House holiday rentals in Happy Valley

4.92 out of 5 average rating, 159 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

Relax in a Gladstone oasis overlooking an untouched trail and forested area. A cozy, bright, and private spot. I hope you connect with my affinity for vintage art and clean lines! You’ll have the entire house and 1/3 acre to yourself. Less than 30 mins from most anywhere in Portland Metro, 10 mins to Oregon City, and 1 hr to Mt. Hood. This is a dog friendly (no cats), non-smoking house. The large yard is on a dead-end street, though not fenced. *Some uneven paths and slip hazards are present

A spacious bed is framed by a wooden headboard, complemented by crisp white linens and fluffy pillows. A light beige quilt covers the bed, providing a soft texture. Next to the bed, a simple nightstand with a glass lamp adds a functional touch to the design.

4.94 out of 5 average rating, 175 reviews

Milwaukie Easy-Centrally located, Close to PDX

Our home is a spacious cozy contemporary home, complete with an outdoor deck, and a beautifully decorated interior with contemporary pieces that complete the design of our home. Windows in living & dining space are across from each other bringing in ample light. Our space is furnished with various mid-century, modern and contemporary pieces that complete the home. Shared Spaces •Parking area •On site laundry shared with other tenant, tenant has a separate living area with no other shared spaces

4.85 out of 5 average rating, 254 reviews

The entrance features a covered porch with a wooden frame and decorative pillars. Colorful flower baskets and potted plants adorn the space, while a bench rests on the wooden deck. Large windows provide visibility into the home, enhancing the welcoming appearance.

Home in Clackamas

Miranda's Lodge- cozy place with hot tub

Miranda's farm has been popular camping destination place in Molalla, OR during the summer. We decided to open Farm Lodge that will be welcoming guests all year around and close to the city, only 10min downtown Portland, 15min Airport. This dream home has been created with lots of love, imagination and farm style décor. Its cozy, sunny, happy, comfortable and healthy home, close to shopping and restaurants. Private entrance and fenced yard. Everything is brand new, you will want to stay forever.

4.96 out of 5 average rating, 114 reviews

A detached guest house is highlighted, featuring a blue exterior with large windows and a front door. A small patio area with a wooden table is visible, surrounded by lush greenery and decorative plants. A wooden fence provides additional privacy.

Home in Milwaukie

Secluded Studio

This a fully private and detached guest house is quiet and relaxing. Walk down your very own pathway to a completely private, safe and secure patio with a quaint garden, a small yard and outdoor seating. With tall ceilings and a large nice bright kitchen, this place is very comfortable. Blackout curtains. Close to many desirables: Max Orange Line Commuter Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk or run along the Springwater Corridor.

4.91 out of 5 average rating, 137 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 Happy Valley

RoofTop FirePit, HotTub & Outdoor Theater

Our large (1,500sq ft) space (private access), has a bedroom, bathroom, living room w/ a fireplace, hot tub, full gym as well as a kitchenette w/ full sized fridge, keurig, microwave, air fryer, toaster oven, single burner, and laundry facility. Smart tvs, hammocks and a rooftop firepit are in the outdoor entertainment area. LGBT & BIPOC friendly. Gym, hot tub and laundry are shared with owners but guests have priority access. Close to Mt Hood Wilderness (45mins) & Downtown Portland (15mins).

5 out of 5 average rating, 158 reviews

A single-level home is presented, featuring a light blue and gray exterior with a combination of brick and siding. The front yard is manicured with greenery, and a driveway leads to a two-car garage. A clear blue sky serves as the backdrop.

Home in Clackamas

Peaceful Spacious Single Level Home

Look no further if you are looking for a clean & spacious home with all the amenities for a comfortable stay. Single level with a walk in ADA shower in the primary bathroom. Dedicated office/den with excellent wifi. Remote work & family friendly. 5 minutes away from the Clackamas mall, Costco warehouse/gas, Target, REI, restaurants, Kaiser hospital. Clackamas is a suburb of Portland, only 25 min. drive of downtown and airport. *Co-hosts conveniently live nearby to assist whenever needed

Superhost

Home in Happy Valley

4.89 out of 5 average rating, 378 reviews

Mid Century Villa w/Mountain View & Movie Theater

Just relisted as we had long-term renters due to total fire loss. 3400 sq ft hillside retreat decked out with rare furnishings. Take in the Cascade Mountains from the wraparound deck and lounge under giant maple trees. You'll love the 125” Hi-Def movie theater (w/ 200+ movies)! Two large primary suites with king bed and large showers. One additional queen bedroom and one large office. Close to urban and nature, 20min to the airport, with daytrip opportunities to all the PNW must-see spots.

A welcoming living area features dark leather seating with cozy accent pillows. A patterned area rug anchors the space, complementing the warm-toned walls. Soft lighting from two lamps enhances the inviting atmosphere, and an open doorway leads to another room.

4.87 out of 5 average rating, 148 reviews

Urban Cabin on Mt Scott

Close to the city and close to nature, this is the best of both worlds! Tucked into forested Mt Scott on the edge of Portland, a very popular stay! 20 minutes from downtown and convention centers, 5 minutes from the freeway, 5 minutes from several food cart pods, 20 minutes from four major rivers, 30 minutes from the famous Columbia River Gorge waterfalls, and an hour from Mt Hood skiing and Timberline Lodge. Enjoy this entire guest house to yourself with shared driveway parking in front.

The living room features a comfortable grey sofa and a blue armchair, with a decorative woven basket adding texture. A smart television displays a vibrant arcade game, while a fireplace with stacked logs sits beneath a brick wall. Natural light enters through a window draped with sheer curtains.

4.95 out of 5 average rating, 140 reviews

Happy To Be Home

Welcome to Andy’s home. Here you will find a clean cozy half basement guesthouse with everything you need when traveling with family and friends - full kitchen, washer, dryer, street parking or off street parking. It is a half basement level so usually a little colder. Convenient location near public transportations. Short distance to grocery stores, restaurants, shopping malls, movie theater, bowling alley. 17 minutes to downtown and 15 minutes to airport by car.

4.93 out of 5 average rating, 263 reviews

Home in Vancouver

Explore. Play. Sneak home. Safe, Quiet & walkable

Stay where style meets location. The entire main floor is yours — a private, airy space tucked in Vancouver’s sought-after Historic Uptown Village. This peaceful, walkable neighborhood puts you just three blocks from buzzing Main Street, where you’ll find craft coffee, foodie-approved restaurants, indie shops, and more. Craving the water? The fabulous Vancouver Waterfront is just 1.6 miles away — perfect for sunsets, cocktails, and weekend vibes.

A spacious living area is highlighted by a light-colored sectional sofa positioned near a coffee table. Soft lighting fixtures are mounted on a navy blue accent wall, contributing to the room's inviting ambiance. Natural light filters through sliding doors that lead to a dining area.

4.91 out of 5 average rating, 149 reviews

Relaxing Home w/ Fire Pit, BBQ and Game Room

Welcome to our contemporary two bedroom home designed with comfort in mind to make your Portland stay unforgettable. Enjoy a prime location just 15 minutes from Portland International Airport, 20 minutes from the iconic Multnomah Falls, and 50 minutes from Mt Hood Ski Bowl and Timberline Lodge for skiing and snowboarding adventures. Whether you are here for business, relaxation, or outdoor exploration, this is the perfect base for your visit.