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$25,109 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.

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Top guest favorite
A spacious deck features several light wooden chairs arranged for outdoor seating. Potted flowers add color, while the river and distant landscape are visible in the background, illuminated by warm sunset hues.
Home in Florence

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
Top guest favorite
A cozy fire pit encircled by log seating is visible in the foreground, surrounded by lush greenery. The two-story guest house and main house are positioned nearby, each featuring large windows and warm lighting, creating an inviting outdoor space as evening sets in.
Home in Lakeside

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
Guest favorite
An older mobile home is shown, surrounded by gravel parking. The structure features a wooden ramp leading to the entrance, with large windows allowing natural light. Tall trees provide shade, creating a serene outdoor environment.
Home in North Bend

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
Guest favorite
The exterior of a single-story home is featured, characterized by brown siding and a peaked roof. A wooden fence surrounds the front yard, and an American flag is displayed near the entrance. Soft evening light casts a warm glow over the inviting porch area.
Vacation home in Reedsport

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
Top guest favorite
Two glasses of red wine sit on a wooden railing beside a bottle, overlooking a tranquil duck pond. Lush greenery surrounds the water, with ducks visible in the background, providing a serene setting for relaxation.
Home in Lakeside

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.

4.99 out of 5 average rating, 141 reviews
Top guest favorite
A bright and airy living room is furnished with a comfortable beige sofa and a recliner. A white coffee table is centered on a blue area rug. The space features two side tables with lamps and a television mounted above a modern electric fireplace.
Apartment in Reedsport

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
Top guest favorite
Two hot tubs are showcased under soft, ambient lighting, surrounded by rustic wooden walls. The water reflects a calming blue hue, adding to the serene atmosphere. A fire pit glows warmly in the background, enhancing the relaxing environment.
Tower in North Bend

Hot Tub + Cold Plunge | Bay Views | The Tower

Some places entertain you. Some places change how you feel. The Tower was built for the second one. It’s four stories tall and completely its own thing. You’ll wake up above the bay, drink your coffee while you enjoy breathtaking views, put a record on instead of the TV, soak in the hot tub, brave the cold plunge and probably spend more time than you planned on the rooftop. Perfect for a romantic weekend for two—or two couples traveling together who still want their own space.

4.93 out of 5 average rating, 215 reviews
Top guest favorite
A spacious deck features several dark wooden Adirondack chairs facing the water, offering an unobstructed view of the bay and distant hills. Sunlight reflects off the water's surface, creating a serene atmosphere for relaxation.
Home in North Bend

Coastal Charm & Views - Near Oregon Dunes & Golf

Bayview House is located in a quiet historic neighborhood with amazing views . A place to relax and unwind. Enjoy beautiful sunrises, storm watch, barbecues on the deck or hang out by the fire with friends and family. Enjoy all the coast has to offer: fishing, crabbing, clamming, beach combing, hiking, kayaking, ATV-ing and golf. Bayview House has easy access to Bandon Dunes golf resort and several state parks including Shore Acres and Oregon Dunes National Recreational Area!

4.99 out of 5 average rating, 158 reviews
Superhost
Home in Reedsport

'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
Guest favorite
A covered outdoor seating area is presented with bright orange chairs and a white table, offering views of Tenmile Lake and the surrounding greenery. The clear blue sky enhances the serene atmosphere. Lush trees frame the picturesque backdrop while sunlight creates a warm ambiance.
Home in Lakeside

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, 523 reviews
Top guest favorite
A spacious bedroom is depicted, featuring a large bed dressed in white and navy linens. A dresser and mirror are positioned near windows that allow natural light to fill the room. A cozy chair and decorative plants add a touch of warmth.
Guest suite in Florence

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
Top guest favorite
A serene harbor scene at dusk features docked boats reflecting in calm water. Soft lights illuminate the marina, creating a peaceful ambiance. Wooden pylons stand in the water, contributing to the tranquil setting surrounded by forested hills.
Home in Winchester Bay

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 reviews

Popular amenities for Winchester Bay family-friendly rentals