Holiday 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.

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.

4.98 out of 5 average rating, 129 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

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

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 ✨

Guest house in Friday Harbor

4.93 out of 5 average rating, 653 reviews

Peaceful Cottage on 15 acre Farm Pprovo-14-0016

Comfortable one bedroom cottage with sun-room (in the winter months it is very pleasant on a sunny day, allowing you to relax after a day of exploring the island). There is also a back patio with a great view overlooking the lower pasture and wetland. BBQ and comfortable outdoor furniture. On a hot day the patio offers good shade. It comfortably fits two and is centrally located. An easy 15 minute drive to most attractions. Dog friendly with pet fee (please reach out if you have questions).

4.97 out of 5 average rating, 168 reviews

Home in Friday Harbor

Twin Palms at Forbidden Island Motor Lodge

Welcome to Twin Palms, your passport to midcentury glamour and jet age style! Pass through sunny yellow doors into a tropical garden where Desert Modern meets Polynesian Pop. This completely private courtyard includes a propane fire pit, soaking tub and a pass-through bar, all sheltered by towering palms. Step inside your swank living room flanked by kitchen and bar areas. Beyond lies a bedroom featuring his and hers closets and a bathroom with heated floors and dual shower heads.

4.83 out of 5 average rating, 130 reviews

Cottage in Eastsound

FoxGlove Cottage Private Beach Sleeps 4 Wifi Pets

FoxGlove Cottage is nestled into the shoreline of Deer Harbor on Orcas Island. You will enjoy coffee or wine on the back deck with one of the most epic views this island offers. Walk out your back door to the beach, the marina or for local fare. This cottage newly updated. It is charming and quaint and ready to make memories for your family. We are pet friendly with pre approval. You are able to fly into Deer Harbor on Kenmore Air or use the Washington State Ferry System.

4.97 out of 5 average rating, 250 reviews

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.

4.89 out of 5 average rating, 125 reviews

Guest suite in Eastsound

Entire Guest Suite on Orcas Golf Course

🌟 Introducing our new private bedroom with a private bathroom: 🛏️ Enjoy a comfortable stay with 1 king bed. 🚪 The space has its own private entry for your convenience. 🌳 Located directly on the Orcas Island Golf Course, perfect for golf enthusiasts! 🍽️ While there's no kitchen, amenities include a small fridge/freezer combo, microwave, and access to an outdoor grill. Experience relaxation and convenience at Orcas Island – book your stay now! 🏌️‍♂️

5 out of 5 average rating, 248 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.

4.94 out of 5 average rating, 333 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

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Popular amenities for San Juan County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in San Juan County

4.97 out of 5 average rating, 116 reviews

water view cottage above West Sound

miriamRating, 5 stars2 days ago

We really enjoyed our 3 nights in this wonderful cottage.. enjoyed watching the birds in the garden.. looking out on to the water.. and the location was so private and peaceful.. we were very comfortable in the cottage and enjoyed a couple peaceful relaxing afternoons in the cottage as weather was a bit cloudy and cool. Miriam and Tom live in house right next to the cottage but we still felt very private... they were available for any needs but not intrusive either.. delightful couple and enjoyed meeting them and chatting a bit. The main bed is only a full size so we chose to use the futon for a 2nd bed and i was very comfortable on that for my sleep.. (and i didnt have to hear my hubby snore.. win win!!) Location was great for us.. right up the street from Kingfish restaurant on west end but not far from East sound either.. we would totally return and stay next time we go to Orcas Island..

KarenRating, 5 stars2 weeks ago

New place to stay

Sunset Hideaway-Oceanfront Bliss

This was a bit of an older Home, but I don't think there's anywhere else on the island that would compare. First of all when we arrive Jennifer, the owner was filling our rooms with fresh flowers, the place was impeccable, it was charming… The view was amazing you see Canada - Vancouver and the mountains from the backyard. While we were there there was a mother deer with two phones, eight River otters wrestling for about 45 minutes, a buck and a doe a few random river otters and then bald eagles it was simply amazing.

4.78 out of 5 average rating, 9 reviews

Romantic Oceanfront Getaway/Hot tub/Chef Kitchen

KyleRating, 5 stars1 month ago

This may be our favorite bnb we've stayed at on the islands and will probably be an annual thing. Such a perfect location and so quiet! Parking at the home is great, kitchen is fully loaded, living room is incredibly cozy, and all the seating from kitchen, to front window, to couch was perfect. We've stayed in places that were cool and fun locations, but there is rarely places to really cozy up and enjoy your stay in. The home was truly inspiring for someone who wants to build a tiny cabin one day. I wouldn't change a thing, cannot wait to get back!

5 out of 5 average rating, 43 reviews

Cabin in Lopez Island

Water and mountain views in a cozy wooded retreat

RichardRating, 5 stars1 month ago

We enjoyed our stay so much. It was such a relaxing atmosphere. The house was private but easy to travel and explore from.

4.95 out of 5 average rating, 276 reviews

Luxe Beachfront, Hot Tub, Kayaking, Walk to Town

AdamRating, 5 stars2 weeks ago

The house was exactly as described. Extremely clean, beautiful landscaping and design. The patio and hot tub were perfect. One previous review did mention it was near a main road, which it is, but that did not affect our stay at all. Could not have asked for a better place to stay and enjoy our anniversary. Would definitely book again. Thanks!

5 out of 5 average rating, 13 reviews

Home in Friday Harbor

Sunny Eagle Cove Waterfront Lookout

OliverRating, 5 stars5 days ago

What a wonderful location to get the best of the San Juan islands. Incredible views, nearby beach and trails. It is a short term minute drive to all that Friday Harbor has to offer. Chris and Diane were wonderful, communicative hosts and everything was in great shape. We can't wait for our next trip!