Family-friendly holiday rentals in Winchester Bay

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.

Cozy River Cabin

Sitting on nearly two acres of river front land, this tiny cabin is packed with charm. Enjoy the view of the beautiful Siuslaw River out of the large picture windows. This property is the perfect place to unplug from technology and plug into the great outdoors. Relax in the jacuzzi nestled in a grove of mature firs. Wander the orchard and taste the sun ripened seasonal fruits. Bring your fishing pole and catch a fresh salmon for supper. Leave your worries behind and come unwind at the cabin.

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.

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.

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!

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!

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 are a boater, we have towels in the garage to wipe your boat off.

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.

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.

Cozy Coastal Cottage

Keep it simple at this peaceful and centrally-located place. Easy walk to Bay Street and all the charm, great eats and fun that Old Town Florence offers! Stroll to the Exploding Whale Memorial Park in moments, walk along the sandy river "beach" and through its magical forest, as you look across at the Oregon dunes that inspired the book and movie series, "Dune". A large grocery store is close by, too. Breathe the air and relax!

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.

☆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.