House holiday rentals in Bainbridge Island

Beautiful Crystal Springs - Private Beach & Views

Featured in Cascade PBS Hidden Gems, our completely renovated 1930's beach front cottage is located in the island's south end, sunny Crystal Springs neighborhood. Featuring a chef's kitchen, vaulted great room, wood burning fireplace and stunning Puget Sound view where you can take in sunsets from the covered lanai, deck or relax on 100 feet of private no bank waterfront. One of the few homes with a private, fenced yard and beach. Enjoy nearby trails & Pleasant Beach Village just minutes away.

The Perch @ Eagle Harbor

Enjoy pristine views of Eagle Harbor and serene sounds of the Puget Sound at this recently remodeled spacious one-bedroom with a living room and a library/den. Set at the end of a private road, a separate entrance, patio and garden add to the tranquility and privacy of this oasis. The cozy dwelling is complete with outdoor chaise lounges, dining table, and a fire table to enjoy views of the marina. A short walk to the beach and close to Winslow, The Perch captures the best of Bainbridge.

Winslow Oasis with Sunroom and Fireplace

Stylish condo walking distance from the Bainbridge Ferry and in the heart of town. The condo is close to everything but still feels secluded and private. There is some road noise due to the location. Enjoy cooking your meals in the well appointed kitchen or walk across the street to enjoy an array of dining options. The sunroom provides a private and warm oasis from which to enjoy your morning coffee or relax surrounded by lush greenery. Both bedrooms have queen beds with quality linens.

Canyon Creek Cabins: #1

Perched high on a granite ledge, you will find this cabin overlooking a rushing river that weaves its way through the dense, lush forest of the North Cascade mountains. The unique asymmetrical A-frame structure is both unexpected and familiar, with its wood-clad walls, exposed beams, and large geometric windows. Whether you are playing whiskey-fueled card game by the fire, or lounging in the hottub while listening to the nearby rushing creek, this cabin offers the ultimate cabin experience.

Conifer House Hideaway at Wing Point

Welcome to this beautifully appointed home nestled among the trees on Bainbridge Island! The neighborhood offers quiet privacy, while being just a 5-minute drive from bustling Winslow and the ferry terminal. The home provides gracious hospitality, a design-forward aesthetic, and plenty of space for multi-generational families to stay together. From hiking, to beachcombing, kayaking, wine tasting, and meals from award-winning chefs, the Kitsap and Olympic Peninsulas have so much to offer!

Simple Living at Modern Farmhouse on Bainbridge

Your adventure begins... in a new, modern and fresh space with tons of natural light and privacy. Imagine waking to the sounds of farm animals, sipping morning coffee on your covered porch as sunlight breaks through the big leaf maples, wandering miles of forested trails, biking island roads, kayaking, paddle boarding or combing sandy beaches of Puget Sound while searching for sea treasures. When nighttime falls, share stories around a bonfire and count stars as they fall from the sky.

Water View | Deck, Luxury Space | Families & Pets

Traveling with kids and/or your dog? You've found your place. Welcome to Sunrise Oasis - a family- and pet-friendly mid-century modern retreat built with both in mind. Wake to breathtaking sunrises over Puget Sound from oversized windows and the expansive deck, then stroll to Rolling Bay's winery, and local market just down the road. A thoughtfully laid-out home where little ones, dogs, and grown-ups all find their happy spot - and where the view never stops being the star.

Whidbey & Chill - Mid-Century Modern Waterfront

A lovingly restored classic Mid-century Modern Waterfront home with JAW DROPPING VIEWS. The nearly 270 degree westside view spans Mt. Rainier, downtown Seattle, the Olympics, Port Townsend, and the San Juan islands. Sitting on nearly an acre with privacy so difficult to find, this home features a circular driveway, full length deck, master suite with its own private deck, a chef's kitchen with high end appliances, and close proximity to all that Whidbey Island has to offer.

Enchanted Forest Cottage

Escape to the cozy cottage in the forest of big trees. Ecologically built, a healthy environment with everything you need for a comfortable stay. Large picture windows make you feel like you are part of the forest. Enjoy visiting the Norwegian town of Poulsbo, yet Seattle is not far away. There are also many hiking and mounting-biking trails, parks and beaches nearby, and the Olympic National Forest is just a javelin-throw away. Experience the magic of the big trees!

Tideline Bainbridge Luxury Waterfront

Tideline Bainbridge has natural beauty and comfort in every detail. Inside, luxuriate in a new home with high-quality everything. Casper mattresses, OLED TV, Italian cookware, the list goes on... The primary bedroom is jaw dropping, guest room is lovely, and the den is cozy. Outside, enjoy two levels of decks, our private no bank beach, kayaking, and sweeping views of Seattle, ships, and mountains. Get lost in the Puget Sound, with regular sea life sightings.

Dahlia Bluff: Luxe Retreat/Stunning Views, EV Chg

Dahlia Bluff Cottage overlooks Puget Sound with unforgettable 180° views of the water, Mount Baker, and Seattle. Enjoy the panoramic deck and pristine saline hot tub, meticulously serviced before each guest’s stay. A short walk to espresso, pastries, wood-fired pizza, and Italian takeout. Fully equipped kitchen and luxe comforts make this tranquil retreat a magnificent vacation spot or perfect work-from-home escape. Minutes to Manitou Beach by car or on foot.

Luxury Waterfront w/ Private Dock + Kayaks

True waterfront on Point Monroe with private dock and panoramic Bay views. Launch the provided kayaks and paddleboards from your own shoreline, bring your boat, and unwind around the firepit as seals and eagles pass by. Newly remodeled with open-concept living that flows directly to the water. Walk to Fay Bainbridge Park and reach the Seattle ferry in just 15 minutes. A rare Bainbridge stay where the water isn’t just the view — it’s your backyard.