House holiday rentals in Raleigh Hills

4.96 out of 5 average rating, 117 reviews

Home in Multnomah

Portland Modern

Welcome to our Midcentury Modern – a true masterpiece inspired by the iconic Frank Lloyd Wright. Nestled on a lush 1/3 acre private retreat, this architectural gem is just minutes away from Multnomah Village and Gabriel Park. Immerse yourself in the timeless beauty of this completely renovated mid-mod marvel, where high vaulted open beamed wood ceilings adorn every room on the main floor. This house is perfect for friend groups, families or corporate retreats. Note: 4 bedroom, 2 bath, 2 kitchen.

4.98 out of 5 average rating, 555 reviews

Home in Kenton

Loft in Kenton- Hot tub, MAX line, Weed friendly

House with 650 sq ft and patio to yourself. The loft, with vaulted ceilings and beautiful tile and woodwork throughout, is settled behind the main house, and includes a comfortable king bed, modern decor, fold down couch, well functioning kitchen, and access to hot tub. Kenton has great food, retail shops, and bars two blocks away, and guests are a short MAX train ride to Downtown. LGBTQ+ and rec. marijuana friendly. This home is not suitable for any guests under 18. Please read pet policy.

4.9 out of 5 average rating, 202 reviews

Home in Maplewood

Portland Vintage Hideaway

Portland Vintage Hideaway is a lovely, private, completely self-contained unit in our light-filled 1950's day-ranch basement. Enjoy 600+ sq.ft., queen bed with memory foam topper, double sofa bed, TV with streaming, workspace area, wi-fi, and adorable fully appointed kitchenette! The private, gated garden and patio offer a serene and lovely setting in which to hang out for meals & enjoy a glass of wine. We accept a maximum of two dogs and there is a pet fee. Please see details in the listing.

4.99 out of 5 average rating, 257 reviews

Hidden Garden Cottage

This 850 sf. cottage is a century old but was completely updated 12 years ago with era-appropriate furnishings, giving it a period (and safe) feel. Breakfast goodies, art, books, and a woodstove make it cozy. It sits on half an acre so lots of room for kids . It's in SW Portland, minutes from downtown. It's quiet, great for working or vacationing. An outdoor fire pit and gardens make it unique. There's even a zip line for kids. Family gatherings also fine. (Note: There is a $60 fee per dog.)

4.85 out of 5 average rating, 170 reviews

Charming home on private street with hot tub

Keep it simple at this conveniently situated retreat, just a 10-minute drive from downtown Portland and moments away from Multnomah Village. Nestled at the end of a private street in a desirable neighborhood, this charming home offers a spacious interior (with recently added centralized A/C) and inviting shared outdoor spaces. Relax and unwind in the hot tub, gather around the barbecue, or enjoy the patio and fireplace. Remote worker? Come be productive in our sitting/standing desk station.

4.9 out of 5 average rating, 136 reviews

SW Portland Retreat, Full amenities, kitchen + W/D

Welcome to the Relaxing SW Portland Getaway! We are proud to offer our beautiful home nestled in the Sylvan Highlands. Inside you will find accommodations designed to help our guests recharge and prepare for a full day exploring the beautiful city. This is a great landing point for your trip to PDX with close proximity to hotspots such as: The Oregon Zoo, Washington Park, Japanese Gardens, & Downtown Portland (all are within an 8-12 minute drive / UBER) We look forward to having you!

4.96 out of 5 average rating, 129 reviews

Home in Beaverton

Conveniently Located Home For Vacation or WFH

We are back after 2 years break due to Covid! Whether you are travelling for business or pleasure, this sparkling clean, well-equipped home will definitely make your trip memorable. The individual ductless HVAC unit in each bedroom offers a restful evening after a full day of activities. This renovated home is minutes away from our premier Washington Square shopping mall, groceries & restaurants. It is centrally located for a day trip to the Oregon coast, Columbia River Gorge, or Mt. Hood.

4.96 out of 5 average rating, 274 reviews

Cozy modern staycation workplace close to downtown

Entire space is very private. Enjoy the cozy modern 1 bedroom queen bed, 2 large sofas that are comfortable to sleep on, oversize soaking tub large walk-in closet , 2 TVs, Blue Ray player, stereo, gorgeous private garden with table seating & tranquil water, feature, & private entry. 5 minute drive to downtown, 2 minute walk to get to Forest Park trails. Several amazing restaurants just minutes away. There is a pet fee or $40 each pet. Preferably just one pet or the fee is $70 for two.

5 out of 5 average rating, 135 reviews

Home in Tigard

Mama J's

For whatever brings you to Oregon, stay at Mama J’s comfortable, peaceful, safe and convenient spot. Portland is just ten miles away, the closest beaches, Columbia River Gorge and Mt. Hood are all about an hour, and there are numerous hikes from the forest right down the street to Silver Falls and beyond. The neighborhood is peaceful and your private patio is the perfect place for a beverage and some bird and squirrel watching. If it rains, hang out in the gazebo! Hope to host you here!

4.97 out of 5 average rating, 433 reviews

Portland Southwest Suite Stay

Cozy suite in quiet, safe neighborhood with private, digital key-coded entrance for convenience. Private kitchenette & bathroom/shower, comfy queen sized bed, fold-out sofa, air-bed, pack & play, high chair & change table. Lots of closet space, included continental breakfast, and private covered outdoor sitting area. Very close to bus stops, so you won't need car. Walking-distance to parks, grocery, and restaurants. Close to downtown, Zoo, Japanese, Chinese & Rose Gardens, OHSU, OMSI.

4.93 out of 5 average rating, 245 reviews

Spacious Forest Retreat w/ Hot Tub & Views

In the woods, next to a creek, but still in Portland! Forget your worries in this spacious and serene space. There is a private entrance to this large two story guest suite, which includes a family room, living area with dining area and kitchenette, bedroom and bathroom, central AC, and private balcony. Located in a quiet neighborhood, close to hiking trails in Woods Memorial Park. A 3-minute drive or 1 mile walk to popular Multnomah Village; 15 minutes from Downtown Portland.