Shelter Island Beach Vacation Rentals(31)
Gorgeous Home in Beach Community with Heated Saltwater Pool
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$5,950
per week
7 - 31 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 10
Romantic Waterfront Hideaway
- 4 Bedrooms,
- 7 Bathrooms, Sleeps 14
$5,500
per week
7 night Minimum Stay
- 4 BR,
- 7 BA,
- Sleeps 14
Airy + Light Island Retreat, Walk to Sunset Beach -MEM DAY WKND AVAIL !
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 7
$500
per night
3 - 7 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 7
Luxury,Quiet, Pool,Spotless, Beach,Main+Guest House,June Still Avail!
- 6 Bedrooms,
- 7 Bathrooms, Sleeps 14
$5,000 -
$7,395
per week
2 - 7 night Minimum Stay
- 6 BR,
- 7 BA,
- Sleeps 14
Contemporary Home With Old Vocabulary In Walking Distance To Beaches
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$6,000 -
$11,000
per month
28 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 8
Design and Comfort Come Together in this Island Beach Home
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 7
$2,800 -
$4,750
per week
7 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 7
Shelter Island Renovated Barn Hideaway Pool • Water Access • Hamptons
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$11,029 -
$19,375
per month
14 - 31 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 6
Two Acre Waterfront Estate with Renovated Historic Home, Shelter Island NY
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 7
$2,700 -
$10,000
per week
7 - 28 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 7
Beautiful, Secluded, Waterfront with Wrap-around Porch and Roof Deck
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 9
$1,000
per night
3 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 9
Spacious Shelter Island Escape within walking distance to pristine beach
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 10
$2,250 -
$2,650
per week
7 night Minimum Stay
- 4 BR,
- 2 BA,
- Sleeps 10
Charming, Historic Cottage
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$250 -
$300
per night
2 - 7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Tranquil Island Refuge Nestled Among Towering Trees and Near Private Beach
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$1,900 -
$2,575
per week
3 - 7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Winner of Best of Citysearch- Beach/Pool, 4+ Bedroom Hamptons Vacation
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$400 -
$695
per night
3 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 10
Stylish Shelter Island Home with Pool and Walk to Beach.
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
ROMANTIC Hamptons Beach Cottage! Seclusion, Waterfalls
- 2 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
$335 -
$495
per night
2 - 7 night Minimum Stay
- 2 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Rustic house w/ pool on 2 private acres
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$8,000 -
$15,000
per month
3 - 28 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Charming Water View Victorian ' Eden Roc ' in Park-like-Setting
- 5 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 6
$30,000 -
$35,000
per month
7 night Minimum Stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 6
Breathtaking & Charming Shelter Island Oasis 5BR 3.5BA on Private Acre
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$4,000 -
$7,000
per week
28 night Minimum Stay
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
Waterfront Charmer on idyllic Shelter Island for summer rental
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 8
- 3 BR,
- 3 BA,
- Sleeps 8
Sun Worshipers Paradise
- 3 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
- 3 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Peace and Quiet on Shelter Island
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
September on Shelter Island is the perfect place at the perfect time!
- 1 Bedrooms,
- 1 Bathroom, Sleeps 3
- 1 BR,
- 1 BA,
- Sleeps 3
9 More choices from HomeAway International Websites
Beautiful Beach Cottage
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$4,193
per week
7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Shelter Island Waterfront Beach House - Private Beach Perfect Sunsets
- 4 Bedrooms, Sleeps 10
$12,000
per month
14 night Minimum Stay
- 4 BR,
- Sleeps 10
Boater's Delight
- 5 Bedrooms,
- 2 Bathrooms, Sleeps 9
- 5 BR,
- 2 BA,
- Sleeps 9
Art Loving Sailors' Zen Retreat--Waterfront 5 Bedroom House
- 5 Bedrooms, Sleeps 12
- 5 BR,
- Sleeps 12
Hampton's Waterfront with Dock. Best Location in Shelter Isla.
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$1,200
per night
2 - 7 night Minimum Stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Waterfront Home with Beach & Deep-Water Dock
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 10
- 4 BR,
- 4 BA,
- Sleeps 10
Charming Country 4 BR/4 BA Retreat Available July & August
- 4 Bedrooms, Sleeps 8
- 4 BR,
- Sleeps 8
Fabulous Easy Living Waterfront with Dock
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
- 4 BR,
- 3 BA,
- Sleeps 10
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