Family-friendly holiday rentals in Oak Grove

4.8 out of 5 average rating, 357 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.

4.91 out of 5 average rating, 336 reviews

Upstairs Rustic 1940s styled Studio Apartment

Great for water loving people! Private unit. Self checkin. Outdoor patio & yard. Wifi. Pet/animal free, allergy safe. Smoke free. Linens washed with Defunkify perfume free soap. Fully stocked kitchenette. .75 Bathroom (sink, toilet, large shower) Stocked w/ toiletries. AC in summer. Complimentary snacks! 1940's vintage furniture. Quiet neighborhood. Semi-industrial parking, as we run a pressure washing biz. Your unit is around the back on the 2nd floor. 1/4 mi to bus route at top of hill.

4.92 out of 5 average rating, 139 reviews

Guest house in Milwaukie

Spacious Studio near Historic Milwaukie/Sellwood

No cleaning fees! Unique retro inspired LARGE studio Private entrance, driveway parking. One Full sized bed and a comfy twin sized cot (set up upon request). Bright sunny space with skylights and beautiful details. Uncluttered, quiet and clean. Full sized fridge and plenty of kitchen amenities. Large dining room table and sitting space. Located in peaceful neighborhood, close to Historic Downtown Milwaukie, 15 min to downtown Portland, minutes away from SE Portland attractions!

4.94 out of 5 average rating, 108 reviews

Home in Oak Grove

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!

4.99 out of 5 average rating, 309 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.

4.99 out of 5 average rating, 422 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.

4.88 out of 5 average rating, 710 reviews

Cabin in Milwaukie

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.

4.99 out of 5 average rating, 347 reviews

Guest house in Milwaukie

River Forest Guest House, All new+Riverfront Patio

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.

4.96 out of 5 average rating, 500 reviews

Home in Oak Grove

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!

4.96 out of 5 average rating, 267 reviews

Cozy, Private Studio

This beautifully remodeled studio with private bathroom, entrance and off-street parking is nestled in a quiet, relaxed neighborhood in Milwaukie- a neighborhood south of Portland. Extremely comfortable queen bed will provide you with an excellent nights sleep. Great atmosphere for those traveling for business or vacation. Located 5 minutes from I-205 and a 10-minute drive to downtown Portland.

4.97 out of 5 average rating, 193 reviews

Flat in Milwaukie

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.