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.

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

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.

Cozy Clean Getaway

Cozy MIL style studio, in a private garden setting. Perfect for the solo traveler or couples getaway. Close to downtown, shopping, eateries, entertainment, parks, trails & more! Equipped with a fully stocked kitchenette, hair dryer, toiletries etc. Access to washer, dryer, & additional amenities upon request. Twin hide-a-bed provides extra sleeping space in a pinch. Easy walk to town (0.7 miles) 1.1 mile from Ferry. Early check in & late check out okay whenever possible, check with host.

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.

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.

Froggy Heights - An English Cottage on Bainbridge

A picturesque two-bedroom cottage approached by a secluded road sits on a hill with stunning views of rolling lawns and treetops to the east. You’ll wake to the sunrise light streaming through the tall picture windows in the romantic bedroom. The separate living room offers ample space to relax with a good book and enjoy tea and cake! The adorable second bedroom provides a special place for children to feel right at home, or a private spot to unwind.

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.

walking distance to the ferry Studio Katsura

Welcome to Studio Katsura, one of four studios at Vineyard Lane Condo community. This is 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.

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.