Holiday rentals in Portland

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Top-rated holiday rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of a two-story studio is framed by lush greenery and trees. The building features a spiral staircase leading to a private balcony with black railings. A shared garden area is visible below, with a hammock and various plants around the space.
Guest house in Piedmont
4.98 out of 5 average rating, 243 reviews

Spacious, bright garden studio on Peninsula Park

Explore the world-class restaurants, coffee shops and bars in the nearby Williams and Mississippi districts. Take a stroll around the award winning (and oldest) rose garden in the City of Roses across the street in Peninsula Park. At home, this second story studio has extra space in the meditation loft, a full kitchen, fast internet, and projector for streaming. Enjoy your private deck over the shared garden with hammock and H/C outdoor shower. Bus and train nearby with ample on-street parking.

Top guest favourite
A spacious living area is highlighted by mid-century furnishings, including a white sofa and a modern rocking chair. A brick fireplace serves as a focal point, complemented by built-in shelves lined with books. Soft lighting enhances the inviting atmosphere of the room.
Guest suite in Roseway
4.97 out of 5 average rating, 213 reviews

Scandinavian-modern private studio

Studio apartment designed with the essentials for relaxing. Get cozy by the gas fireplace with a book from our little library, work on your laptop in the desk nook or make an outdoor fire + star-gaze on the patio. Enjoy the mid-century furnishings, the nice sheets + towels and be sure to write a letter - letterpress cards + stamps are for your use. Quiet neighborhood with good coffee (Bison!), steps from breakfast (Beeswing), and near Beaumont Village (Pip's Donuts!). Only 10 mins to airport!

Top guest favourite
Home in Vernon
5 out of 5 average rating, 100 reviews

Modern Home — Prime Alberta Arts

This new home is steps from lively Alberta Street, the heart of NE Portland. It's perfect for couples, business travelers, and anyone looking to explore Northeast, Portland's best neighborhood. Plush king-size bed, open kitchen and living room, 1.5 bathrooms, and private yard. Explore awesome restaurants, bars, and shops around the corner, while staying on a quiet residential street. This home is just 15 minutes from the airport, and close to downtown (transit friendly!). Hablamos español.

Top guest favourite
A charming greenhouse features a clear glass structure with a black entrance door. The concrete base supports a light-filled space, showcasing lush greenery inside. Natural stone pathways lead to the entrance, with surrounding plants adding to its inviting appearance.
Guest suite in Woodlawn
4.94 out of 5 average rating, 508 reviews

Private Greenhouse Suite for 1 or 2 Guests

Elegant, private king bedroom suite with magical private greenhouse, private entrance, desk and ensuite bathroom. Enjoy radiant tile floor heat, charming greenhouse seating nook, spacious 2-person shower and an amenities cabinet with microwave, mini-fridge, teakettle & flatware - ideal for simple breakfasts or reheated leftovers. This spacious room is ideal for 1 or 2 guests who want an entirely separate private space and charming "interior garden" porch, but who don't need a full kitchen.

Top guest favourite
A sunlit living area features a cozy brown sofa, a glass dining table with metal chairs, and a mounted television. A circular mirror reflects light from the windows, enhancing the atmosphere. A fireplace is situated beneath the mirror, while sliding doors lead to an outdoor space.
Guest suite in Northwest District
4.95 out of 5 average rating, 133 reviews

Wilson Heights Studio at Forest Park

Welcome to your home away from home in the heart of Northwest Portland. This studio has a private entrance on a quiet street and has been newly renovated with a full kitchen, gas fireplace, laundry unit, and bath. You'll find this unit in a beautiful area of NW Portland - within walking distance to hiking & bike trails of Forest Park, fantastic restaurants and breweries in Portland Slabtown, a New Seasons Market, NW 23rd shopping district, the Pearl District, and more.

Top guest favourite
Guest suite in Overlook
4.98 out of 5 average rating, 163 reviews

Spacious Suite - Private Entry - Hip Kitchenette

Enjoy North Portland’s most loved shops, bars, and restaurants from this fresh and recently renovated suite. The 800sf immaculately clean space features a private entry, one bedroom, a bathroom, kitchenette, and sitting room. You’ll love its easy parking, proximity to downtown (10 min. drive or 2 blocks to the light rail), and convenient access to the freeway (explore the Columbia Gorge or the Oregon Coast). —> Reservations must reflect the correct number of guests.<—

Top guest favourite
A charming two-story house is framed by lush greenery and blooming plants. Tall windows allow natural light to fill the interior, while stone steps lead up to the welcoming entrance. Bright sunlight filters through the leaves overhead, enhancing the inviting atmosphere of the home.
Flat in Kerns
4.96 out of 5 average rating, 388 reviews

Studio in Walkable Foodie Heaven

We're on a quiet side street – right around the corner from a dynamic restaurant scene in Kerns, the 5th coolest neighborhood in the world. Stroll to parks, live music, vintage shops, and a vintage movie theater. Walk, Lyft/Uber, bicycle, or use Portland’s amazing public transportation everywhere. Tall windows overlook greenery and a cozy porch. Our family's 1900 house has been divided into separate apartments. Its like an artsy hotel room, but much more homey!

Top guest favourite
A warm sleeping area features a spacious bed framed by two wooden nightstands with lamps. A bright yellow throw blanket lays across the bed. The walls are painted a deep teal, and natural light enters through a window with a beige shade. A decorative piece on the wall adds character.
Guest house in Sullivan's Gulch
4.99 out of 5 average rating, 468 reviews

Cozy, Stylish Bungalow w/ Fireplace & Full Kitchen

Enjoy a comfy retreat in this cozy and bright studio with a private bathroom, air conditioning, fireplace, full kitchen and work desk. Conveniently located within walking distance to local restaurants, coffee shops, retail stores, and parks. Centrally located in Portland and just 3 miles from downtown. Take a stroll through Historic Irvington and enjoy some of the most beautiful homes and old growth trees that Portland has to offer.

Top guest favourite
An outdoor patio area is illuminated by soft lights, featuring a pathway of pavers and surrounded by lush greenery. The structure showcases large glass doors that provide a glimpse into the inviting interior space.
Guest house in Overlook
5 out of 5 average rating, 326 reviews

Colorful, spacious, light-filled guesthouse on MAX

Welcome to Juniper House! We designed our backyard guesthouse to be a bright, cozy loft, full of sunlight, exposed wood, tasteful furnishings and colorful finishes. Enjoy a private, 600-sq-ft space with an outdoor patio in a quiet, close-in Portland neighborhood, just blocks from light rail and within walking distance to a wide variety of great restaurants and watering holes. Perfect for couples and longer stays.

Top guest favourite
Guest house in Buckman
4.98 out of 5 average rating, 897 reviews

Cozy Portland Studio Apartment

The space is a well appointed, comfortable studio apartment. It is an ADU at the back of the main house. All the amenities that one would desire are provided (wifi, internet, TV, washer & dryer, fridge, dishwasher, stove, microwave, AC, cooking utensils, etc., etc). It is also very modern and clean, with a private entrance and keyless entry. Close to many restaurants, bars and coffee shops.

Top guest favourite
A spacious window offers a view of distant hills covered in greenery and autumn colors. A cozy chair sits nearby, creating a comfortable spot to enjoy the scenery. The room is softly illuminated, enhancing the serene ambiance while allowing natural light to flow in.
Flat in Pearl District
4.96 out of 5 average rating, 144 reviews

Free Parking/Gym/Rooftop/Pearl District/Downtown

Akoya, one of the four types of Pearls in the world. Welcome to Pearl District in PDX! Simple yet elegant, the Akoya Stay combines convenience and style. Location is extremely walkable and offers quick access to Whole Foods and the MAX Light Rail. Simply step out of the building and get lost in the brewery blocks, fine dining, entertainment & premier retail shopping.

Top guest favourite
Guest house in Concordia
4.99 out of 5 average rating, 656 reviews

Contactless Clean Private Treetop Studio

Majestic, unattached and sparkling clean, treetop studio in vibrant, accessible, and friendly neighborhood. New space whit lots of custom unique features. Great nearby restaurants, parks, coffee, and good vibes. On check out all we ask you to do is load the dishwasher and put dirty towels in one place.

Popular amenities for Portland holiday rentals

When is the best time to visit Portland?

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Avg. price$123 SGD$124 SGD$127 SGD$127 SGD$132 SGD$140 SGD$149 SGD$149 SGD$138 SGD$135 SGD$137 SGD$135 SGD
Avg. temp5°C7°C9°C12°C15°C18°C21°C21°C19°C13°C8°C5°C

Frequently Asked Questions

  • What are the best places to stay in Portland?

    Explore vibrant neighborhoods like the Pearl District, known for its galleries and eateries, Alberta Arts District with street art and cafés, or Nob Hill, which has tree-lined streets and boutique shops. Each area adds a distinct character to your visit.

  • What are the best things to do in Portland with kids?

    Families often visit the Oregon Zoo, explore interactive exhibits at OMSI, or roam the Portland Japanese Garden. These sites combine hands-on learning, animal encounters, and peaceful garden strolls.

  • What are some of the best things to do in Portland?

    Explore Powell’s City of Books, stroll through the International Rose Test Garden, or sample food at local markets. Art, gardens, and culinary experiences shape the city’s energy.

  • How is the weather in Portland?

    Portland has cool, rainy winters with temperatures from 36–47°F (2–9°C) and dry summers often reaching 82°F (28°C). Pack layers and rain protection—umbrellas are common, but locals often prefer waterproof jackets.

  • What are the best places to visit in Portland?

    Locals frequently suggest Forest Park’s trails, Lan Su Chinese Garden, and Portland Art Museum. Wander green spaces, discover art collections, and relax in tranquil gardens around the city.

  • What are some hiking trails in Portland?

    Portland has wooded paths in Forest Park, riverside trails in Oaks Bottom Wildlife Refuge, and scenic loops in Tryon Creek State Natural Area. These routes invite exploration in diverse natural settings.

  • What are some family activities we can do in Portland?

    Enjoy hands-on science at OMSI, picnic and play at Washington Park, or pedal along the waterfront on bike paths. Families also gather for open-air movies and seasonal farmers’ markets.

  • What are some of the best day trip ideas from Portland?

    Explore waterfalls in the Columbia River Gorge, taste wine in Willamette Valley, or wander historic streets in Hood River. Nearby nature and small towns add variety to your stay.

  • Are there any pet friendly accommodations available in Portland?

    Portland has many pet-friendly vacation rentals, especially around Alberta Arts, Sellwood-Moreland, and Mississippi Avenue. Parks and walking trails help make stays comfortable for travelers with pets.

  • What are some local tips for visiting Portland?

    Locals often use public transit or bikes, and rain is frequent—waterproof outerwear is practical. Food carts are popular for quick meals, and tap water is safe to drink throughout the city.

  • What is Portland known for?

    Portland is known for its craft beer, food carts, and vibrant arts scene. The city values sustainability, local makers, and green spaces, shaping a community-focused atmosphere.

  • What are the best hidden gems to explore in Portland?

    Discover quiet corners like Crystal Springs Rhododendron Garden, quirky boutiques on Mississippi Avenue, or murals along Alberta Street. These locally rooted spots cultivate creative energy.

  • What are the best foods to try in Portland?

    Taste fresh Pacific Northwest seafood, locally made artisan donuts, and inventive vegan dishes. Portland’s food carts and independent coffee roasters are frequently suggested by residents.

  • What should I bring for a trip to Portland?

    Pack waterproof jackets or umbrellas for wet weather, along with layers for shifting temperatures. Walking shoes and a reusable water bottle are practical for exploring markets, parks, and local trails.

  • What is the nightlife in Portland like?

    Neighborhoods like Hawthorne and Old Town mix live music, casual bars, and late-night eats. Craft breweries, music venues, and creative spaces add to the city’s inclusive night scene.

  • What are the most popular events or festivals in Portland?

    Portland has the Rose Festival in late spring and the Waterfront Blues Festival during summer, both widely attended city traditions. There are also local food and brew gatherings that attract many visitors throughout the year.

  • Are there family friendly vacation rentals in Portland?

    Family-friendly vacation rentals can be found in neighborhoods like Sellwood-Moreland, Laurelhurst, and Richmond. These areas have parks, playgrounds, and markets close by, making them welcoming for travelers with children.

  • When is the best time to visit Portland?

    Late spring to early autumn is often recommended for warmer temperatures and lower rainfall. Gardens and parks are especially lively when flowers bloom and festivals fill outdoor spaces.

Quick stats about holiday rentals in Portland

  • Total holiday rentals

    Explore 6,450 holiday rentals in Portland

  • Verified guest reviews

    Over 608,740 verified reviews to help you choose

  • Family-friendly holiday rentals

    2,690 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 2,240 rentals that welcome pets

  • Holiday rentals with a pool

    200 properties feature pools

  • Rentals with dedicated workspaces

    3,980 properties have a dedicated workspace

  • Wifi availability

    6,380 of Portland holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Monthly stays, Self check-in and Gym across Portland rentals

  • 4.8 Average rating

    Portland stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Portland’s top spots include Moda Center, Oregon Zoo and Powell's City of Books

Destinations to explore

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