Vacation rentals with a kayak in Douglas County

Valley's End Guesthouse

Newly refurbished, charming 3-bedroom, 2-bath house in the exquisite Umpqua Valley wine country. 6 adults, 2 children. Private hot tub, AC, woodstove, EV charger, decks with gorgeous rural views. Stocked kitchen with granite countertops, big screen TV, W/D, high speed wi-fi, games and hammock. Private river beach a quick walk away on a calm section of the Umpqua River, with guest kayaks. Perfect for small family reunions or romantic getaways! Additional Airbnb rental available on property.

Outdoor spaces · Value · Nearby

The Osprey Nest: Private Umpqua Riverfront

The Osprey Nest is so much more than a cabin nestled in the wooded mountains. It is a private, peaceful getaway on the Umpqua river; perfect for multiple families wanting to gather together. The newly remodeled home has large windows and multiple decks offering fantastic views of the river and surrounding mountains. The Boathouse: an outdoor pavilion with grills, sink & outdoor shower. 300 ft private waterfront. This area is known for its fishing, vineyards, waterfalls and hot springs

Outdoor spaces · Location · Parking

The Red Door Retreat at Our Shangra la

The Red Door Retreat is part of Our Shangra la LLC. We overlook the Circle Bar Golf course. Quiet, water features on four sides. 6 month creek flows into the North Fork of the Willamette. Tree frog pond and waterfall in the Grape arbor. We put up our own grape juice. Heated Exercise Pool with a current also enclosed to keep the pool area pleasant. A HOT SPRINGS hot tub. Multi car parking. Koi and frog pond. A Treehouse with stairs and adult swing set.

Outdoor spaces · Value · Skiing

Secluded Hidden Gem Mazama House near Crater Lake

The Mazama house is a beautiful two story home perfect for a family. The home features hard wood floors with area rugs throughout. The living room has nice corner windows with a beautiful view for star gazing, bird watching, or taking in the view of the property and the mountains. The kitchen is stocked with all the kitchenwares and utensils you would need to prepare a meal, as well as a Keurig coffee maker. The porch has many windows and is a bright and sunny spot for morning coffee.

Outdoor spaces · Value · Nearby

Lakeshore Manor

A beautiful country-French estate on the pristine Woahink Lake in Florence - perfect for family gatherings. Inside, enjoy large living and dining rooms, a cozy library, a sunny breakfast room, and a well-equipped kitchen. Outside, relax on the dock, paddle the lake, or soak in sunsets. Secluded yet minutes from beaches, dunes, trails, and Old Town. A rare blend of charm, space, and coastal adventure. Sleeps 14 comfortably and also has a smaller bunk in a bedroom for two children.

Location · Outdoor spaces · Family

Riverfront Hideaway - Hot Tub - Private Entrance

Kick back and relax in this calm, stylish retreat tucked along the river in the heart of wine country. With peaceful river views and private river access just steps away, you’ll feel immersed in nature—yet still enjoy the convenience of being only a quick 10-minute drive into town. Fishing, agriculture, local activities, and abundant wildlife surround our tranquil hideaway, and it’s easy to see why we fell in love with this special place. Come unwind and soak in the serenity.

Location · Value · Wifi

Tide's Reach of the Umpqua

**NEW GLAMP DOME DESIGN!*** Pics will update soon! Nooked in Oregon Coastal Mountains at edge of inland tidal waters. Set to the background of a small historic rural town, tucked just out of sight of the beaten route to/from the Pacific Ocean and Oregon Dunes a short 16mi away at Reedsport.  Year-round floating dock and river access all to yourself, different experience with each tide change, and kayaks provided. Otter, eagle, seal, fish, etc : a nature theme park!

Location · Outdoor spaces · Family

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.

Outdoor spaces · Value · Condition

Upper Rogue Cool Creek Cottage

Relax with the whole family at this peaceful place to stay. COOL CREEK COTTAGE Welcoming Cool Creek Cottage is situated in the mountains of the Rogue River Siskiyou National Forest, along Oregon Highway 62 on the Rogue River, in the heart of Prospect Oregon, population 500. Located 45 miles from Medford, Oregon, and just 32 miles from, Crater Lake National Park South entrance, Prospect is the gateway to year-round natural beauty and recreational opportunities.

Value · Location · Sleep quality

Stay In Lakeside - Lake Front Oasis

Take it easy **Enchanting Lakeside Retreat with Private Dock and Spectacular Views** Discover the magic of Tenmile Lake at our exquisite lakeside home, nestled in the serene community of Lakeside, Oregon. This luxurious 4-bedroom, 4.5-bathroom haven, including a charming detached bunkhouse with its own full bath, promises an unforgettable escape filled with relaxation, adventure, and breathtaking natural beauty at this unique and tranquil getaway. CD-24-141

Location · Value · Decor

Lake Front Family Retreat Home/ Boat House

Discover the ultimate family vacation at our stunning lake house rental on the Pacific Coast. With 5 bedrooms, plus a futon and two rollaways, 3.5 bathrooms, a cozy game room and breathtaking views, this home offers luxury and relaxation. Enjoy kayaking or stand-up paddle boarding on the provided equipment. The Pacific Ocean is just 3 miles away for a change of scenery. Book now and create unforgettable memories in Florence, Oregon and the Surrounding Areas.

Location · Outdoor spaces · Pets

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.

Location · Outdoor spaces · Grill