Villas with a pool Long Island | Apartments to rent with swimming facilities | Holiday Lettings

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116 Holiday homes

Filters applied: Swimming pool (117)

Travellers going to Long Island are booking May dates now. Secure your holiday home today and have the perfect trip.

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+
Heated pool, hot tub, deck, screened porch, landscaped gardens, close to beach, private, large basement, huge garage.  …see more

from £692 / night

£4839 / week

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from £692 / night

26

Holiday 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 £564 / night

£3629 - £4517 / week

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from £564 / night

10

Holiday 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 £1076 / night

£7527 / week

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from £1076 / night

9

Long Island holiday 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 £1613 / night

£11291 / week

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from £1613 / 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 £1345 / night

£9409 / week

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from £1345 / night

11

Holiday 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 £5761 / night

£40323 / week

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from £5761 / 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 km
  • Swimming pool

 …see more

from £231 / night

£1613 - £4033 / week

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from £231 / night

29

Long Island / Shirley

4 12 Min stay varies

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

 …see more

from £484 / night

£2904 - £4936 / week

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from £484 / 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 £323 / night

£2259 / week

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from £323 / 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 £888 / night

£4517 - £6210 / week

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from £888 / 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 £323 / night

£2259 - £3388 / week

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from £323 / night

23

Hamptons / Amagansett

3 6 Min stay varies

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

 …see more

from £565 / night

£3388 / week

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from £565 / 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 £283 / night

£1210 - £5323 / week

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from £283 / 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 £121 / night

£1210 - £29436 / week

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from £121 / 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 £202 / night

£1130 - £2823 / week

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from £202 / 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 £462 / night

£290533 - £403912 / week

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from £462 / 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 km
  • Swimming pool

 …see more

from £464 / night

£2823 - £7259 / week

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from £464 / night

(3) Excellent 

71

Hamptons / Hampton Bays

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 11 km
  • Swimming pool

 …see more

from £646 / night

£4436 - £5000 / week

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from £646 / night

18

Hamptons / East Quogue

5 8 7 nights min

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

 …see more

from £577 / night

£4033 / week

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from £577 / night

23

Hamptons / Southampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £2218 / night

£13710 - £21371 / week

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from £2218 / night

(2) Excellent 

16

Long Island / Huntington

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £69 / night

£444 - £726 / week

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from £69 / night

(2) Excellent 

33

Hamptons / Water Mill

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 8 km
  • Swimming pool
  • Child friendly

 …see more

from £807 / night

£5646 / week

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from £807 / 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 £605 / night

£3323 - £7057 / week

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from £605 / 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 £565 / night

£3952 / week

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from £565 / 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 km
  • Swimming pool

 …see more

from £202 / night

£1210 / week

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from £202 / 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 km
  • Swimming pool

 …see more

from £444 / night

£3359 - £3924 / week

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from £444 / night

13

Hamptons / Bridgehampton

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool

 …see more

from £807 / night

£5646 - £6049 / week

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from £807 / night

16

Hamptons / Southampton

5 12 14 nights min

  • 5 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £1556 / night

£10888 / week

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from £1556 / night

(2) Excellent 

18

Hamptons / East Hampton

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £859 / night

£6013 / week

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from £859 / night

26

Hamptons / Quogue

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 4 km
  • Swimming pool
  • Child friendly

 …see more

from £1210 / night

£4033 - £6049 / week

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from £1210 / night

(1) Excellent 

7

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £299 / night

£2097 - £2904 / week

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from £299 / 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 km
  • Swimming pool

 …see more

from £242 / night

£1694 - £2097 / week

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from £242 / night

(2) Excellent 

17

Hamptons / Quogue

4 8 1 night min

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

 …see more

from £323 / night

£2017 / week

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from £323 / 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 km
  • Swimming pool

 …see more

from £238 / night

£1593 - £5081 / week

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from £238 / night

(4) Excellent 

28

Hamptons / Sag Harbor

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

 …see more

from £1729 / night

£12097 / week

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from £1729 / 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 £346 / night

£2420 / week

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from £346 / night

16

Hamptons / East Quogue

3 6 2 nights min

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

 …see more

from £384 / night

£2682 / week

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from £384 / night

24

Hamptons / Southampton

4 8 30 nights min

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

 …see more

from £148 / night

£1035 / week

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from £148 / night

11

Hamptons / East Quogue

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £404 / night

£2823 / week

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from £404 / night

20

Hamptons / Water Mill

7 10 14 nights min

  • 7 bedrooms
  • Sleeps 10
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £2305 / night

£20323 / week

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from £2305 / night