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Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
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Jacuzzi or hot tub
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Private tennis court
Cot available
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Solarium or roof terrace
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Staffed property
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Linen provided
Towels provided
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Housekeeping Included

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Pets
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Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
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Water sports
Horse riding
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Golf course on site or within 15 min walk
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Beach or lakeside relaxation
Golf within 30mins drive
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146 Houses

Sort by:

Waterfront Charmer on idyllic Shelter Island

Shelter Island house

3 bedrooms
3 bathrooms

sleeps 8

Price per night from

$1,064

Great rentals within 20 miles that match your search

Hamptons Getaway on the water with gorgeous sunsets

East Hampton house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$779

Hampton Bay Home 2 Miles from Beach & Dune Road

Hampton Bays house

3 bedrooms
2 bathrooms

sleeps 8

Price per night from

$693

Exquisite Hamptons Mansion Retreat

Water Mill house

10 bedrooms
10 bathrooms

sleeps 20

Price per night from

$635

HAMPTON'S WATERFRONT HOUSE STEPS TO PRIVATE BEACH

East Quogue house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$1,443

Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool

East Hampton house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$345

Southampton Village home/Heated Pool/July availability

Water Mill house

3 bedrooms
2 bathrooms

sleeps 12

Price per night from

$2,654

Idyllic North Fork Waterfront Home with Pool

Mattituck house

5 bedrooms
3 bathrooms

sleeps 14

Price per night from

$431

Boutique Waterfront Home with Pool in Heart of North Fork

Southold house

4 bedrooms
3 bathrooms

sleeps 12

Price per night from

$431

Wine Country Retreat w/ Dock & Pool on Mattituck Inlet

Mattituck house

6 bedrooms
4 bathrooms

sleeps 14

Price per night from

$431

House for Rent North Fork Long Island

Mattituck house

3 bedrooms
3 bathrooms

sleeps 8

Price per night from

$1,379

Architecturally Unique Summer Home in Southampton. Mins from the beach!

Southampton house

3 bedrooms
4 bathrooms

sleeps 6

Price per night from

$1,379

Lushly Landscaped Contemporary With Pool East Hampton North

East Hampton house

4 bedrooms
2 bathrooms

sleeps 8

Price per night from

$573

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$2,519

Beachy Keen - East Hampton NY

East Hampton house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$1,374

Romantic Getaway in Southampton (private room/bathroom)

Southampton private room

1 bedroom
1 bathroom

sleeps 2

Price per night from

$355

Airy, Woodsy, Walk to Beach, New Saltwater Pool!

East Hampton house

3 bedrooms
2 bathrooms

sleeps 7

Price per night from

$1,064

Charmimg Beach cottage in Sagaponack

Southampton house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$655

Relax at our East Hampton home

East Hampton house

3 bedrooms
2 bathrooms

sleeps 8

Price per night from

$900

Mint Southampton Village 5-BR South of the Highway w Heated Pool

Southampton house

4 bedrooms
5 bathrooms

sleeps 9

Price per night from

$1,718

Weekly Summer Beach Rental

Old Lyme house

4 bedrooms
2 bathrooms

sleeps 12

Price per night from

$328

East Hampton Summer Rental

East Hampton house

5 bedrooms
4 bathrooms

sleeps 12

Price per night from

$1,145

Architect Designed Home in Waterfront Village

Greenport house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$409

Southampton Water Front Retreat

Southampton cottage

4 bedrooms
10 bathrooms

sleeps 10

Price per night from

$3,272

Large Beach Bungalow next to Fresh Water Pond

Montauk house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$745

Amagansett House with Pool near Village & Beach

Amagansett house

4 bedrooms
4 bathrooms

sleeps 8

Price per night from

$1,309

SOUTHAMPTON POOL & TENNIS

Southampton house

5 bedrooms
5 bathrooms

sleeps 12

Price per night from

$3,272

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$982

East Hampton Village Classic , South of Highway

East Hampton house

7 bedrooms
9 bathrooms

sleeps 12

Price per night from

$12,268

Montauk Oceanfront Estate

Montauk manor house

5 bedrooms
8 bathrooms

sleeps 10

Price per night from

$17,175

Dream house vacation on the Long Island Sound

Orient house

4 bedrooms
3 bathrooms

sleeps 6

Price per night from

$1,088

SEASHELLS BY THE SEA SHORE

Hampton Bays house

8 bedrooms
6 bathrooms

sleeps 20

Responds fast! avg. 3 hours 16 minutes

Price per night from

$1,219

Elegance,Privacy, French Farm House

East Hampton farmhouse

3 bedrooms
2 bathrooms

sleeps 8

Price per night from

$1,088

Shorecrest Beach House, 4 bedroom private beach front, new renovation

Southold house

4 bedrooms
2 bathrooms

sleeps 10

Price per night from

$915

Hampton Accommodations

Springs private room

1 bedroom
2 bathrooms

sleeps 2

Price per night from

$344

The Seashell House

Sag Harbor house

4 bedrooms
3 bathrooms

sleeps 10

Price per night from

$974

Historic Cottage Near Beach!

Greenport house

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$382

ONE-OF-A-KIND VILLA NESTLED ALONG THE SHORE

Southampton villa

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$1,023

Viewing 38 of 146
rentals in Shelter Island

Also consider

Southampton 56 properties
East Hampton 21 properties
Sag Harbor 11 properties
Montauk 11 properties
Amagansett 8 properties
Westhampton Beach 8 properties
Hamptons 136 properties
North Fork 28 properties
Wading River 20 properties
Fire Island 11 properties
Baiting Hollow 7 properties
Long Island 253 properties
Catskill Region 237 properties
Lake Placid 50 properties
Chautauqua County 30 properties
Cattaraugus County 27 properties
Lake George 24 properties
Westchester County 16 properties
Otsego County 15 properties
Wilmington 15 properties
St. Lawrence County 12 properties
Hartwick 11 properties
Severance 10 properties
Albany 10 properties
Fort Plain 9 properties
Olcott 9 properties
Erie County 9 properties
Bolton Landing 8 properties
Hudson 6 properties
Old Forge 6 properties
Hillsdale 5 properties
Wells 5 properties

Shelter Island Rentals

Per night

146 Houses

Viewing 38 of 146rentals in Shelter Island

Also consider

Viewing 38 of 146
rentals in Shelter Island