Family-friendly vacation rentals in Damascus

4.96 out of 5 average rating, 179 reviews

The exterior of a two-story house is presented, featuring a red and gray façade with white trim. A welcoming porch with decorative railings extends along the front, surrounded by lush greenery. A chimney rises from the roof, complementing the home's charming architectural details.

Guest suite in Gresham

Sweet Private Suite in Historic Home

Mary and I love hosting people who appreciate a comfortable experience and beautiful space. Our Private Suite is located in an idyllic setting central to all the activities, great food and nature that the greater Portland area is known for, but without the "junk" that comes with being in the city. Short drives to Portland, Mt Hood hiking and skiing, the Columbia River, Multnomah Falls and great entertainment at McMenamin's "Edgefield (15 Min)" and "Grand Lodge" (35 min.). Infants 0-2 welcome.

4.89 out of 5 average rating, 150 reviews

A serene bedroom features a spacious bed adorned with an assortment of decorative pillows. Two modern bedside lamps flank the bed, providing soft light. A piece of abstract artwork hangs above the headboard, complemented by greenery on the side, creating a relaxing atmosphere.

Guesthouse in Damascus

Hygge House-luxurious secluded 3BR guesthouse

The Hygge House PNW is a place to unwind, get cozy and enjoy the company of those you love. Cuddle up with a cup of tea or a good book and enjoy a restful retreat. Enjoy country vibes while being moments away from Happy Valley City Center. Whether you're in town visiting friends and family or looking to experience everything Portland has to offer, the Hygge House has you covered. We hope you enjoy your time spent here and leave feeling relaxed and more connected with the ones you love.

4.91 out of 5 average rating, 498 reviews

A charming storybook cabin is framed by lush trees, adorned with hanging lights that warm the inviting facade. Flower boxes beneath the windows add color, while a pink door and decorative accents enhance the whimsical aesthetic. An ornamental fence encloses a neat garden area.

Farm stay in Oregon City

Romantic ‘Glamping’ Farm Tiny Cottage

Glamping at its finest! This adorable, warm and cozy, artistic, and truly unique storybook cabin is nestled in a quiet, close-in farm setting (but only 30 min to DT PDX). You’ll love the magical vibe, artwork, decor, lighting, coffee bar, comfy bed, cute outhouse w/cold water sink, and a private outdoor heated shower! We welcome ALL colors, LGBTQ, and outdoor tobacco friendly. Cannabis flower allowed indoors in separate, fun and funky TV/game shed. You'll LOVE it here!

4.91 out of 5 average rating, 622 reviews

A serene garden scene features a waterfall cascading over natural stone, surrounded by lush greenery and colorful flowers. A small pond is visible at the base of the waterfall, complemented by a tranquil statue. Various plants add vibrant textures and colors throughout the landscape.

Guest suite in Damascus

Oasis Between City, River & Mountain. Damascus OR

A large & private guest house on lower level of home only 30 min. to Portland. Mt. Hood, Gorge Waterfalls & Scenic hikes within 60 min drive. Super comfortable bed, quiet nights, recliner sofa & relaxing atmosphere make this an ideal place to hang out and rest. We welcome ALL colors, LGBTQ. Must Read all info, house rules & details prior to booking please. Informed guests are happy guests. Can accommodate 3pm check in every day of the week except Tuesdays.

4.93 out of 5 average rating, 174 reviews

A cozy living area features a sectional couch adorned with decorative pillows. A wooden dining table with sturdy chairs is positioned nearby. Art prints are displayed on the walls above the couch, and a floor lamp adds soft illumination to the space.

Home in Damascus

Foxglove Farm Private Guest Suite

Enjoy a stay in a ground level suite in our two acre country home. Experience the privacy and quiet of the countryside, yet shopping and restaurants are just moments away. We are 30 minutes from PDX and downtown Portland, less than an hour from Mt. Hood and the beautiful Columbia River Gorge, and 90 minutes from the Oregon Coast. You will have your own private entrance, and have access to a porch and deck with scenic views.

4.92 out of 5 average rating, 780 reviews

The entrance to the tiny house features a vibrant green door framed by natural wood, leading to a small porch area. A chair sits to the side, with lush greenery surrounding the property, enhancing the connection with nature.

Tiny home in Damascus

Quaint Tiny House In The Trees. Damascus, Oregon.

150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to SE Portland, 45 to PDX, One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th. Can accommodate a 3pm check-in all days except Tuesdays.

4.98 out of 5 average rating, 454 reviews

Tiny home in Montavilla

Monta-Villa Garden Cottage & Furry Farmstead

Private cottage with views of the garden & cats. High ceilings, lots of natural light & warm accents. 🥰 Four, friendly cats and four, suspicious hens in the garden chickens coop. 🐈‍⬛🐓 Tranquil garden with bubbling fountain, chimes, & sheltered, cozy seating. ⛲️ Nearby food, drink, shopping & recreation options. 🍷 Local recommendations. 🌟 Ask about renting our Toyota Sienna. 🚐 Your home away from home! 🏡

4.89 out of 5 average rating, 108 reviews

A modern kitchen is arranged with sleek cabinets and stainless steel appliances, featuring an island with a round dining table. Four black chairs complement the wood flooring, while a plant adds a touch of greenery in the corner. Light enters through a window, enhancing the bright atmosphere.

Apartment in Damascus

Modern Townhouse

Newly built gated Modern Townhouse. Beautiful and scenic drive to Timberline Lodge / Mt. Hood Ski Bowl. 25 minute drive to downtown Portland. 15 minute drive to Clackamas Town Center. Minutes away from 172nd / Sunnyside shopping center and restsurants. Close drive to Multnomah Falls. Close drive to Vista House view point. Lots of hikes and trails nearby.

4.93 out of 5 average rating, 538 reviews

Two elegant cocktail glasses filled with ice are displayed on a wooden railing. In the background, a panoramic view of a lush green landscape and rolling hills can be seen, with the prominent snow-capped peak of Mt. Hood against a clear blue sky.

Apartment in Oregon City

Sunday Quiet, awesome Hood view, hot tub!

Welcome to our country home a mile to the Clackamas River, with panoramic view of Mt Hood from deck and hot tub. Advertised rate is for a private room and king bed with its own entrance in the lower level of our two story home. You enter along a garden path onto private deck.. 14 mins to I-205, a mile to restaurants, 30 mins to airport (PDX).

4.75 out of 5 average rating, 155 reviews

A cozy seating area is presented with a full-size daybed/couch, accompanied by a framed mirror and a wall-mounted television. A rug with geometric patterns enhances the space, while a lamp provides soft illumination. An accent pillow showcases a welcoming phrase.

Condo in Troutdale

Modern Studio Apartment Near Edgefield!

Fantastic location close to Edgefield & downtown, historic Troutdale. Features a full size daybed/couch and a small kitchen with a modern look. Comfortable, uniquely designed space. Features 1 BD/LVG RM, 1BA Studio with private entrance. Relax in this calm, stylish space after enjoying a concert at The Edgefield or a day exploring the Gorge!

4.95 out of 5 average rating, 154 reviews

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

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.

Guesthouse in Oregon City

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.

5 out of 5 average rating, 600 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 Damascus family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 432 reviews

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

River Forest Lake Apt w/hot tub. HOT find!

4.84 out of 5 average rating, 131 reviews

A vibrant pool area is highlighted with colorful lights and surrounded by lush greenery. Lounge chairs are positioned for relaxation, and an umbrella offers shade. String lights create a warm ambiance over the space, enhancing the inviting atmosphere.

Guesthouse in Portland

Cascadia Cabana | Poolside Suite with Spa

4.97 out of 5 average rating, 122 reviews

A spacious covered patio features a rustic wood bar with barrel bases, accompanied by wooden seating and a table. Natural light filters in, illuminating the surrounding greenery. A barbecue grill stands ready for outdoor cooking, enhancing the inviting space for relaxation and gatherings.

Guest suite in Damascus

Unique Underground Speakeasy with hot tub

4.94 out of 5 average rating, 251 reviews

A spacious family room features a large L-shaped couch with comfortable seating. A plush green ottoman rests on a striped rug, complementing a contemporary armchair. Natural light filters through multiple windows, illuminating the room, which includes a TV and a cozy gas-lit fireplace.

Home in Portland

Spacious Forest Retreat w/ Hot Tub & Views

4.88 out of 5 average rating, 251 reviews

A bedroom features a queen bed with a decorative metal frame, dressed in light bedding with green accents. Two bedside lamps provide gentle illumination, and French doors open to a balcony, offering views of the surrounding greenery. Soft carpeting adds warmth to the space.

Apartment in Milwaukie

Indulge in Rare Riverside Retreat

Tiny home in Foster-Powell

4.87 out of 5 average rating, 486 reviews

Margaux | Airstream Glamping in the Heart of PDX

4.87 out of 5 average rating, 101 reviews

A fire pit is illuminated in the foreground, casting warm light on the surrounding stones. In the background, a colorful sunset paints the sky with shades of orange and pink, while trees and distant hills create a serene landscape.

Home in Lents

RoofTop FirePit, HotTub & Outdoor Theater

Guest suite in Cedar Mill

The living area features a soft brown sofa adorned with patterned cushions, situated on a neutral-toned area rug. Two stylish chairs with orange accents flank the sofa. Warm light is provided by two lamps, enhancing the cozy atmosphere of the room.

4.99 out of 5 average rating, 123 reviews

Jason & Susie's private guest suite w/ kitchenette

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 143 reviews

The open living space features a sectional couch with cushions, a wooden dining table, and chairs in a well-lit area. A television is mounted on the wall, with kitchen and dining areas visible in the background, illuminated by natural light from large windows.

Home in Gladstone

Forested Hygge House Getaway

4.97 out of 5 average rating, 964 reviews

The bathroom features a jetted tub surrounded by elegant tiles and candles. A large mirror enhances the space, while neatly arranged towels and plush robes are visible. Soft lighting and natural light from the window create a serene environment, emphasizing the calm aesthetic.

Guest suite in Troutdale

Amazing VIEW & Private Entry/Jetted Tub near Falls

4.96 out of 5 average rating, 222 reviews

A cozy studio space is depicted, showcasing a comfortable seating area with a neutral-toned sofa. An open kitchen with bar seating is visible in the background, alongside large glass doors leading to a fenced backyard. A television stands against the wall, ready for entertainment.

Guesthouse in Lents

Bright, Private & Cozy with Yard

4.94 out of 5 average rating, 903 reviews

A spacious studio cottage is bathed in natural light. Wooden beams adorn the vaulted ceiling, while a queen size bed with a floral green coverlet occupies one side. A kitchen area, a small table, and two chairs are visible, with warm yellow curtains framing the windows.

Guesthouse in Mt. Tabor

The Cedar Cottage

4.94 out of 5 average rating, 358 reviews

Guest suite in Richmond

Spacious Loft in the Heart of Southeast PDX

4.89 out of 5 average rating, 674 reviews

A tranquil pond surrounded by smooth stones and lush green plants is situated in front of a rustic wooden building. A wooden deck with patio furniture and an umbrella is visible, offering an inviting outdoor space amidst the serene natural setting.

Farm stay in Sandy

Green Acres Private Studio Apartment

4.81 out of 5 average rating, 101 reviews

A compact kitchenette features dark cabinets and a sink, complemented by a small seating area visible through an open door to a fenced yard. A pullout couch with cushions and a nearby wall-mounted table are also included in the cozy space.

Guest suite in Troutdale

Fresh + Clean, Walk to Edgefield and Town

4.92 out of 5 average rating, 179 reviews

A charming blue cottage is framed by a welcoming front porch with wooden railings. Lush green plants and purple flowers decorate the landscape. An American flag is displayed on the railing, and a car is parked in the driveway alongside the property.

Bungalow in Gladstone

The Wee Humble Cottage

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 210 reviews

The spacious bedroom features a large bed with a blue quilt and neutral pillows. Two windows allow natural light to fill the room, accented by greenery and decorative wall hangings. A wooden dresser and a traditional clock add a touch of charm to the space.

Guest suite in Welches

Spacious Mt. Hood Studio Retreat

Guest suite in Rose City Park

The kitchenette features sleek white cabinetry, a stainless steel refrigerator, and modern appliances. A round black table with two colorful chairs is situated on a patterned rug, complemented by open shelving displaying cups and utensils. The space is illuminated by natural light from a nearby doorway.

4.95 out of 5 average rating, 462 reviews

Rose City Retreat

4.96 out of 5 average rating, 107 reviews

A bright yellow door welcomes guests, set against exposed brick and green wall textures. Stone steps lead up towards the entrance, framed by potted plants. The inviting doormat displays the word 'WELCOME', enhancing the cheerful entrance to the apartment.

Guest suite in Eliot

Garden Apartment in the Heart of Portland

5 out of 5 average rating, 473 reviews

A golfer stands on a green tee-off area, facing a serene landscape filled with tall trees and lush grass. A small bucket of ice is positioned nearby, amidst the tranquil surroundings of a picturesque outdoor space.

Guesthouse in Newberg

Wine Country Spa House - Hot Tub/Sauna/Pool

4.98 out of 5 average rating, 214 reviews

A charming treehouse is suspended between large fir trees, featuring a wooden deck with multiple seating areas. Large windows provide natural light, and the surrounding forest greenery adds to the tranquil setting. The pathway beneath is lined with gravel, leading to the entrance.

Treehouse in Mt Hood

Beautiful, Magical, Treehouse

4.97 out of 5 average rating, 143 reviews

An airy kitchen features sloped ceilings with wooden beams and warm wood cabinetry. A vintage-style aqua refrigerator complements stainless steel appliances. Natural light filters through three windows, while a vibrant rug adds a pop of color to the space.

Home in Overlook

Rose City Hideaway

4.97 out of 5 average rating, 174 reviews

The exterior of the cabin is highlighted by warm wooden siding and large windows. A stone pathway leads to a circular arrangement of wooden chairs gathered around a fire pit, with an outdoor dining area set under a sunshade. Lush greenery surrounds the space.

Home in Rhododendron

Zen Cabin - Sauna, Hot Tub, Fireplace & Game Room!