Family-friendly holiday rentals in Port Orchard

Custom home with panoramic Puget Sound views.

This special place is close to everything, making it easy to plan your visit. A short walk to the best restaurants in Port Orchard. A very short walk to foot ferry to Seattle or downtown Bremerton, or the Navy base. The home is filled with unique custom woodwork and it has all you need for a short visit or an extended stay. One bedroom with a queen bed, spacious bathroom, living room, fully equipped kitchen, and full laundry closet. Fast wifi, TV and DVD player. 1 private parking space in front.

NIRVANA by the bay

Enjoy the scenic Olympic Mountains from the deck, or watch the tall ships engage in mock cannon battles. Bremerton Naval Shipyard provides a backdrop with the Pacific Fleet docked across the bay. Have your own boat? Moor at beautiful Port Orchard Marina only a 5 minute walkaway. A fast ferry to Seattle- no need for a car. Watch the sun set over the Olympics, go for a scenic drive to Hood Canal, or just relax and enjoy a bottle of wine from the deck.Go for a stroll along the waterfront boardwalk.

Chesnut Cottage - writers retreat @ Harper's Hill

The Chesnut Cottage is the perfect quaint romantic getaway or rustic writer's retreat. One of three AirB&B listings on our 10-acre property atop Harper's Hill, it is surrounded by woods and a short walk up from the Puget Sound where you can fish from Harper pier or kayak over to Blake Island. The Southworth ferry terminal is just over a mile away providing direct access to both Seattle and Vashon Island. Harper is the perfect base camp for exploring the beautiful Kitsap and Olympic Peninsulas.

Cozy stay with Panoramic Puget Sound View

Bring in the fall season and holidays at our cozy Airbnb with beautiful views of the Puget Sound, Seattle, and on clear days, Mt. Rainier. Watch the weather change through large windows while you relax in comfort. We’re minutes from the ferry to downtown Seattle and close to charming small towns. The walkable neighborhood offers a pub, library, food options, and a coffee shop/convenience store, plus peaceful spots to stroll and enjoy the scenery. Perfect for a quiet seasonal getaway retreat too

Dotty’s Place Downtown

Dotty’s Place Downtown is a unique 1910 all refurbished large studio apartment. Private entrance with views of the Sinclair Inlet. One block from downtown Port Orchard, two blocks from the foot ferry to Bremerton & Seattle. Dotty’s is conveniently located to restaurants, bars, shopping and the waterfront Marina. This space is cozy with modern amenities, cotton linens with a comfy memory foam queen size bed. The living room has a smart TV & internet with a comfy sofa. With a new full kitchen!

Cozy Retreat w/ Vintage Charm & Puget Sound Views

Kickback and relax in the 120-year-old Harper Beachside Escape. This tranquil home was craftly restored to hold its original charm while still catering to the tastes of a modern society. Sitting on a private beach next to a public fishing pier. You can sit under the covered porch enjoying views of Blake Island and the local sea otters. Bring your boat and anchor it out front while you explore all the Puget Sound has to offer. Worried about charging your electric vehicle? We got you covered!

Carriage House - Spacious, Charming, and VIEWS!

The Carriage House is attached to the owner-occupied house by a shared wrap-around porch. As you'll see from the pictures, we are up on a hill overlooking Sinclair Inlet and the majestic Olympic Mountains. We are downtown Port Orchard, so restaurants and a myriad of cute shops are just steps away, as is the lovely waterfront. You'll have the house to yourself to relax in the serenity you deserve. You can get to and from Port Orchard by ferry from Seattle, so a getaway with no car is doable!

Salish Sea Cottage-2 BR Waterfront in Port Orchard

The Salish Sea waterfront two bedroom cottage is sure to meet your expectations for a romantic getaway, small family trip, or solo work retreat! Just minutes from Downtown Port Orchard sits this adorable, stylish cottage perched over the Sinclair Inlet with breathtaking views to watch wildlife, Seattle ferries, and city views! Weather you stay local and explore downtown Port Orchard or catch the ferry to Seattle just 15 minutes from the house - You will surely find plenty to do in the area!

Take a Break at Wye Lake - 2 BR Lakefront Cabin

Come take a break at Wye Lake! Sitting directly on the lake, this home is fully remodeled and waiting for you to grab a drink and come relax on its huge private dock or take a spin around the lake in the provided pedal boat or kayaks! This home is stocked with all the needed essentials; from its fully stocked kitchen and bathrooms, to the comfy beds with quality linens and throws to keep you cozy. Come enjoy swimming, fishing, boating, and so much more at this tranquil property!

Lake House Retreat Kid & Dog Friendly

Updates: new grill and new solid doors for added privacy and sound proofing. This is a place where stress melts away the moment you step inside. Wake up to misty lake views, sip coffee on the deck as eagles soar, and soak in the hot tub under the stars. Spend your days kayaking, roasting marshmallows by the fire, or just unwinding in the cozy living space. I love sharing this space and can’t wait for you to experience it. Note: If bringing a pet, see pet rules below.

Cozy Country Cottage * Near Hiking & Beaches

Newly renovated, cozy cottage in a beautiful country setting. A peaceful refuge from the hustle and bustle of the city, this comfortable & stylish cottage offers views of nature and all the amenities of a full size home. The covered deck is a perfect place to enjoy the views with a relaxing seating area & propane BBQ grill. Or gather on the patio around the fire table, surrounded by nature and a sky full of stars. Shooting stars are a frequent sight in late summer.

Lakefront l Kayaks, Fire Pit, New Deck | Seattle

Escape to a private lakefront retreat on Horseshoe Lake, perfect for families or friends. Paddle the kayaks or paddle boards, fish from the dock, or sip coffee on the new deck. Evenings feature a fire pit for s’mores, a cozy theater room for movie nights, or a game room with plenty of puzzles and games for all to enjoy. Just a short drive (or ferry ride) to Seattle and Tacoma, ideal for weekend escapes, family getaways, and memorable celebrations.