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, 158 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, 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
The modern two-story home features a light exterior with vertical siding and a covered porch. Two chairs are positioned near the entrance, while vibrant pumpkins and landscaped flowers enhance the welcoming atmosphere. A garage is visible to the right.
Home in Oak Grove
4.95 out of 5 average rating, 117 reviews

Cozy, Modern Farmhouse, King Bed, Great Yard, Pets

Enjoy your stay in the quaint, Oak Grove neighborhood of Portland a block from the old historic trolly trail. Minutes to the river, close to downtown, ample dog parks make this spot perfect for your getaway. Our family poured our hearts into designing a modern and cozy space that our family loves to visit. We're so very excited that we get to share that with you! We've got a yard that the whole family will love and I know you'll make some priceless memories here, just as we have. Welcome!

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
4.97 out of 5 average rating, 118 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, 314 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.

Top guest favorite
A warm dining area is showcased with a wooden table at its center, surrounded by decorative plants. An archway leads into a cozy living room featuring a gas fireplace, comfortable seating, and large windows that invite natural light into the space.
Home in Milwaukie
4.98 out of 5 average rating, 111 reviews

Oak Grove Easy-Centrally located w/King Bed

Welcome to this updated and comfortable, light filled home in the Oak Grove neighborhood of Portland. A short distance to the river, downtown, parks, restaurants and all things Portland-make this a perfect vacation space for your family and guests. We put a lot of love in to designing the interior to be stylish, yet comfortable and seamless to ensure you feel right at home. Ample space in our park-like backyard to relax , entertain or play a summer game of corn hole!

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, 445 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, 446 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.

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, 729 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.

Top guest favorite
The exterior of the home features a well-maintained gray facade, accented by a wooden deck. Surrounding greenery includes grass and a few trees, creating a serene outdoor space. The driveway is visible beside the house, leading to additional structures in the background.
Home in Oak Grove
4.96 out of 5 average rating, 510 reviews

Oak Grove Getaway Retreat

Welcome to our remodeled 2,350 sqft home in a peaceful, friendly neighborhood! This cozy, modern retreat is perfect for families or groups. A short walk or drive to grocery stores, restaurants, and an 8-screen cinema. Downtown Portland is near for a fun day trip. Enjoy local trails and events. With an updated, inviting interior, it’s your ideal base for Portland’s charm. Book now for a relaxing stay with exciting discoveries!

Top guest favorite
A charming red cottage is nestled among lush greenery, with large windows framed in gray. A moss-covered tree stands nearby, adding to the serene woodland setting. Soft light emanates from the cottage's windows, suggesting a cozy atmosphere inside.
Guesthouse in Oregon City
5 out of 5 average rating, 606 reviews

Cottage in the Country

At the end of a long driveway through large evergreen trees sits this 600 sq ft cottage studio at the edge of the woods, ready to provide you with a relaxing country retreat. Enjoy this lovely remodeled guest house with a woodland landscape outside your doors.

Popular amenities for Oak Grove vacation rentals

When is the best time to visit Oak Grove?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$20,082 GYDG$20,918 GYDG$20,709 GYDG$21,964 GYDG$22,801 GYDG$25,311 GYDG$24,474 GYDG$25,311 GYDG$20,918 GYDG$24,474 GYDG$22,173 GYDG$24,474 GYD
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Frequently Asked Questions

  • Do house rentals in Oak Grove have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Oak Grove. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Oak Grove have wifi?

    Absolutely! We offer over 10 guesthouse 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 private suite rentals in Oak Grove have a kitchen?

    Absolutely! We offer over 10 private suite 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 House Rentals in Oak Grove?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with air conditioning, over 60 homes with free parking, over 60 homes with a kitchen, over 60 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$4,184 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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