Family-friendly holiday rentals in Bainbridge Island

Light-filled Guesthouse in the Woods

Sleep near the stars and wake up to the birds in this private, studio guesthouse. Top to bottom this is a special place. Vaulted ceilings and sky lights allow natural sunlight to filter in above. Rustic hardwood floors, milled from the properties maple trees, gleam at your feet below. Open, modern kitchen complete with granite counters, stove, cooktop, refrigerator, microwave, coffee maker, toaster and everything you need to cook and eat at home. Private entrance and deck with outdoor seating allow you to enjoy nature as deer roam through the garden and birds dart around the trees.

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.

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.

Artist's Studio

This light, open and inviting space with sweeping Puget Sound views is fully furnished and available for rent. Natural light from abundant windows maximize the view, while the wall space tastefully showcases original art from local artists. This getaway is steps away from Fay Bainbridge Park, a beachcomber's delight. Explore all that the island has to offer or relax in the sun on your own private deck. On a rainy day snuggle up by the fire with a book.

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.

Froggy Heights - An English Cottage on Bainbridge

Tucked away at the end of a quiet lane, Froggy Heights is a charming two-bedroom cottage surrounded by trees and gardens. Wake to beautiful sunrise light streaming through the picture windows, relax with a book in the cozy living room, or enjoy a cup of tea overlooking the peaceful greenery. Thoughtfully designed for couples, friends, or small families, it's a tranquil Bainbridge Island retreat just minutes from Winslow.

The Private Peaceful Cottage

WELCOME to this delightful, comfy and cozy cottage with pocket views to the Seattle skyline, Cascade Mountains and Puget Sound shipping lanes. Less than 2 miles from the ferry terminal and downtown and only 3/4 mile from a public beach, you're surrounded by tall evergreen trees, resident bald eagles and gardens. A propane fireplace adds ambience and warmth. A comforting poodle mix, Bodhi, would likely greet you.

Secluded Hideaway in the Forest

This idyllic cottage on a private road is a few steps away from a trail into the Grand Forest yet the ferry terminal is less than ten minutes away. It is surrounded by majestic cedars and next to a quietly babbling brook on protected wetlands. The main house is further down the driveway. Please note that the internet connection here in the forest is generally decent but can be temperamental at times.

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.

Bainbridge Island, Crystal Springs Shangri-La.

Whole 2 bedroom cottage on half acre of land, with many amenities. Great retreat to refresh and relax in privacy. Shared beach, water and west facing views from large deck. Plenty of tables and seating inside and out. Fire pit between house and your own private hot tub. Additional tables and fire pit on beach. Kayaks and SUPs available if prequalified. Hammock for afternoon naps...