Pet-friendly vacation rentals in Milwaukie, OR

Explore 10 pet-friendly vacation rentals, homes, and villas in Milwaukie, OR for your next getaway or business trip. Bring your pet along and enjoy the comfort and privacy of a home with premium amenities such as Air Condition Homes, Best Affordable Homes and Great for Groups. Throughout your stay, settle in together, enjoy more space to relax, and experience your destination side by side. With options starting as low as $142 per night and homes offering up to 10 bedrooms and 12 bathrooms, it's easy to book a comfortable stay personalized for your taste. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next pet-friendly adventure and enjoy the journey together.

10 Pet-Friendly Homes in Milwaukie

Palais de Leon

Lake Oswego, OR, US
10 Bedrooms 20 Guests
Aug 31 - Sep 2
$2,199 night

Welcome to the Palais de Leon, a one-of-a-kind private riverfront estate—a breathtaking retreat where luxury, space, and unforgettable experiences come together on nearly three secluded acres along the Willamette River in beautiful Lake Oswego. From the moment you pass through the gated entrance and arrive at the grand circular driveway, it becomes clear this is not simply a home—it’s an extraordinary destination designed for unforgettable gatherings, retreats, and celebrations. Spanning nearly 20,000 square feet, this estate offers an unparalleled blend of elegance, entertainment, and resort-style living. With multiple living spaces, dramatic architectural details, and sweeping river views, every corner of the property invites you to slow down and savor the moment. A Private Resort Designed for Entertaining -- Inside Palais de Leon, you’ll discover an incredible collection of spaces designed for both grand entertaining and quiet relaxation. Host unforgettable movie nights in the private theater room, complete with soaring ceilings, a dramatic fireplace, and its own stage. Gather around the billiards room and full bar, or enjoy time in the library, home gym, and multiple lounge areas that make the home feel like a private luxury resort. Whether you’re planning a corporate retreat, milestone celebration, or extended family getaway, the home offers space and amenities rarely found anywhere else. *Please note that any events hosted at the property must be approved in advance and will incur additional event fees, occupancy requirements, and security deposits. *Extraordinary Outdoor Living* -- Step outside and the experience continues. The estate’s outdoor spaces are truly spectacular, featuring: ★ A resort-style swimming pool and in-ground spa ★ Expansive terraces and courtyard gathering spaces ★ A private pond and lush landscaped grounds ★ A pool house for relaxing between swims ★ Specially curated decor and furnishing ★ Direct Willamette River frontage with a private dock ★ Spend mornings watching mist rise over the river, afternoons lounging by the pool, and evenings enjoying sunset reflections across the water. The setting feels peaceful and secluded, yet you’re just minutes from the charming shops and restaurants of downtown Lake Oswego. Space for Everyone -- With 10 bedrooms and over a dozen bathrooms, the estate comfortably accommodates large groups while still providing privacy and quiet spaces to unwind. With multiple living rooms, gathering areas, and entertainment spaces, guests can spread out, connect, and create memories without ever feeling crowded. A Setting That Feels Truly Rare -- Properties like this simply don’t exist in typical vacation rentals. It’s the kind of place where: Morning coffee happens overlooking the river Afternoons are spent poolside under the Oregon sun Expansive manicured lawns for enjoyment Evenings become unforgettable dinners and celebrations And every guest leaves feeling like they experienced something extraordinary. This estate is more than a home—it’s a private riverfront sanctuary designed for unforgettable stays. We truly want you to enjoy your time and make some wonderful memories with your group. That being said, this is not a party or gathering house for groups that can’t control their noise levels. We have relationships with all of our neighbors who have our direct contact information. Quiet time is 10:00 pm to 8:00 am. Please stay indoors during this time, keep the windows and doors closed and keep the volume to an enjoyable but reasonable level. If it is loud enough to be heard outside in these conditions, it is too loud for you to remain our guest. This property includes a noise alert monitoring system in order to ensure that neighborhood noise levels are respected. Again, please realize we want every group to enjoy their time, laugh, have fun and make memories. These devices are only to ensure noise levels don’t reach a threshold that bothers our neighbors. Also, please note there is no electronic video surveillance monitoring pools or spas, or on the interior of the house. PET FRIENDLY: **There is a $100 pet fee per pet with a maximum of $300 (3 pets). Although we are pet-friendly please note your pet must not be left unattended at the house without you present, even if in a crate/kennel. Failure to adhere to the house rules as it pertains to pets may result in cancellation of the booking with no refund. ** ★ Private gated estate ★ Nearly 3 acres of riverfront grounds ★ Resort-style pool, spa, and pool house ★ Private theater, bar, billiards, gym, and library ★ Private dock on the Willamette River ★ Minutes to downtown Lake Oswego To keep the landscaping pristine, service is scheduled every Thursday morning. Please note that any events hosted at the property must be approved in advance and will incur additional event fees, occupancy requirements, and security deposits.

Portland Home w/ Private Hot Tub: 9 Mi to Downtown

Milwaukie, OR, US
4 Bedrooms 8 Guests
Aug 30 - Sep 1
$153 night

Pets Welcome w/ Fee | Fenced-in Backyard | 1,660 Sq Ft Just 9 miles from downtown, this 4-bedroom, 2.5-bath vacation rental invites you to experience Portland like a local! Take advantage of the nearby Trolley Trail or Milwaukie Park & Ride Station, where you can enjoy easy access to downtown Portland, additional MAX Lines, and endless attractions. After exploring the beautiful Spring Water Trail, return home for a relaxing evening in the backyard. -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed (split king adjustable bed) - Bedroom 2: 1 king bed - Bedroom 3: 1 queen bed - Bedroom 4: 1 full sleeper sofa - Additional Sleeping: 1 portable crib, 1 queen air mattress MAIN FEATURES - Flat-screen TV w/ Roku - Children’s game room, board games - Dining table, laptop-friendly workspace - Private hot tub, fenced-in backyard KITCHEN - Fully equipped w/ cooking basics & spices - Coffee maker, espresso machine, coffee grinder - Side-by-side refrigerator w/ ice maker & filtered water, dishwasher - Toaster - High chair GENERAL - Free WiFi - Central air conditioning/heat - Linens/towels - Trash bags/paper towels FAQ - Pet fee (paid pre-trip) - 1 exterior security camera (facing driveway) - Homeowner next door ACCESSIBILITY - 2-story home, 1 step to enter PARKING - Driveway (4 vehicles) - Free street parking (first-come, first-served) -- THE LOCATION -- - 6 miles to Oak Amusement Park - 6 miles to Crystal Springs Rhododendron Garden - 8 miles to OMSI - 11 miles to Oregon Zoo - 18 miles to Portland Int’l Airport -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - Pet friendly with $100 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story home requires a step to enter - Guests are not permitted to park in/enter the garage during their stay - The property sleeps 6 guests on 3 beds, but the maximum occupancy is flexible up to 9 with sleeping arrangements available on the queen air mattress - The homeowner lives next door, in a completely separate unit, and may be present during your stay - The homeowner has additional amenities in their yard, including a sauna, cold plunge, and fire pit, that may be available during your stay. The owner often travels and will allow guests to use the amenities when they are not home. Additional Charges will apply. Please reach out to the Guest Contact after booking for further information - Your safety matters. This property features 1 exterior security camera located on the front door, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion. It will record when it first senses motion and 30 seconds after the last motion is detected Licence number: 750-20

River Forest Retreat

Milwaukie, OR, US
5 Bedrooms 12 Guests
Aug 23 - 25
$344 night

On the main level there are three beautifully appointed bedrooms all with king beds. The one furthest back is slightly larger and has an entire wall of windows with more unbelievable river views. Descending downstairs, you’ll find the lower-level lounge and media area. This cozy and quite room is where the group can sit back and relax while streaming your favorite shows. There are two additional spacious bedrooms with king beds on the lower level as well. They share the second full bathroom. You will also find the washer and dryer on this level if needed. One of the most special parts of this home is the backyard oasis. A new hot tub has been installed allowing you to soak your troubles away while enjoying the sights and sounds of this riverside paradise. Whether you want a competitive game of cornhole or just to relax around the firepit, there is something for everyone. Please don’t hesitate to reach out if you have any questions. We are excited for you to be one of our first guests at the River Forest Retreat. We truly want you to enjoy your time and make some wonderful memories with your group. That being said, this is not a party or gathering house for groups that can’t control their noise levels. We have relationships with all of our neighbors who have our direct contact information. Quiet time is 10:00 pm to 8:00 am. Please stay indoors during this time, keep the windows and doors closed and keep the volume to an enjoyable but reasonable level. If it is loud enough to be heard outside in these conditions, it is too loud for you to remain our guest. This property includes a noise alert monitoring system in order to ensure that neighborhood noise levels are respected. Again, please realize we want every group to enjoy their time, laugh, have fun and make memories. These devices are only to ensure noise levels don’t reach a threshold that bothers our neighbors. Also, please note there is no electronic video surveillance monitoring pools or spas, or on the interior of the house. PET FRIENDLY: **There is a $100 pet fee per pet with a maximum of $300 (3 pets). Although we are pet-friendly please note your pet must not be left unattended at the house without you present, even if in a crate/kennel. Failure to adhere to the house rules as it pertains to pets may result in cancellation of the booking with no refund. ** *Sleeping Arrangements: Bedroom 1 (main level): King bed Bedroom 2 (main level): King bed Bedroom 3 (main level): King bed Bedroom 4 (lower level): King bed Bedroom 5 (lower level): King bed Amenities: ★ Incredible panoramic Willamette River views ★ Hot tub on covered patio (We strive to make sure hot tubs are working at all times. If they are not working due to circumstances outside of our control, unfortunately we cannot provide any type of refund for the inconvenience.) ★ Fire-pit ★ Cornhole ★ New décor and furnishing throughout ★ 3 Gas Fireplaces Location: ★ Steps away from banks of Willamette River ★ 1 Mile to groceries, restaurants, and entertainment ★ 6 Mile to Oaks Amusement Park ★ 7 Miles to West Linn ★ 9 Miles to downtown Portland ★ 17 Miles to Portland International Airport

Dog-Friendly Milwaukie Home: 9 Mi to Dtwn Portland

Lake Oswego, OR, US
3 Bedrooms 6 Guests
Aug 31 - Sep 3
night

Your next PNW adventure awaits at this Milwaukie, OR, vacation rental. This centrally located 3-bedroom, 2-bathroom home puts you close to all of the Portland area’s best attractions, with access to the Willamette River just 2 miles away and Downtown’s breweries, venues, and museums only 9 miles away. Spend time by the water at Rivervilla Park, catch some Blazers basketball at the Moda Center, or make a day trip to Mt. Hood National Forest for beautiful hikes with your furry friend. -- THE PROPERTY -- Newly Remodeled | Shared Yard | ~ 2 Mi to Willamette River | 1,600 Sq Ft Bedroom 1: Queen Bed | Bedroom 2: King Bed | Bedroom 3: Queen Bed SHARED AMENITIES: Patio, gas fire pit INDOOR LIVING: Smart TV, board games, books, dining table, breakfast bar, walk-in closet KITCHEN: Cooking basics, dishware/flatware, dishwasher, refrigerator, stove, microwave, coffee maker, coffee/tea, blender, toaster GENERAL: Free WiFi, central heating & A/C, ceiling fans, complimentary toiletries, linens/towels, washer/dryer, laundry detergent, iron/board, hangers, hair dryer, trash bags/paper towels FAQ: Pet fee (paid pre-trip) ACCESSIBILITY: 2 steps required to access, 2-story home, bedroom/full bathroom on 1st floor PARKING: Driveway (2 vehicles), street (first-come, first-served) ADDT’L ACCOMMODATIONS: There is an additional property available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- LOCAL HOTSPOTS: Oaks Amusement Park (6 miles), OMSI (8 miles), Revolution Hall (9 miles), Portland Art Museum (9 miles), Moda Center (9 miles), Oregon Convention Center (9 miles), Providence Park (10 miles) WILLAMETTE RIVER: Rivervilla Park (2 miles), Elk Rock Island (2 miles), Spring Park Natural Area (2 miles), Milwaukie Bay Park & Boat Launch (3 miles) PARKS & OUTDOORS: Crystal Springs Rhododendron Garden (7 miles), Mount Talbert Nature Park (7 miles), Portland Japanese Garden (11 miles), Oregon Zoo (11 miles), Powell Butte Nature Park (14 miles), Mt. Hood National Forest (31 miles) AIRPORT: Portland International Airport (17 miles) -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - Pet friendly w/ $50 fee (+ fees & taxes, dogs only, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This 2-story home requires 2 steps to enter but features a bedroom and full bathroom on the 1st floor - NOTE: There is another bookable vacation rental on-site with some shared amenities; other travelers may be present during your stay

Oak Shore Haven

Milwaukie, OR, US
7 Bedrooms 14 Guests
Aug 17 - 20
$891 night

Oak Shore Haven | Luxury Riverfront Retreat with 270° Water Views Welcome to Oak Shore Haven, one of the Pacific Northwest’s most exceptional riverfront escapes. Perfectly positioned along the water’s edge, this remarkable six-bedroom, five-bathroom retreat offers breathtaking 270-degree river views, luxurious finishes, and an incredible collection of amenities designed for unforgettable gatherings. From the moment you arrive, you’ll be captivated by the home’s stunning setting. Expansive windows frame the river from nearly every angle, while the massive outdoor deck invites you to relax, dine, and soak in the ever-changing scenery. Whether you’re enjoying your morning coffee, watching boats drift by, or unwinding in the hot tub beneath the stars, the sights and sounds of the river create a truly magical backdrop. Inside, every detail has been thoughtfully curated to blend modern luxury with warmth and comfort. The open-concept great room features soaring ceilings, designer furnishings, and wall-to-wall views that bring the outdoors in. The chef’s kitchen is fully equipped with premium appliances, expansive countertops, and ample seating, making it the perfect place to prepare meals for family and friends. Entertainment abounds throughout the home. Challenge your group to a game of pool, test your skills on the shuffleboard table, or gather in the dedicated karaoke room for a night of music and laughter. With multiple gathering spaces spread throughout the property, there’s plenty of room for everyone to relax, connect, and create lasting memories. Featuring seven spacious bedrooms and five full bathrooms, Oak Shore Haven comfortably accommodates large families, corporate retreats, reunions, and special celebrations. The home’s generous layout ensures everyone has room to spread out while still enjoying the many shared spaces that make this property so special. Whether you’re planning a weekend getaway, celebrating a milestone event, or simply seeking an unforgettable riverfront experience, Oak Shore Haven delivers luxury, comfort, and unparalleled natural beauty in one extraordinary destination. This home has security cameras at the entrance for security. We’re excited to host you and hope your stay is full of fun and great memories. To keep things peaceful for our wonderful neighbors, we observe quiet hours from 10:00 pm to 8:00 am. During this time, please stay indoors with windows and doors closed, and keep noise at a comfortable indoor level. The home includes a noise‑monitoring system that measures volume only—it simply helps us ensure the neighborhood stays calm and enjoyable for everyone. Thanks for helping us keep this a welcoming place for all guests. PET FRIENDLY: **There is a $100 pet fee per pet with a maximum of $300 (3 pets). Although we are pet-friendly please note your pet must not be left unattended at the house without you present, even if in a crate/kennel. Failure to adhere to the house rules as it pertains to pets may result in cancellation of the booking with no refund. ** Highlights: ✔ Spectacular 270° river views ✔ Six bedrooms & five full bathrooms ✔ Expansive riverfront deck ✔ Private hot tub overlooking the water ✔ Chef’s kitchen with premium finishes ✔ Pool table & shuffleboard ✔ Dedicated karaoke room ✔ Designer furnishings and curated décor throughout ✔ Multiple indoor and outdoor gathering spaces ✔ One of the Pacific Northwest’s premier luxury vacation homes Limited Parking (4 spaces) - please carpool as much as possible. If you choose to enjoy the river during your stay, we encourage you to do so safely. The river offers a wonderful opportunity for recreation and relaxation, and we recommend bringing properly fitted life jackets for anyone planning to swim, kayak, or participate in water activities. Come experience Oak Shore Haven—where luxury meets the river, and every stay becomes a memory worth sharing.

Portland Vacation Rental Near Parks & Downtown!

Portland, OR, US
3 Bedrooms 5 Guests
Dec 26 - Jan 25
$143 night

Spend this season exploring ‘Rose City’s’ most beautiful gardens, nature trails, and neighborhoods, when you stay at this 3-bed, 3-bath, vacation rental in Portland! Stroll, bike, or horseback through Tryon Creek State Park, hike thickly wooded ravines at Forest Park, or sample your way through Oregon’s wine country. No matter how you spend your day, return to your home away from home in the downstairs unit, where a Smart TV, kitchen, and an outdoor dining area with a gas grill await! -- THE PROPERTY -- Outdoor Dining Area w/ Gas Grill | In-Unit Laundry | 8 Mi to Downtown Portland | Downstairs Unit Bedroom 1: Queen Bed | Bedroom 2: Twin Bed | Bedroom 3: Twin Bed w/ Twin Trundle INDOOR LIVING: Smart TV, electric fireplace, dining table, laptop-friendly workspace, 2 en-suite bathrooms w/ walk-in showers KITCHEN: Stove/oven, microwave, dishwasher, refrigerator w/ ice maker, dishware/flatware, drip coffee maker (starter coffee provided), electric kettle, toaster oven GENERAL: Free WiFi, washer/dryer, linens/towels, complimentary toiletries, central air conditioning/heating, hair dryer, laundry detergent ACCESSIBILITY: Single-story home, stairs required to enter PARKING: Gravel driveway (1 vehicle), street parking -- THE LOCATION -- DOWNTOWN PORTLAND (8 miles): Portland Art Museum, Keller Auditorium, Pioneer Courthouse Square, Arlene Schnitzer Concert Hall, OMSI, Revolution Hall NEARBY ATTRACTIONS: Oaks Amusement Park (6 miles), Providence Park (8 miles), Portland Japanese Garden (9 miles), Moda Center (9 miles), The Freakybuttrue Peculiarium and Museum (9 miles), Oregon Zoo (9 miles), Pittock Mansion (10 miles) OUTDOORS: Tryon Creek State Natural Area (2 miles), George Rogers Park (5 miles), Sellwood Riverfront Park (5 miles), International Rose Test Garden (8 miles), Washington Park (9 miles) VISITING: Portland Community College Sylvania (0.8 miles), Lewis & Clark College (3 miles), Portland State University (7 miles), OHSU Hospital (7 miles) AIRPORT: Portland International Airport (15 miles) -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - Pet friendly w/ $50 fee (+ fees & taxes, 1 dog max, no cats) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The single-story property requires using an outdoor staircase to enter

Maison Ananda Oswego

Lake Oswego, OR, US
5 Bedrooms 12 Guests
Aug 17 - 19
$863 night

Ananda means bliss, and that is what we set out to create here. Tucked behind a private gate in the Uplands neighborhood, Maison Ananda is a five-bedroom, three-and-a-half-bath estate designed for traveling guests who want space, privacy, and quiet. Long weekends where the kids disappear into the game room and the adults claim the heated patio. Slow mornings with coffee in the yard before anyone else is up. Evenings can wind down in the media room without anyone feeling on top of each other. The home comfortably hosts your traveling party of up to 12 registered guests, with the calm, private feel of a true residential retreat. Exceptional ratings across all booking sites. Maison Ananda is one of Lake Oswego’s most consistently top-rated luxury rentals. Location ★ 9-minute walk to Lake Oswego Indoor Tennis Center ★ 10 minutes to downtown Lake Oswego (dining, boutique shopping, lake access) ★ 20 minutes to downtown Portland ★ 35 minutes to Portland International Airport (PDX) ★ Easy day trips to Willamette Valley wine country, Mount Hood, and the Oregon coast What makes this home different ★ Fully gated, fully fenced front and back, parking for up to 6 vehicles ★ Heated indoor-outdoor living area with fireplace, usable year-round ★ Garage converted into a dedicated game room with ping pong, pop-a-shot basketball, and more ★ Media room with full sleeper sofa for movie nights or an extra crash space ★ Expansive chef’s kitchen, ideal for cooking together ★ Private home office for the occasional working guest ★ Two king en-suites, one on each floor, ideal for two couples traveling together or multigenerational travel parties ★ Designer furnishings and high-end finishes throughout ★ Central air conditioning, in-unit washer and dryer ★ Self check-in via keypad, high-speed WiFi, propane BBQ grill ★ Pet friendly with full disclosure Sleeping arrangements (sleeps up to 12) ★ Bedroom 1, main floor: King with en-suite bath ★ Bedroom 2, main floor: Queen ★ Bedroom 3, second floor: King with en-suite bath ★ Bedroom 4, second floor: King ★ Bedroom 5, second floor: Twin-over-full bunk, plus rollaway and crib ★ Media room: Full sleeper sofa The neighborhood The Uplands is one of Lake Oswego’s most established residential pockets, quiet, leafy, and walkable to local trails and the indoor tennis center. Downtown Lake Oswego, ten minutes away, offers waterfront dining, boutique shopping, and access to the lake itself. Oswego Lake Country Club is six minutes away, and Waluga Dog Park is four minutes by car. The home is centrally located for guests visiting family in the area, attending events at Nike or Intel campuses, exploring Portland, or starting a wine country trip. A note on who this home is for Maison Ananda is a guest-favorite home, and we work hard to keep it that way. It is built for traveling families, multigenerational travel parties, business travelers, and couples celebrating something special. It is not a party house, an event venue, or a place to host gatherings. Beyond that, we want you to relax, spread out, and enjoy every corner of the home. Our neighbors know us, quiet hours are 10 PM to 8 AM, and the home is monitored by an exterior noise sensor and four exterior security cameras (three at the front, one at the back, none inside, none at the pool or spa). House rules at a glance ★ Traveling party of up to 12 registered guests. Overnight stays are limited to the registered guests on the booking. Please disclose your full party at the time of booking. ★ Day visitors are welcome for daytime visits, meals, and casual time together. We just ask that visitors not stay overnight and that the home does not become a venue for gatherings, parties, or events. Total people on the property at any time should remain reasonable for a residential home. ★ No parties, gatherings, or events of any kind, including birthdays, showers, bachelor or bachelorette events, or work offsites. ★ No smoking, vaping, or marijuana use anywhere on the property ★ Pet friendly with full disclosure required: $100 per pet, max 3 pets ($300). Pets cannot be left unattended in the home, including in a crate ★ Quiet hours 10 PM to 8 AM. Please stay indoors during these hours with doors and windows closed ★ 12 guests maximum overnight Other things to note We may collect additional guest information after booking (typically an email address) to comply with local Lake Oswego short-term rental regulations. Book your stay at Maison Ananda and see why guests keep coming back.

Woodstock Townhouse

Portland, OR, US
4 Bedrooms 8 Guests
Aug 17 - 19
$354 night

Welcome to Woodstock Townhouse, a thoughtfully curated retreat nestled in the heart of Southeast Portland. Designed for families and groups seeking a stylish and comfortable home base, this spacious townhome blends modern design with local charm, offering easy access to Portland’s best neighborhoods while providing a peaceful escape from the downtown bustle. Step inside and you’ll immediately notice the attention to detail. The decor is fresh and contemporary, with custom finishes and furnishings sourced to create an ideal blend of style and relaxation. Many of the art pieces and design touches were commissioned by local Portland artists, adding a unique and authentic vibe that celebrates the city’s creative spirit. The main level features an open-concept kitchen, dining, and living area perfect for gathering and entertaining. The fully stocked kitchen offers bar seating at the island, and the adjacent dining area provides the perfect setting for shared meals and conversations. The cozy living room invites you to kick back and stream your favorite show after a day of adventures. There’s also a full bathroom and a bedroom on this level, ideal for guests who prefer fewer stairs. Upstairs, you’ll find bright and inviting bedrooms along with two full bathrooms, offering plenty of privacy and space for everyone. The upstairs family room is a guest favorite, complete with a large smart TV, comfy seating, and a collection of games for late-night fun or a relaxing day in. Downstairs, the lower level includes a laundry room, another full bathroom, and a charming seating nook with a hand-painted mural—a fun and picture worthy spot for selfies and snapshots to remember your stay. Whether you’re in town to explore Portland’s food scene, visit local wineries, or set off on Pacific Northwest adventures, Woodstock Townhouse is your perfect launchpad. We’ve poured our hearts into every detail of this home, and we can’t wait to share it with you. PET FRIENDLY: **There is a $100 pet fee per pet with a maximum of $300 (3 pets). Although we are pet-friendly please note your pet must not be left unattended at the house without you present, even if in a crate/kennel. Failure to adhere to the house rules as it pertains to pets may result in cancellation of the booking with no refund. ****There is a ring doorbell at this location** Sleeping Arrangements: Upper level: Bedroom 1: Queen bed + Queen bed Bedroom 2: King bed Amenities: ★ Brand new décor and design throughout ★ Countless custom commissions from local artists ★ Huge open floor plan with tons of flexibility for sleeping arrangements ★ Four full bathrooms Location: ★ 1-4 blocks to food and coffee options ★ 5 blocks to Trader Joes ★ 3/4 Mile to Reed College ★ 1 Mile or less to countless restaurants, shopping and entertainment ★ 4 Miles to downtown Portland ★ 12 Miles to Portland International Airport ★ 50 Miles to Mt. Hood ★ 80 Miles to the Oregon Coast Additional Property Information: We truly want you to enjoy your time and make some wonderful memories with your group. That being said, this is not a party or gathering house for groups that can’t control their noise levels. We have relationships with all of our neighbors who have our direct contact information. Quiet time is 10:00 pm to 7:00 am. If it is loud enough to be heard outside in these conditions, it is too loud for you to remain our guest. This property includes a noise alert monitoring system in order to ensure that neighborhood noise levels are respected. Again, please realize we want every group to enjoy their time, laugh, have fun and make memories. Special Information and Rules: A maximum of 8 guests may stay at any time. "Use of all outdoor spaces by ASTR guests is prohibited between the hours of 10 p.m. and 7 a.m. all days, except when entering or exiting the house. The hours of outdoor space use must be listed in the House Rules and may be more but not less restrictive. The ASTR use must comply with City Title 18, Noise Control. Among other regulations, Title 18 sets limits on sound levels that impact residential properties. Section 18.12.020.B addresses permissible levels of sound producing or reproducing equipment. The following activities are in violation of Title 18: Operating or permitting the use or operation of any device designed for sound production or reproduction in such a manner as to cause a noise disturbance; or operating or permitting the operating or use of any such device between the hours of 10 p.m. and 7 a.m. so as to be plainly audible within any dwelling unit which is not the source of sound. Commercial meetings are prohibited. Commercial meetings include luncheons, banquets, parties, weddings, meetings, charitable fund raising, commercial or advertising activities, or other gatherings for direct or indirect compensation." License: 2021_097982_000_00_LU

1920s Farmhouse | 4BR/2BA | Foodie District

Portland, OR, US
4 Bedrooms 8 Guests
Aug 17 - 19
$611 night

✨ Sun-Filled Farmhouse Steps from Division St ✨ 🏡 Renovated 1920s Sears kit house with vintage charm 🛏️ 4 bedrooms, 2 baths — sleeps 8 comfortably 🍳 Quartz counters, dishwasher & full cookware 🛋️ Original hardwood floors & modern updates throughout 💻 Laptop-friendly workspace with fast WiFi ❄️ Ductless mini-split A/C & heat 🔒 Private 4BR farmhouse; backyard is shared with tiny homes 🍺 Walk to Division St restaurants & Hub Brewery. Free street parking. Freshly remodeled from top to bottom - this home blends original character with modern upgrades throughout. MAIN FLOOR: Open-concept kitchen, living, and dining area Quartz countertops with new top-of-the-line appliances Refinished hardwood floors throughout One bedroom with queen bed Full bathroom with original cast iron clawfoot tub Tall ceilings preserving the home’s classic charm SECOND FLOOR: Three additional bedrooms, each with a queen bed Full bathroom with shower RECENT UPGRADES: ✔ New quartz countertops and stainless appliances ✔ Ductless mini-split A/C and heat ✔ Updated plumbing and electrical ✔ Refinished hardwood floors ✔ Fast WiFi throughout This booking is for the private 4BR farmhouse. The indoor living areas are not shared, and the backyard/courtyard is shared with the tiny homes behind the house. 🔑 Self check-in with smart lock - arrive on your schedule 🧺 Basement laundry accessed from outside 📶 High-speed Wi-Fi throughout 🚗 Free street parking Everything you need for a comfortable stay is already set up. If anything comes up, we’re a quick message away. 🚶 Walking — This neighborhood sits between the Division and Hawthorne corridors, two of Portland’s best streets for dining and shopping — both within easy walking distance. 🚌 Bus — TriMet Route 2 (Division) and Route 75 (Cesar Chavez) provide frequent service to downtown (~15 min). 🚲 Biking — BIKETOWN bike-share stations nearby. Portland’s bike lane network makes cycling easy and safe. 🚗 Driving — Free street parking available (read signs for restrictions). Rideshare (Uber/Lyft) typically arrives in under 5 minutes. ✈️ Airport — PDX is about 18 minutes by car or a quick MAX + bus connection. 🏘️ The Property Our home shares the backyard with a tiny home village - they’re also vacation rentals! Each space is completely separate, and there’s very little interaction between guests. It’s quieter than you’d expect 👉 Interested in booking a tiny home or the entire property for your group? Message us for details! ⏰ Quiet Hours 10 PM – 7 AM (building + city ordinance) 🚭 No Smoking or Vaping Smoking and vaping are not allowed anywhere on the property, indoors or outdoors. Guests who wish to smoke or vape must leave the property completely.

Farmhouse + Tiny Home Village | 7BR/5BA| Sleeps 14

Portland, OR, US
7 Bedrooms 14 Guests
Sep 1 - 3
$1,160 night

✨ Sprawling 7-Bedroom Farmhouse Compound in SE Portland ✨ 🏡 Main farmhouse + backyard tiny house village 🛏️ 7 bedrooms, 5 baths — sleeps 14 comfortably 🍳 Full kitchen with dishwasher & coffee bar 🛋️ Cozy living room with original fireplace & TV 🌳 Garden courtyard & outdoor seating for gatherings 🐾 Pet-friendly — bring the whole family ❄️ AC & heating for year-round comfort 🔒 Full compound is yours — farmhouse + all 3 tiny homes 📍 Heart of SE Portland, minutes to cafés & shops. Free street parking. Our charming and rustic farmhouse has been lovingly restored to retain its original character while incorporating modern amenities for your comfort. Highlights include a cozy living room with a fireplace, a fully equipped kitchen, and comfortable bedrooms. What truly sets our property apart is the enchanting backyard tiny house village. Nestled in a beautifully landscaped garden, this village features several thoughtfully designed and decorated tiny houses, each offering a cozy and eco-friendly lodging experience. Each tiny house includes a comfortable bed, a mini kitchen, and a private bathroom, providing the perfect place to relax and unwind after a day of exploring Portland. Located in the Brooklyn neighborhood, our property is unbeatable for its relaxed and friendly vibe, tree-lined streets, and proximity to the city’s top attractions. You’ll be just a short drive or bike ride away from some of Portland’s best restaurants, bars, and shops. Don’t wait! Book your stay at our farmhouse with a backyard tiny house village today and experience the best of Portland in style! This booking includes the full SE 24th compound: the main farmhouse and all three tiny homes in the backyard village. Each space has its own private entrance, and the courtyard/garden areas are included with your group booking. 🔑 Self check-in with smart locks - arrive on your schedule 🧺 In-unit washer & dryer 📶 High-speed Wi-Fi throughout 🚗 Free street parking Everything you need for a comfortable stay is already set up. If anything comes up, we’re a quick message away. 🚶 Walking — This neighborhood sits between the Division and Hawthorne corridors, two of Portland’s best streets for dining and shopping — both within easy walking distance. 🚌 Bus — TriMet Route 2 (Division) and Route 75 (Cesar Chavez) provide frequent service to downtown (~15 min). 🚲 Biking — BIKETOWN bike-share stations nearby. Portland’s bike lane network makes cycling easy and safe. 🚗 Driving — Free street parking available (read signs for restrictions). Rideshare (Uber/Lyft) typically arrives in under 5 minutes. ✈️ Airport — PDX is about 18 minutes by car or a quick MAX + bus connection. ⏰ Quiet Hours 10 PM - 7 AM (building + city ordinance) 🚭 No Smoking or Vaping Smoking and vaping are not allowed anywhere on the property, indoors or outdoors. Guests who wish to smoke or vape must leave the property completely.

Vacation Rentals in Milwaukie by Amenities & Features

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Vacation Rentals Near Milwaukie

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