Holiday rentals in Cypress Island

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.

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

Byrd's Nest Guesthouse

Byrd’s Nest is a retreat nestled among the trees. This custom-built guesthouse was completed in June 2025. It spans 357 sq. ft. and features a studio layout with a kitchen and bathroom. Surrounded by evergreen trees and approx. 30 feet from the main house, it offers a charming treehouse-like experience. The whole property is 6.6 acres at an elevation of over 200 ft. Views of Mount Baker, the North Cascade Mountain range, the Skagit Bay, and forest land can be seen from the guesthouse.

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.

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.

DenPNW with Sauna

DenPNW is a recently curated space that will indulge your desire for beauty and romance. A modern design with tile and wood walls and free standing stove. The studio has a comfortable king sized bed, built in office space and full kitchen with island. Shared sauna included. The studio is adjacent to another unit and owners live upstairs. You may hear faint noises from shared living and light footsteps upstairs. This space is not suitable for children or infants

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!

Eagles' Bluff

Watch eagles soar over the Salish Sea with the Olympic Mountains and San Juan Islands in the background. You will enjoy beautiful vistas and spectacular sunsets from the porch of the cabin. Our cozy studio cabin is located halfway between the charming town of Anacortes and Deception Pass. Enjoy hiking, fishing, kayaking, and whale watching as well as dining and shopping - just be back in time to watch a gorgeous sunset unfold.

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.

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 Summer Saturday Market. Kayaking and great hiking right from the beach!

Oceanfront Home- Just Steps from Private Beach

Escape to this idyllic beach house nestled on the shore just a stone's throw away from your own private beach. Enjoy the unobstructed panoramic views of the ferry sailing by, Mount Baker, Bellingham Bay and Portage Island. The journey down the many winding stairs is not for the faint of heart, but is completely worth the trek once you find yourself in your own private haven.

Charming Guemes Island Getaway w/ Hot Tub & View

Just a 6 min ferry ride from Anacortes to beautiful Guemes Island. Spot eagles and watch the working waterfront from the south facing patio with gas grill. Enjoy a relaxing dip in the sparkling clean hot tub with beautiful views. From your front door you can walk or drive to Cook's Cove, Guemes Mountain trail, and beach access trail. You'll love it here!