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