Holiday rentals near Shelter Island Whale's Tail
We found 3,786 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals near Shelter Island Whale's Tail that can be your home away from home. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you expect for your stay, which might include a garden and hot tub. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Shelter Island Whale's Tail
Showing deals for:10 Jul - 17 Jul
Image gallery for Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Orient
8% off
Price is NZ$21,490
NZ$21,490
for 7 nights, 1 room
NZ$3,070 per night
includes taxes & fees
Image gallery for Everything in Hamptons special discount available for weekly and monthly renters
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Everything in Hamptons special discount available for weekly and monthly renters
Water Mill
8% off
Price is NZ$116,166
NZ$116,166
for 7 nights, 1 home
NZ$16,595 per night
includes taxes & fees
Image gallery for AMAGANSETT 2 ACRE, 3000 Sq Ft 4 BDR MODERN W/ 20 x 40 POOL, NEAR BEACH & TOWN
9.89.8 out of 10, Exceptional, (73 reviews)
Exceptional
(73 reviews)
AMAGANSETT 2 ACRE, 3000 Sq Ft 4 BDR MODERN W/ 20 x 40 POOL, NEAR BEACH & TOWN
East Hampton
8% off
Price is NZ$34,373
NZ$34,373
for 7 nights, 1 home
NZ$4,910 per night
includes taxes & fees
Image gallery for Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
9.89.8 out of 10, Exceptional, (92 reviews)
Exceptional
(92 reviews)
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Sag Harbor
16% off
Price is NZ$28,701
NZ$28,701
for 7 nights, 1 home
NZ$4,100 per night
includes taxes & fees
Image gallery for Private Custom Built Beach Home with Heated Pool Short Walk to Ocean Beach
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Private Custom Built Beach Home with Heated Pool Short Walk to Ocean Beach
Montauk
8% off
Price is NZ$38,062
NZ$38,062
for 7 nights, 1 home
NZ$5,437 per night
includes taxes & fees
Image gallery for Modern Family Retreat with Heated Pool, Playground and Peloton
9.89.8 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Modern Family Retreat with Heated Pool, Playground and Peloton
Hampton Bays
8% off
Price is NZ$14,450
NZ$14,450
for 7 nights, 1 home
NZ$2,064 per night
includes taxes & fees
Image gallery for Cottage near the beach
9.89.8 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)
Cottage near the beach
Niantic
8% off
Price is NZ$3,845
NZ$3,845
for 7 nights, 1 cottage
NZ$549 per night
includes taxes & fees
Image gallery for Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village
9.89.8 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village
East Hampton
12% off
Price is NZ$27,185
NZ$27,185
for 7 nights, 1 home
NZ$3,884 per night
includes taxes & fees
Image gallery for WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
East Hampton
8% off
Price is NZ$30,271
NZ$30,271
for 7 nights, 1 home
NZ$4,324 per night
includes taxes & fees
Image gallery for Beautiful designer modern luxury home - steps from beach
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Beautiful designer modern luxury home - steps from beach
East Hampton
8% off
Price is NZ$18,962
NZ$18,962
for 7 nights, 1 home
NZ$2,709 per night
includes taxes & fees
Image gallery for Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!
Mattituck
15% off
Price is NZ$5,911
NZ$5,911
for 7 nights, 1 cottage
NZ$844 per night
includes taxes & fees
Image gallery for Northfork Long Island House Rental-US Open-Shinnecock, Family Vacation, Wineries
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Northfork Long Island House Rental-US Open-Shinnecock, Family Vacation, Wineries
Riverhead
8% off
Price is NZ$11,518
NZ$11,518
for 7 nights, 1 home
NZ$1,645 per night
includes taxes & fees
Image gallery for Spacious Contemporary Home with Pool and Tennis
8.48.4 out of 10, Very good, (10 reviews)
Very good
(10 reviews)
Spacious Contemporary Home with Pool and Tennis
Sag Harbor
36% off
Price is NZ$25,257
NZ$25,257
for 7 nights, 1 home
NZ$3,608 per night
includes taxes & fees
Image gallery for Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Jamesport
12% off
Price is NZ$13,012
NZ$13,012
for 7 nights, 1 home
NZ$1,859 per night
includes taxes & fees
Image gallery for Elegant and spacious North Fork home; near beaches, vineyards, farms and dining.
1010 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)
Elegant and spacious North Fork home; near beaches, vineyards, farms and dining.
Jamesport
8% off
Price is NZ$14,182
NZ$14,182
for 7 nights, 1 home
NZ$2,026 per night
includes taxes & fees
Image gallery for Retreat to Nature with the best of both worlds - Beaches & Hiking Trails
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Retreat to Nature with the best of both worlds - Beaches & Hiking Trails
Montauk
8% off
Price is NZ$22,415
NZ$22,415
for 7 nights, 1 home
NZ$3,202 per night
includes taxes & fees
Image gallery for UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
1010 out of 10, Exceptional, (74 reviews)
Exceptional
(74 reviews)
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
Westbrook
8% off
Price is NZ$10,168
NZ$10,168
for 7 nights, 1 home
NZ$1,453 per night
includes taxes & fees
Image gallery for Southampton Village Gem
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Southampton Village Gem
Southampton
8% off
Price is NZ$27,818
NZ$27,818
for 7 nights, 1 home
NZ$3,974 per night
includes taxes & fees
Image gallery for Kenneys Beach retreat by the Wineries
9.89.8 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
Kenneys Beach retreat by the Wineries
Southold
7% off
Price is NZ$10,427
NZ$10,427
for 7 nights, 1 home
NZ$1,490 per night
includes taxes & fees
Image gallery for Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
9.69.6 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
Southampton
7% off
Price is NZ$29,821
NZ$29,821
for 7 nights, 1 home
NZ$4,260 per night
includes taxes & fees
Image gallery for Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport
East Marion
8% off
Price is NZ$16,608
NZ$16,608
for 7 nights, 1 home
NZ$2,373 per night
includes taxes & fees
Image gallery for Best View + Private Beach + Putting Green
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Best View + Private Beach + Putting Green
Hampton Bays
8% off
Price is NZ$17,099
NZ$17,099
for 7 nights, 1 home
NZ$2,443 per night
includes taxes & fees
Image gallery for Perfect Family home, AC, Heated Pool, 3BR 2Bath
9.89.8 out of 10, Exceptional, (37 reviews)
Exceptional
(37 reviews)
Perfect Family home, AC, Heated Pool, 3BR 2Bath
East Hampton
21% off
Price is NZ$13,257
NZ$13,257
for 7 nights, 1 home
NZ$1,894 per night
includes taxes & fees
Image gallery for Prime East Hampton Village Location. Heated Pool. Walk To All!
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Prime East Hampton Village Location. Heated Pool. Walk To All!
East Hampton
12% off
Price is NZ$35,832
NZ$35,832
for 7 nights, 1 home
NZ$5,119 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Shelter Island Whale's Tail
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Sleeps 12 · 5 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptional
exceptional
33 reviews
(33 reviews)
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Sleeps 12 · 4 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptional
exceptional
147 reviews
(147 reviews)
WALK OR BIKE TO THE VILLAGE OF EAST HAMPTON AND ROUND SWAMP FARM
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderful
wonderful
20 reviews
(20 reviews)
10 Bedroom Hampton House with a regulation size Pickleball court
Sleeps 25 · 10 bedrooms · 3+ bathrooms
1010 out of 10
Exceptional
exceptional
32 reviews
(32 reviews)
Gorgeous private Hamptons house with pool and volleyball court
Sleeps 15 · 5 bedrooms · 3+ bathrooms
7.07.0 out of 10
Good
good
29 reviews
(29 reviews)
Architects' Own Perfect Hideaway With Pool
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptional
exceptional
28 reviews
(28 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value