Family-friendly holiday rentals in Winchester Bay

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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

Guest suite in Reedsport

4.99 out of 5 average rating, 823 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 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.

Guest favourite

Loft in Florence

4.94 out of 5 average rating, 226 reviews

Sylvia's Sanctuary

Upscale recently renovated private loft in quiet wooded neighborhood. High ceilings, deep carpet, glass and ceramic tile, roomy shower. Luxury linens & comfortable Cal King bed Free WiFi, new 50" smart TV. Kitchenette with dishes, utensils, cookware. New 1800 watt cooktop Pantry has snacks and goodies. Private entrance and deck up stairs. Country feeling right in town. Minutes from shopping, Old Town, beach, dunes, trails. Respectful owners onsite. Raised Aerobed available for 3rd guest.

Top guest favourite

Flat in Reedsport

4.96 out of 5 average rating, 114 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.

Top guest favourite

Guest house in Florence

4.93 out of 5 average rating, 165 reviews

Evergreen Oasis

Welcome to Evergreen Oasis, a labor of love meticulously crafted from the ground up by my wife and me. As you step into this charming retreat, you'll be embraced by the warmth of wood walls, the elegant contrast of a chic black ceiling, and a peaceful ambiance. Our cozy oasis invites you to unwind, recharge, and immerse yourself in its charm, a haven created just for you to enjoy and cherish. We're happy to share our special place with you and hope your stay brings wonderful memories!

Guest favourite

Barn in Lakeside

4.96 out of 5 average rating, 455 reviews

ALL NEW!-Barnhaus-Spa+11 Acres+EV+Gym+Lake Access

The Barnhaus at Treetop Lodge—formerly The Studio—was completely and meticulously renovated for 2025. This handcrafted retreat sleeps 7 (2 kings, 1 bunkbed and a sofabed) with luxe TVs, a high-speed gaming PC, hot tub, firepit, EV Charging and gym. Set on 11 private acres with hiking trails through the forest that lead to a secluded lakefront. The private hot tub with string lighting is where rustic charm meets high-tech comfort—surrounded by nature and built for relaxation or play.

Guest favourite

Home in Reedsport

4.94 out of 5 average rating, 256 reviews

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!

Guest favourite

Cabin in Lakeside

4.94 out of 5 average rating, 122 reviews

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.

Superhost

Flat in Coos Bay

4.81 out of 5 average rating, 130 reviews

#StayinMyDistrict Historic Heritage House Apt

#StayinMyDistrict Downtown Coos Bay! Beautiful and quiet residential neighborhood close to downtown Coos Bay Shopping, Dining & Entertainment. (6-8 blocks walking distance). This 1 bedroom- 1 bath apartment sleeps up to (4). This private residence with updates and amenities throughout offers a comfortable place to stay in Coos Bay. Fully furnished, Cable & WIFI, full kitchen, WD and FREE parking. Private back porch and shared outdoor space.

Top guest favourite

Guest suite in Florence

4.95 out of 5 average rating, 508 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.

Top guest favourite

Home in Winchester Bay

4.99 out of 5 average rating, 134 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.

Top guest favourite

Guest suite in North Bend

4.97 out of 5 average rating, 264 reviews

☆Sully's Sanctuary☆ Centrally located/North Bend

** Discount applied when you stay 2 nights or more! Also, ask about National Education Association or Oregon Education Association membership discounts.** Enjoy a stay on the Oregon coast in this spacious guest suite (508 sq. ft.), complete w/ private entrance, comfy queen-size bed, large private bathroom & eating area. A mini-fridge/freezer, microwave, wi-fi, smart TV/DVDs & dedicated parking are provided.

Top guest favourite

Home in North Bend

4.94 out of 5 average rating, 144 reviews

Forested Retreat Close to Dunes/Beach/Town

Enjoy unmatched privacy with over an acre of land all to yourself and close proximity to town, the dunes and beach! Located 5 minutes from Hwy 101, 10 minutes from downtown North Bend and 15 minutes from Horsefall Beach! Relax on the expansive deck by the fire-pit with your coffee/wine or BBQ a feast while soaking in the country like setting. If your lucky a momma deer with her fawns may make an appearance!