Discover a selection of 1,000 vacation rentals in Lake Oswego, OR that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $90 per night, and houses and condos are popular options for a stay in Lake Oswego. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Lake Oswego
Destination guide

An oasis, but not where you'd expect it

While "the 'burbs" might not evoke the perfect getaway, this suburban neighborhood just 30 minutes south of Portland is exactly that. After a scenic drive, visitors can breathe in the fresh air, and enjoy the locally owned boutiques and restaurants situated on the banks of Lake Oswego. Art galleries and theaters bring new life to the area, too, with constantly changing exhibits, productions, and performances. As one of Portland's most affluent suburbs, there are plenty of upscale Lake Oswego vacation rentals to please even the most discerning of travelers.

Things to do

Food, art, and culture thrive on the banks of Lake Oswego

If someone claimed Lake Oswego invented farm-to-table, you just might believe them. Nearly every restaurant touts its "farm fresh" quality, and those eager to learn more about the local organic and sustainable agriculture scene should pay a visit to the city-run Luscher Farm. Cultural highlights include an outdoor public art exhibit called the Gallery Without Walls, and the annual theater season at the Lakewood Center for the Arts. Visitors looking to get even further away from city life will enjoy scenic drives through nearby wine country, or hiking one of the city's 5 main trails that loop around Lake Oswego.


Where nature lovers and culture vultures unite

Whether escaping the city in search of small town charm and local hidden gems, or just seeking some fresh air, Lake Oswego delivers. Nature lovers will enjoy the city's surrounding hiking trails and the many public parks and gardens. Culture vultures, meanwhile, will stay busy hopping from boutiques to galleries, or taking in a show or concert. Everyone can end the day with a delicious meal at one of the town's many charming lakefront restaurants, or in the comfort of a Lake Oswego vacation rental.


Don't let the rain get you down

Like Portland, Lake Oswego is known for its rainfall - but don't let that stop you! April showers certainly bring a burst of May flowers, while the summer is your best bet for sunny and dry days that aren't too hot. The fall is perfect for a flash of autumnal color, but keep in mind that a spot of rain is usually on the horizon, too. Winter visitors should use the gray, damp weather as the perfect excuse to hole up in a Lake Oswego vacation rental with an Oregon-made Pinot Noir or a locally-brewed craft beer.

Natural features

Small-town charm in this lakefront gem

Situated on the banks of its namesake lake, Lake Oswego is practically picture perfect. With sprawling homes nestled among the hills and hiking trails that loop around the town, it's the perfect place to escape the hustle and bustle of Portland. The town has the added bonus of being on the edge of wine country and under 2 hours from the coast, for any travelers interested in venturing just a bit further to explore the rocky coastline of the Pacific Northwest.

How to get there

Traveling to and around Lake Oswego

The nearest airport is in Portland International Airport (PDX), located 12.2 mi (19.7 km) from the city center.

What are the top vacation rentals in or near Lake Oswego?

The heart wants what it wants, and right now that's a vacation. Now's the time to pack your suitcase and head for one of these top vacation rentals in or near Lake Oswego:

  • Around 4 miles from the center of Lake Oswego, you'll love staying at "Lovely Apartment In The Heart Of Sellwood". It has 1 bedroom and a host of amenities including air conditioning and cookware, dishware and utensils.
  • Another enticing choice is "Carefully Restored Wilsonville Farmhouse Next To Parks And Trails", which is around 9 miles from Lake Oswego. Offering 3 bedrooms, a microwave oven and lowered locks, it has everything you need to make your visit comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Lake Oswego vacation rental for you.

What are the best tiny house vacation rentals in or near Lake Oswego?

You need only step foot inside one of Vrbo's tiny house vacation rentals in Lake Oswego to figure out that awesome things really do come in little packages. Smartly designed to maximize every spare inch of space, these pint-sized digs deliver a big vacation experience:

  • Take a couple of days off to recharge at "Custom Tiny House With Boho Vibes". Located in Kerns, heating and towels are included here.
  • "Custom Tiny House With Bamboo Vibes" in Portland is another good choice. Air conditioning and a hair dryer will make your getaway here more comfortable.

What are the top-rated vacation rentals for weekend getaways in or near Lake Oswego?

Those chores can wait, because weekends were made for having fun. Make your way to one of these weekend getaways in and around Lake Oswego and enjoy all the awesome things to do nearby:

  • Spend your whirlwind break at "Modern, Beautifully Located Reed College 2 Bedroom Apartment With Private Patio", which is around 6 miles to the northeast of central Lake Oswego. There's plenty of nature and adventure to discover around here. Go hiking and biking and basketball or simply delight in the sights of Wahkeena Falls and Fantasy Trail.
  • "Peaceful Garden Cottage, Close To Mt. Tabor Park And Downtown Bus" is another dream escape to consider. Around 9 miles northeast of Lake Oswego, use it as a base to do a little golf or hiking and biking. Park Mountain Lane Trailhead and Gabriel Park also have to be on your must-do list while you're here.

Can I find studio apartments for rent in and around Lake Oswego?

Studio apartments are tough to beat when it comes to location, convenience and character. Get cozy in one of these studio apartments for rent in or near Lake Oswego and immerse yourself in the local vibe and energy:

  • Make "Lovely Apartment In The Heart Of Sellwood" your home for a couple of days or more. This appealing vacation rental comes with amenities including a fridge and towels.
  • Alternatively, organize a stay at "Peaceful Garden Cottage, Close To Mt. Tabor Park And Downtown Bus", which comes with conveniences such as WiFi and a TV.

There are lots of highlights around Lake Oswego to put on your must-do list. Feed the culture vulture within and visit Antoinette Hatfield Hall and Makah Cultural and Research Center.

Can I find short term rentals in or near Lake Oswego?

Now and then, you just need to take a well-earned breather, even if it's only for a few days. Experience a delightful combination of exploring and relaxing at one of these short-term rentals in or around Lake Oswego:

  • If you'd love to be near the action, "The Multnomah Guest House" will be just the thing. It's within reach of the center of Lake Oswego and a handy base to discover attractions like Oregon Zoo and Veterans Memorial Coliseum.
  • Roll out of bed, make a coffee and then plan what to explore around "Stylish And Modern 3 Bedroom Townhome In The Heart Of Vibrant Alberta Arts District". Portland State University and Portland Japanese Garden are must-do's if you stay at this popular rental.

What are the best romantic weekend getaways in or near Lake Oswego?

Whether spent in a cabin, a cottage or a treehouse, a romantic weekend getaway is a fantastic way to say "I love you." Whisk your partner off for a couple of leisurely days at one of these enticing escapes in or near Lake Oswego:

  • Put on some soft tunes and slow dance the nights away at "Lovely Apartment In The Heart Of Sellwood". Around 4 miles from Lake Oswego, this property has everything you need for a romantic getaway, including a fireplace and air conditioning.
  • Another place where you can spend a few dreamy days together is "Carefully Restored Wilsonville Farmhouse Next To Parks And Trails". Located around 9 miles from Lake Oswego, winery tours and a fireplace add to the atmosphere here.

What are the best large group vacation rentals in or near Lake Oswego?

Big groups mean massive fun. They also mean finding a place that'll effortlessly fit your whole crew. Browse our large group vacation rentals in or around Lake Oswego and get your loved ones together under one roof:

  • You'll have loads of space to move around at "Stunning Modern Home In Trendy And Hip Mississippi District". Around 10 miles north of Lake Oswego, this sizable retreat has 5 bedrooms that sleep up to 12 guests. Quality amenities include a kitchen and a water park.
  • "Super Clean, Sanitized, Centrally Located" is another fantastic option. It's around 11 miles to the north of Lake Oswego, has 4 bedrooms and sleeps up to 16 guests. A garden and a nearby river are just a couple of things designed to make your group getaway more comfortable.

What are the best houses for rent with a pool in or near Lake Oswego?

Nothing spells fun like a pool. Blow up your inflatable flamingo and browse these houses in or near Lake Oswego that come with this must-have amenity:

  • Pack your swim gear and take a break at "The Multnomah Guest House". There are also lots of other great amenities here, including a video library and coffee and tea making facilities.
  • Alternatively, enjoy a more leisurely pace of life at "Designer Owned House On Vibrant Williams Avenue Near Mississippi". Along with a refreshing pool, make use of a separate dining area and books.

Lake Oswego has a mediterranean climate, with average summertime temperatures ranging from 55 ºF to 80 ºF. But there's no need to wait until summertime to visit. Check out the search bar at the top of the page and adjust the filters to find the ideal Lake Oswego vacation rental and organize your getaway for whenever you like.

What are the best large family vacation rentals in or near Lake Oswego?

It's always more fun when you share those memorable moments with the people you care about the most. Whether you're planning a family catch-up or taking time out with your best friends, Vrbo has a large vacation rental that's right for you. These are two of our best in and around Lake Oswego:

  • Sleeping up to 8 guests in 3 bedrooms, "Carefully Restored Wilsonville Farmhouse Next To Parks And Trails" is the ideal place for some family time. This retreat is 9 miles to the southwest of Lake Oswego and has amenities that include a DVD player and nearby birdwatching activities.
  • "The Portland Villa - In The Heart Of Ne Portland" also offers the space you need to share special moments with loved ones. This option is around 11 miles to the north of Lake Oswego, and accommodates 9 guests in its 4 bedrooms. Outdoor furniture and coffee and tea making facilities will help keep everyone comfortable and happy.

If you want to see some family-friendly attractions around the area, you're spoiled for choice. Oregon Zoo, International Rose Test Garden and Portland Children's Museum offer fun for all ages.

Can I find family cabin rentals in or near Lake Oswego?

Cozy up with the kids in a family cabin rental in or near Lake Oswego and get set to make some beautiful new memories together. Here are some we think you'll love:

  • "Private Tiny Forest Cabin Near Portland And Local Wineries" - Located around 7 miles west of the center of Lake Oswego, this family-friendly escape offers amenities like a fridge and books.
  • "Newly Renovated Urban Boho 5bedroom Cabin In Private 6 Acre Forest" - This property has also been designed with families in mind and is around 8 miles northwest of Lake Oswego. Offering coffee and tea making facilities, a microwave oven and more, it'll get your group's nod of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Lake Oswego vacation rental that's perfect for your needs.