
Holiday rentals in Pearl District
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Top-rated holiday rentals in Pearl District
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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.

Accessible, AIA-Award Winning, Urban Garden Oasis
A nurturing place with abundant light, garden views, & access to the best Portland food. “The best Airbnb I’ve ever stayed in!” - frequent guest comment. - American Institute of Architects Award to designer Webster Wilson - Upscale amenities & European fixtures - Quiet NoPo neighborhood tree-lined street, minutes from downtown - Fully equipped kitchen w/ fresh local coffee - Indoor & outdoor dining - See photo captions for more details - Trained Service Animals welcome; no pets nor ESAs

Wes Anderson inspired historical private apt.
Turn of the century/Wes Anderson Inspired converted lower level basement of an 1890s house. Great proximity to Downtown and public transportation, as well as all the cool stuff to do in N Portland. We are a block away from Mississippi Ave. and close to N. Williams and Freeway access to I-5. You will have a private entry from the front of the house. Our place is good for couples, business travelers, friends, and families (with kids). We do not allow smoking of any substances in the home.
Close-in, private Overlook retreat.
The Overlook neighborhood is one of Portland's hidden gems. Quiet, tree lined, yet only a few minutes from all the action Portland serves up. Walk or ride to meals, brewpubs or shopping in the Mississippi and Williams districts. Hop a train (three blocks away) to all quarters. Or, to unwind, walk to Overlook or Mocks Crest parks for sweeping views of downtown Portland, Forest Park and the Willamette River. Please read on to see if the studio's lower ceiling is the right fit for you.

Queen Anne Guest Apt. In Historic District
Enjoy this private guest apartment on the bottom floor of our historic four story home. Located footsteps from Portland's best restaurants, shops, and our beloved Timbers and Thorns soccer stadium, you'll be central of NW 21st/23rd commercial districts, the Pearl district and downtown Portland. Whether traveling to visit loved ones, see a show, a game or enjoy some culinary maximalism, this is your hotel like home away from home. Business travelers will also love this central location.

Modern Apt | Close to Everything
Located within the trendy Boise neighborhood and only minutes to central Portland is this chic sun-filled apartment that offers all the modern comforts of home. With stylish décor and bright open plan living, the apartment features a fully equipped kitchen, soft comfortable furnishings, a spacious master bedroom and a sparkling modern bathroom. Walk to the popular Williams and Mississippi streets with its top restaurants, coffee shops and Portland’s world-famous food carts.

Pet Friendly NW Nob Hill High End Private Apt.
Beautiful high end modern private apartment built in a historic 1904 Craftsman in Nob Hill. Walk two blocks to NW 23rd for a wide variety of stellar restaurants and shopping or take a 10min walk to get to the heart of the city or to the famous trails of forest park. Easy access to transportation all over the city just steps away. View Mt. Hood from the front porch or relax with your own large private yard and let your pets run. Listed on VRBO 395585, excellent reviews.

The Green Door PDX: A European Inspired Cottage.
A bolthole created from passion by Kaemingk Collection, The Green Door PDX was designed to provide a unique respite from the energy of Portland while being conveniently located only minutes from downtown and popular shopping/eating districts. We have taken queues from Europe and built a traditional field cottage tucked into the landscape at the front of the property and surrounded it with mature greenery for an inviting welcome and ultimate privacy for our guests.

Melrose Place
Light, bright, and airy modern corner townhouse with an abundance of windows looking out to a quiet maple tree lined street. Freshly remodeled house with no detail overlooked. Cook in the Chef’s kitchen or eat out at the numerous restaurants and food carts within blocks of the house. Forest park and hiking trails are just a couple blocks up the street! The house is a great spot to work from home, relax, cook and serve as your home base to see the best of Portland!

Renovated 1BR - Historic Charm - Great Locale
Flooded with natural light, this stylish suite blends timeless charm with modern comfort in one of Portland’s best neighborhoods. Nestled just off NW 23rd Ave, enjoy boutique shopping, top-rated restaurants, and tree-lined strolls right outside your door. Inside, you’ll find a curated living space with a plush sofa, full kitchen, fast WiFi, smart TV, and comfy queen bed—perfect for cozy nights in or recharging after a day exploring the city.

Large Studio in Historic Isam White House
Super Clean third floor suite in the historic Isam White House. Includes bed area, living and dining area, kitchenette with microwave, hot water kettle, dishes and small fridge and private bathroom with tub/shower. This is one of the last grand mansions downtown that hasn't been converted to condos or offices. We are at the shopping and restaurant districts of Northwest 21st and 23rd Avenues. Walkability score of 97!

Bright 1BR - Walk to Coffee, Food & Shopping
This bright and stylish one-bedroom apartment is located in one of Portland’s most walkable and desirable neighborhoods. Just steps from NW 23rd Avenue, you’ll have the city’s best restaurants, shops, and cafés right outside your door. Inside, enjoy a thoughtfully furnished space with a queen bed, Smart TV, fast WiFi, and a full kitchen - ideal for cozy nights in or urban adventures.
Popular amenities for Pearl District holiday rentals
Other great holiday rentals in Pearl District

2 Bedroom Apt. in Historic NW Portland Warehouse

Modern City Apartment with Gym and Parking

New Luxury 2BR • Walk to Dining • Best Location

Walkable, lively 'hood; pet-friendly and permitted

The PDX

Luxury Living in Prime Location FREE Airport Rides

Elegant 1bed 1bath •Free Parking •Rooftop

Walkable NW 23rd Retreat – Style & Comfort
When is the best time to visit Pearl District?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $129 SGD | $129 SGD | $137 SGD | $141 SGD | $139 SGD | $143 SGD | $156 SGD | $145 SGD | $135 SGD | $144 SGD | $135 SGD | $129 SGD |
| Avg. temp | 5°C | 7°C | 9°C | 12°C | 15°C | 18°C | 21°C | 21°C | 19°C | 13°C | 8°C | 5°C |
Quick stats about holiday rentals in Pearl District

Total holiday rentals
Explore 110 holiday rentals in Pearl District

Nightly prices starting at
Pearl District holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 2,500 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
110 of Pearl District holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Pearl District rentals

4.7 Average rating
Pearl District stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Moda Center
- Laurelhurst Park
- Oregon Zoo
- Timberline Lodge
- Providence Park
- Silver Falls State Park
- The Grotto
- Portland Japanese Garden
- Mt. Hood Skibowl
- Wooden Shoe Tulip Festival
- Beacon Rock State Park
- Wonder Ballroom
- Hoyt Arboretum
- Powell's City of Books
- Tom McCall Waterfront Park
- Pumpkin Ridge Golf Club
- Oaks Amusement Park
- Domaine Serene
- Wings & Waves Waterpark
- Portland Art Museum
- Skamania Lodge Golf Course
- Bridal Veil Falls State Scenic Viewpoint
- Battle Ground Lake State Park
- Arlene Schnitzer Concert Hall