Vacation rentals with a kayak in Portland

Underground Art Suite

Spacious underground art suite/apartment in the sunlit basement of our 1926 bungalow in the lively SE Foster Powell Neighborhood. We partner with local artists to bring rotating artwork to the space. Enjoy a relaxing guest suite with a private entrance, parking and access to nearby food carts, restaurants, bars, galleries, and shops featuring local wares art & food. The space is a newly finished one bedroom modern guest suite with full kitchen, located in a quiet yet fun and funky neighborhood.

River Forest Lake Apt w/hot tub. HOT find!

*No smoking, no parties, no drugs or pets on premises* total/Max 4 guests; included in this total are infants/children, no more than 2 or3 children under 12, as long as only 4 total guests. FYI: Incline driveway Welcome to our newly remodeled daylight basement apartment. Tucked into the quiet peaceful River Forest neighborhood of Milwaukie on River Forest Lake. Conveniently located to shopping, restaurants, hwy 99, freeways to Portland, Oregon City, historic Sellwood, the Gorge, Mt Hood, etc.

Oxberg Lake Retreat, lake & farm view in wine ctry

A storybook oasis with lake/farm views. Enjoy morning coffee or evening wine watching lake wildlife, sheep and chickens. One loft bedroom, a full bath, large living room/kitchen. Hosts live in attached home, but you have full privacy. * 5 min to George Fox * 2 min to The Allison Inn & Spa * 50+ wineries within 10 min drive *Walk to Wolves and People or Encore for a brew, Starbucks, Mod Pizza and others at Crestview Crossing *Canoeing, catch and release fishing, fire pit, games *roll-away bed

Hockinson Carriage House - You Won't Want to Leave

Your stay can be as peaceful and relaxing as you desire. The property invites exploration at your leisure. The Carriage House is private and comfortable. You are a mile from the little town of Hockinson with a store, gas and a tap room. You are 6 miles from Battleground which offers all services and a neat downtown for shopping, antiquing, a winery and multiple restaurant options. Stay a night or stay and use as a base to explore Portland, Columbia River Gorge, Multnomah Falls, Vancouver.

RoofTop FirePit, HotTub & Outdoor Theater

Our large (1,500sq ft) space (private access), has a bedroom, bathroom, living room w/ a fireplace, hot tub, full gym as well as a kitchenette w/ full sized fridge, keurig, microwave, air fryer, toaster oven, single burner, and laundry facility. Smart tvs, hammocks and a rooftop firepit are in the outdoor entertainment area. LGBT & BIPOC friendly. Gym, hot tub and laundry are shared with owners but guests have priority access. Close to Mt Hood Wilderness (45mins) & Downtown Portland (15mins).

River Garden Cottage.

Charming cottage apartment on a garden and forest hill. Next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

Recreational Family Fun & Adventures Await

Entertain outdoors in a covered lit patio with grill and cooler. Stay warm with 2 propane firepits or by the campfire pit. Fenced in yard is pet friendly. Nearby Rec Center offers a Gym, Splash Pad, and Indoor Pool with Water Slide ($7 Day Pass). Enjoy basketball, baseball, soccer, and tennis all walking distance with our sports equipment. Explore many nearby parks with playgrounds and trails with our bicycles. Short drive to Washington Square Mall, restaurants, grocery stores, and more!

Milwaukie Riverfront Guest House

Incredibly majestic river-front guest house. This is the ultimate romantic getaway and peaceful retreat. Large windows and double french doors look out on the Willamette river from the cottage living room and loft sleeping area. It includes a semi-private rocky beach, and a large manicured lawn with fire pit. Kayaks are available for use, and guests are welcome to bring their own too! The guesthouse has its own drive-way, and is completely separate from the main-house grounds for privacy.

Portland Hillside Retreat near OHSU & river

This comfortable home, nested in a forest setting and located in a great central, and safe neighborhood. The space is functional, and well appointed. You’ll have a super functional kitchenette, private bathroom, living room / work space / dining area, along with two, full bedrooms, and a very comfortable pull-out sofa that offers the space of a queen. Well stocked amenities with customization available on request. Within walking distance of the river, park, trails, and OHSU.

Blue Heron Sanctuary · Private Riverfront Cottage

Welcome to Riverfront Cottage, a serene retreat set along the Willamette River within a protected natural habitat rich with wildlife and seasonal beauty. Originally built in 1944 and thoughtfully updated, this private guesthouse blends vintage character with modern comfort. Enjoy peaceful mornings, river views, and a quiet setting shaped by blue herons, songbirds, and river life. A perfect place to slow down and unwind just minutes from town.

River Forest Guest House, River and Dock access

Tasteful and brand new guest house, beautiful neighborhood on the river. Guests have private deck facing yard and separate outdoor sitting area on the Willamette river (behind main house). Watch the birds, boats and riverboat cruise from the patio with fire pit. 2 miles from lightrail station, restaurants and shopping nearby and 15 mins. to downtown Portland. All are welcome! We are on the east side of the river, Milwaukie area.

1st floor, Sleek, Nature Lover's Studio

Kick back and relax in this calm, stylish, non-smoking studio. Because of our allergies, it is an animal free listing. Allergy safe, smoke free. There is no smoking, vapping, dabbing, or loud noise permitted. This is a quiet place to unplug. Lay by the lake or under the tall trees. Watch eagles, herons, and wild life.