Vacation rentals in Cypress Island

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Top-rated vacation rentals in Cypress Island

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Guest favorite

A spacious deck extends over the water, featuring a rustic wooden table and inviting adirondack chairs in vibrant green. Soft lighting provides a warm ambiance, while scenic views of the shore and distant trees are visible across the calm water.

Home in Eastsound

4.94 out of 5 average rating, 118 reviews

The Lodge: Private beach, kayaks, hot tub, bikes,

Book w/Confidence! Buy Trip Insurance. We have 4 rooms in which you can sleep (see photos). Stunning views, private beach just steps from our 40 ft deck, hot tub, bikes, kayaks, row boat, crab pots, fire pit, ping pong table, BBQ. You will have the ultimate vacation on Orcas Island. Inside you will find a luxurious master bedroom, 2 bathrooms, 2 bedrooms, 2 "bonus" rooms, 6 beds. Pet Fee: $100 first pet. $50, second pet. We require a signed rental agreement prior to check-in. PCUP000-16-0032

Top guest favorite

A vibrant sunset paints the sky with shades of orange, pink, and purple, transitioning into deep blue hues. Silhouetted trees and a gentle landscape outline the scene, creating a serene backdrop against the dramatic cloud cover.

Guesthouse in Friday Harbor

4.96 out of 5 average rating, 137 reviews

Park Place

1,000 sq. ft. custom cottage 4 miles from town. Hosts Chris & Tom take pride in sharing their oasis with you. Nicely decorated, spacious, open living area with vaulted ceiling, a full kitchen with granite counter tops. Two bedrooms separated by a bathroom & laundry room ensure privacy & restful sleep. Ideal for 2 couples. Located halfway between the town & American Camp with easy access to miles of hiking trails & bicycle routes. Although only minutes from town you experience the country side.

Guest favorite

A deck area features a bistro table with two chairs and an additional chair, surrounded by tall trees. The view includes water and distant hills, creating a peaceful outdoor space for relaxation.

Cottage in Eastsound

4.97 out of 5 average rating, 283 reviews

WaterView,Impeccable Studio Cottage, Walk to Town

With stunning views of East Sound on Orcas Island, our charming studio cottage was fully updated in 2019! Just a short walk to restaurants, shopping, and Eastsound Waterfront Park, you can enjoy the sunrise from the deck, cozy sofa, or comfortable queen-size bed in this lovely 300 sq. ft. space. Perfect for a solo retreat or a couple's getaway, our cottage features all-new appliances, quartz countertops, a tiled bathroom, comfy bedding, and new flooring. Your island escape is ready for you 🏝️✨

Top guest favorite

A bright living area features large windows with sweeping views of the water and sunset. A cozy sofa sits atop a wooden floor, complemented by a coffee table. A dining area with wooden chairs is positioned near the window, allowing for scenic dining experiences.

Cabin in Oak Harbor

5 out of 5 average rating, 184 reviews

Sunset Beach Haven- Whidbey "Seriously Waterfront"

5-Star: Highest rated! In the words of our Guests: "It's Like Living on a Boat", "Seriously Waterfront", "Magical Place", "Sunrise & Sunset Heaven"! Sunset Beach Haven is a classic 2 bedroom, one bath beach cabin, updated with modern comforts and new state of the art kitchen! NEW! Seasonal AC bedroom window units. Enjoy phenomenal views of the Olympic Mountains, the Straight of Juan de Fuca, the San Juan Islands, and Swantown Lake (yes, 360 water views). Enjoy the wild side of Whidbey!

Guest favorite

A deck area features outdoor furniture, including chairs and a table, providing a clear view of the surrounding landscape. The scene captures the ocean in the distance, framed by lush trees and a serene sky.

Home in Eastsound

4.94 out of 5 average rating, 112 reviews

The Red Harbor: Retreat/Refresh/Rekindle

Perfect location for a restful getaway on one of the most beautiful islands in the country! We are new owners to this property, and have done everything possible to make it a special place to relax and enjoy family and friends! Complete with 3 bedrooms and two bathrooms (one bdrm and bath on main level and two bdrms and one bath upstairs). The master bedroom is huge with a deck, where views of the Sound and mountains are pristine! Don’t hesitate to book this sweet spot! You won’t regret it!

Guest favorite

A small table holds a bottle of wine and two glasses on a balcony overlooking the serene waterfront. Views of the calm sea and lush green hills are visible in the distance, with scattered clouds framing the scenic landscape.

Loft in Eastsound

4.95 out of 5 average rating, 311 reviews

The Windward Studio at SeaStar Lofts

Enjoy gorgeous views from this beautifully appointed condo perched right on the shore! Every convenience for your stay: fine linens, eco-friendly amenities, compact kitchen, locally roasted coffee, tasteful furnishings, and more. SeaStar Lofts are in the heart of charming Eastsound Village, with shops and restaurants just steps away. MARCH 2020 UPDATE: due to Corona Virus concerns we're offering a full refund should you need to cancel. And rest assured, we THOROUGHLY disinfect between guests.

Guest favorite

A spacious outdoor deck is visible, featuring comfortable seating options including a blue bench and a single chair. Lush greenery and a serene waterway are framed by trees in the background, providing a scenic view of the natural landscape.

Home in Port Hadlock-Irondale

4.9 out of 5 average rating, 135 reviews

Oasis By The Sea

Unwind and breathe in the fresh ocean air as you enjoy scenic views of the Puget Sound. This quiet oceanfront getaway is the perfect retreat for rest and relaxation. Beautifully situated only steps from the waterfront or a quick 20 minute drive to Port Townsend; The stunning views of the gorgeous sunrises and majestic mountains are magical; come and indulge in everything the Olympic Peninsula has to offer, from tourist activities to soothing sunset strolls on the beach. Your oasis awaits.

Guest favorite

A dining area is set with a round wooden table surrounded by light-colored chairs. At the center, a vase filled with greenery rests atop a woven placemat. Large glass doors frame a stunning view of the water and a colorful sunset.

Cottage in Mukilteo

4.96 out of 5 average rating, 107 reviews

Waterview Rabbit Hill Cottage

Escape to this charming cottage with stunning water views from almost every room & a cozy atmosphere. You’ll feel instantly at peace as you settle in to enjoy your vacation. Cozy up by the fireplace or cook a delicious meal in the fully equipped kitchen. The plush beds & soft linens in the beautiful bedrooms offer ultimate comfort. As the sun sets, immerse yourself in the warm bubbles of the hot tub & let your worries melt away or gather around the flickering flames of the fire pit.

Guest favorite

A spacious deck is shown with a dining table surrounded by several chairs. The scene is complemented by a lush yard and an unobstructed ocean view under a bright sky. Green trees provide a natural backdrop, enhancing the outdoor space.

Home in Friday Harbor

4.92 out of 5 average rating, 135 reviews

Friday Harbor Delight - Spacious Home w/Ocean View

Enjoy the stunning Ocean View from his 3 BR home that has it all. In Town location, Master Suite w/King bed and en suite bath. Second BR w/ Queen Bed and adjacent full bath. 3rd BR with bunk beds and a trundle for the kids. Large Deck for lounging with Dining Table, BBQ, and Hot Tub. Fully stocked Kitchen, Highest WI-FI speed on the island, Office with printer/scanner. The Kids will love the huge yard. Oh, and the view...did I mention the view?

Guest favorite

A view of the dock extending into the calm water, featuring a colorful kayak and paddleboard resting on the platform. Adjoining wooden chairs create a cozy seating area, surrounded by lush grass and trees, offering a serene atmosphere for relaxation by the waterfront.

Cottage in Eastsound

4.98 out of 5 average rating, 120 reviews

The Cottages at Twin Coves, Orcas Island (#1 of 2)

NEW in 2024 - COVERED OUTDOOR cooking perfect for preparing your own meals! Twin Coves offers serene seclusion with 400 feet of private shell beaches on West Sound. Two seaside firepits. Catch and release crabbing for kids, beachcombing, boating, swimming, hiking, and ample acreage for sports and games. Free use for registered guests: five kayaks seating six + toddler, two stand up paddleboards, and life vests in every size.

Guest favorite

A wooden staircase descends toward a tranquil beach landscape, leading to a pebbled shore. Calm waters stretch out to the horizon under a blue sky with wispy clouds.

Cottage in Sequim

4.89 out of 5 average rating, 342 reviews

6-Romantic Waterview-Hot tub-Private beach-Kitchen

Romantic Waterfront Cabin Getaway • Private Beach Access: Just steps away. • Relaxation: Cozy up indoors or enjoy your private hot tub with stunning sunsets. • Compact Kitchen: Perfect for intimate meals. • Nearby Attractions: Lavender fields, Dungeness Spit, Olympic National Park, Olympic Game Farm, and Victoria ferry. • Serene Escape: Ideal for romance and tranquility. Minutes from town, this is your perfect getaway!

Guest favorite

A well-maintained grassy area features a stone pathway leading towards the sea. Several white chairs are positioned in an inviting circle under the shade of tall trees. Views of the water are visible beyond the garden, framed by lush greenery.

Cottage in Friday Harbor

4.89 out of 5 average rating, 125 reviews

Cottage by the Sea

Lovely cottage by the sea with private beach access. Amazing views with the whales coming by often. You will also get daily eagle sightings and sunsets like no other. (We also have FAST fiber optic WiFi for those looking to take meetings remotely.) This spot is one of the best you'll find on the island. Come enjoy this nestled gem on Sunset Point!