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A long, low dock has an inflatable boat and a sailboat tied to it. A higher, railed dock runs above it. An ornate white streetlight has a planter hanging from it.
Friday Harbor.

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10 weird and wonderful San Juan Islands vacation rentals

From nautical accommodations to fairytale retreats

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The San Juan Islands are one of the Pacific Northwest’s most beloved destinations. On the islands accessible by ferry—many are not—cute, small towns punctuate vast forests and farmland. They’re one of the absolute best places to watch for orcas right from the shore without the need to hop on a sometimes disruptive whale-watching boat.

The appeal is also in the culture of the San Juans, though. Those that live on the island full-time tend to be creatives, farmers, and artisans—and totally offbeat. So when they build places to stay for the island’s many guests, things get really inventive. Think treehouses, cabins made from dirt, fairy-tale hideaways, and, of course, boats.

All of these rentals are on ferry-accessible islands, but remember: Check that ferry schedule carefully and early. If you must drive, there are no guarantees of getting on that boat unless you make a reservation first—spots get released two months, two weeks, and two days from sailing. As a pedestrian or cyclist, though, it’s not difficult at all getting on the ferry. Orcas, San Juan, and Lopez all have cabs (or a water taxi!), too, although service moves a little (read: a lot) slower out there.

Island life is a little different, and so are these rentals.

A red cabin with a slanted roof has a protrusion on the right side like the bow of a boat, and a spiderweb-like window in the front. Evolve

Madrona Cove Cottage in Friday Harbor, San Juan Island

Evolve | $125 per night

This converted artist studio has water views through a dramatic front window, or outside from the front patio or a wide lawn over a bluff. A unique design makes for a fun roofline inside—and a great backdrop for your already stunning San Juan Island vacation photos. It sleeps two in a queen bed.

A rounded, covered deck along a rounded, wood-panel wall with two red-trim windows and a red door. There’s a selection of wooden chairs and a log railing. Courtesy of Doe Bay Resort

Treehouse at Doe Bay Resort on Orcas Island

Doe Bay Resort | $229 per night

Doe Bay is a relaxing and arty destination, with yoga classes, massages, soaking tubs, a cafe, and an annual music festival. Its collection of lodgings allows you to choose your own adventure, including tent sites, yurts, and cabins. But the standout is a treehouse built by DIY Network’s Treehouse Guys. It sleeps four people, has views of the Rosario Strait, has a private bath, and is powered—not always a given with that treehouse life.

Gnome House Chalet on Deer Harbor, Orcas Island

VRBO | $165 per night

Feel like you’re part of a fantasy novel in this storybook home, full of weird, fun pockets: a cupboard bed, a domed dining nook, and a built-in sleigh bed. It’s accented by meticulous, whimsical woodwork, including exposed roof beams and half-timbering. It sleeps up to six (up to four adults), and sits on 140 acres that include a hot tub, a play structure, and a campfire pit.

Lotus tents on Mount Baker Farm, Orcas Island

Mount Baker Farm | $218 to $348 for two nights

Mount Baker Farm sits on 80 acres within walking distance of Eastsound, which visitors can explore by train—a previous wealthy, eccentric owner installed train stations on either side of the property and ran track between them, which the current owners have maintained for use. There’s a petting zoo, too. The farm offers the full glamping experience with Lotus Belle and Bud tents available to rent, complete with beds, rugs, hammocks, stove, and fire pit. If you want to BYOTent, small campsites start at $40.

A treehouse with wooden walls and a shingled gable roof, high above water and surrounded by trees, viewed from a suspension bridge leading to the front door. Airbnb

Hilltop Treehouse Retreat on Lopez Island

Airbnb | $249 per night

Another treehouse sits above Lopez Island—smaller, but still ferry-accessible. This one, designed by Tom Froning of Soundesign, is mounted between two large Douglas firs in a way that allows it to rock in the wind while still staying stable. It’s accessible by suspended bridge for optimal privacy (and whimsy), sleeps three, and includes an bathroom and an outdoor shower. The design uses salvaged materials, including a porthole and cabinets made from a chuck wagon.

A white sailboat with metal railings and a lowered, navy blue sail on the water. In navy blue, the side reads, “NAMASTE, SEATTLE, WA.” Airbnb

S/V Namaste in Deer Harbor, Orcas Island

Airbnb | $94 per night

The idea of living on a sailboat is dreamy, but upkeep can be... a lot. Fortunately, this 42-foot sailboat is here for you to live out that fantasy for a while. It can sleep up to four guests in three cabins, although there’s room for six to hang out. You can’t leave the dock, but there’s kayak rentals—and a heated pool—nearby for getting in the water.

A room has clay walls with tiny bits of colorful glass embedded in it, plus two larger, more traditional windows. There’s a multicolored rug on the floor and a bed with a blue blanket on the far wall. Airbnb

The Foxes Den in Friday Harbor, San Juan Island

Airbnb | $119 per night

Really get back to nature in this cabin, built from earth and salvaged materials—including colorful glass embedded in the clay to light up the interior. It doesn’t have power, save for some battery-operated lights, but there’s a flush toilet and a hot shower in a nearby bathhouse. If an off-grid cabin isn’t away-from-it-all enough, the hosts offer a giant hammock 15 feet above the ground for your forest hangs. An added bonus: The hosts bring by baked breads, fruit, juice, and coffee or tea each morning.

Two structures (one ten-sided, one twelve-sided) with wood-slat walls emerge from an elevated deck, surrounded by evergreen trees. Flipkey

Forest House on Orcas Island

Flipkey | $175 per night

The exceedingly ornate Forest House serves magical vibe and a treehouse sensibility within a network of decks. Decagon and dodecagon-shaped wings—including a separate, two-story tower—are covered in tall windows with Gothic arches, domed ceilings, and skylights. Live-edge-wood decor gives it an even more sylvan vibe. It sleeps up to three.

An octagonal bedroom with green walls and a center log column. A bed is along a far wall in front of an arched window. Airbnb

Garden Cottage on Lopez Island

Airbnb | $93 per night

This bright little one-bedroom cottage, which sleeps two, gets its charm from octagonal shapes anchored by skylights. It’s walkable to shops and restaurants—not always a guarantee, especially on the smaller islands—but has a cozy wood stove and patio seating for staying in.

The exterior of a home with weathered, exposed-wood siding and glass French doors at entry. There’s a small covered front porch with a windchime dangling from it. VRBO

The Roost on Orcas Island

VRBO | $143 per night

This airy abode is a converted barn, the former home of horses, cars, and even a stained glass studio. Plenty of interior and exterior windows and a high ceiling bring in plenty of light, despite being tucked in the woods, and the grounds include a tranquil garden with a waterfall and koi pond. It can sleep up to four.