Holiday rentals near Pioneer Courthouse Square

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October 2025

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Choose the right private holiday rental that's near Pioneer Courthouse Square. Holiday homes offer the best amenities for you and your friends, family or even pets, such as a fireplace and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Pioneer Courthouse Square

Showing deals for:30 Jan - 6 Feb

Exceptional

(47 reviews)

Cozy Modern Farmhouse, King bed, great yard, pets!

Milwaukie, OR

17% off

for 7 nights, 1 room

AU$467 per night

includes taxes & fees

Exceptional

(8 reviews)

Cozy Getaway w/Hot tub, Fireplace, Firepit & A/C

Portland, OR

7% off

for 7 nights, 1 home

AU$351 per night

includes taxes & fees

Exceptional

(12 reviews)

Charming 1-Bedroom Entire Condo Loft in Scenic Mountain Park

Lake Oswego, OR

8% off

for 7 nights, 1 apartment

AU$269 per night

includes taxes & fees

Very good

(10 reviews)

Full remodeled home on 1/3rd Acre! Close to Nike WHQ and central Beaverton.

Beaverton, OR

8% off

for 7 nights, 1 home

AU$441 per night

includes taxes & fees

Excellent

(20 reviews)

Stylish, New & Clean 1b apt w/ King Bed+Pool+Gym+Parking

Beaverton, OR

6% off

for 7 nights, 1 apartment

AU$234 per night

includes taxes & fees

Exceptional

(5 reviews)

Beautiful, family-friendly Portland home, walk score of 94!

Portland, OR

7% off

for 7 nights, 1 home

AU$581 per night

includes taxes & fees

Exceptional

(51 reviews)

❤️ CLEAN | LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ LARGE PATIO

Portland, OR

7% off

for 7 nights, 1 home

AU$310 per night

includes taxes & fees

Exceptional

(25 reviews)

New Build, Great Value near Downtown Vancouver & Waterfront

Vancouver, WA

8% off

for 7 nights, 1 home

AU$168 per night

includes taxes & fees

Exceptional

(14 reviews)

Casa Tropical Jungle in the Couve close to DT

Vancouver, WA

11% off

for 7 nights, 1 home

AU$206 per night

includes taxes & fees

Exceptional

(18 reviews)

Patio w/ fire pit home ✶ 10min to DT → Has it all!

Portland, OR

7% off

for 7 nights, 1 home

AU$523 per night

includes taxes & fees

Wonderful

(33 reviews)

The "Old Barn" in the woods. Peace, Romance, Ahhh

Portland, OR

8% off

for 7 nights, 1 cottage

AU$266 per night

includes taxes & fees

Exceptional

(240 reviews)

Peaceful Garden Cottage, Close to Mt. Tabor Park & Downtown Bus

Portland, OR

6% off

for 7 nights, 1 cottage

AU$257 per night

includes taxes & fees

Exceptional

(41 reviews)

Spectacular Choice: Sleeps 6, Your Dog Welcome Too

Tigard, OR

7% off

for 7 nights, 1 home

AU$286 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Pioneer Courthouse Square

Pioneer Courthouse Square

Find the best place to stay - Pioneer Courthouse Square

The Clyde Hotel Portland by Kasa Living

Sleeps 2 · 1 bedroom

Top rated rentals - Pioneer Courthouse Square

Modern & Great Location

Had a great stay with my kids here, having the bedrooms on opposite sides was very helpful. The place was cozy, clean, and great location. Would stay here again!

Brittagh L.

Stayed Jan 2025

Queen sized bed with both feather and foam pillows, fireplace, tv, stereo, etc.

Premier Host

Portland stopover

Vicki is a very helpful and obliging host who has thought of every comfort that we might need for our stay. We were very warm and comfortable.

Marilyn B.

Stayed May 2024

Brick House Beautiful is on Nat. Historic Register - 24 different brick pattern

Premier Host

Perfect place to stay when visiting Portland

Bob was such a lovely fella, very friendly, accommodating and he even gave us a tour of the house, which is stunning. The space downstairs where we stayed had everything you could need and was very comfortable. As with the house, the backyard was lovely and perfect to unwind at the end of the day. The neighbourhood was one of the nicest I've come across. Highly recommend staying here.

Andrew S.

Stayed May 2022

fully private and lovely guest home with private deck and dimmable lights

Premier Host

Great home away from home

We loved our stay in this beautifully appointed apartment. Heaps of space, comfy beds, quiet, and walking distance to a big selection of eateries. Would definitely stay again 😊

Craig T.

Stayed June 2019

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Holiday rentals near Pioneer Courthouse Square

Holiday rentals with weekly discounts - Pioneer Courthouse Square

Image gallery for Cozy Modern Farmhouse, King bed, great yard, pets!

Cozy Modern Farmhouse, King bed, great yard, pets!

Find spaces that suit your style

Find properties near top attractions in Pioneer Courthouse Square

Map Attractions

Pioneer Courthouse Square

Find the best place to stay - Pioneer Courthouse Square

The Clyde Hotel Portland by Kasa Living

Top rated rentals - Pioneer Courthouse Square

Modern & Great Location

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near Pioneer Courthouse Square

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