Vacation rentals in San Juan County

4.83 out of 5 average rating, 588 reviews

Farm stay in Eastsound

Rose Cottage - Deer Harbor, Orcas

PPROVO-14-0015 Our charming old fashioned cottage is private and quiet, overlooking meadows where our horses graze and bird life abounds! Full kitchen with dining table and day bed. Living room with surround windows, wifi, Best suited for a couple & kids 5+ . Flowers and herbs surround the private, sunny patio. Love Horses? Take some Horse Lessons with our mustangs. Great walks right from the door and a mile to the Deer Harbor dock & beach for kayaking, whale watching, sailing. SORRY NO PETS.

Superhost

A vibrant garden area features a variety of plants and flowers in full bloom, including irises and greenery. An archway is visible in the foreground, leading towards the charming red barn, which is surrounded by lush foliage and additional outbuildings in the background.

4.88 out of 5 average rating, 400 reviews

Garden Cottage w/Pool at the Sunburnt Mermaid

Stay at the Sunburnt Mermaid Cottages by boat (nearby marina), ferry or plane. Hot tub with views of sparkling waters of Westsound. Early arrival/late departure at $25/hour when available. Heated Pool (May 15-Sept 25th) ,Fire Pit, outdoor barbecue/ kitchen. Kayak rentals available. Enjoy our Organic vegetable gardens and fruit orchard. Guest rooms have microwave, toaster, fridge, tea kettle, hot plate, internet and ROKU TV. Private exclusive hot tub use October through April 30. Max 2 adults.

The cabin stands illuminated against the night sky, a soft glow emanating from its windows. The moon reflects on the water nearby, while dark trees frame the structure, creating a serene setting by the shore.

4.98 out of 5 average rating, 131 reviews

Waterfront Guest Cabin on private beach estate

See our other two available cabins listed on this waterfront estate by clicking my host profile. Welcome to the vintage 100 year old original guest Cabin, nestled over the Salish Sea on a private estate with two cabins, beach, camp fire, kayaks & paddle boards. Seals, otters, eagles and deer are your neighbors. Walk to Turtleback Mountain south trailhead for grand views above. The secluded Hot Tub is tucked under cedar trees, over the beach, private for either cabin, but not at the same time.

4.98 out of 5 average rating, 176 reviews

A spacious dining area features a wooden table surrounded by comfortable chairs, positioned near large windows that invite natural light. Outside, a deck with patio furniture is visible, nestled among the trees. A modern light fixture complements the inviting atmosphere.

Home in Eastsound

Stylish, Gourmet Kitchen, Minutes to Moran Park

Tree Haven is the perfect getaway for friends and small families! 🌲 Located near Eastsound, Moran State Park, and the Rosario Resort Marina, adventure is just minutes away. Our well-appointed home features an open floor plan and a separate media room for lounging or extra guests. Enjoy amazing outdoor dining on the deck, all nestled among tall, beautiful trees. Tree Haven offers a peaceful retreat while still being close to shops, beaches, trails, and kayaking. Your island adventure awaits!🏖️

4.97 out of 5 average rating, 295 reviews

A spacious deck features a bistro table with four chairs, offering a serene setting among tall trees. Scenic views of the water can be seen in the distance, with soft light filtering through the branches. The deck provides an inviting space for outdoor relaxation.

Cottage in Eastsound

WaterView,Impeccable Studio Cottage, Walk to Town

With beautiful views of the Salish Sea, our charming cottage is perfect for a solo retreat or a couple's getaway. Just a short walk to restaurants, shops, and a waterfront park, you can enjoy the convenience of town while waking each morning to sunrises from the deck, or the comfy queen-size bed in this perfectly designed studio. Our studio cottage features: ☀️ All-new appliances ☀️ Quartz countertops ☀️ Custom-tiled bathroom ☀️ Luxury linens and amenities Your island escape is ready for you ✨

4.97 out of 5 average rating, 269 reviews

A vibrant bouquet of flowers is displayed in a textured, turquoise vase on a black countertop. The arrangement includes peonies, daisies, and other assorted blooms, adding a touch of color and life to the kitchen space, illuminated by natural light from nearby windows.

Apartment in Eastsound

Wake up to this! Near Eastsound!

Cozy Studio space with an AMAZING water view up the straight and memorable sunsets. Kitchen, full bathroom, Queen Bed & TV. Located in woods up steep, gravel road. This space is attached to our home with private entrance and deck. We do have a three night minimum, as of 6/5/25 we have these two night openings: 6/20- 6/21--check out by 11am on 6/22 7/11-7/12-- check out by 11am on 7/13 8/20-8/21--check out by 11am on 8/22 9/4-9/5--check out by 11am on 9/6 message me! PPROVO-15-0022

4.93 out of 5 average rating, 252 reviews

A charming wooden cottage with a sloped roof is nestled among tall trees. The porch features a railing lined with potted plants, and steps lead to the entrance. Sunlight casts a warm glow on the rustic exterior, showcasing moss-covered shingles and a weather vane atop the roof.

Cabin in Eastsound

Cottage-in-the-Barn on Dragonfly Farm

Pure tranquility is yours on Dragonfly Farm! Centrally located, yet extremely private, with garden, greenhouse, chickens, orchard and pond to paddle around in our kayaks or canoe. Charming decor with leather sofa, high ceilings, fine linens, cozy propane heating stove, tasteful furnishings, barbecue and more. SJC Permit #00PR0V77. MARCH 2020 UPDATE: due to Corona Virus concerns we're offering a full refund in the event you need to cancel. We thoroughly disinfect between guests.

4.97 out of 5 average rating, 250 reviews

An orange-shingled bungalow is framed by lush greenery. A welcoming wooden front door is complemented by a large window. Outdoor seating is provided by a circular table surrounded by four chairs, set on a peaceful lawn, with stone pathways leading to the entrance.

Cottage in Eastsound

Farm cottage, close to Eastsound!

Buckhorn Farm Bungalow is located on ten-acres near the north shore of Orcas Island. This family vacation cottage enjoys a wonderful country-farm atmosphere but is only a 5 minute drive from the village of Eastsound, our island's version of “downtown.” Guests can easily walk or ride bicycles along level roads to restaurants, shops or to the nearby semi-private beach to enjoy beach strolls, tide-pooling and spectacular views from Mt. Baker to Vancouver Island.

A fluffy owl perches on a tree branch, surrounded by a soft blur of natural foliage. The owl’s plumage appears thick and textured, blending shades of gray and white, while soft moss hangs from the branches, enhancing the serene forest atmosphere.

5 out of 5 average rating, 249 reviews

Orcas Island Sunset Retreat

Relax on Orcas Island in this quiet and peaceful guesthouse high up on Buck Mountain. Enjoy gorgeous views and spectacular sunsets, south to Olympic Mtns and west to Vancouver Is. This 900 sq ft guesthouse has a rustic elegance and is comfortably furnished. Ten foot high ceilings add to the grand and spacious feeling of the guesthouse. Hand waxed pine plank floors and dark woodwork give a lustrous sense and air of old and timeless beauty.

An inviting sleeping area features a spacious bed with neutral bedding against a backdrop of natural wood beams. A window allows natural light to fill the room, while a small desk and chair are placed near the bed, providing a functional space.

4.94 out of 5 average rating, 334 reviews

Northbeach Cabin

Sweet cedar shingled cabin on Sunset Avenue just a short walk to town, and an even shorter walk to the beach! Queen size bed tucked upstairs under the vaulted ceiling with peek-a-boo view of the water. Freshly renovated, old school Orcas style. Hardwood & Marmoleum floors throughout, pine paneling & subway tile in kitchen and bathroom. French door slider opens to deck, perfect for enjoying your morning coffee. #weaccept. PPROVO-17-0042

4.98 out of 5 average rating, 282 reviews

A spacious wooden deck is depicted, extending towards the water, with a scenic view of the lake and trees in the background. A single rocking chair is positioned invitingly on the deck, and additional seating can be seen, enhancing outdoor relaxation.

Guest suite in Eastsound

The Salish Waterfront Retreat

Fishing Bay. Ground-level suite. On the water right next to the village of Eastsound. No Pets or ESA with hair or dander. An exclusive location with amazing views, private beach, kayak launch, above water deck, a Japanese Soaking Tub, and outdoor fire pit. All within a five minute walk to Eastsound. Kayaks, bicycles, mooring buoy, and crab trap are available for free on site for use with a signed Release of Liability.