Beachfront holiday rentals in Shelter Island
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Top-rated beachfront rentals in Shelter Island
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Popular amenities for beachfront rentals in Shelter Island
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
25 Oct – 1 Nov
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
14–21 Apr
Home in Greenport
5.0 out of 5 average rating, 18 reviewsWalk to Beach or to Town …
16–23 Nov
Home in Sag Harbor
4.98 out of 5 average rating, 88 reviewsPerfection in Sag Harbor 5 Br 1 block from water
4–11 Nov
Home in East Hampton
5.0 out of 5 average rating, 14 reviewsHistoric East Hampton Home - Private Beach Access
3–10 Oct
Home in Peconic
5.0 out of 5 average rating, 3 reviewsPeaceful in Peconic
8–15 May
Cottage in Montauk
4.97 out of 5 average rating, 31 reviewsSharkey Cottage
15–22 Oct
Beachfront home rentals with a pool
Apartment in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
20–27 Jul
Apartment in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
26 Oct – 2 Nov
Apartment in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
5–12 Jan
Apartment in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
8–15 Apr
Villa in Greenport
4.84 out of 5 average rating, 32 reviewsYear-Round Heated Pool Villa - 3 blocks from town
21–28 Jan
Home in Old Saybrook
5.0 out of 5 average rating, 24 reviews3BR Private Cottage w/ Pool in Old Saybrook
10–17 Oct
Flat in Greenport
4.75 out of 5 average rating, 4 reviewsJunior Suite One King + Sofa Bed
9–16 Jun
Flat in Montauk
4.86 out of 5 average rating, 95 reviewsRecharge at our Renovated ocean front unit
15–22 Jul
Private beachfront home rentals
Flat in Greenport
4.96 out of 5 average rating, 24 reviewsVintage 1880 Victorian gem.
30 Aug – 6 Sep
Guest suite in Southold
4.94 out of 5 average rating, 99 reviewsComfortable Suite, a walk to the beach
13–20 Oct
Cottage in Greenport
4.84 out of 5 average rating, 38 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
11–18 Oct
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
7–14 Sep
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
Cottage in Old Saybrook
5.0 out of 5 average rating, 13 reviewsLittle cottage of gratitude
11–18 Dec
Guest house 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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- Beachfront rentals Suffolk County
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