Beachfront holiday rental in Shelter Island
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Top-rated beachfront accommodation in Shelter Island
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.
Holiday 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
22–29 Dec
Cottage in New Suffolk
4.94 out of 5 average rating, 48 reviewsBeach Cottage 3 - New Suffolk | NY
20–27 Sep
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
1–8 Jan
Home in Greenport
5.0 out of 5 average rating, 18 reviewsWalk to Beach or to Town …
16–23 Nov
Home in East Hampton
5.0 out of 5 average rating, 14 reviewsHistoric East Hampton Home - Private Beach Access
6–13 Mar
Home in Peconic
5.0 out of 5 average rating, 3 reviewsPeaceful in Peconic
7–14 May
Home in Greenport
5.0 out of 5 average rating, 3 reviewsWaterfront Greenport Boathouse
14–21 Dec
Cottage in Montauk
4.97 out of 5 average rating, 31 reviewsSharkey Cottage
6–13 Oct
Beachfront home rentals with a pool
Condo in Montauk
4.8 out of 5 average rating, 231 reviewsMontauk Royal Atlantic Beach Resort North
20–27 Jul
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
25 Oct – 1 Nov
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
28 Sep – 5 Oct
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
4–11 Jan
Apartment in Greenport
4.75 out of 5 average rating, 4 reviewsJunior Suite One King + Sofa Bed
9–16 May
Home in Old Saybrook
5.0 out of 5 average rating, 24 reviews3BR Private Cottage w/ Pool in Old Saybrook
12–19 Jun
Apartment in Montauk
4.86 out of 5 average rating, 95 reviewsRecharge at our Renovated ocean front unit
15–22 Jul
Home in Hampton Bays
5.0 out of 5 average rating, 3 reviewsWaterfront Paradise - 6Bd 4.5Ba!
20–27 Dec
Private beachfront home rentals
Apartment in Greenport
4.96 out of 5 average rating, 24 reviewsVintage 1880 Victorian gem.
20–27 Oct
Guest suite in Southold
4.94 out of 5 average rating, 99 reviewsComfortable Suite, a walk to the beach
11–18 Jan
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
3–10 May
Cottage in Greenport
4.84 out of 5 average rating, 38 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
10–17 Oct
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
6–13 Jan
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
11–18 Jun
Home in Greenport
5.0 out of 5 average rating, 35 reviewsBeachfront Greenport Villa
7–14 Apr
Guesthouse in Sag Harbor
5.0 out of 5 average rating, 6 reviewsRomantic studio cottage; Walk to town
1–6 Dec
Destinations to explore
- New City Holiday rentals
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