San Juan Island Cottage Rentals & Holiday Homes
Find the best cottages in San Juan Island - We found 288 exact matches
About San Juan Island Luxury Rental on Wine Country Villas
Searching for cottages to rent near San Juan Island? Wine Country Villas features more than 288 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in San Juan Island have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Wine Country Villas’s cottage listings come in all shapes and sizes for large groups, friends, or couples in San Juan Island.
Are you planning to travel to the lakeside, beach, or mountain area? Wine Country Villas’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Wine Country Villas boasts of 288 holiday cottages and places to stay in San Juan Island. The site provides unique Airbnb, VRBO, Wine Country Villas-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About San Juan Island Cottage Rentals
What are the top rated Cottage Rentals in San Juan Island?
There are a lot of options in San Juan Island. If you plan on staying in the San Juan Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in San Juan Island:
- Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.
- Peaceful waterfront cottage, close to town!
- Custom Waterfront Home near Roche Harbor. n Aug. 29-Sept 3 still available
- WATER VIEWS of Puget Sound and the Olympic Mountains in a Garden Setting
- Hot Tub! Beautiful Water View Home! (WVP)
- Waterfront Cove, West Side Of San Juan Island, Sandy Beach, Prime Orca location
- Spectacular West side views of Strait, Olympics, Victoria, south to Mt Rainier.n
- Perfect location to relax, unwind, renew and enjoy San Juan Island
- Secluded & light-filled Pacific NW Waterfront home on SJI with views of Speiden Island
- Beautifully Appointed 2 Bedroom Condo in the Heart of Friday Harbor.
How much does it cost to rent a cottage in San Juan Island?
The average cost for a cottage rental in San Juan Island is $544 per night. Winecountryvillas has a wide list of great cottages near San Juan Island that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in San Juan Island that allow pets?
Yes, here are the top cottage rentals in San Juan Island that allow you to bring your pet:
- Golf Course Guesthouse , Friday Harbor, San Juan Isl.
- Tucker House Inn
- Trumpeter Inn
- Waterfront! Hot Tub! - (Stonecliff)
See all pet-friendly vacation rentals in San Juan Island on Winecountryvillas
Do you have any rental cottages in San Juan Island that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in San Juan Island to find one that works for you.
Are there quality cottages in San Juan Island that have indoor swimming pools?
As of 2026, the data from Winecountryvillas shows that there are Over 288 private swimming pools or cottages with indoor pools in the San Juan Island area along with other great amenities.
