50 Best Long Island Apartments on Holiday Lettings - Condos

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327 Vacation rentals

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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 $700 / night

$4500 - $5601 / week

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from $700 / 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  …see more

from $2000 / night

$12001 / week

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from $2000 / 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 $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 $901 / night

$6001 / week

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from $901 / 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

$4601 / week

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from $658 / night

9

Long Island Vacation home rental

Hamptons / Southampton

5 12 90 nights min

  • 5 bedrooms
  • Sleeps 12
  • 90 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Stunning Bay Front Stone Home with breathtaking views of the Bay, close to Southampton Village & Beaches. The Bay Front has 5 Bedrooms & 4 Bathrooms a Chefs Kitchen with views of the Bay. Vaulted Ceilings floor to ceiling Fireplace in Great Room. All Rooms have  …see more

from $2000 / night

$14000 / week

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from $2000 / 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

7

Home rental in Long Island

Hamptons / Southampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spectacular view await you with this Charming Water Front Cottage a short distance from Southampton Village & Beaches! All the ammenities you need for a Summer to remember! Teak Furnishings for your out door dining Al Fresco & a heated unite pool for comfortable  …see more

from $1667 / night

$11667 / week

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from $1667 / night

10

Vacation home in Long Island

Hamptons / Southampton

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous newly renovated sprawling Contemporary with 2 acres of Privacy! All weather Tennis Court, heated Pool & hot Tub, open floor plan leads to a beautiful Blue Stone Patio perfect for entertaining. Walk to the Bay Beaches & close to the Village of Southampto  …see more

from $1334 / night

$9334 / week

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from $1334 / 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

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 $301 / night

$1201 - $2201 / week

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from $301 / 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 $600 / night

$3601 - $6120 / week

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from $600 / night

(9) Excellent 

18

North Fork / Cutchogue

2 6 4 nights min

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

 …see more

from $151 / night

$951 - $1231 / week

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from $151 / 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 $230 / night

$1451 / week

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from $230 / 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 $1100 / night

$5601 - $7700 / week

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from $1100 / night

(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 $151 / night

$801 - $1081 / week

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from $151 / 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 $475 / night

$3326 / week

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from $475 / 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

$2793 - $4894 / week

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from $399 / night

10

North Fork / Greenport

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $551 / night

$3000 - $10625 / week

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from $551 / 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 $301 / night

$2100 - $2601 / week

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from $301 / night

27

Long Island / Hempstead

4 6 4 nights min

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

 …see more

from $286 / night

$2002 / week

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from $286 / 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 $215 / night

$1500 - $3500 / week

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from $215 / night

(1) Excellent 

28

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly

 …see more

from $301 / night

$1951 - $5001 / week

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from $301 / 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 $750 / night

$3800 / week

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from $750 / 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

 …see more

from $155 / night

$926 / week

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from $155 / 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 $551 / night

$4165 - $4866 / week

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from $551 / 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

(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 - $5001 / week

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from $286 / 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 $295 / night

$1295 - $5501 / week

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from $295 / 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 $250 / night

$1401 - $3500 / week

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from $250 / night

25

North Fork / Greenport

3 8 Min stay varies

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

 …see more

from $225 / night

$3000 - $5501 / week

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from $225 / night

23

Hamptons / East Hampton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Car not necessary

 …see more

from $250 / night

$1750 / week

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from $250 / night

16

Long Island / Levittown

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 19 mi
  • Child friendly
  • Air conditioning

 …see more

from $56 / night

$386 / week

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from $56 / 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

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

$2701 - $6294 / week

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from $450 / night

(3)  

15

Long Island / Westhampton Beach

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $151 / night

$1500 - $36501 / week

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from $151 / night

24

Long Island / Northport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $125 / night

$875 - $1576 / week

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from $125 / night

20

Hamptons / Wainscott

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $1801 / night

$9000 / week

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from $1801 / night

(1) Excellent 

18

Long Island / Amityville

1 4 1 night min

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

 …see more

from $100 / night

$694 / week

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from $100 / 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 $250 / night

$1500 / week

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from $250 / night