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Family-friendly holiday rentals in Winchester Bay

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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 $166 AUD 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.

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Top Guest favourite
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 favourite
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, 107 reviews
Guest favourite
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
Top Guest favourite
A sweeping view of the Umpqua River surrounded by lush greenery and rolling hills under a clear blue sky. The vibrant landscape features a mix of water and grasslands, with wooded areas lining the riverbanks, creating a serene natural setting.
Guest suite in Reedsport

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 spacious, 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, 887 reviews
Guest favourite
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.
Holiday 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, 139 reviews
Top Guest favourite
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, 139 reviews
Top Guest favourite
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, 158 reviews
Guest favourite
The exterior of a two-story duplex is seen, featuring a light-colored siding and multiple large windows. A small garage is located to the right, and a fenced yard provides privacy. The sky displays soft hues during sunset, enhancing the calm ambiance.
Home in Reedsport

The Salty Duplex (Right Side)

We are located uptown, only 4 minutes from Winchester Bay! The neighborhood is very quiet and comfy. There is a fully stocked kitchen with lots of gadgets, a Keurig coffee pot with a random assortment of kcups, and gas BBQ, and a bar for good conversation. In the Livingroom we have Spectrum cable TV and high speed WiFi. There are 2 bedrooms with one king and one queen bed both upstairs. There is plenty of room for an air mattress in the Livingroom, which is in the closet downstairs!

4.94 out of 5 average rating, 287 reviews
Top Guest favourite
A two-level chalet is surrounded by vibrant greenery and blooming flowers. Large windows allow natural light to fill the interior. A patio area with outdoor seating and a fire pit is visible in the yard, enhancing the inviting outdoor space.
Cabin in Lakeside

Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

Looking to create a “Lifetime Memory?” Welcome to Treetop Lodge—a renovated two-level A-frame on 14 private acres. Nestled in the hills of Lakeside, it feels secluded but is just minutes from town. Hike private forest trails that end at at the lake, soak in the Jacuzzi under the stars, toast marshmallows by the firepit, or curl up in the cozy loft for the ultimate movie night. Whether you're chasing adventure or seeking calm, the experience is yours to create.

4.95 out of 5 average rating, 690 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
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

4.88 out of 5 average rating, 276 reviews
Top Guest favourite
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, 578 reviews

Popular amenities for Winchester Bay family-friendly rentals

KitchenWi-FiFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
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

4.93 out of 5 average rating, 210 reviews
Guest favourite
The entrance of the round nature retreat features a welcoming wooden porch framed by two columns. A sturdy front door is flanked by two turquoise chairs, while neatly trimmed shrubbery creates a lush, inviting landscape. Steps lead up to the porch from a gravel pathway.
Home in Florence

Nature Retreat- in Old Town!

4.96 out of 5 average rating, 291 reviews
Guest favourite
A cozy living space is captured, featuring a glass dining table surrounded by four chairs. A plush sofa, adorned with striped cushions, is positioned beside a wooden entertainment unit and a mounted television. Soft light is provided by a hanging pendant light.
Cottage in Dunes City

Hot Tub Ocean access river Dock Coast Cottage

4.83 out of 5 average rating, 329 reviews
Top Guest favourite
The image captures a serene lake at dusk, reflecting vibrant hues of orange and purple skies. Silhouettes of trees line the background, while a dock extends into the calm waters, creating a tranquil atmosphere. Soft clouds are visible above, enhancing the peaceful scenery.
Guesthouse in Florence

Woahink Lake Studio Retreat - Pirate’s Cove

4.97 out of 5 average rating, 151 reviews
Guest favourite
Large windows allow natural light to fill the space, framed by dark curtains. A view of the courtyard is visible, featuring greenery and outdoor seating. The cozy ambiance of the room is complemented by a plush bed in the foreground.
Guest suite in Coos Bay

Spacious, Secluded 1BR Apt w/HotTub near Mingus Pk

4.92 out of 5 average rating, 458 reviews
Guest favourite
The exterior of a two-story white building is displayed, featuring a black front door and black shutters on the upper windows. Flower boxes with red blooms add a touch of color. The garage door is visible, with a paved entryway leading to the door.
Apartment in Florence

Welcome to The Seal Cove. Relax and rejuvenate.

4.95 out of 5 average rating, 151 reviews
Guest favourite
A serene outdoor space features a lush green lawn bordered by ferns. A rustic red bench sits in the foreground, overlooking the Siuslaw River and surrounded by tall trees providing shade. The peaceful setting showcases the natural beauty of the property.
Guesthouse in Mapleton

Cozy River Cabin

4.89 out of 5 average rating, 434 reviews
Guest favourite
Cottage in Florence

Sea Star Spa – Hot Tub, Walk to Beach

4.88 out of 5 average rating, 108 reviews

Family- and pet-friendly home rentals

Top Guest favourite
An insulated dome interior showcases a cozy space with a plush brown blanket draped over a spacious bed. A stone hearth is centrally positioned, with wood-fired heating. Two tall tables with chairs and a sectional sofa are located near expansive windows that provide views of the outdoors.
Dome in Scottsburg

Tide's Reach of the Umpqua

4.97 out of 5 average rating, 181 reviews
Guest favourite
A floating cabin exterior is shown, featuring a deep red wooden façade with large windows. Solar panels are mounted on the slanted roof. The cabin rests on a wooden deck overlooking the calm waters of Siltcoos Lake, surrounded by greenery and distant trees.
Houseboat in Dunes City

Siltcoos Floating Cabin

4.89 out of 5 average rating, 281 reviews
Superhost
A welcoming home exterior features a well-maintained driveway with lush greenery surrounding the property. The garage door complements the house's design, set within a quiet, serene environment. Natural light filters through the trees, creating a peaceful atmosphere.
Home in Florence

Extended Stay Deals! Home Near Ocean & Dunes

4.87 out of 5 average rating, 159 reviews
Top Guest favourite
An outdoor terrace is set with a wooden table and several chairs, surrounded by potted plants and vibrant flowers. The Pacific Ocean can be seen in the background, with clear blue skies and greenery enhancing the peaceful setting.
Cottage in Florence

Ocean View Retreat, Florence/Yachats, OR

4.98 out of 5 average rating, 334 reviews
Top Guest favourite
The exterior of a two-story green home is presented, featuring a double garage and a concrete driveway. Surrounding trees provide a natural backdrop, enhancing privacy. The architecture is modern, with large windows allowing for ample light. An additional structure is visible to the left.
Home in Florence

3- Bedroom home close to beach,dunes,shops

4.99 out of 5 average rating, 132 reviews
Top Guest favourite
A sunroom featuring large windows that offer expansive views of the slough and surrounding trees. An L-shaped sofa provides ample seating, complemented by a round table at the center. Natural light fills the space, creating a bright and airy atmosphere.
Home in Coos Bay

Serene Lake View Retreat

4.98 out of 5 average rating, 125 reviews
Guest favourite
A modern exterior is depicted, featuring a single-story structure with muted gray siding. A covered porch extends along the front, supported by wooden columns. The entrance is framed by a white door, and a small window provides natural light. A well-maintained lawn surrounds the area.
Home in North Bend

Bay & Dune Haven | Oregon Coast

4.91 out of 5 average rating, 100 reviews
Top Guest favourite
A corner of a room is highlighted by a wooden side table featuring a decorative lamp. The lamp, adorned with a nature-themed shade, provides soft illumination. A small decorative object is placed beside the lamp, with a mirror reflecting the ambient light.
Apartment in Coos Bay

Ms. Ellie’s Estate

4.96 out of 5 average rating, 142 reviews

Family-friendly home rentals with Wi-Fi

Top Guest favourite
A cabin-style home is surrounded by towering conifers, with a spacious deck overlooking a lush green lawn. The structure features a combination of wood siding and a pitched roof, reflecting a blend of natural elements and rustic charm. Clear blue skies enhance the serene atmosphere.
Home in North Bend

Forested Retreat Close to Dunes/Beach/Town

4.95 out of 5 average rating, 176 reviews
Top Guest favourite
An aerial view of a modern, two-story home with a dark exterior. The property features a spacious driveway and landscaped yard. Large windows allow natural light to brighten the interior. A vibrant sunset casts a colorful backdrop, enhancing the peaceful setting.
Home in Winchester Bay

BayView Villa On Sunset. Dune access, Ocean views

4.94 out of 5 average rating, 65 reviews
Top Guest favourite
A well-appointed living area is featured, showcasing a dark blue couch and a matching armchair. A wooden entertainment unit holds a flat-screen TV, while a decorative clock adorns the wall. Natural light enters through a window with closed blinds, and a small tree adds a touch of decor.
Home in Winchester Bay

Winchester bay Dungeness & dunes

4.94 out of 5 average rating, 51 reviews
Superhost
A covered porch extends from the home's exterior, featuring wooden railings and ample seating. A black grill is positioned on the side, with outdoor furniture nearby. The lawn is spacious and well-maintained, surrounded by trees in a peaceful setting.
Home in Winchester Bay

Little House w/ Creek in Backyard near Ocean

4.74 out of 5 average rating, 68 reviews
Guest favourite
The exterior of a large two-story home is positioned amid lush greenery, showcasing a navy blue façade and multiple windows. A spacious driveway leads to the entrance, with surrounding gardens featuring shrubs and trees, creating a sense of privacy and tranquility.
Home in Reedsport

Ranch Road Retreat 3 bd 2.5 bath Sleeps 6

5.0 out of 5 average rating, 21 reviews
Superhost
Home in Winchester Bay

Winchester Bay Coastal Retreat | Dog-Friendly Home

4.67 out of 5 average rating, 6 reviews
Top Guest favourite
Home in Reedsport

Coastal Forest Rendezvous Suite for Two!

5.0 out of 5 average rating, 17 reviews
Top Guest favourite
A single-story home is enclosed by a white picket fence, with manicured greenery and shrubs visible in the front yard. Two tall conifer trees stand prominently on either side of the house, complemented by a clear blue sky overhead.
Home in Reedsport

Wish You have a pleasant stay & wonderful trip.

4.89 out of 5 average rating, 62 reviews