Waterfront vacation rentals in Lake Oswego

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Top-rated waterfront rentals in Lake Oswego

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
The exterior of the cottage is showcased, featuring a bright orange facade and white trim. Two windows are visible on the side, with a glass door that leads to the patio. Surrounding greenery includes tall grasses and various plants, contributing to a natural setting.
Guesthouse in Westmoreland
4.97 out of 5 average rating, 606 reviews

Dream Cottage! Springwater Bike/Walking Path!

Explore, recharge, dream in your own quiet & inspiring country-in-the-city cottage. Sellwood is a great riverside neighborhood, featured in Sunset’s Best Places to Live in the West. Set off on a bike path adventure or start your novel at the writer’s desk. Walk to coffee shops, restaurants & New Seasons Market grocery. Ideal for College visits: drive times, 10 min to Reed, 10 min to Lewis & Clark, 15 min to PSU. Note: PLEASE ASK about weekly or monthly discounts if you're planning extended stay!

Guest favorite
A spacious living area features a large sectional sofa adorned with soft pillows. Natural light fills the room through expansive glass doors that open to a deck. A coffee table and decorative items add an inviting touch to the open-concept layout, which leads to a modern kitchen.
Home in North Plains
4.97 out of 5 average rating, 158 reviews

2 Acre, Pond View Home, with Hot-tub & BBQ FOR 16

Relax in this calm, stylish space. Enjoy beautiful nature views OR catch up on your favorite flicks, with Tv's in every room. Enjoy the large deck with your favorite beverage, while taking in the beauty of nature. It's also the perfect place to grill. The hot tub is a lovely place to unwind. Relax in the warm bubbly water. Our space offers something for people of all ages. We can't allow indoor pets at this time due to family allergies. Also, no smoking allowed inside Thanks for looking!

Top guest favorite
A serene entrance features a wooden archway draped with greenery, leading to a tranquil lake. The lush yard is complemented by a carved bear statue, and mature trees provide shade. The calm water reflects the surrounding greenery, creating a peaceful atmosphere.
Guest suite in Milwaukie
4.95 out of 5 average rating, 436 reviews

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.

Guest favorite
A tranquil guest house is nestled alongside a serene river, framed by tall trees with autumn foliage. Sunlight filters through the leaves, illuminating the exterior of the house while reflecting off the calm water, creating a peaceful ambiance.
Guesthouse in Clackamas
4.97 out of 5 average rating, 227 reviews

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

Guest favorite
A serene river view is visible, framed by lush trees and greenery. The clear water reflects the sky, while a gentle wake from a boat creates ripples. A sandy beach area is located in the foreground, alongside a manicured lawn and a fire pit.
Guesthouse in Milwaukie
4.88 out of 5 average rating, 183 reviews

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.

Guest favorite
A private deck features two chairs and a small table, surrounded by lush greenery. The space is shaded by an overhead structure, with a vibrant area rug adding pattern to the wooden flooring. Scenic views of the landscape and trees are visible in the background.
Guesthouse in Gladstone
4.96 out of 5 average rating, 130 reviews

The River House - Waterfront Retreat w/Fireplace

Experience the serenity of riverside living in our private, enchanting retreat nestled on the tranquil banks of the Clackamas River. This guest suite offers 1500 square feet of living space, boasting a private entrance and a spacious deck that grants breathtaking views of both the serene pond and the majestic river. Step inside to discover a haven of comfort and elegance. The gourmet kitchen features SS appliances, sleek granite countertops, and is fully stocked for your culinary needs.

Guest favorite
A cozy outdoor deck area is furnished with a glass-top table and two chairs. Lush green grass and trees are visible in the background, along with a serene stream that meanders through the landscape.
Home in Portland
4.87 out of 5 average rating, 684 reviews

A River (stream) Runs Through It

Okay, well, it's a stream, but it's all yours to enjoy. For the nature lovers we have deer, beavers, ducks, nutria, fish, etc. (think wetlands). For everyone, the house (duplex) is fully equipped with a fireplace, BBQ, hot tub central gas heat and central AC. This is a bright, clean and cozy space to land for folks who love the suburbs (not in the city city but we are close drive to the city center) but want to be surrounded by nature. With ambient noise from the creek and highway.

Guest favorite
A spacious family room features a large L-shaped couch with comfortable seating. A plush green ottoman rests on a striped rug, complementing a contemporary armchair. Natural light filters through multiple windows, illuminating the room, which includes a TV and a cozy gas-lit fireplace.
Home in Portland
4.93 out of 5 average rating, 261 reviews

Spacious Forest Retreat w/ Hot Tub & Views

In the woods, next to a creek, but still in Portland! Forget your worries in this spacious and serene space. There is a private entrance to this large two story guest suite, which includes a family room, living area with dining area and kitchenette, bedroom and bathroom, central AC, and private balcony. Located in a quiet neighborhood, close to hiking trails in Woods Memorial Park. A 3-minute drive or 1 mile walk to popular Multnomah Village; 15 minutes from Downtown Portland.

Guest favorite
The cabin, nestled among towering cedar trees, features a rustic exterior with warm lighting from the windows. A serene creek flows nearby, with smooth stones and mossy patches lining the water's edge. A wooden bridge connects to the surrounding natural landscape.
Cabin in Milwaukie
4.89 out of 5 average rating, 730 reviews

Rustic Creekside Cabin

This tranquil hideaway feels like you're in the middle of the forest, but is just minutes from Portland. Relax next to the burbling creek surrounded by towering cedar trees. The MAX Orange line and downtown Milwaukie are only five minutes away. Built in 1928, the cabin has one bedroom and bathroom, living room, full kitchen and central heat. The bedroom has one queen bed and an en suite bathroom. There is a pull-out queen futon in the living room.

Top guest favorite
A spacious living area features light green walls and hardwood flooring. A gray sofa and a blue accent chair offer comfortable seating, complemented by a wooden coffee table. The open kitchen is visible in the background, showcasing modern appliances and warm wood cabinetry.
Guesthouse in Milwaukie
4.99 out of 5 average rating, 351 reviews

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.

Superhost
Condo in Portland
4.89 out of 5 average rating, 122 reviews

South Portland Luxury Condo, City & Mountain Views

Discover our South Portland penthouse condo, where luxury meets comfort. Enjoy views of the city skyline and distant mountain views from this bright, 1350 sq ft space. Perfect for leisure or work, our condo offers a spacious bedroom, office, and top amenities in a secure, family-friendly area. Steps away from shopping, dining, and transport, with secure parking included. Experience the best of Portland in style!

Guest favorite
A cozy cabin interior features a wood stove providing warmth. A small kitchenette with a mini fridge is visible, alongside a dining table with two chairs. The wooden floor adds warmth, while a large window allows natural light to illuminate the space.
Guesthouse in Beavercreek
4.97 out of 5 average rating, 294 reviews

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautiful cozy cabin that is heated exclusively by a wood stove, on the edge of a magical old growth cedar forest on our 11 acre farm and vineyard. Relax on the deck built into the trees, and sleep peacefully in the loft bed, as you soak in the nature around you. The cute out house is just down the path and the cedar hot tub/ outdoor shower is next to the garden.

Popular amenities for Lake Oswego waterfront rentals

When is the best time to visit Lake Oswego?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR3,053 ZARR3,707 ZARR3,070 ZARR3,254 ZARR3,439 ZARR3,355 ZARR3,355 ZARR3,355 ZARR3,170 ZARR2,986 ZARR3,204 ZARR3,321 ZAR
Avg. temp5°C7°C9°C12°C15°C18°C21°C21°C19°C13°C8°C5°C

Quick stats about waterfront rentals in Lake Oswego

  • Total vacation rentals

    Explore 20 vacation rentals in Lake Oswego

  • Nightly prices starting at

    Lake Oswego vacation rentals start at R671 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 1,650 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Lake Oswego vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lake Oswego rentals

  • 4.8 Average rating

    Lake Oswego stays are highly rated by guests—averaging 4.8 out of 5!

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