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

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119 Holiday homes

Filters applied: Swimming pool

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 £686 / night

£4800 / week

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from £686 / night

6

Home rental in Long Island

Hamptons / Southampton

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a gorgeous newly renovated hamptons shingled farm style home. 4 bedrooms 3 full bathrooms plus one in the basement, huge kitchen for entertainers, dining room & living rooms Heated Pool, fireplace, deck for entertaining, lots of space and plenty of natural  …see more

from £320 / night

£2240 / week

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from £320 / 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 £5715 / night

£40000 / week

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from £5715 / 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 £400 / night

£2800 / week

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from £400 / 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 £560 / night

£3920 / week

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from £560 / 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 £229 / night

£1600 - £4000 / week

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from £229 / 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 £320 / night

£2240 / week

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from £320 / 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 £480 / night

£2880 - £4896 / week

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from £480 / 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 £460 / night

£2800 - £7200 / week

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from £460 / 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 £200 / night

£1120 - £2800 / week

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from £200 / 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 £600 / night

£3296 - £7000 / week

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from £600 / 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 £320 / night

£2000 / week

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from £320 / 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 £380 / night

£2660 / week

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from £380 / 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 £880 / night

£4480 - £6160 / week

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from £880 / 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 £240 / night

£1680 - £2080 / week

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from £240 / 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 £560 / night

£3360 / week

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from £560 / night

(1) Average 

5

Hamptons / Montauk

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £240 / night

£1680 / week

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from £240 / 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 £2200 / night

£13600 - £21200 / week

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from £2200 / 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 £458 / night

£288208 - £400680 / week

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from £458 / 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 £280 / night

£1200 - £5280 / week

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from £280 / night

16

Hamptons / East Hampton

5 10 Min stay varies

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

 …see more

from £1120 / night

£7840 - £8960 / week

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from £1120 / 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 £236 / night

£1580 - £5040 / week

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from £236 / 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 £68 / night

£440 - £720 / week

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from £68 / night

38

Hamptons / Amagansett

5 10 Min stay varies

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

 …see more

from £680 / night

£4760 / week

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from £680 / 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 £120 / night

£1200 - £29200 / week

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from £120 / night

22

Long Island / Westhampton Beach

4 6 14 nights min

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

 …see more

from £800 / night

£5600 / week

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from £800 / 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 £800 / night

£5600 / week

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from £800 / 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 £320 / night

£2240 - £3360 / week

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from £320 / 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 £440 / night

£3332 - £3892 / week

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from £440 / 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 £1200 / night

£4000 - £6000 / week

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from £1200 / 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 km
  • Swimming pool

 …see more

from £1715 / night

£12000 / week

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from £1715 / 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 £1543 / night

£10800 / week

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from £1543 / 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 £572 / night

£4000 / week

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from £572 / night

50

Hamptons / Southampton

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 2 km
  • Swimming pool
  • Child friendly

 …see more

from £880 / night

£5200 - £6880 / week

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from £880 / 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 £296 / night

£2080 - £4720 / week

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from £296 / night

3

Hamptons / East Hampton

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £80 / night

£748 / week

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from £80 / night

31

Hamptons / East Hampton

3 6 Min stay varies

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

 …see more

from £280 / night

£2000 / week

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from £280 / night

14

Hamptons / Hampton Bays

6 12 14 nights min

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

 …see more

from £800 / night

£5600 / week

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from £800 / night

(1) Excellent 

16

Hamptons / Sag Harbor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

 …see more

from £556 / night

£3892 / week

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from £556 / night

(2) Excellent 

30

Hamptons / Quogue

4 8 30 nights min

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

 …see more

from £1200 / night

£8400 / week

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from £1200 / night