday Lettings - Condos

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House rentals Hamptons
226 properties
Vacation rentals North Fork
30 properties
House rentals Fire Island
12 properties
House rentals Westhampton Beach
9 properties
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6 properties

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327 Vacation rentals

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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 finis  …see more

from $858 / night

$6001 / week

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from $858 / 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

$6001 / 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 permitte  …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

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 $1001 / night

$7001 / week

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from $1001 / 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

$50001 / week

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from $7143 / night

29

Long Island / Shirley

4 12 Min stay varies

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

 …see more

from $601 / night

$3601 - $6121 / week

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from $601 / night

29

Long Island / Baiting Hollow

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $249 / night

$2000 - $4059 / week

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from $249 / night

(1) Excellent 

23

Fire Island / Cherry Grove

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $401 / night

$2801 - $4201 / week

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from $401 / night

23

Hamptons / Amagansett

3 6 Min stay varies

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

 …see more

from $700 / night

$4201 / week

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from $700 / night

24

Hamptons / Sag Harbor

2 6 Min stay varies

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

 …see more

from $450 / night

$2700 - $6293 / week

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from $450 / night

(1) Excellent 

16

Long Island / Long Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 0.5 mi
  • Car not necessary
  • Air conditioning

 …see more

from $89 / night

$623 / week

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from $89 / night

(2) Excellent 

6

North Fork / East Marion

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $426 / night

$2801 / week

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from $426 / 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

 …see more

from $751 / night

$3800 / week

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from $751 / night

(7) Excellent 

14

North Fork / Greenport

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $300 / night

$2100 - $2600 / week

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from $300 / night

(4) Excellent 

16

Long Island / Long Beach

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $1101 / night

$5600 - $7700 / week

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from $1101 / night

19

Hamptons / East Hampton

3 6 Min stay varies

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

 …see more

from $350 / night

$1500 - $6601 / week

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from $350 / night

18

Hamptons / East Hampton

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Ask about children

 …see more

from $501 / night

$2000 - $2500 / week

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from $501 / night

15

Hamptons / East Hampton

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $501 / night

$2000 - $6001 / week

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from $501 / night

27

Hamptons / Hampton Bays

3 12 3 nights min

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $572 / night

$360260 - $500850 / week

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from $572 / night

15

Hamptons / Water Mill

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden

 …see more

from $601 / night

$3601 / week

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from $601 / 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

 …see more

from $295 / night

$1750 - $3326 / week

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from $295 / night

31

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

 …see more

from $350 / night

$2500 / week

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from $350 / 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

 …see more

from $749 / night

$4121 - $8751 / week

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from $749 / night

(6) Excellent 

24

Hamptons / Montauk

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

 …see more

from $576 / night

$3501 - $9001 / week

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from $576 / night

(1) Excellent 

10

North Fork / East Marion

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $426 / night

$2801 / week

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from $426 / 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

 …see more

from $300 / night

$1201 - $2201 / week

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from $300 / night

(3) Excellent 

11

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+

 …see more

from $251 / night

$1500 - $2551 / week

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from $251 / night

21

Fire Island / Fair Harbor

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $851 / night

$5000 / week

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from $851 / night

28

Hamptons / Hampton Bays

2 4 3 nights min

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

 …see more

from $401 / night

$2801 / week

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from $401 / 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

 …see more

from $229 / night

$1451 / week

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from $229 / night

27

Long Island / Hempstead

4 6 4 nights min

  • 4 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning

 …see more

from $271 / night

$1897 / week

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from $271 / 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

 …see more

from $286 / night

$2000 - $5000 / week

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from $286 / 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

 …see more

from $800 / night

$5501 - $6200 / week

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from $800 / night

(1) Excellent 

19

Hamptons / East Hampton

2 4 7 nights min

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

 …see more

from $429 / night

$3001 / week

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from $429 / night

24

Hamptons / Water Mill

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $700 / night

$4900 / week

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from $700 / 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

 …see more

from $401 / night

$3001 / week

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from $401 / night

(4) Excellent 

21

Hamptons / Sag Harbor

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $496 / night

$2600 - $2950 / week

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from $496 / night

18

Hamptons / East Quogue

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool

 …see more

from $715 / night

$5000 / week

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from $715 / night

13

North Fork / Mattituck

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Ask about children

 …see more

from $895 / night

$3501 - $9101 / week

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from $895 / night