50 Best Long Island Apartments on Holiday Lettings - Condos

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House rentals Hamptons
222 properties
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31 properties
House rentals Fire Island
11 properties
House rentals Westhampton Beach
8 properties
Long Beach
6 properties

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334 Vacation rentals

(1) Very Good 

6

Long Island / Great Neck

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 40 mi
  • Ask about children

 …see more

from $152 / night

$807 - $1089 / week

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from $152 / 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

 …see more

from $252 / night

$1512 / week

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from $252 / 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 $303 / night

$1210 - $2218 / week

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from $303 / night

8

North Fork / Greenport

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets

 …see more

from $404 / night

$2823 / week

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from $404 / night

22

Long Island / Wading River

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Ask about children

 …see more

from $429 / night

$2999 / week

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from $429 / night

(1) Excellent 

17

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

 …see more

from $131 / night

$911 / week

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from $131 / night

(1) Excellent 

24

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 $404 / night

$2823 - $4234 / week

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from $404 / night

16

Hamptons / East Quogue

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

 …see more

from $479 / night

$3352 / week

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from $479 / 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

 …see more

from $399 / night

$2794 - $5076 / week

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from $399 / night

13

Hamptons / East Hampton

3 6 Min stay varies

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

 …see more

from $404 / night

$1512 - $6048 / week

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from $404 / night

(2) Very Good 

20

Hamptons / Bridgehampton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Child friendly

 …see more

from $137 / night

$953 - $1165 / week

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from $137 / 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 finis  …see more

from $864 / night

$6048 / week

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from $864 / 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

24

Hamptons / Sag Harbor

2 6 2 nights min

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

 …see more

from $451 / night

$2700 - $4500 / week

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from $451 / night

26

Vacation home with swimming pool in Hampton Bays

Hamptons / Hampton Bays

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Please check -rental agreement- that has to be signed at check in (click Book now and then at bottom in blue on page with payment info) and inquire with your details for availability. Min. 3 weekdays will consider 2 regular week-end nights for family(2+ X) or group ad  …see more

from $705 / night

$3930 - $5645 / week

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from $705 / night

(2) Excellent 

17

Hamptons / Quogue

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

 …see more

from $404 / night

$2520 / week

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from $404 / night

(1) 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

 …see more

from $86 / night

$555 - $908 / week

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from $86 / night

(1) Excellent 

14

Hamptons / Shelter Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning

 …see more

from $298 / night

$1306 - $5544 / week

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from $298 / 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 $756 / night

$3831 / week

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from $756 / 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 $404 / night

$2823 / week

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from $404 / 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 $807 / night

$5645 - $7762 / week

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from $807 / 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 $429 / night

$2823 / week

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from $429 / 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 $663 / night

$4637 / week

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from $663 / 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 $251 / night

$2016 - $4091 / week

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from $251 / night

29

Hamptons / East Hampton

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $449 / night

$2695 - $6993 / week

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from $449 / night

35

Vacation villa in Sag Harbor

Hamptons / Sag Harbor

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Only for the very discerning renter. It is a designer's own home . Minimum rental is 14 nights. Please, please read rental rates before inquiring. Please Do NOT inquire about weekends . No parties whatsoever will be permitted. This elegant 6000 square foot home feat  …see more

from $2016 / night

$12096 / week

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from $2016 / night

(1) Very Good 

9

North Fork / Jamesport

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 2 mi
  • Car not necessary
  • Air conditioning

 …see more

from $252 / night

$1764 / week

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from $252 / night

(1) Excellent 

18

Long Island / Glen Cove

5 9 5 nights min

  • 5 bedrooms
  • Sleeps 9
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

 …see more

from $555 / night

$4199 - $4904 / week

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from $555 / night

6

Long Island / Kings Point

1 4 7 nights min

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

 …see more

from $252 / night

$1412 - $3528 / week

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from $252 / night

(5) Very Good 

11

North Fork / Greenport

3 4 2 nights min

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

 …see more

from $197 / night

$1412 - $2470 / week

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from $197 / 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

 …see more

from $580 / night

$2016 - $3528 / week

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from $580 / night

11

Hamptons / Montauk

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $706 / night

$4939 / week

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from $706 / night

18

Hamptons / Westhampton

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $782 / night

$4536 / week

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from $782 / 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 $231 / night

$1462 / week

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from $231 / 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 $908 / night

$6048 / week

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from $908 / 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 $706 / night

$4234 / week

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from $706 / night

(1) Excellent 

22

Hamptons / East Hampton

3 6 Min stay varies

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

 …see more

from $298 / night

$1991 - $6350 / week

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from $298 / night

18

Hamptons / Montauk

2 5 2 nights min

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

 …see more

from $504 / night

$3024 - $6048 / week

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from $504 / night

12

Long Island / East Setauket

5 10 21 nights min

  • 5 bedrooms
  • Sleeps 10
  • 21 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

 …see more

from $994 / night

$6955 / week

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from $994 / night

22

Hamptons / Montauk

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

 …see more

from $108 / night

$756 - $2823 / week

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from $108 / night