
Family-friendly holiday rentals in Winchester Bay
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Winchester Bay

Total holiday rentals
Explore 20 holiday rentals in Winchester Bay

Nightly prices starting at
Winchester Bay holiday rentals start at $206 NZD per night before taxes and fees

Verified guest reviews
Over 690 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Winchester Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Winchester Bay rentals

4.8 Average rating
Winchester Bay stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Winchester Bay
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Bayview Cottage - Charming Family Friendly Home With a View
Enjoy beautiful views of the bay and wildlife including deer and a variety of birds from the large picture windows that welcome you to Bayview Cottage. Gather around the waterfront fire pit after a day of adventures to enjoy s’mores and stunning sunsets. Everything you’ll need to prepare a gourmet meal or a quick snack is provided in the fully equipped kitchen including spices, bakeware, a variety of kitchen appliances, and other cooking essentials. All three beds feature memory foam and cozy bedding to provide a wonderful night’s sleep. The house is fully stocked with Smart televisions including cable, high speed wifi, a washer and dryer, toiletries, and plenty of books, puzzles, toys and games. Bayview Cottage is an ideal home for families or a group of friends enjoying the beautiful Southern Oregon Coast! Bayview Cottage may also be rented in conjunction with Bayview House, a larger home that sleeps 4 guests and is located right next door. Consider renting both homes together for larger parties or a gathering where families may want their own space. Together both homes can accommodate parties of 8 and each home has a full kitchen and a washer/dryer! This waterfront property is great for cozy evenings around the firepit. During low tide clam from the property or take a nature hike around the bay. Large picture windows provide views of the incredible sunsets while staying warm and cozy indoors. Along with the cottage, enjoy the deck with lawn chairs as well as the waterfront fire pit in the private backyard. I am available by phone, text or email at anytime during your stay. I live nearby if you need anything while you are at the cottage. The cottage is located just a few blocks from Downtown North Bend, a small coastal town with shops, restaurants, antique stores and pubs. Located at the end of a quiet road next to a nature park providing ample opportunity to observe wildlife including deer and many birds. A short drive to several beaches and sand dunes for a day full of outdoor adventures. Plenty of parking for your toys including boats and trailers is available. World famous Bandon Dunes Golf Course is less than a 30 minute drive away! Conveniently located just a few blocks off of the Scenic Coastal Highway and a quick 5 minute drive to the North Bend airport.
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GEM ON THE OREGON COAST
Looking over the river, sand dunes and the ocean, this 2 story - 3 bd Cape Cod home captures views from every room!! The open floor plan and interior decor makes it easy to entertain with a chef’s kitchen. The patio is exposed to the elements of the Oregon Coast and captivates it’s wildlife and natural beauty. This home is equipped for entering inside and out with a jacuzzi situated off the master bedroom. Don’t forget to enjoy the river rock fireplace for those cooler evenings. We welcome you!
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Home + Guesthouse ~Dunes Nearby, Gated ATV parking
Whispering Pines is a main house PLUS guesthouse and game room! Blocks from town, yet privacy among trees. Ride to the dunes from this property on the PAVED ATV Route! Enjoy the lake. Gated parking for boats, ATVs. Chill by the fire. Cozy fireplace. Soak in the deep clawfoot bathtub. Book the tiny home next door too (Tiny Pines is a separate listing). Whether you are looking for adventure getaway, romantic weekend, or peaceful vacation, Whispering Pines is a special Oregon Coast Oasis getaway!
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Saunders Lakefront Retreat 600ft from Dunes
Lakefront home on Saunder’s Lake. Located 600ft from the dune entrance and a five minute ATV ride to the beach. Purchased property to build new home in a few years. We enjoy staying there so much that we decided to rent out the current older mobile as an opportunity to stay lakefront 600ft from the sand until construction begins for a fraction of what the price will be after we build. Please keep in mind that this is an older mobile as the price reflects so don’t expect a newly remodeled home.
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Coastal Shenanigans!
This home is right in the middle of everything to do on the coast. Whether it's fishing the Umpqua river or the ocean, riding the dunes or shopping old town Florence. It's all 10- 30 minutes away. Go for a sunset walk on the beach! There is a nice little coffee shop close and some very good restaurants close by. There is free parking on the premises and on the street. Our driveway is 38' L x 20' W. If you're a boater, we have towels in the garage to wipe your boat off. Dog friendly-NO cats.
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The Casita on Duck Pond: Dune Access
Direct dune access!! Coastal adventure meets quiet retreat! This hidden gem of a home sleeps 4 and offers direct dune access, a short walk to Tenmile Lake, and quick drives to beaches and trails. Ride your ATVs, fish for bass, hike the coast, or simply relax by the pond with the ducks and a good book. Bring your ATVs, fishing boat, hiking boots, or stack of books and enjoy this peaceful spot to unwind after the day’s fun. Perfect for couples or small families seeking the best of both worlds.
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Ridgeway Hideaway
This stylish place to stay is in the middle of everything. You are a short walk away from the disc golf course, Reedsport golf course and the hospital. A short drive (2-miles) from Winchester Bay where crabbing, fishing, the beach, and dunes are located. Minutes from downtown restaurants, shopping and boat launches. If you're a fisherman or ATV'r there is room to park your trailer in the spacious driveway. You will be able to keep a watchful eye on your trailer just outside your door.
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'DOLLHOUSE 2' (4 br) R&S Vacation Homes
Located in Reedsport Oregon. 20 miles south of Florence and 20 miles north of Coos Bay/North Bend. The central hub of the Southern Oregon Coast. Only minutes away from all your coastal enjoyments. The town of Reedsport is a quaint little town full of its own entertainment. The Dollhouse is located only two blocks off Hwy.101 and minutes from the beach. Reedsport is complete with it's own Restaurants, Shopping Centers, and Old Town for all your other needs.
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Secluded Lakefront Mini-Cabin W/ Paddleboards
Remote lakefront retreat—boat access only. We provide all arrival details after booking. Tucked away on North Tenmile Lake, this peaceful mini-cabin is perfect for a romantic escape or quiet writer’s retreat. Features a full kitchen, full bathroom with shower/tub combo, loft with king bed and lake views. Enjoy a private dock, paddleboards, high-speed WiFi, fishing, stargazing, and morning coffee by the water. The perfect mix of peace, privacy, and nature.
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Tenmile Lakeview Retreat
Escape to the Oregon Coast and soak up stunning views of Tenmile Lake from this modern, cozy getaway. Sip your morning coffee on the full deck, gather around the backyard fire pit, or relax indoors while enjoying the lake view and streaming your favorite shows on the Smart TV with high-speed WiFi. Here, you’ll find the perfect balance of relaxation and convenience. Come unwind, recharge, and create unforgettable memories at this lakeside retreat.
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Quiet, serene retreat near stream, lakes, & ocean
Relax and renew in our private coastal guest suite with its own entrance. Enjoy a large sunlit bedroom, spacious bathroom with double vanity, sitting room with desk, and outdoor patio. Watch deer nibble blackberries outside your picture windows. Just minutes from beaches, dunes, lakes, and the charming town of Florence— The stars don't get brighter or the days more peaceful than at this quiet, secluded spot. Your peaceful retreat awaits.
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Beautiful home with spectacular harbor view
Make some unforgettable beach memories at this unique and family-friendly place. Mid-century meets the 21st in this lovingly renovated home with spectacular harbor view. Within walking distance of the beach, dunes, lighthouse, harbor, and restaurants. Beautiful enclosed garden room provides sheltered space for dining and relaxing. Young children will love the one-of-a-kind alcove beds. Well-behaved dogs are welcome.
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Popular amenities for Winchester Bay family-friendly rentals
Family-friendly home rentals with a hot tub

Hot Tub + Cold Plunge | Bay Views | The Tower
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Nature Retreat- in Old Town!
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Hot Tub Ocean access river Dock Coast Cottage
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Seagate, The Gold Standard in Coos Bay
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Woahink Lake Studio Retreat - Pirate’s Cove
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Spacious, Secluded 1BR Apt w/HotTub near Mingus Pk
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Welcome to The Seal Cove. Relax and rejuvenate.
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Cozy River Cabin
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Family- and pet-friendly home rentals

Tide's Reach of the Umpqua
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Siltcoos Floating Cabin
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3- Bedroom home close to beach,dunes,shops
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Extended Stay Deals! Home Near Ocean & Dunes
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Ocean View Retreat, Florence/Yachats, OR
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Bay & Dune Haven | Oregon Coast
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Coos Bay Getaway, Crabbing, Fishing, Golf, Dunes!
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Ms. Ellie’s Estate
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Family-friendly home rentals with Wi-Fi

Forested Retreat Close to Dunes/Beach/Town
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The Elk View Suite- 5 min to town, 15 min to Beach
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BayView Villa On Sunset. Dune access, Ocean views
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Winchester bay Dungeness & dunes
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Little House w/ Creek in Backyard near Ocean
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Coastal Forest Rendezvous Suite for Two!
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Cozy Coastal Getaway
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Wish You have a pleasant stay & wonderful trip.
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