Family-friendly holiday rentals in Bainbridge Island

Contemporary Bainbridge Island Apartment

Light, airy, warm and cozy open concept, modern 2nd floor apartment with vaulted ceilings and contemporary styling. Spacious 600 sqft living, dining and kitchen area. Elegant private bedroom with queen bed, and walk in closet. Bathroom with shower. Access to sunny deck for coffee and dining. Prime location on Bainbridge Island - 5 minutes walk to beach, 15 minute walk to the Seattle Ferry and all the amenities of Winslow. Charming place to explore Bainbridge Island, Seattle and the Puget Sound.

Cozy guesthouse on tranquil family farm.

You’ll sleep great in this light-filled king-size suite at the B-hive. Freshly updated, centrally located on Bainbridge Island, situated on the 26 acre Bountiful Farm. Sometimes used as a wedding venue, surrounded by a pastoral setting with mature landscaping, flowers, & animals galore. An artist's retreat, family excursion, farm animal experience or just a relaxing getaway from the city, we think you’ll find just what you need at the B-hive! BI WA Short-Term Rental Certificate # P-000059

Tranquil Studio Dogwood - Downtown Winslow

Welcome to Studio Dogwood, one of four studios at Vineyard Lane Condo community, the perfect location to begin exploring beautiful Bainbridge Island. Walking distance to Winslow's fine dining, shopping and waterfront trails, you'll enjoy this comfortably appointed studio w/ king bed, fireplace, flatscreen smart tv, mini-fridge, Keurig coffee and tea. Ideal for those looking for a peaceful getaway. *This studio has vaulted ceilings and is on the upper level of our building, accessed by stairs.

Etoille Bleue -A Water View/Sauna Retreat

17 windows & 4 skylights flood this modern 900 sq ft space with light & offer stunning views of majestic pines framing the water. Enjoy a 2 min walk to beach & 10 min walk to Battle Point Park. Relax in indoor sauna, enjoy oversized rain shower with hand wand. Bathroom inc double vanity & radiant floor heating. Enjoy cooking/entertaining in a fully equipped kitchen with large island bar, Chef's gas cooktop, double oven & full sized fridge/freezer. Pack light! Equipped with washer/dryer.

Luxury Farmhouse-Style Living in the Heart of Bainbridge

Completely separate and private guest suite walking distance to downtown Winslow (1/2 block), the ferry (.6 miles), the harbor and the 8.5 acre Moritani Preserve (1 block) away Easy access via a code. I am always available for questions.. I live in the main house in the front but you will have complete privacy. It's a very safe area and people are warm and friendly. Check out the farmers' market on Saturdays at Bainbridge Performing Arts. You have space to park one car in the carport.

Roundhouse in the Fairytale Grand Forest

Listen to the trees and rain, in the Fairytale Roundhouse! Warm and cozy, sip some wine, enjoy nature! Trails to the Grand Forest and Battle Point Park, are at your doorstep. Cuddle up in the media loft & fall asleep on the wonderful pillow top King. All hail "The Queen" bed is below and a full Prince or Princess bed in the blue room. A "Jack n' Jill" bathroom with comfy white towels, Soap, Shampoo and Conditioner. No Pets or Assistance animals due health issues. Absolutely No Smoking!

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.

Guest House with a view above the beach.

Come explore beautiful Bainbridge Island and stay in our comfortable guest home. Located 5 miles from the ferry on the Northeast side of the island. This home is a separate dwelling with it's own driveway and private entrance located on our property. The short walk to the beach is about 5 minutes where you can have a beach fire, build a fort or simply relax and enjoy the views of the shipping lanes, Mt. Rainer, herons, eagles, orcas and our neighborhood sea lions.

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.

Stylish Guest Apartment Suite on Bainbridge Island

Just a short walk from this stylish, modern, cozy and private second story suite down a private drive lies the beach on coveted Crystal Springs. Take a stroll along the water or explore one of the islands numerous walking trails. Conveniently located to South End attractions such as Pleasant beach Village, historic Lynwood Center, and Islandwood, you are sure to find something that strikes your fancy.