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Houses for Rent in Shelter Island NY with a Swimming Pool - 7 Homes

15 Montclair Ave

15 Montclair Ave, Shelter Island, NY 11964
1 / 5
$75,000

6 Beds, 4.5 Baths, 4,600 sq ft

Pool Smoke Free
104 S Ferry Rd

104 S Ferry Rd, Shelter Island, NY 11964
1 / 5
$30,000

5 Beds, 5.5 Baths, 4,040 sq ft

Pool Smoke Free
3 Lakeview Dr

3 Lakeview Dr, Shelter Island, NY 11964
1 / 5
$14,000

4 Beds, 2 Baths, 1,720 sq ft

Pets Allowed Pool Smoke Free
5 Bay Ave

5 Bay Ave, Shelter Island, NY 11964
1 / 5
$18,000

3 Beds, 3 Baths, 1,675 sq ft

Pool Smoke Free
28 Gardiners Bay Dr

28 Gardiners Bay Dr, Shelter Island, NY 11964
1 / 5
$50,000

3 Beds, 3 Baths, 3,000 sq ft

Pool Smoke Free
61 Peconic Ave

61 Peconic Ave, Shelter Island, NY 11964
1 / 5
$40,000

5 Beds, 5.5 Baths, 4,000 sq ft

Pool Smoke Free
15 N Cartwright Rd

15 N Cartwright Rd, Shelter Island, NY 11964
1 / 5
$30,000

4 Beds, 4 Baths, 3,100 sq ft

Dogs Allowed Pool Smoke Free
More Rentals Near Shelter Island, NY

We found 18 more rentals that closely match your search.
248 5th Ave

248 5th Ave, Greenport, NY 11944
1 / 5
$3,800

2 Beds, 1 Bath, 1,306 sq ft

Pool Smoke Free
10 Wickatuck Dr

10 Wickatuck Dr, Sag Harbor, NY 11963
1 / 5
$12,000

2 Beds, 1 Bath, 710 sq ft

Pool Smoke Free
424 4th St

424 4th St, Greenport, NY 11944
1 / 5
$4,000

1 Bed, 1 Bath, 1,000 sq ft

Pets Allowed Pool Smoke Free
950 Blue Marlin Dr

950 Blue Marlin Dr, Southold, NY 11971
1 / 5
$20,000

4 Beds, 4 Baths, 3,200 sq ft

Dogs Allowed Pool Smoke Free
46 Bayview Ave

46 Bayview Ave, Sag Harbor, NY 11963
1 / 5
$25,000

3 Beds, 2 Baths, 10,890 sq ft

Pool
28 Parkway Dr

28 Parkway Dr, Sag Harbor, NY 11963
1 / 5
$75,000

4 Beds, 3.5 Baths, 2,800 sq ft

Pool Smoke Free
446 6th St

446 6th St, Greenport, NY 11944
1 / 5
$5,000

4 Beds, 1.5 Baths, 1,400 sq ft

Pool Smoke Free
415 6th Ave

415 6th Ave, Greenport, NY 11944
1 / 5
$20,000

4 Beds, 2 Baths, 1,650 sq ft

Pool Smoke Free
23 Marjorie Ln

23 Marjorie Ln, Sag Harbor, NY 11963
1 / 5
$35,000

2 Beds, 2 Baths, 1,092 sq ft

Pool Smoke Free
324 5th Ave

324 5th Ave, Greenport, NY 11944
1 / 5
$3,500

3 Beds, 2 Baths, 1,600 sq ft

Pool Smoke Free
130 6th St

130 6th St, Southold, NY 11944
1 / 5
$20,000

5 Beds, 2 Baths, 2,600 sq ft

Pool Smoke Free
3389 Noyack Rd

3389 Noyack Rd, Sag Harbor, NY 11963
1 / 5
$22,000

3 Beds, 2 Baths, 1,421 sq ft

Pool Smoke Free
165 Sterling St

165 Sterling St, Greenport, NY 11944
1 / 5
$15,000

3 Beds, 2 Baths, 1,700 sq ft

Pool Smoke Free
905 9th St

905 9th St, Greenport, NY 11944
1 / 5
$18,000

3 Beds, 3 Baths, 1,800 sq ft

Pool Smoke Free
32 Sunset Dr

32 Sunset Dr, Sag Harbor, NY 11963
1 / 5
$115,000

4 Beds, 3 Baths, 1,572 sq ft

Pool
18 North Dr

18 North Dr, Sag Harbor, NY 11963
1 / 5
$190,000

4 Beds, 4.5 Baths, 3,160 sq ft

Pool Smoke Free
10 Spring Ln

10 Spring Ln, Sag Harbor, NY 11963
1 / 5
$4,900

3 Beds, 1 Bath, 1,000 sq ft

Pool Smoke Free
308 Wiggins St

308 Wiggins St, Greenport, NY 11944
1 / 5
$30,000

3 Beds, 2 Baths, 1,800 sq ft

Pool Patio Hardwood Floors Waterfront Smoke Free Deck

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Shelter Island, NY Homes with Pool for Rent

Find the perfect house for rent with a pool in Shelter Island. Whether you're looking for houses with neighborhood swimming areas or a home with a private pool, you can experience comfort, convenience, and relaxation just steps from your back door. Elevate your lifestyle by unwinding in the sun after a long day or hosting poolside gatherings with friends and family. Stay active with invigorating swims or simply enjoy a moment of tranquility by the glistening water.

Dive in at your leisure - when you rent a house with a pool, you make the schedule. You won't have to adhere to restricted swimming hours or wait for summer crowds to thin out. Embrace the freedom of having a pool at your fingertips, available for you to enjoy whenever you want! If you're hoping to swim even when the summer heat begins to cool off, consider searching for rentals with an indoor pool for year-round access. Start searching now. Browse 7 houses for rent with a pool and find your new home today.