Family-friendly holiday rentals in San Juan County

Heather Waterfront Guest Cabin on private estate

See our other two available cabins listed on this waterfront estate by clicking my host profile. Welcome to the vintage 100 year old original guest Cabin, nestled over the Salish Sea on a private estate with two cabins, beach, camp fire, kayaks & paddle boards. Seals, otters, eagles and deer are your neighbors. Walk to Turtleback Mountain south trailhead for grand views above. The secluded Hot Tub is tucked under cedar trees, over the beach, private for either cabin, but not at the same time.

Haro Sunset House

Winding through a Madrona forest hillside on the coveted Westside of San Juan Island, Haro Sunset House greets you with sweeping views from Vancouver Island to Salt Spring Island to the North. This home is known for its stunning views from the expansive deck and with amazing wildlife viewing. The home is near San Juan County Park for beach access and the iconic Lime Kiln Light House. The owner’s home is located next door, yet separated by two garage structures, leaving a feeling of seclusion.

Private Pond, Dog-Friendly, Peaceful, Golfing

Dragonfly Pond is a spacious, light-filled home with high ceilings and comfy furnishings. Sip coffee on the deck while ducks glide across your private pond. Enjoy total privacy with close proximity to hiking, paddle boarding, shopping and cafes. 🔹Dog and Kid Friendly with a big yard 🔹Fully stocked kitchen 🔹Fast WiFi 85 Mbps 🔹Large Dining and Living Room 🔹Pond views 🔹Private 7 acre wooded setting 🔹 4 min to Eastsound Village 🔹14 min to Orcas Ferry Landing 🔹 9 min to Moran State Park

Luxe Beachfront, Hot Tub, Kayaking, Walk to Town

Welcome to Beach House, our exceptional waterfront retreat where nature and luxury come together for a perfect romantic getaway. What You’ll Love Wake to waterviews and end your night in the hot tub under the stars. 🔹 On Crescent Beach waterfront 🔹 3 min to Eastsound Village 🔹 7 min to Moran State Park 🔹Private hot tub with bay views 🔹 King suite with deck access 🔹 Radiant heated floors 🔹 Gas fireplace 🔹 Walkway to sandy beach 🔹 Dedicated workspace & WiFi 🔹 Zen garden setting

Waterfront San Juan Island Retreat | Beach & Views

Wake up to sweeping waterfront views at Westward Cove, a spacious beach house on the west side of San Juan Island. Perched on one of the island’s rare sandy beaches, our home is the perfect spot to relax, soak in the hot tub, or simply enjoy the sound of the waves. From the deck, you’ll have front-row seats to the island’s incredible wildlife. Just 10 minutes to Friday Harbor and Lime Kiln State Park, this peaceful retreat blends comfort, nature, and unforgettable views. Sleeps up to 6.

Sunrise Waterfront Retreat w/Hot Tub, Beach Access

Escape to Sunrise Retreat and enjoy the tranquil setting of Lopez Sound. This waterfront hillside cabin has an open concept floorplan with a sleeping loft for up to 5 and is a cozy place to relax and enjoy amazing panoramic water views and sunrises. This retreat features a new kitchen, a new bath with a spa-like shower, and beautiful hardwood flooring. Enjoy grilling and hot tubbing on the wrap-around deck, out door fire pit, and short walks to the private community beach.

Get away to the quiet island

I built this house as a place for my family to escape to. Open floor plan lots of room on the porch. Fantastic sunset view over water. There is room for many, though during the phase 3 of CoViD-19, San Juan County only allows me to groups of 6 or less. Rental includes access to the 8.3 acres. There is a flat lawn suitable for croquet, and yard games. Most of the place is wooded with paths. Some paths lead to ne of the best swimming ponds on the island.

Puffin Island - San Juan Tiny Suite

Escape to tranquility at our charming tiny home in the heart of Friday Harbor, WA. This cozy retreat offers a unique getaway experience, combining comfort and convenience in a compact space. Immerse yourself in the island lifestyle as you unwind on the deck, surrounded by lush greenery. Explore the island's natural beauty with ease, as downtown Friday Harbor and its vibrant shops, restaurants, and attractions are just a mile away. Great Territorial Views.

Luxury Waterfront & Views, Private Beach, Golfing

Welcome to Eastsound Shores, our spacious designer home overlooking the Salish Sea! 🌊 Enjoy expansive decks for outdoor living and dining, a fantastic Chef's kitchen, and cozy evenings by the fire with games and a wet bar. Each ensuite bedroom features a luxurious bathroom, perfect for family and friend gatherings. Plus, explore the private beach trail and unique rocky shore right at your doorstep. We can’t wait to host you for an unforgettable getaway!

Large Private Retreat on Orcas Golf Course

Spacious and private suite on the scenic Orcas Island Golf Course ⛳—ideal for families or groups. Features a large main bedroom, separate attached room, and full bathroom. ✔ King bed, queen sofa bed, and 2 twin beds 🛌 ✔ Wi-Fi 📶, smart TV 📺, heating 🔥 ✔ Mini fridge ❄️, microwave, coffee maker ☕ ✔ Outdoor grill access 🔥 & shared porch with golf views ⛳ Close to hiking 🥾, whale watching 🐋, and Eastsound. Book your island escape!

Garden Cottage A, heart of Lopez Village.

Come enjoy our beautiful cottage on peaceful Lopez Island. Our cottage is located in the heart of the Village. Kitchen is well stocked with appliances and all that you might need to pack a nice picnic with or stay in for a light romantic dinner. Plenty of towels and soaps, 100% cotton sheets, down pillows and duvet. Nice outdoor deck seating to enjoy nature and a short walk to restaurants, shops and store.

The Fox Den a whimsical Earthen Glamping Cabin

Glamping on San Juan Island. The Foxes Den is a whimsical Earthen sleeping cabin, nestled in amongst a Douglas fir forest. Fifteen minutes drive from Friday Harbor and less then a 10 minute drive from Lime Kilm state park. The cabin sleeps 2 on a comfy queen bed and features a small sitting area and access to a separate designated bath house, complete with flushing toilet and hot shower. PPROV0-17-0021