Beachfront vacation rentals in Shelter Island
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Shelter Island
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Shelter Island beachfront rentals
Beachfront home rentals with a pool
Condo in Montauk
4.8 out of 5 average rating, 231 reviewsMontauk Royal Atlantic Beach Resort North
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
Home in Sag Harbor
4.98 out of 5 average rating, 88 reviewsPerfection in Sag Harbor 5 Br 1 block from water
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
Home in Old Saybrook
5.0 out of 5 average rating, 24 reviews3BR Private Cottage w/ Pool in Old Saybrook
Apartment in Greenport
4.75 out of 5 average rating, 4 reviewsJunior Suite One King + Sofa Bed
Beachfront home rentals with a hot tub
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Vacation home in Flanders
4.96 out of 5 average rating, 68 reviewsAmazing Waterfront Bungalow
Villa in Greenport
4.84 out of 5 average rating, 32 reviewsYear-Round Heated Pool Villa - 3 blocks from town
Villa in Guilford
4.91 out of 5 average rating, 11 reviewsPrivate Luxury Waterfront Home
Home in New Haven
4.96 out of 5 average rating, 79 reviewsBeach Haven - waterfront, near Yale, sunsets
Home in Hampton Bays,
4.95 out of 5 average rating, 56 reviewsLovely Year Round Vacation Home in the Hamptons
Home in Hampton Bays
4.89 out of 5 average rating, 45 reviewsHamptons Round Beach House - 60 secs walk to beach
Guest suite in Remsenburg-Speonk
5.0 out of 5 average rating, 14 reviewsHamptons Waterfront King Suite
Pet-friendly beachfront home rentals
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
Cottage in New Suffolk
4.94 out of 5 average rating, 48 reviewsBeach Cottage 3 - New Suffolk | NY
Home in Greenport
5.0 out of 5 average rating, 18 reviewsWalk to Beach or to Town …
Home in East Hampton
5.0 out of 5 average rating, 14 reviewsHistoric East Hampton Home - Private Beach Access
Home in Peconic
5.0 out of 5 average rating, 3 reviewsPeaceful in Peconic
Cottage in Montauk
4.97 out of 5 average rating, 31 reviewsSharkey Cottage
Home in Greenport
5.0 out of 5 average rating, 3 reviewsWaterfront Greenport Boathouse
Vacation home in Greenport
4.96 out of 5 average rating, 24 reviewsWalk to town, Marina Views, Greenport Village
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