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

Total vacation rentals
Explore 20 vacation rentals in Winchester Bay

Nightly prices starting at
Winchester Bay vacation rentals start at G$25,106 GYD per night before taxes and fees

Verified guest reviews
Over 690 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Winchester Bay vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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.
4.95 out of 5 average rating, 561 reviews
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!
4.99 out of 5 average rating, 123 reviews
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!
4.99 out of 5 average rating, 108 reviews
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.
4.81 out of 5 average rating, 151 reviews
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.
4.91 out of 5 average rating, 140 reviews
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.
4.96 out of 5 average rating, 159 reviews
The Elk View Suite- 5 min to town, 15 min to Beach
The views of the Umpqua River and Elk Reserve are breathtaking from this cozy studio! The location is a perfect launching pad for adventures, but is also a relaxing place to stay & unwind. We provide quality amenities, a high level of cleanliness and personal touches to ensure a fabulous experience. Enjoy a cup of coffee or glass of wine on custom made furniture stationed right outside your door! Located 15 minutes from local beaches & only 30 min from either Coos Bay or Florence.
4.99 out of 5 average rating, 892 reviews
'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.
4.83 out of 5 average rating, 104 reviews
Nestled in the Pines Lakefront Retreat W/Kayak
Perfect for writers, creatives, or those seeking peaceful solitude to recharge. - Private Dock & Kayak for 2 - Fishing, boating, and kayaking right at your doorstep. - Cozy Indoor Amenities - King bed - Wood stove . - Hot shower - With High-speed WiFi - With Smart TV - Outdoor Cooking - Propane grill to cook your catch of the day or enjoy a meal under the stars. - Stargaze from the dock or enjoy the serene, quiet atmosphere. Ideal for Solo Retreats
4.88 out of 5 average rating, 276 reviews
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.
4.96 out of 5 average rating, 522 reviews
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.
4.96 out of 5 average rating, 584 reviews
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.
4.99 out of 5 average rating, 167 reviewsPopular amenities for Winchester Bay family-friendly rentals
Family-friendly home rentals with a hot tub

Hot Tub + Cold Plunge | Bay Views | The Tower
4.93 out of 5 average rating, 215 reviews
Hot Tub Ocean access river Dock Coast Cottage
4.83 out of 5 average rating, 332 reviews
Nature Retreat- in Old Town!
4.96 out of 5 average rating, 296 reviews
Seagate, The Gold Standard in Coos Bay
4.95 out of 5 average rating, 100 reviews
Sutton Lake Area Cottage, North Florence
4.81 out of 5 average rating, 151 reviews
Woahink Lake Studio Retreat - Pirate’s Cove
4.97 out of 5 average rating, 153 reviews
Spacious, Secluded 1BR Apt w/HotTub near Mingus Pk
4.92 out of 5 average rating, 459 reviews
Welcome to The Seal Cove. Relax and rejuvenate.
4.95 out of 5 average rating, 153 reviewsFamily- and pet-friendly home rentals

Tide's Reach of the Umpqua
4.97 out of 5 average rating, 181 reviews
3- Bedroom home close to beach,dunes,shops
4.99 out of 5 average rating, 132 reviews
Siltcoos Floating Cabin
4.89 out of 5 average rating, 285 reviews
Ocean View Retreat, Florence/Yachats, OR
4.98 out of 5 average rating, 334 reviews
Coos Bay Getaway, Crabbing, Fishing, Golf, Dunes!
4.87 out of 5 average rating, 114 reviews
Ms. Ellie’s Estate
4.97 out of 5 average rating, 143 reviews
Extended Stay Deals! Home Near Ocean & Dunes
4.86 out of 5 average rating, 160 reviews
Bay & Dune Haven | Oregon Coast
4.91 out of 5 average rating, 100 reviewsFamily-friendly home rentals with Wifi

#StayinMyDistrict Cape Arago Sanctuary at the Sea
4.86 out of 5 average rating, 408 reviews
The Casita on Duck Pond: Dune Access
4.99 out of 5 average rating, 141 reviews
BayView Villa On Sunset. Dune access, Ocean views
4.94 out of 5 average rating, 65 reviews
Winchester bay Dungeness & dunes
4.94 out of 5 average rating, 51 reviews
Winchester Bay Coastal Retreat | Dog-Friendly Home
4.67 out of 5 average rating, 6 reviews
Little House w/ Creek in Backyard near Ocean
4.74 out of 5 average rating, 68 reviews
Ranch Road Retreat 3 bd 2.5 bath Sleeps 6
5.0 out of 5 average rating, 21 reviews
Wish You have a pleasant stay & wonderful trip.
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