Family-friendly holiday rentals in Oak Grove

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Top-rated family-friendly rentals in Oak Grove

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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A cozy living room features a brick fireplace at the center, emanating a warm glow. The space is furnished with a dark sofa and adorned with decorative pillows. A vibrant area rug lies on the green carpet, providing contrast and comfort. Bookshelves line the walls, showcasing various items.
Flat in Milwaukie
4.77 out of 5 average rating, 117 reviews

My Cozy Place- For the Budget Traveler-29 day max!

This cozy unit is a converted rec room located on the bottom floor of a two story house that includes a living room, a separate bedroom, a bathroom with shower, and a small kitchenette /laundry room (cold water). The kitchenette includes a microwave, toaster oven, hot plate, coffee pot, utensils, and refrigerator. The unit can be locked with key. STEPS are required for entry. Not recommended for guests with mobility issues. Extra guests are each charged $5 per day. NO smoking/vape inside.

Top guest favourite
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, 433 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.

Top guest favourite
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.
Guest house in Lake Oswego
4.97 out of 5 average rating, 116 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 favourite
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, 313 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 favourite
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, 109 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!

Top guest favourite
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, 442 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 favourite
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, 725 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 favourite
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, 509 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 favourite
A comfortably appointed studio features a queen bed with decorative pillows and a soft blanket. A seating area includes a modern chair beside a sleek storage unit, with a coffee setup and a mini refrigerator. Natural light filters through sheer curtains, enhancing a relaxed atmosphere.
Guest suite in Milwaukie
4.96 out of 5 average rating, 272 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.

Top guest favourite
A vibrant tiny home with a red exterior and blue trim is framed by a cluster of blooming pink flowers in the foreground. The welcoming entrance is highlighted by warm lighting, complementing the colorful garden that surrounds the property.
Tiny home in McLoughlin
4.95 out of 5 average rating, 158 reviews

Tiny Sequoia House

Feel refreshed when you stay in this rustic gem. With a full heated outdoor yet private shower, lofted queen bed and fold-out couch, walking distance to tons of restaurants and shops, 15 - 25 minutes into Portland proper depending on where you're going and very close to the wilderness and hiking.

Top guest favourite
The bedroom features two twin beds dressed in light blue and white striped linens. A small bedside table with a lamp is positioned between the beds, complemented by decorative pillows. Framed floral art is displayed on the wall, enhancing the cozy atmosphere.
Guest suite in Milwaukie
4.86 out of 5 average rating, 175 reviews

Why Not Stay?

This charming Basement Apartment is in a beautiful Ranch Style home in a quiet tree lined neighborhood of Milwaukie, Oregon. It offers it's own ground level entrance from an ample parking area. You will have a private bedroom, bath and kitchenette.

Guest favourite
A welcoming entrance features a vibrant red door bordered by large planters filled with green plants. Flanking the sides are bamboo and ferns, creating a calming atmosphere. The pathway leads to the entrance, showcasing a serene, nature-inspired setting.
Guest house in West Linn
4.94 out of 5 average rating, 450 reviews

Sunlit Oasis

This private, renovated art studio has skylights and quiet views of nature. As an interior designer, I loved creating a space that is as much an experience as a night away from home...and only 10 miles from downtown Portland!

Popular amenities for Oak Grove family-friendly rentals

When is the best time to visit Oak Grove?

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Avg. price$191 SGD$186 SGD$180 SGD$178 SGD$202 SGD$241 SGD$250 SGD$260 SGD$215 SGD$217 SGD$217 SGD$211 SGD
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Quick stats about holiday rentals that are family-friendly in Oak Grove

  • Total holiday rentals

    Explore 50 holiday rentals in Oak Grove

  • Nightly prices starting at

    Oak Grove holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,380 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Oak Grove holiday rentals include wifi 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!