Home Vacation Rentals By Owner In Lake Oswego, OR

Showing 20 Of 51 Vacation Rentals
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$92.58

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Private Vacation Home

Executive ADU overlooking 9th Fairway at Oswego Lake Country Club. 31+ days min.

Lake Oswego, Oregon, United States

In Lake Oswego's most exclusive and desirable location overlooking the lush greens of Oswego Lake Country Club, this custom built 2007 European inspired home has all the modern safety features (fire sprinkler system w/dedicated alarm, and C02 detector), a fully equipped eat-in kitchen, full bath, cedar-lined closet, and extra storage. Secure off-street parking and only 25 minutes from PDX. brbrJust outside its door is the entrance to the 54 acre Iron Mountain nature trail - a walk through the majestic old growth woods, once a rail line for mining iron ore. A walkable mile to town with restaurants, shops and a seasonal Saturday Market. In a serene and peaceful setting, it is the perfect balance of tranquility and accessibility.brbrThis home has meticulously landscaped grounds with a gravel pathway leading to the unit. A regulation bocce ball court is available for your enjoyment. It is the perfect spot to call home during a visit to the Northwest, a household move, a remodel, a home flood or fire, or a job relocation to the Portland Metro Area. Located just 20 minutes to Portland metro hospitals make this a quiet and serene environment for a medical recovery.brbrThis unit is available for a minimum of 31 days due to local regulations that access a $20,000 system development fee for ADU rentals under 31 days. (Please note that the 6% local accommodations tax for transient lodging tax for short-term rentals of 30 days and under, is not charged on this unit since it is a long-term rental of 31 days or more).
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Exceptional(22)

$390.3

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Private Vacation Home

Lake Oswego Home w/ Covered Patio: Near Portland!

Lake Oswego, Oregon, United States

Your next Pacific Northwest getaway begins at this 3-bedroom, 2-bath vacation rental in Lake Oswego, OR! With a full gourmet kitchen, a cozy interior, and a covered patio with outdoor seating, this home offers the perfect place to relax with loved ones. Explore the nearby Willamette River for outdoor adventures, visit the Lake Oswego Farmers' Market for local treats, or venture into downtown Portland. When evening comes, kick back on the living room sofa and enjoy the warmth of the fireplace.brbr-- THE PROPERTY --brbrMovie Projector & Big Screen | Quiet Neighborhood | Outdoor Seating | Proximity to Willamette RiverbrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bunk BedbrbrMAIN FEATURES: Covered patio, fireplace, home theater system, 6-person dining tablebrKITCHEN: Cooking basics, refrigerator, stove/oven, microwave, dishwasher, dishware & flatware, blender, coffee maker, ice maker, toaster, toaster oven, water filterbrGENERAL: Free WiFi, linens/towels, central A/C & heating, in-unit washer/dryer, hair dryers, hangers, iron/board, trash bags/paper towels, complimentary toiletriesbrACCESSIBILITY: 5 steps required to enter, 2 bedrooms on 1st floor, 2-story homebrPARKING: Driveway (2 vehicles), free street parking (first-come, first-served)brbr-- THE LOCATION --brbrAREA HIGHLIGHTS: Downtown Lake Oswego (2 miles), Lake Theater & Cafe (2 miles), Lake Oswego Farmers' Market (2 miles), Sykart Indoor Racing (6 miles), Oaks Amusement Park (7 miles)brGET OUTSIDE: George Rogers Park (2 miles), Willamette River (2 miles), Tryon Creek State Natural Area (4 miles), Tom McCall Waterfront Park (10 miles), Hoyt Arboretum (13 miles), Molalla River State Park (16 miles), Forest Park (19 miles)brPORTLAND SPOTS (~10 miles): Powell's City of Books, Portland Japanese Garden, Washington Park, Oregon Zoo, OMSI, Portland Art MuseumbrAIRPORT: Portland International Airport (23 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The 2-story property requires 5 steps to enter and additional stairs to access the 2nd-floor bedroombr- NOTE: The lake is not available for guest use
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$320.48

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Private Vacation Home

Single-Story|Cozy 3B3B|Street Parking Available|Flex-Lease| Workspace n #42366

Lake Oswego, Oregon, United States

The house requires a minimum 30-day stay and utilities are not included.brNestled in Lake Oswego’s prime location, this 3-bedroom, 3-bathroom home blends privacy and sophistication. The primary suite serves as a private sanctuary, featuring an ensuite bathroom and patio access that opens to lush lower-level living areas. The heart of the home is defined by a grand living room with soaring 24-foot vaulted ceilings and a gas fireplace, seamlessly flowing into the open-concept kitchen equipped with professional-grade appliances, a quartz island, and ample culinary workspace. Two secondary bedrooms offer serene views through patio access, while versatile spaces like the den and sunroom invite natural light to dance across hardwood floors and custom carpets.brbrGuest Accessbr• Clean, Fully Furnished and Decorated Home Located in Lake Oswegobr• Single-story home with all bedrooms on the main floorbr• Remodeled Kitchen Equipped with Granite Countertops and a Spacious Center Islandbr• 1 bedroom comes equipped with a desk and chair, providing ideal spaces for working or studying from homebr• 3 Full Bathrooms for Your Conveniencebr• Hardwood Flooring Throughout The Homebr• Spacious Backyard With Relaxing Patio Areabr• Only Street Parking AvailablebrbrLocationbrPerfectly positioned for Pacific Northwest living, this home places you minutes from premier amenities: Walk to top-rated Lake Oswego High School (9/10) and Forest Hills Elementary (10/10) via wooded trails, while downtown’s boutique shops (Zupan’s Market) and waterfront dining at Lakewood Center await a 5-minute drive. Healthcare needs are covered with Providence Willamette Falls Medical Center 12 minutes away and OHSU Health 15 minutes north. Embrace outdoor adventures with direct Oswego Lake access (kayaking/sailing), 5 minutes to Iron Mountain Park trails, and 20 minutes to Portland’s iconic Washington Park (zoo/Japanese Garden). Commuters thrive with an 18-minute drive to downtown Portland via SR-43, 30 minutes to PDX Airport, and seamless I-5 access for Seattle/Salem getaways—blending lakeside serenity with urban efficiency.
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Condo

Condo on Lake Oswego, a rare find. Pet friendly!

Lake Oswego, Oregon, United States

This home is directly on Lake Oswego with a short walking distance to cafes, dining, shopping, theaters, parks, bus stops, grocery and more.brbrYou will love living here for the stunning beauty and central location.brbrThis sweet and upscale community offers plenty of dining, shopping, and theater opportunities. brbrIt's very walkable and has lots of great people-watching opportunities while still being a small town of under 40,000.brbrEach bedroom has a bed, TV, dedicated workspace, and storage.brbrThe living room features a very comfortable sofa and an oversized chair by Lazyboy, both of which recline. Guests can enjoy the new 55 LG OLED Smart TV with included Wi-Fi and Amazon Prime.brThe dining room offers a nice dining table and four chairs. The coffee table in the living room doubles as a seating so the table sits six comfortably.brbrThe kitchen has been newly remodeled and features all new state-of-the-art appliances. The island offers extra seating and storage.brbrYou have a private yard that is highly valued; it provides a great place to hang out and gives your dog (if you have one) a nearby place to go out. This space is only for you to use and cannot be accessed by anyone else.brbrThe condo feels light and bright and Airy and open and has all of the appliances large and small that you could want. With plenty of space to store food and goods you can relax and simply enjoy life on the lake.brbrYou will have one dedicated parking space and open street parking.brThe Guest spaces are upon availability. brbrThe common dock is available for your use. The lake access is for resident owners or tenants on a 6 month minimum lease. brbrbrbr
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$323.6

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Private Vacation Home

The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors

Lake Oswego, Oregon, United States

​Welcome to the OMG House—an extraordinary overnight experience crafted by local artists, designed to transport you to another dimension. This unique 3-bedroom home features a fully mirrored room equipped with immersive sound and mood lighting, perfect for both play and restful sleep. Additionally, enjoy a whimsical cat meme lounge in the media room, an experience that has earned Best-in-Show honors at Rose City Comic Con.​brbrRecognized as one of Oregon's top stays by Willamette Week, the OMG House offers more than just a place to sleep—it provides an unforgettable journey. brbrWe've got over 180 five star reviews by families, couples and friends.brbrBedroom Setup:brbrMaster Bedroom: Features a queen-sized bed with luxurious linens, ample closet space.​brSecond Bedroom is the mirrored room: Offers a cozy Japanese style tatami mat for two , immersive mirror, and easy access to the shared bathroom.​brThird Bedroom: Includes two twin beds, perfect for families or groups, with playful design elements that spark imagination.​brbrHome Amenities:brbrFully Mirrored Experience Room: Immerse yourself in a room adorned with mirrors, complemented by customizable sound and mood lighting, ideal for both relaxation and entertainment.​brbrCat Meme Lounge: Unwind in the media room, themed around popular cat memes, providing a fun and lighthearted atmosphere.​brbrModern Kitchen: Equipped with state-of-the-art appliances, cookware, and utensils, perfect for preparing meals during your stay.​brbrLiving Area: Comfortable seating arrangements with artistic touches, creating a welcoming environment for gatherings.​brbrHigh-Speed Wi-Fi: Stay connected with complimentary high-speed internet throughout the property.​brbrLaundry Facilities: Washer and dryer available for guest use, ensuring convenience for longer stays.​brOutdoor Features:brbrPrivate Patio: Enjoy outdoor dining or relaxation on the furnished patio under a circus tent, (not pictured for your surprise) surrounded by lush greenery.​brbrPrivate Lake Access (Seasonal): From June 17 to August 27, guests have exclusive access to a private lake just blocks away, perfect for swimming or simply soaking up the sun.​brbrOn-Site Parking: Ample parking space available for guests, accommodating multiple vehicles.​brbrLocation: Conveniently located just 15 minutes from Portland via I-5, the OMG House offers easy access to urban attractions while providing a serene retreat. Explore nearby dining, shopping, and entertainment options, or venture out to experience Oregon's natural beauty.​brbrBook your stay now and step into a world where art, comfort, and adventure converge.
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Exceptional(29)

$348.63

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Private Vacation Home

#StayInMyDistrict Lake Oswego Honey Bee Cottage

Lake Oswego, Oregon, United States

Summary:br#StayinMyDistrict Lake Oswego Honey Bee Cottage. Live like a local while experiencing the trendy Lake Oswego District! 5 blks to coffee shops, restaurants, shopping & local hot spots! Convenient to West Linn, SW Portland & Tigard Neighborhoods. Private Cottage nestled in the trees, and furnished to create a comfortable and charming space! Historic 1 bed/1bath (+sofa bed & Futon) King Suite, Kitchen, W/D, Private Patio & Fenced Yard. FREE Parking. Pre-Approved Dogs w/addt’l $50 per pet fee.brbrThe Space:br#StayinMyDistrict Lake Oswego Honey Bee Cottage. This single level, free-standing cottage, is a comfortable retreat surrounded by trees. The large windows and tall ceilings, make the space bright & light and bring nature from the outside in. Beautiful wood grained vinyl floors throughout and warm colors create a feeling of warmth and comfort in the living area. Walk to downtown Lake Oswego and explore the many local coffee shops, dining and shopping. Less than 1 mile to the waterfront and Lake Oswego Farmers MarketbrbrCompact, full kitchen is stocked and ready for preparing meals from home. Refrigerator, stove & oven, dishwasher, microwave, Drip and cold press coffee makers. Utensils & cookware are included to make eating in, convenient and enjoyable. Enjoy breakfast, lunch, or dinner seated at the dining table or at the kitchen bar! brDining table can pull out to accommodate up to (4) and there are (2) stools at the bar for seating up to (6). French doors close off the dining room, and make it a perfect private area to set up a computer for working remotely. brbrSnuggle up with a book or watch a movie on the sofa OR futon. (BOTH pullout for sleeping). Perfect for relaxing at home. Smart TV, set up for streaming, and wireless Internet. Sofa also pulls out to a sofa bed for additional guests and there is additional seating in living area.brbrBedroom has a comfortable King bed with quality linens, and a spacious closet for guests personal items. There is a smart TV for streaming and bedside lamps for guests comfort. brbrBathroom has plenty of space for your personal items and a full bathtub/shower. Essentials, paper products and high quality linens, are provided for guest. A hair dryer and an iron complete the necessities.brbrA pack and play and children’s kitchen items make this home a comfortable space for families to enjoy.brbrThere is a quaint private patio with a wood burning firepit (bring your own wood), & seating. Perfect for your morning coffee or glass of wine on a nice evening. There is a second covered patio out the French door off the living area with (2) chairs and a small table. There is ALSO a large fully fenced, separate yard that guests can use (perfect for dogs) but it is NOT maintained. It is offered as an additional space. brbrThis property is Dog Friendly and accepts up to (2) Pre-approved Dogs with an additional $50.00 per pet fee. PLEASE read and understand our Pet Policy before booking. brbrThe cottage entrance is from the alley and there are (2) parking spaces in a small driveway.brbrGuest Access:brGuests have access to the entire space. The large backyard area is NOT maintained but is accessible to guests. The owner does live in the neighborhood. Parking & Entrance to the cottage is alley access ONLY.brbrThe Neighborhood:brFollow the Willamette River south, past Portland State University and Lewis & Clark College, and you’ll eventually reach the sylvan hills of Lake Oswego. In the early days — back when it was a humble assemblage of iron smelters, lumberyards and homesteaders — travelers could only reach Lake Oswego via the lazy river or bumpy dirt roads. Perhaps that’s why, though only 20 minutes from downtown Portland, the city still feels a world away. brBuilt along the Lake Oswego shoreline, the historic Lake Theater and Cafe has been showing movies since 1940 and recently expanded to offer a full bar, café menu and live music. For a post-flick drink, sample a flight of brews at adjacent Stickmen Brewing Company, where an enticing outdoor patio hovers over the shimmering lake.brIf you’re in town on Sunday, be sure to visit the picturesque Oswego Hills Vineyard and Winery for a complimentary wine tasting. Perched atop a grassy hill, the vineyard offers sweeping views of the surrounding area, including Luscher Farms, an urban farm-cum-park with walking paths and gardening plots. Walk the 4.4 mile (7 km) loop through the farm and over Cook’s Butte, keeping an eye out for blackberries when they’re in season.brbrIf you prefer to stroll through downtown, the Arts Council of Lake Oswego organizes a walking tour of its Gallery Without Walls, a collection of over 60 sculptures scattered about town. Or wander around Millennium Park, the site of Lake Oswego’s cheery farmers’ market spring through fall, and outdoor movies and concerts in the summer.brOne of the most city’s most popular attractions, the loamy Lake Oswego Public Golf Course features a cheery creek meandering through its 18 holes, as well as gorgeous views of Mount St. Helens and Mount Adams. To explore the tree-shrouded hills of Lake Oswego via the many miles of pathways the city has created, take advantage of Lakeside Bicycles’ bike rental program or allow the family-run business to fit you for your very own dream cycle.brbrGetting Around:brApprox. 30 min from the PDX Airport, 20 min from Downtown Portland and 10-15 min from Tigard, West Linn and SW Portland/Beaverton area. The cottage is .3 miles from the Lake Oswego Transit Center. Trimet can take you anywhere in the city, and is a quick way to get downtown. The Max is another great option that you can get to starting with the bus. This location is also incredibly bike-friendly and a walkable neighborhood. Safe well-lit streets and sidewalks make it a great neighborhood to explore on foot. It has a bike score of 76 and a walk score of 82! There is a single cruiser bike at the property and you are welcome to ride at your own risk. We cannot guarantee regular maintenance but there is a bike shop downtown that can do a quick flat repair if needed. There are also Portland Bike Town bikes throughout the city that can easily be rented if you prefer to explore the city on bike.brbrOther Things to Note:brWe require that guests provide Full Name of ALL adult guests. This will be required before check in. Please provide this information with your confirmed booking.br~ You must be over the age of 25 to rent any of our properties.br~You may be required to provide a photo of your Drivers License or Government ID directly to the host. This is for the safety and security of both guests & property Owners, and will be requested at the discretion of Stay in My District. br~ No additional guests and visitors/guests that are not registered on the reservation booking are allowed to be on the property after 10pm. br~ Smoking anywhere on the property will result in forfeiture of your entire deposit plus can result in additional fees up to $500 for smoke removal.br~ Housekeeping is required and provided every 15 days for an additional charge on all stays over 15 nights.br~This property accepts up to (2) pre approved dogs. Undeclared Pets will result in a $250 additional cleaning fee. brWe are happy to welcome your well behaved, and house trained dog into our home! We do NOT accept Cats due to allergies. There is an additional pet fee of $50 per pet, as per my listing details. We will go ahead and request the fee via an alteration request after the booking is confirmed. Please accept ASAP to confirm authorization.brPlease also be aware of our pet policy:br-Up to (2) pre approved dogs allowed. br-Pets should not be left unattended at the property inside or outdoors. We do have kennels available on request for an additional fee. br-Please pick up after your pets in outdoor areas immediately. br-Pets are NOT allowed on furnishings or linens. Evidence of pets on furnishings or linens will result in additional cleaning fees to guest.br-Pet fee accounts for additional cleaning and normal wear & tear due to hosting pets. Pet fee does NOT cover damage or additional cleaning above and beyond reasonablebrbrInteraction with Guests:brGuests have access to the entire cottage with private entrance. We are a local Mgmt Company and we manage for the Owners who live on the same block. We are available via booking platform, phone or text, or in person if needed.
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$92.58

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Private Vacation Home

Oswego Lake Country Club by 9th Fairway; nThe Bentley - An ADU for 31+ days

Lake Oswego, Oregon, United States

Overlooking the greens of the Oswego Lake Country Club this executive suite is in a private peaceful setting in one of the most exclusive and desirable locations in Lake Oswego. An ideal, yet short distance from the sound of boats on the lake and the whistle of the train that runs along Oswego Lake's North Shore makes this a most ideal, quiet and serene place to stay. Enjoy secure off-street parking, easy access to the transportation center, and a 25 minute drive to Portland International Airport. brbrThis home provides clean, upscale, safe and secure interim housing for those who are between homes due to a household move, a home flood or fire, a remodel, or a job relocation to the Portland Metro Area. Located just 20 minutes to Portland metro area hospitals makes this a quiet and serene environment for a medical recovery. For those living in the desert in the winter, there is nothing like Oregon in the summertime. The City of Lake Oswego is located mid-point from Mt. Hood and the Oregon Coast.brbrA walkable country mile along the lake makes it very convenient to shop, dine or visit the Saturday Market in downtown Lake Oswego. This location is 1.25 miles to Lakewood Center for the Arts, which has a regional theatre and 2-stage venue for plays & musicals, with an upscale thrift shop, and local art gallery. Lakewood Center is host to the Lake Oswego Festival of The Arts, a significant and noteworthy Art Festival in Mid-June. The City of Lake Oswego has the official City of Arts designation.brbrTwo entrances are on the lower ground level of a private 2007 custom-built European inspired Old Oswego style home on 5/8 acre. Just outside your door is the entrance to the 54 acre Iron Mountain Trail - a 3/4 mile walk through the majestic old grown woods, once a rail line for mining iron ore. Along the Willamette River and less than 2 miles from this home are the remnants of the iron smelter at Foothills Park, and the refurnished furnace at George Rogers Park, a symbol of the City of Lake Oswego. The City of Lake Oswego has the official designation as a City of Trees.brbrThis suite is not a studio as it has a fully-equipped eat-in kitchen and laundry area, full bath, generous cedar lined closet, and a wine cellar which provides space for storage. Included are a ladies desk & Herman Miller desk chair, a comfortable chaise sofa and 52 Smart TV. The large suite has a ceiling drapery room divider to easily separate the sleeping area from the living space if desired. A queen bed with a gel foam topper & featherbed have guests raving about its comfort. Clean mattress & pillow protectors are over spotless bedding, and new white towels are provided for the discerning guest.brbrThis custom home has a dedicated and monitored burglar/fire alarm, zoned HVAC, and a fire/sprinkler system. The grounds are meticulously maintained by the owner and a regulation bocce ball court is outside your door for your enjoyment. Your host lives on site, and is congenial while making your privacy a priority, and is well-traveled and experienced in residential and commercial real estate. Also living on-site is an Estate Caretaker.brbrDue to the local regulations on Short Term Stays in SDU/ADU's, this property is available only for 31 days or longer. On short term stays of less than 31 days, the City of Lake Oswego will assess a $20,000 System Development Charge. This unit is often booked every month of the year and does not have frequent turn-over. It is clean, pristine and is not shop worn; it has been priced in a sweet spot making it very affordable for those needing interim housing.
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