Vacation rentals in Shelter Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Shelter Island

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

Guest favourite
Guest suite in Sag Harbor
Artists Sag Harbor Village Retreat
January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.
14 – 21 Nov
4.88 out of 5 average rating, 308 reviews
Guest favourite
Condo in Greenport
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
1 – 8 Apr
4.91 out of 5 average rating, 107 reviews
Guest favourite
Apartment in Sag Harbor
Updated apartment in historic village home
Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!
1 – 8 May
4.99 out of 5 average rating, 127 reviews

Popular amenities for Shelter Island holiday rentals

Stay near Shelter Island's top sights

SALT Waterfront Bar & Grill34 locals recommend
Mashomack Preserve70 locals recommend
Ram's Head Inn19 locals recommend
Marie Eiffel Market41 locals recommend
South Ferry Inc.6 locals recommend
The Islander10 locals recommend

Other great holiday rentals in Shelter Island

Guest favourite
Apartment in Greenport
Greenport Village View - Walkable 2BR Stay
7 – 14 Nov
4.97 out of 5 average rating, 193 reviews
Guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
19 – 26 Jan
5.0 out of 5 average rating, 50 reviews
Guest favourite
Guest suite in Shelter Island
Private two-bedroom stay on Shelter Island
31 Aug – 7 Sept
4.89 out of 5 average rating, 28 reviews
Guest favourite
Guesthouse in Shelter Island
Lovely Island Cottage
16 – 23 Nov
4.95 out of 5 average rating, 22 reviews
Guest favourite
Guesthouse in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
31 Aug – 7 Sept
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
23 – 30 Mar
4.92 out of 5 average rating, 52 reviews
Guest favourite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
13 – 20 Nov
4.88 out of 5 average rating, 16 reviews
Guest favourite
Home in Shelter Island
Spacious house with pool.
1 – 8 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Shelter Island
Family Friendly Oasis Steps to Water - Heated Pool
8 – 15 Dec
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
8 – 15 June
4.96 out of 5 average rating, 90 reviews
Guest favourite
Home in Shelter Island
Charming 4BR Cottage on Shelter Island
26 Nov – 3 Dec
4.88 out of 5 average rating, 68 reviews
Guest favourite
Home in Greenport
The Sandy Shack - Coastal Escape
14 – 21 Feb
5.0 out of 5 average rating, 10 reviews

Quick stats about holiday rentals in Shelter Island

Total rentals

140 properties

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

100 properties are a good fit for families

Total number of reviews

3K reviews

Nightly prices starting at

$183 AUD before taxes and fees

Destinations to explore