Holiday rentals in Cypress Island

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Top-rated holiday rentals in Cypress Island

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Guest favourite

The image captures a vibrant sunset over the ocean, framed by tall trees. The sky displays rich hues of orange, pink, and purple, reflecting on the water. Silhouetted islands and distant mountains enhance the natural beauty of the scene.

Home in Olga

Two story cedar home with incredible oceanview.

Bungalow 252 is a secluded hilltop cedar home getaway. Magnificent 130 degree view of the ocean, Mt. Baker and the Cascades. Hardwood flooring. Eagles, bats, deer and raccoons abound. BBQ, watch boats and occasionally orcas from the deck. Nicely stocked full kitchen. Wood stove. Pod coffee maker with coffee, chai, hot chocolate. Two 3D HDTVs with streaming. High speed WIFI (100 MBPS upstairs, slower downstairs), cell service. Games, books, DVDs, binoculars, telescope. Soap, shampoo, conditioner.

4.95 out of 5 average rating, 736 reviews

Guest favourite

Tiny home in Anacortes

The Eagle's Nest w/ Hot Tub & Water Views

⸻ This tiny home’s most captivating feature is its breathtaking view down Guemes Channel. Imagine soaking in the hot tub while taking in the peaceful trees and water scenery — kick back, relax, and truly unwind. Thoughtfully designed touches throughout make this small space feel warm, inviting, and perfectly suited for a relaxing getaway. This incredible location offers the best of all worlds. Romantic, serene, and unforgettable — you’re sure to make lasting memories at The Eagle’s Nest.

4.97 out of 5 average rating, 155 reviews

Top guest favourite

A modern black structure stands amid lush greenery, characterized by large windows and a flat roof. A picnic table is positioned on the grassy area in front, surrounded by tall trees. Sunlight filters through the foliage, illuminating the natural setting.

Cabin in Anacortes

Cozy Modern Cabin - The Dragonfly on Guemes Island

Escape to a pet-friendly paradise on Guemes Island! This 2-bed, 1-bath open floor haven sprawls across 2.5 lush acres. Imagine: industrial-grade steel meets polished concrete, inviting nature inside through expansive windows. A glass reading nook, a balcony for forest views, and a woodfire stove providing cozy comfort. Embrace the outdoors inside and revel in the flood of natural light. This is your private retreat—full access to a nature-infused getaway! We are pet-friendly w/no pet fees

5.0 out of 5 average rating, 129 reviews

Top guest favourite

Cottage in Guemes Island

Guemes Is Seaside-easy access to San Juan Islands

Love beach combing, sunsets, and sealife? This island escape is for you! King bed, Starlink wifi, kids & pets welcome, mooring offered. A 5-minute ferry ride will bring you to our whimsical west-beach cottage & property on Guemes Island with its panoramic views and magical sunsets...perfect for relaxing, taking beach walks, finding treasures, hiking our mountain & local trails, exploring your favorite water sports, and spotting herons, seals, bald eagles, & occasionally whales & more.

4.97 out of 5 average rating, 272 reviews

Top guest favourite

A well-lit studio space features a modern design with large windows offering views of the outdoor greenery. A spacious bed is complemented by a cozy seating area with an accent chair and a coffee table. A dining table and kitchen area are visible, enhancing the functionality.

Flat in Anacortes

Island Gateway Anacortes Studio and Sauna

Bright, beautiful studio with full kitchen, coffee bar, private bath and outdoor fire pit. Adjacent outdoor cedar sauna that we share with our guests in both units. Minutes from the Anacortes Ferry Terminal. Note: We live upstairs in a totally separate part of the house and the studio is adjacent to another unit. We have soundproofed the house as well as we can, but there are normal noises that come with shared living. The studio has one queen sized bed. We don't accept children.

4.98 out of 5 average rating, 871 reviews

Top guest favourite

The cabin exterior is showcased amid tall trees, featuring a warm wooden structure alongside a treehouse. An inviting cedar hot tub is situated on a stone patio, with red Adirondack chairs arranged in a circle nearby. The landscape is brightened by the soft sunlight filtering through the foliage.

Cabin in Lummi Island

Lakeside Cabin in the Trees with Views & a Hot Tub

Heron’s Nest Cabin sits on a wooded hillside above Hale Passage and Bellingham Bay — a two-bedroom island retreat where towering firs, filtered water views, and a cedar hot tub under the trees set the tone from the moment you arrive. Guests consistently call this one of the most restorative places they’ve ever stayed: a soaking cedar hot tub, a wood stove to curl up beside, heated bathroom floors, vaulted ceilings, and a fully outfitted kitchen for slow mornings and easy dinners.

4.96 out of 5 average rating, 155 reviews

Guest favourite

A hillside cabin is nestled among trees, featuring a spacious wrap-around deck. The structure combines dark wood and light wood elements, with large windows providing views of Lopez Sound. A wooden pathway leads up to the entrance, surrounded by lush green grass.

Cabin in Lopez Island

Sunrise Waterfront Retreat w/Hot Tub, Beach Access

Escape to Sunrise Retreat and enjoy the tranquil setting of Lopez Sound. This waterfront hillside cabin has an open concept floorplan with a sleeping loft for up to 5 and is a cozy place to relax and enjoy amazing panoramic water views and sunrises. This retreat features a new kitchen, a new bath with a spa-like shower, and beautiful hardwood flooring. Enjoy grilling and hot tubbing on the wrap-around deck, out door fire pit, and short walks to the private community beach.

4.92 out of 5 average rating, 249 reviews

Top guest favourite

A sunny meadow is occupied by grazing cows, with the Field House visible in the background. The house features solar panels on the roof and large windows, surrounded by lush greenery and trees. The open lawn invites exploration within the working farm setting.

Farm stay in Lopez Island

The Field House Farm Stay on Midnight's Farm

Step into island life, relax into the land on a 100 acre working farm. This sunny home invites you to read in the window seat, grill on the patio, cozy up to the woodstove or get creative in the well-stocked kitchen. Explore the pastures, marsh, and ponds. Use the yoga studio. Fire up the sauna. Charge your EV. Nestled next to the pond and removed from the activity of barn and market garden the Field House invites you to enjoy your own retreat or engage with the farm.

4.99 out of 5 average rating, 253 reviews

Top guest favourite

An outdoor seating area features multiple chairs around a stone fire pit, set against a backdrop of lush greenery and distant water views. A wooden deck extends from the home, providing access to the space while surrounded by well-maintained landscaping.

Home in Lopez Island

Spectacular View Home, 4 Bedrooms on 16 Acres

Beautiful four bedroom home at the top of a hill with a spectacular view overlooking acreage and the water. Very private, nestled on 15 acres that deer & bald eagles love to call their home. Plan to have a great time hiking, biking, playing horseshoes, basketball, flying kites, beach combing, or simply enjoying a stroll along the beach. Above all, If you savor privacy, beautiful views, relaxing, smelling & breathing salt water air - you will love this getaway home.

4.91 out of 5 average rating, 202 reviews

Top guest favourite

Home in Eastsound

Luxury Waterfront & Views, Private Beach, Golfing

Welcome to Eastsound Shores, our spacious designer home overlooking the Salish Sea! 🌊 Enjoy expansive decks for outdoor living and dining, a fantastic Chef's kitchen, and cozy evenings by the fire with games and a wet bar. Each ensuite bedroom features a luxurious bathroom, perfect for family and friend gatherings. Plus, explore the private beach trail and unique rocky shore right at your doorstep. We can’t wait to host you for an unforgettable getaway!

4.99 out of 5 average rating, 122 reviews

Guest favourite

Snow-capped mountains rise majestically in the distance, reflecting soft hues of pink and blue in the early morning light. The tranquil water of the Puget Sound gently laps against scattered rocks in the foreground, providing a serene connection to the landscape.

Home in Decatur Island

Hobby Farm Remote private island! Escape Seattle!

Best views in all of the San Juan Islands! Take a private ferry 20 min from Anacortes to remote Decatur island! 20 acres of deer trails and a private beach. This is a hobby farm where dogs are welcome. Gorgeous trails, fire pit and amazing hikes. Enjoy this perfect natural hideaway! Play golf, hike the beach, or visit the old fashioned Country Store for milkshakes and coffee. We also have a great Farmers Market! Kayaking from the beach!

4.91 out of 5 average rating, 281 reviews

Top guest favourite

Two Adirondack chairs are positioned facing a serene waterfront view. A sailboat glides across the calm water, set against a backdrop of rolling hills and trees. Lush greenery and ornamental rocks frame the scene, enhancing the natural beauty.

Guest house in Anacortes

Waterfront Guesthouse Guemes Is., San Juan Islands

Our thoughtfully equipped waterfront mini guesthouse is just steps away from our beachfront on the Guemes Island. Located on the scenic western shore of the island, you can enjoy extraordinary sunsets, panoramic island views, miles of beach combing, and abundant wildlife. Our mini guesthouse, "The Seldom Inn" measuring 12 ft. x 14 ft. in size, is approximately 150 feet from our private beach and is located behind our main home.

4.97 out of 5 average rating, 367 reviews