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Vacation rentals in Oak Grove

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Top-rated vacation rentals in Oak Grove

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

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Top guest favorite
An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.
Guesthouse in West Linn
4.96 out of 5 average rating, 153 reviews

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

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, 432 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 spacious studio suite features a queen bed with a patterned blanket and soft lighting. A cozy seating area includes a gray couch and round coffee table. A small dining table for two is positioned near the window, enhancing the inviting atmosphere.
Guest suite in Ardenwald
4.8 out of 5 average rating, 360 reviews

Clean & Cozy "Private" Studio Suite

Private studio suite (500 sq ft). The unit is on the lower half of this 2 level duplex (host lives upstairs), private entry is on the ground level, self check-in, off street parking. There is a kitchenette, private bathroom with a stand-up shower, washer & dryer, queen bed, high speed internet, expanded cable, Netflix/Amazon Prime. Also, there is a lovely private patio for your enjoyment with a fire table. The space is warm and inviting, very safe location, great neighborhood and dog friendly.

Top guest favorite
A serene garden scene captures early morning fog enveloping vibrant fall foliage. Lush greenery is interspersed with colorful autumn leaves, providing a peaceful backdrop. The landscape features a variety of shrubs and trees, adding depth and texture to the tranquil environment.
Guest suite in Milwaukie
4.96 out of 5 average rating, 179 reviews

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.

Top guest favorite
The kitchen features white cabinetry and a modern countertop with a sink. A coffee maker and tea kettle are visible. Natural light fills the space through nearby windows. A cozy living area can be seen in the background, adding warmth to the environment.
Guesthouse in Lake Oswego
4.96 out of 5 average rating, 112 reviews

Secluded Willamette River Apartment in Lake Oswego

Enjoy a private stay full of nature with a river view! Newly remodeled 1 bedroom private apartment secluded and quiet. Apt is completely separate from main house. 10 min wlk to Mary's Woods Ret. Comm, 20 mins to George Rogers Park, 10 more to DT Lake Oswego w/shops, restaurants and theaters. Private, wooded property along the Willamette River. Fully rmld kit. & BR, LR with large 50” Smart TV, fast wifi. Q-bed + twin in sunroom, table/work area + wa/dr below. 8 stair entrance at back.

Top guest favorite
A bright, modern room features a Queen Murphy bed with crisp white linens and yellow accent pillows. Two windows allow natural light, with views of a fenced outdoor space, enhancing the airy atmosphere. A small built-in sofa is positioned beside the bed, offering additional seating.
Guest suite in Milwaukie
4.99 out of 5 average rating, 312 reviews

The Room In Between

Private and secure entrance to this modern and 5-Star space! Comfortable Queen Murphy bed that converts to a sofa. Fast Wifi and Smart TV w/access to Netflix & Prime Video. Fenced yard with security gate entrance, off of private paved driveway, to lead you to your own private patio & room entrance. Self check-in is at 2pm or later. Check out is 11am. No pets. Smoking allowed on the outside patio only. Flat entrance pathway is well lit from your parking space to your room & patio.

Guest favorite
A charming guesthouse is nestled within a lush garden, surrounded by colorful flowering bushes and sculpted hedges. The structure features large windows that offer a glimpse of the serene interior. The path leading to the guesthouse is intertwined with greenery, enhancing the tranquil atmosphere.
Cottage in Portland
4.92 out of 5 average rating, 440 reviews

Secret Garden Guesthouse!!

Secret garden guesthouse is located 1 mile from downtown Lake Oswego and 2 miles from Lewis and Clark. Ideal hideaway for parents weekend, visiting the college, or guest lecturers. Also great location for exploring the amazing city of Portland and its surrounds. 50 minutes to Mt Hood, 40 minutes to wine country! Located in SW Portland and just a few miles from downtown Portland food scene. 1 mile from Lake Oswego. Friendly pets are welcome with a $40 pet fee.

Top guest favorite
The exterior of a garden studio is illuminated by string lights, creating a warm ambiance at night. An inviting patio features two wooden chairs and floral greenery, while blooming white flowers add a touch of natural beauty to the space.
Guest suite in Milwaukie
4.99 out of 5 average rating, 438 reviews

Light Filled Garden Studio

Our wonderfully bright garden studio is perfect for a short stay or for visitors looking to explore Portland for an extended visit. It has a full, well-stocked kitchen, ideal for those looking to stay in and cook, but it’s also just a 20 minute drive from downtown, for those looking to explore the wonderful restaurant scene Portland offers. Keyless entry and private entrance through the side yard gate provide renters with complete autonomy during their visit.

Top 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, 722 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 serene outdoor space features a patio area with two Adirondack chairs positioned around a stone fire pit. An umbrella provides shade over the seating. Lush greenery surrounds the space, and a lighted petanque court is visible in the background.
Guest suite in West Linn
5 out of 5 average rating, 252 reviews

Arbor Suite Apartment - Washer/Dryer, Desk, A/C!

There is a private entrance to this 725 sq ft. bright, CLEAN, and SANITIZED guest apartment within a home, in a well established neighborhood on the border of West Linn and Lake Oswego. Spacious, beautifully furnished one bedroom with an office/den (includes fiber optic internet & monitor ) in a quiet and desirable suburb of Portland that offers a lush treed garden with a gas fire pit and patio. YouTube TV available. Close to Mary's Woods!

Top guest favorite
An open living area is highlighted by a cozy sofa with patterned cushions and a spacious bed dressed in soft linens. A wooden dining table with chairs is set near a window, enhancing the light, airy feel of the space. An inviting side cabinet adds functionality.
Apartment in Milwaukie
4.98 out of 5 average rating, 200 reviews

Milwaukie Retreat in the Woods

Your private apartment is located on a wood filled lot with a private outdoor area, shade and even deer on occasion. We are 12 miles from the airport, near freeways with easy access to downtown, and to make your way to the coast or the Columbia Gorge, Mt Hood and the Willamette Valley for wine tasting. We have added extra cleaning procedures to help fight against Covid 19.

Guest favorite
A cozy sleeping area features a spacious bed dressed in crisp white linens. A large window allows natural light to fill the room, framed by soft gray curtains. A flat-screen television is mounted on the wall opposite, and a small table holds a decorative plant.
Guest suite in Lake Oswego
4.96 out of 5 average rating, 147 reviews

Peaceful Tree-Lined, Private ADU Retreat

You'll feel at home in this quiet, tree-lined cul de sac. The attached ADU is completely private with a separate entrance, private balcony, off-street parking and access to our 1/4 acre property. Come enjoy the peaceful setting, minutes from downtown Portland and Lake Oswego.

Popular amenities for Oak Grove vacation rentals

When is the best time to visit Oak Grove?

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Avg. priceG$20,090 GYDG$20,927 GYDG$20,718 GYDG$21,974 GYDG$22,811 GYDG$25,322 GYDG$25,531 GYDG$27,205 GYDG$24,485 GYDG$24,066 GYDG$22,183 GYDG$24,485 GYD
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Frequently Asked Questions

  • Do guesthouse rentals in Oak Grove have air conditioning?

    Absolutely! We offer over 10 guesthouse rentals with air conditioning in Oak Grove. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oak Grove have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Oak Grove. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Oak Grove?

    Four-legged friends are welcome in Oak Grove. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Oak Grove?

    Yes! Work meets play with ease at over 50 vacation rentals in Oak Grove featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Oak Grove?

    Oak Grove has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do guesthouse rentals in Oak Grove have a kitchen?

    Absolutely! We offer over 10 guesthouse rentals with a kitchen in Oak Grove. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Oak Grove have free parking?

    Absolutely! We offer over 10 guesthouse rentals with free parking in Oak Grove. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Oak Grove?

    Make yourself at home in Oak Grove by choosing from our most frequently booked neighborhoods. We have over 530 vacation rentals in Oak Grove, over 1,440 vacation rentals in Lake Road, and over 460 vacation rentals in Foothills.

  • How much does it cost to stay in house rentals in Oak Grove?

    Experience the best of Oak Grove with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Private Suite Rentals in Oak Grove?

    Enhance your stay in our Private Suite Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Oak Grove

  • Total vacation rentals

    Explore 100 vacation rentals in Oak Grove

  • Nightly prices starting at

    Oak Grove vacation rentals start at G$4,185 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,810 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Oak Grove vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oak Grove rentals

  • 4.9 Average rating

    Oak Grove stays are highly rated by guests—averaging 4.9 out of 5!

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