Vacation rentals in Shelter Island Heights

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Top-rated vacation rentals in Shelter Island Heights

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 189 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

Jan. 27 – Feb. 3

$1,625 CAD per night
Guest favourite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

May 12 – 19

$345 CAD per night
Guest favourite

Apartment in Greenport

4.95 out of 5 average rating, 122 reviews

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars. It is a week minimum during the peak season ( memorial day weekend until labor day weekend)

Dec. 26 – Jan. 2

$615 CAD per night

Popular amenities for Shelter Island Heights vacation rentals

Stay near Shelter Island Heights's top sights

American Beech52 locals recommend
Lucharitos51 locals recommend
Claudio's39 locals recommend
Claudio's Waterfront44 locals recommend
SALT Waterfront Bar & Grill34 locals recommend
Crazy Beans21 locals recommend

Other great vacation rentals in Shelter Island Heights

Guest favourite

Guest suite in Shelter Island

4.89 out of 5 average rating, 28 reviews

Private two-bedroom stay on Shelter Island

Jun. 5 – 12

$490 CAD per night
Guest favourite

Guesthouse in Shelter Island

4.95 out of 5 average rating, 22 reviews

Lovely Island Cottage

Nov. 26 – Dec. 3

$598 CAD per night
Guest favourite

Home in Shelter Island

4.92 out of 5 average rating, 73 reviews

Family Friendly Island Home

Oct. 25 – Nov. 1

$986 CAD per night
Guest favourite

Home in Shelter Island

5.0 out of 5 average rating, 50 reviews

CASA GYPSEA - a chic and peaceful 3 bedroom house

Jan. 31 – Feb. 7

$906 CAD per night
Guest favourite

Guesthouse in Shelter Island

5.0 out of 5 average rating, 50 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Jul. 22 – 29

$591 CAD per night
Guest favourite

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

Jan. 12 – 19

$614 CAD per night
Guest favourite

Guest suite in Greenport

5.0 out of 5 average rating, 45 reviews

Private Suite in Greenport Historical District

Aug. 23 – 30

$492 CAD per night
Guest favourite

Home in Greenport

5.0 out of 5 average rating, 18 reviews

The Corwin House

Apr. 24 – May 1

$701 CAD per night
Superhost

Home in Shelter Island

4.88 out of 5 average rating, 68 reviews

Charming 4BR Cottage on Shelter Island

May 27 – Jun. 3

$880 CAD per night
Guest favourite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Mar. 7 – 14

$923 CAD per night
Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 76 reviews

Modern, spacious SI home with pool

Mar. 9 – 16

$1,294 CAD per night
Guest favourite

Cottage in Shelter Island

4.96 out of 5 average rating, 90 reviews

3 Bedroom Cottage Gem

Jun. 18 – 25

$1,027 CAD per night

Quick stats about vacation rentals in Shelter Island Heights

Total rentals

290 properties

Rentals with a pool

90 properties have a pool

Pet-friendly rentals

100 properties allow pets

Family-friendly rentals

210 properties are a good fit for families

Total number of reviews

8.5K reviews

Nightly prices starting at

$136 CAD before taxes and fees

Destinations to explore