Beachfront vacation rentals in Shelter Island
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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
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Popular amenities for Shelter Island beachfront rentals
Pet-friendly beachfront home rentals
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
Nov. 30 – Dec. 7
Home in New London
4.89 out of 5 average rating, 132 reviewsOASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS
Jan. 30 – Feb. 6
Home in East Patchogue
4.82 out of 5 average rating, 132 reviewsHouse at water next to Bellport golf course
Mar. 22 – 29
Cottage in New Suffolk
4.94 out of 5 average rating, 48 reviewsBeach Cottage 3 - New Suffolk | NY
Dec. 24 – 31
Home in Greenport
4.95 out of 5 average rating, 20 reviewsWalk to Beach or to Town …
Nov. 16 – 23
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
Mar. 10 – 17
Home in Sag Harbor
4.98 out of 5 average rating, 88 reviewsPerfection in Sag Harbor 5 Br 1 block from water
Apr. 2 – 9
Home in Peconic
5.0 out of 5 average rating, 3 reviewsPeaceful in Peconic
May 12 – 19
Beachfront home rentals with a pool
Condo in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
Aug. 15 – 22
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Oct. 30 – Nov. 6
Condo in Greenport
4.89 out of 5 average rating, 81 reviewsSeaside Escape w Pool, Private Beach & Patio
Dec. 4 – 11
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Sep. 25 – Oct. 2
Home in Old Saybrook
5.0 out of 5 average rating, 24 reviews3BR Private Cottage w/ Pool in Old Saybrook
Feb. 28 – Mar. 7
Villa in Greenport
4.84 out of 5 average rating, 32 reviewsYear-Round Heated Pool Villa - 3 blocks from town
Feb. 17 – 24
Apartment in Greenport
4.75 out of 5 average rating, 4 reviewsJunior Suite One King + Sofa Bed
Jun. 8 – 15
Apartment in Montauk
4.86 out of 5 average rating, 95 reviewsRecharge at our Renovated ocean front unit
Oct. 8 – 15
Private beachfront home rentals
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Dec. 8 – 15
Apartment in Greenport
4.96 out of 5 average rating, 24 reviewsVintage 1880 Victorian gem.
Sep. 3 – 10
Guest suite in Southold
4.94 out of 5 average rating, 99 reviewsComfortable Suite, a walk to the beach
Dec. 12 – 19
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
Sep. 13 – 20
Cottage in Greenport
4.84 out of 5 average rating, 38 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
Oct. 15 – 22
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
Dec. 9 – 16
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Jun. 11 – 18
Home in East Hampton
4.96 out of 5 average rating, 26 reviewsEast Hampton By the Bay - Clearwater Beach
May 2 – 9
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