Waterfront vacation rentals in Shelter Island Heights
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Top-rated waterfront accommodations in Shelter Island Heights
Guests agree: these waterfront accommodations 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 Heights waterfront rentals
Waterfront apartment rentals
Apartment in New Haven
4.89 out of 5 average rating, 466 reviewsFair Haven Heights Entire 1 Bedroom Apartment
Sep. 4 – 11
Apartment in Stonington
4.95 out of 5 average rating, 221 reviewsMystical Ocean View in Historic Stonington Borough
Oct. 20 – 27
Apartment in Montauk
4.89 out of 5 average rating, 325 reviewsStarboard Fort Pond Montauk
Jun. 17 – 24
Apartment in Mystic
5.0 out of 5 average rating, 122 reviewsWaterfront gem! Close to everything. Ultraclean.
Mar. 27 – Apr. 3
Apartment in Greenport
4.75 out of 5 average rating, 4 reviewsJunior Suite One King + Sofa Bed
May 8 – 15
Apartment in Branford
4.89 out of 5 average rating, 9 reviewsStony Crk Studio ideal for trvl nurses…
Dec. 10 – 17
Apartment in Milford
5.0 out of 5 average rating, 49 reviewsThe Pond Mill Retreat w/ 2 Bdrms & Pool
Sep. 13 – 20
Apartment in East Haven
4.97 out of 5 average rating, 65 reviewsCoastal Relaxation Getaway
Mar. 16 – 23
Waterfront house rentals
Home in New Haven
4.99 out of 5 average rating, 188 reviewsQ River House - 2 bdrm, minutes from Yale/Downtown
Dec. 16 – 23
Home in Southampton
4.96 out of 5 average rating, 130 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
Mar. 21 – 28
Home in Groton
4.95 out of 5 average rating, 160 reviewsTrue Ocean Front Vacationing - Groton/Mystic
Aug. 28 – Sep. 4
Home in Milford
4.89 out of 5 average rating, 124 reviewsThe Beach House!
Jun. 10 – 17
Home in Mastic Beach
4.93 out of 5 average rating, 107 reviewsGorgeous Waterfront and Indoor Pool Family Oasis!
Dec. 13 – 20
Home in Greenport
4.94 out of 5 average rating, 85 reviewsMaritime Village Getaway with Backyard
Apr. 8 – 15
Home in Greenport
5.0 out of 5 average rating, 3 reviewsWaterfront Greenport Boathouse
Dec. 14 – 21
Home in Greenport
4.95 out of 5 average rating, 40 reviewsThe North Star: Greenport Waterview Beach Getaway
Jan. 28 – Feb. 4
Waterfront condo rentals
Condo in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
Mar. 24 – 31
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Oct. 25 – Nov. 1
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
Sep. 28 – Oct. 5
Condo in Montauk
4.82 out of 5 average rating, 87 reviewsBeautiful Condo on the Ocean Bluffs
Mar. 26 – Apr. 2
Condo in Montauk
Sun N Sound Resort, Montauk, NY
Aug. 8 – 15
Condo in Shelter Island Heights
5.0 out of 5 average rating, 5 reviewsPeaceful and Relaxing Waterfront.
Mar. 30 – Apr. 6
Condo in Greenport
4.87 out of 5 average rating, 90 reviewsWaterfront Condo C-204 at The Cliffside Resort
Oct. 13 – 20
Condo in New Haven
4.89 out of 5 average rating, 18 reviewsLuxurious 1B, high-ceiling loft in New Haven.
Oct. 23 – 30
Quick stats about waterfront rentals in Shelter Island Heights
Total rentals
30 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
840 reviews
Nightly prices starting at
$273 CAD before taxes and fees
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