Vacation rentals in San Juan County

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Top-rated vacation rentals in San Juan County

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Guest favorite

A white horse is seen walking through a lush green meadow, accompanied by two darker horses in the background. Behind them, a charming red cottage with surrounding windows peeks out from the dense greenery of trees and shrubs.

Farm stay in Eastsound

4.83 out of 5 average rating, 598 reviews

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.

Top guest favorite

A vintage cabin is framed by trees and lush green grass, illuminated by soft evening light. A wooden picnic table sits on the lawn, enhancing the inviting outdoor space. The cabin’s porch leads to scenic views of the nearby water.

Guesthouse in Eastsound

4.99 out of 5 average rating, 136 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.

Guest favorite

The cottage features a spacious deck with several black bistro chairs and a table, surrounded by lush greenery. French doors provide access to the interior, and a gas BBQ is positioned nearby for outdoor cooking.

Cottage in Eastsound

4.97 out of 5 average rating, 302 reviews

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 ✨

Top guest favorite

A spacious wooden deck is shown, featuring two comfortable chairs and a glass table. Potted plants add greenery, while a scenic view of the water and distant mountains can be seen in the background under a clear blue sky.

Apartment in Eastsound

4.97 out of 5 average rating, 276 reviews

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

Top guest favorite

A serene outdoor area features a wooden deck with a dining set and views of the water. Lush greenery and flowering shrubs frame the pathway leading to the house, complemented by rocks and plantings, enhancing the tranquil setting.

Home in Eastsound

4.95 out of 5 average rating, 282 reviews

Luxe Beachfront, Hot Tub, Kayaking, Walk to Town

Welcome to Beach House, our exquisite beachfront retreat where nature and luxury come together for a perfect romantic getaway. Located on the iconic Crescent Beach of Orcas Island, you’ll enjoy miles of sandy beach right out your door. Step inside to a custom-built cottage with a master suite, fireplace and gourmet kitchen. The meticulous gardens and interior have a zen vibe for a refined and peaceful experience. Come and unwind in the hot tub under the stars. Dreaming is encouraged!

Guest favorite

A charming wooden cottage is nestled among tall trees, surrounded by lush greenery. The entrance features a flower box overflowing with colorful plants. A wheelbarrow rests nearby on moss-covered ground, adding to the rustic appeal of this tranquil setting.

Cabin in Eastsound

4.93 out of 5 average rating, 255 reviews

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.

Top guest favorite

A charming cottage with bright orange siding is showcased, surrounded by lush greenery. A round table with four wooden chairs is positioned on a grassy area, inviting relaxation. The entrance features a single door, complemented by windows that allow natural light.

Cottage in Eastsound

4.97 out of 5 average rating, 256 reviews

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.

Top guest favorite

A breathtaking sunset view from a mountain top showcases layers of colorful skies transitioning from orange to pink. Below, tranquil waters reflect the soft hues, while silhouettes of distant islands and lush trees create a striking foreground.

Guesthouse in Eastsound

5 out of 5 average rating, 258 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.

Top guest favorite

A cozy living area features large French doors that open to a deck, allowing natural light to fill the space. Comfortable seating includes a dark chair with a soft throw and a light sofa adorned with decorative pillows. A small wooden coffee table sits on a textured rug.

Guesthouse in Eastsound

4.94 out of 5 average rating, 343 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

Top guest favorite

A serene water view reflects soft pastel hues of pink and blue in the sky, surrounded by lush green hills. The stillness of the water is complemented by distant tree-covered slopes, creating a peaceful natural setting.

Guest suite in Eastsound

4.98 out of 5 average rating, 288 reviews

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.

Top guest favorite

A cozy living room features rich wooden walls and ceiling beams. A large sectional sofa is adorned with various cushions and a soft throw. A coffee table sits at the center, surrounded by potted plants, while a television is mounted on the wall opposite a large window allowing natural light.

Cabin in Eastsound

5 out of 5 average rating, 170 reviews

the Honey BnB

Just a few short miles from Eastsound, the Honey BnB perches on the shore of a small pond teeming with wildlife. From the house you might see ducks, herons, geese, kingfishers, eagles, otters, turkeys, and deer among many other types of birds and beasts. A quick walk to the beach and you'll find plenty of skipping stones and an excellent panoramic view across the water.

Guest favorite

An outdoor stone patio features a fire pit surrounded by six black Adirondack chairs. The sunset casts warm hues over the landscape, with ocean views visible through the trees. A lush lawn leads to the water's edge, emphasizing the serene natural setting.

Home in Eastsound

4.97 out of 5 average rating, 111 reviews

Amazing sunsets, water view, hot tub, near town.

Orcas Sunset Retreat is a tastefully decorated 2900 sq ft home on nearly 3 acres overlooking the Salish Sea. This home boasts high quality furnishing, linens, and cookware. Expansive ocean views can be enjoyed from inside and out. This serene setting is the perfect escape from your everyday life, all the while being just 1.5 miles to the charming village of Eastsound.