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, 232 reviewsMontauk Royal Atlantic Beach Resort North
Aug 1 – 8
Home in New London
4.89 out of 5 average rating, 132 reviewsOASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS
Feb 19 – 26
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Nov 3 – 10
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
Mar 9 – 16
Condo in Greenport
4.89 out of 5 average rating, 81 reviewsSeaside Escape w Pool, Private Beach & Patio
Mar 3 – 10
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Sep 29 – Oct 6
Home in Sag Harbor
4.98 out of 5 average rating, 88 reviewsPerfection in Sag Harbor 5 Br 1 block from water
Dec 29 – Jan 5
Home in Old Saybrook
5.0 out of 5 average rating, 24 reviews3BR Private Cottage w/ Pool in Old Saybrook
Jan 3 – 10
Beachfront home rentals with a hot tub
Home in Bayport
4.84 out of 5 average rating, 156 reviewsExquisite spacious waterfront all modern-sleeps 8
Feb 28 – Mar 7
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Jun 11 – 18
Vacation home in Flanders
4.96 out of 5 average rating, 68 reviewsAmazing Waterfront Bungalow
Aug 1 – 8
Home in New Haven
4.96 out of 5 average rating, 79 reviewsBeach Haven - waterfront, near Yale, sunsets
Jan 16 – 23
Villa in Guilford
4.91 out of 5 average rating, 11 reviewsPrivate Luxury Waterfront Home
Mar 26 – Apr 2
Home in Milford
4.98 out of 5 average rating, 82 reviews3 Bedroom Beach House with Hot Tub!
Mar 22 – 29
Home in Hampton Bays,
4.95 out of 5 average rating, 56 reviewsLovely Year Round Vacation Home in the Hamptons
Dec 19 – 26
Home in Cherry Grove, Fire Island
4.96 out of 5 average rating, 79 reviewsBayfront Fun - 3 BR & 3 Ensuite Bath with Hot Tub!
Apr 26 – May 3
Pet-friendly beachfront home rentals
Cottage in Milford
4.96 out of 5 average rating, 236 reviewsSpring Sale! Cozy Cottage | Walk to Beach | Pet
Oct 10 – 17
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
Dec 25 – Jan 1
Cottage in New Suffolk
4.94 out of 5 average rating, 48 reviewsBeach Cottage 3 - New Suffolk | NY
Dec 28 – Jan 4
Home in East Marion
4.92 out of 5 average rating, 24 reviewsWaterfront Bungalow w/Private Beach on Peconic Bay
Jun 5 – 12
Home in Greenport
4.95 out of 5 average rating, 20 reviewsWalk to Beach or to Town …
Nov 16 – 23
Home in New Suffolk
5.0 out of 5 average rating, 13 reviewsWaterfront Beach Cottage
Dec 26 – Jan 2
Bungalow in Old Lyme
4.86 out of 5 average rating, 92 reviewsInsta-worthy * Couples Retreat
Nov 1 – 8
Home in Peconic
5.0 out of 5 average rating, 3 reviewsPeaceful in Peconic
May 16 – 23
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