Shelter Island Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Shelter Island, San Diego, California, USA

New Oceanview Studio – Walk to Sunset Cliffs
New
1 Bedroom 2 Guests
|
10.0 (18 Reviews)
1 Bedroom 6 Guests
From US $333 per night
10.0 (1 Review)
1 Bedroom 2 Guests
|
10.0 (6 Reviews)
5 Bedrooms 12 Guests
|
9.6 (4 Reviews)
1 Bedroom 2 Guests
|
10.0 (5 Reviews)
1 Bedroom 2 Guests
|
8.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (3 Reviews)
2 Bedrooms 4 Guests
New Renovated Coastal 2BR - Stylish & Bright
From US $933 per night
|
10.0 (2 Reviews)
6 Bedrooms 12 Guests
|
10.0 (2 Reviews)
3 Bedrooms 8 Guests
|
10.0 (2 Reviews)
3 Bedrooms 8 Guests
|
10.0 (2 Reviews)
2 Bedrooms 4 Guests
From US $340 per night
10.0 (209 Reviews)
2 Bedrooms 4 Guests
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (201 Reviews)
2 Bedrooms 4 Guests
10.0 (174 Reviews)
1 Bedroom 4 Guests
|
10.0 (1 Review)
1 Bedroom 4 Guests
10.0 (171 Reviews)
2 Bedrooms 4 Guests
|
10.0 (1 Review)
4 Bedrooms 8 Guests
10.0 (171 Reviews)
1 Bedroom 4 Guests
|
10.0 (1 Review)
4 Bedrooms 12 Guests
From US $244 per night
10.0 (161 Reviews)
1 Bedroom 4 Guests
From US $810 per night
|
10.0 (1 Review)
3 Bedrooms 7 Guests
10.0 (139 Reviews)
2 Bedrooms 4 Guests
9.9 (15 Reviews)
1 Bedroom 5 Guests
10.0 (105 Reviews)
1 Bedroom 3 Guests
|
9.8 (18 Reviews)
1 Bedroom 3 Guests
10.0 (91 Reviews)
2 Bedrooms 4 Guests
From US $460 per night
10.0 (80 Reviews)
2 Bedrooms 4 Guests
10.0 (73 Reviews)
2 Bedrooms 4 Guests
From US $181 per night
10.0 (15 Reviews)
1 Bedroom 2 Guests
|
9.8 (12 Reviews)
1 Bedroom 3 Guests
|
5.0 (2 Reviews)
1 Bedroom 2 Guests
|
9.8 (7 Reviews)
1 Bedroom 4 Guests
10.0 (11 Reviews)
2 Bedrooms 4 Guests
|
9.7 (3 Reviews)
3 Bedrooms 6 Guests
10.0 (11 Reviews)
1 Bedroom 4 Guests
|
9.6 (8 Reviews)
2 Bedrooms 11 Guests
10.0 (10 Reviews)
1 Bedroom 2 Guests
|
9.5 (4 Reviews)
3 Bedrooms 7 Guests
From US $436 per night
10.0 (9 Reviews)
2 Bedrooms 6 Guests
|
9.4 (53 Reviews)
2 Bedrooms 6 Guests
10.0 (9 Reviews)
2 Bedrooms 5 Guests
From US $438 per night
|
9.3 (15 Reviews)
2 Bedrooms 6 Guests
10.0 (9 Reviews)
1 Bedroom 4 Guests
10.0 (7 Reviews)
2 Bedrooms 6 Guests
From US $584 per night
|
9.3 (3 Reviews)
2 Bedrooms 5 Guests
10.0 (7 Reviews)
1 Bedroom 2 Guests
|
9.1 (147 Reviews)
8 Bedrooms 23 Guests

About Shelter Island Vacation Rentals

With more than 1316 Shelter Island vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Shelter Island.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Shelter Island, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Shelter Island. Places to stay near Shelter Island are 829.74 ft² on average, with prices averaging US $458 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Shelter Island with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Other Places to Stay in Shelter Island, CA


Frequently Asked Questions About Shelter Island?

What are the top vacation rentals in Shelter Island?

How many Rentbyowner vacation rentals are available in Shelter Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1316 in the Shelter Island area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Shelter Island. 

Nearby Neighborhood (12)

Neighborhood Property Count
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