House
10.0(557 Reviews)
2 Bedrooms
4 Guests
Parking
Balcony/Terrace
Kitchen
Internet
US $143/Night
7 Nights - US $1,002
Portland Holiday Rentals
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Compare Villas, Resorts, & Rentals in Portland
10.0
Apartment
10.0(7 Reviews)
1 Bedroom
2 Guests
- Parking
- Internet
Child Friendly
Sports/Activities
US $166/Night
7 Nights - US $1,164
Bed & Breakfast
10.0(131 Reviews)
1 Bedroom
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $301/Night
7 Nights - US $2,108
House
10.0(358 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
US $156/Night
7 Nights - US $1,089
Apartment
10.0(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $174/Night
7 Nights - US $1,221
House
10.0(176 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $224/Night
7 Nights - US $1,569
House
10.0(175 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $287/Night
7 Nights - US $2,009
Apartment
10.0(166 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $274/Night
7 Nights - US $1,920
House
10.0(155 Reviews)
1 Bedroom
4 Guests
- Parking
Pool- Balcony/Terrace
- Kitchen
US $236/Night
7 Nights - US $1,654
Luxury Holiday Rentals in Portland
Over 5162+ Luxury Holiday Rentals in or Near Portland
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US $9,107/Night
7 Nights - US $63,751
US $6,459/Night
7 Nights - US $45,210
House
9.8(7 Reviews)
10 Bedrooms
20 Guests
Private Pool- Parking
- Pool
Spa
US $3,864/Night
7 Nights - US $27,045
House
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Internet
- Child Friendly
US $3,399/Night
7 Nights - US $23,790
House
8 Bedrooms
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $3,205/Night
7 Nights - US $22,437
Top-Rated Holiday Rentals with a Pool in Portland
Over 509+ The Best Private Villas and Holiday Rentals in Portland with a Pool
House
10.0(224 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $414/Night
7 Nights - US $2,899
House
10.0(82 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $156/Night
7 Nights - US $1,090
House
10.0(38 Reviews)
1 Bedroom
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $177/Night
7 Nights - US $1,237
House
10.0(29 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $341/Night
7 Nights - US $2,389
Cabin
10.0(25 Reviews)
4 Bedrooms
12 Guests
- Private Pool
Hot Tub- Pool
- Kitchen
US $1,180/Night
7 Nights - US $8,263
House
10.0(22 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $596/Night
7 Nights - US $4,169
House
10.0(19 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $335/Night
7 Nights - US $2,342
House
10.0(17 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $315/Night
7 Nights - US $2,203
House
10.0(13 Reviews)
3 Bedrooms
5 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $449/Night
7 Nights - US $3,142
Pet-Friendly Holiday Rentals in Portland
Over 2117+ Pet-Friendly Holiday Rentals in or Near Portland
House
10.0(96 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $461/Night
7 Nights - US $3,227
House
10.0(4 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $176/Night
7 Nights - US $1,229
House
9.8(14 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $749/Night
7 Nights - US $5,242
Cabin
10.0(91 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $179/Night
7 Nights - US $1,253
House
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $307/Night
7 Nights - US $2,147
House
10.0(73 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $265/Night
7 Nights - US $1,852
House
10.0(43 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $245/Night
7 Nights - US $1,712
House
10.0(36 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $123/Night
7 Nights - US $859
House
10.0(32 Reviews)
1 Bedroom
4 Guests
- Internet
- Pet Friendly
- Child Friendly
Laundry
US $230/Night
7 Nights - US $1,611
Large Holiday Rentals and Private Villas in Portland
Over 535+ Large Holiday Rentals and Private Villas in or Near Portland
Villa
10.0(13 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $301/Night
7 Nights - US $2,106
US $457/Night
7 Nights - US $3,201
House
9.0(4 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $349/Night
7 Nights - US $2,444
Apartment
10.0(2 Reviews)
1 Bedroom
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,495/Night
7 Nights - US $10,465
Villa
10.0(2 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
View- Air Conditioner
US $294/Night
7 Nights - US $2,058
House
9.6(4 Reviews)
2 Bedrooms
11 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $141/Night
7 Nights - US $984
Condo
1 Bedroom
10 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $2,019/Night
7 Nights - US $14,133
Other
1 Bedroom
11 Guests
- Air Conditioner
- Internet
- Child Friendly
Bedding/Linens
US $291/Night
7 Nights - US $2,038
House
10.0(44 Reviews)
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $999/Night
7 Nights - US $6,996
Wheelchair Accessible Holiday Homes in Portland
Over 913+ Wheelchair Accessible Holiday Homes in or Near Portland
Apartment
10.0(24 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $244/Night
7 Nights - US $1,711
Apartment
10.0(3 Reviews)
2 Bedrooms
3 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $265/Night
7 Nights - US $1,856
Hotel
9.8(148 Reviews)
- Breakfast
- Parking
- Pool
- Kitchen
US $165/Night
7 Nights - US $1,153
Condo
10.0(17 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $179/Night
7 Nights - US $1,256
House
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $154/Night
7 Nights - US $1,078
Apartment
10.0(16 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $178/Night
7 Nights - US $1,246
Condo
10.0(13 Reviews)
1 Bedroom
3 Guests
- Kitchen
- Internet
- Child Friendly
Wheelchair Accessible
US $98/Night
7 Nights - US $683
Condo
10.0(7 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $123/Night
7 Nights - US $858
Condo
10.0(6 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
US $94/Night
7 Nights - US $657
Portland Private Villas and Holiday Homes Under $200
Over 2385+ Portland Private Villas and Holiday Homes Under $200
Apartment
10.0(116 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $156/Night
7 Nights - US $1,093
Apartment
10.0(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Internet
- Child Friendly
- Sports/Activities
US $114/Night
7 Nights - US $796
Bed & Breakfast
9.8(144 Reviews)
1 Bedroom
- Breakfast
- Balcony/Terrace
- Kitchen
- Internet
US $152/Night
7 Nights - US $1,064
Apartment
10.0(107 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Internet
- Child Friendly
US $162/Night
7 Nights - US $1,136
House
10.0(3 Reviews)
1 Bedroom
3 Guests
- Parking
- View
- Internet
Security/Safety
US $144/Night
7 Nights - US $1,008
Cottage
10.0(105 Reviews)
1 Bedroom
2 Guests
Oceanfront- Parking
Ocean View- Balcony/Terrace
US $183/Night
7 Nights - US $1,282
Apartment
10.0(92 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $170/Night
7 Nights - US $1,187
Apartment
10.0(91 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $117/Night
7 Nights - US $820
Cottage
10.0(84 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $168/Night
7 Nights - US $1,176
Instantly Bookable Holiday Homes in Portland
Over 2783+ Instantly Bookable Holiday Homes in or Near Portland
Cottage
10.0(143 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $203/Night
7 Nights - US $1,423
US $96/Night
7 Nights - US $672
US $183/Night
7 Nights - US $1,278
Apartment
10.0(136 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $201/Night
7 Nights - US $1,408
Condo
10.0(135 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $365/Night
7 Nights - US $2,558
House
10.0(119 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $203/Night
7 Nights - US $1,424
House
10.0(110 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $271/Night
7 Nights - US $1,896
Apartment
10.0(109 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $239/Night
7 Nights - US $1,672
Apartment
10.0(109 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $205/Night
7 Nights - US $1,438
Book a Last Minute Place to Stay in Portland
About Casai's Private Villas and Holiday Rentals in Portland
Discover more than 5171 vacation rentals available in Portland. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Portland.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Portland, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Portland. On average, places to stay near Portland offer 843.63 ft², with nightly prices averaging US $306.
With Casai, finding and comparing holiday rentals in Portland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Portland, OR
There are 5171 Portland, OR Holiday Rentals
- Prices for a holiday home in Portland start at US $45
- Top rated vacation home in Portland is Exquisite Historic Suite Close to Downtown 14-21673
- Most popular short term in Portland is The Paramount Hotel
- Cheapest place to stay in Portland is Motel 6-Troutdale, OR - Portland East
- Most expensive holiday rental in Portland is Downtown Views | Pet-friendly & In-Room Dining
Recently Booked Holiday Rentals in Portland
Frequently Asked Questions About Portland?
What are the top holiday rentals in Portland?
With numerous options available in Portland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Portland:
- Exquisite Historic Suite Close to Downtown 14-21673
- Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row
- A Handsome Newly Remodeled Vintage Inspired Apartment In Downtown Newberg, OR
- Luxurious Zen Modern in the Historic N. Mississippi District. Sanitized , clean!
- Adorable attic cottage in the heart of Oregon Wine Country.
- Spectacular Sweeping Views of Willamette Valley Vineyards and Surrounding Hills
- THE PORTLAND VILLA - In the heart of NE Portland, Alberta Arts District
- Sunny 1400 SQFT Dutch Colonial in Portland Heights - 5 min to downtown, NW 23rd
- University Park Garden Guest House
- Modern Sanctuary in the heart of Concordia
How many holiday rentals have private pools in Portland?
Discover a selection of holiday rentals with private pools near Portland with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Portland are best for families?
If you're searching for a family-friendly holiday home in Portland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Portland:
How many Casai.com holiday rentals are available in Portland?
As of 2026, Casai boasts over 5171 properties listed in the Portland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Portland.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Portland Vacation Rentals in Portland, Oregon | 237 |
| Northwest Portland Vacation Rentals in Portland, Oregon | 212 |
| Alphabet Historic District Vacation Rentals in Portland, Oregon | 121 |
| Nob Hill Vacation Rentals in Portland, Oregon | 121 |
| Sunnyside Vacation Rentals in Portland, Oregon | 114 |
| Goose Hollow Vacation Rentals in Portland, Oregon | 60 |
| Parkrose Vacation Rentals in Portland, Oregon | 34 |
| Hollywood District Vacation Rentals in Portland, Oregon | 33 |
| Pearl District Vacation Rentals in Portland, Oregon | 32 |
| Old Town Chinatown Vacation Rentals in Portland, Oregon | 31 |
| Cedar Hills Vacation Rentals in Portland, Oregon | 31 |
| Sellwood-Moreland Vacation Rentals in Portland, Oregon | 30 |
| Lloyd District Vacation Rentals in Portland, Oregon | 2215 |
| Tanasbourne Vacation Rentals in Portland, Oregon | 286 |
| Orenco Station Vacation Rentals in Portland, Oregon | 238 |
| Bethany Vacation Rentals in Portland, Oregon | 189 |
