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$25,087 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.

1 of 1 pages1 / 1

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!

KitchenIndoor spacesHospitality

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!

FamilyKitchenAmenities

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.

Indoor spacesFamilyComfort

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.

Indoor spacesFamilyWifi

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.

Indoor spacesKitchenCleanliness

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.

FamilyIndoor spacesWifi

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.

FamilyIndoor spacesComfort

4.94 out of 5 average rating, 216 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.

Indoor spacesFamilyAccuracy

4.83 out of 5 average rating, 104 reviews

Superhost

A wooden dock extends over a calm lake, featuring two folding chairs positioned for serene views of the water and surrounding trees. The bright sky enhances the peaceful atmosphere, inviting moments of solitude and relaxation.

Cabin in Lakeside

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

FamilyIndoor spacesBeach

4.88 out of 5 average rating, 276 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.

Indoor spacesFamilyOutdoor spaces

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.

FamilyIndoor spacesParks

4.96 out of 5 average rating, 585 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.

KitchenIndoor spacesLocation

4.99 out of 5 average rating, 167 reviews