Photo by Linda Cronan

Portland vacation rentals

We found 95 vacation rentals — enter your dates for availability

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August 2025

September 2025

Scroll through and select from vacation rentals in Portland to find one that's perfect for your trip. Vacation rentals provide the amenities you need and want for your family, friends, or furry companion, such as a fireplace and a washer and dryer. You'll be able to choose a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Portland

Showing deals for:Nov 7 - Nov 14

Exceptional

(38 reviews)

Family Friendly, Historic Mansion Row, 5 min from Louisville!

New Albany, IN

10% off

includes taxes & fees

Exceptional

(159 reviews)

Historic Downtown, Walk to Dinner and Shops, Rooftop Patio, Great for Big Groups

New Albany, IN

10% off

includes taxes & fees

Exceptional

(21 reviews)

Unique Loft in Downtown NA, Walk to Dinner & Shops, Poker Table, Bikes & Garage

New Albany, IN

10% off

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Portland

Kentucky Derby 5 Bed Group 12+ Vacation Stay in Louisville Kentucky

Sleeps 17 · 5 bedrooms · 2+ bathrooms

Top rated rentals - Portland

Premier Host

40th Birthday trip

Couldnt have asked for a better home base for 3 days

Brendan I.

Stayed Sep 2024

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, yards and more
More for less
More space, more privacy, more amenities — more value

Find out more about Portland

Traveling to and around Portland

Fly into Louisville Intl. Airport (SDF), the closest airport, located 6.3 mi (10.1 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Louisville, KY (LOU-Bowman Field), which is 7.5 mi (12.1 km) away.

Frequently asked questions

How much does it cost to rent a vacation rental in Portland?

Property type, length of stay and time of year are some things that can influence the price of a vacation home. Simply add your dates of travel to find the ultimate escape. From quaint country cottages to expansive luxury villas, all Vrbo vacation rentals provide amazing value.

How much does it cost to rent a beach house in Portland?

Prices for beach houses in Portland may vary depending on the style and size of the property and when you're traveling. Simply enter your dates of travel into Vrbo and the number of guests to view your rental options and prices. From there you can use our filter tool to narrow down your search by ratings, nearby activities and more.

What are the top attractions for families in Portland?

There are plenty of wonderful things to see and do with the family in Portland, such as:

Louisville Slugger Museum
Louisville Mega Cavern
Kentucky Kingdom

How old do you have to be to rent a vacation rental in Portland?

It's advisable to check with the Portland vacation property you're looking at on Vrbo as age restrictions differ. However, generally it's 16, 18 or 21.

How long can I rent a vacation rental in Portland for?

The amount of time you can stay in a Portland vacation home for differs depending on the property. Simply tap in your travel dates to view options offering extended stays. They have everything you need to make your extended trip more enjoyable like air conditioning and kitchens. Some vacation homes may also offer weekly or monthly discounted prices, so you can hang around longer for less.