Holiday Rentals in Penn

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Penn

Kasa South Side Pittsburgh

4.0 star property
8.6 out of 10, Excellent, (72)
"We had an amazing stay, unfortunately the only parking was in a parking garage and you get charged anytime your vehicle leaves so we spent a pretty penny just to get to and from. Regardless the room and building itself was nice and clean, we also enjoyed the pool! Definitely recommend!"
Kasa South Side Pittsburgh

The Warhola Bloomfield

4.5 star property
5.0 out of 10, (22)
"This place is incredible!! Walking distance to awesome neighborhoods, immaculately clean, comfy furniture and all amenities top-notch! I already want to plan more stays at this spot!!"
The Warhola Bloomfield

Not so tiny house with full kitchen & patio swing

9.6 out of 10, Exceptional, (42)
"Had a great time staying here. I had total confidence in my host, and they made me feel very comfortable which was super important to me. This place had more amenities than I even needed! Very comfortable. However, if you visit in the winter you’ll have to bring a portable heater for the bathroom, as it gets really cold in the mornings!! "
The price is €190
includes taxes & fees
23 Feb - 24 Feb
Not so tiny house with full kitchen & patio swing

Spacious 1-Bedroom Apartment In Pittsburgh (B1)

9.6 out of 10, Exceptional, (19)
"Price, location, facilities, and atmosphere top shelve (for what I needed). "
The price is €190
includes taxes & fees
11 Mar - 12 Mar
Spacious 1-Bedroom Apartment In Pittsburgh (B1)

Melwood Suites Unit 107 Studio

2.0 star property
10.0 out of 10, Exceptional, (11)
"It’s a cute little studio, perfect amount of space. Overall, a great stay! "
The price is €103
includes taxes & fees
26 Feb - 27 Feb
Melwood Suites Unit 107 Studio

Enjoy Urban Living at our Steel City Getaway w/ Hot Tub!

10.0 out of 10, Exceptional, (34)
"Stayed here over a long weekend for a hockey tournament. We commuted to Ice Castle in Castle Shannon at various times of day and it was very reasonable. Neighborhood was quiet and clean. Driveway parking available which we used and had to park an additional vehicle on the street. No issues finding parking. Backyard was fully fenced and clean. Would be super cute in the Spring-Fall time. Salt and shovel were available for us as well as a couple of space heaters should we needed them. I would have...
Enjoy Urban Living at our Steel City Getaway w/ Hot Tub!

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (23)
"We had a lovely stay at the Carey Townhome. Everything was exactly as promised and the location was perfect. There were plenty of bars and restaurants within a 10 minute walk while still being located in a quiet area. Tom was very easy to communicate with as well. I would definitely recommend staying at the Carey Townhome in the future."
❤️Cozy Townhome on Carey with Private Deck Space ❤️

Greenfield Home

10.0 out of 10, Exceptional, (7)
"Very comfortable stay, nice amenities and accurate to the listing"
Greenfield Home

424-Apt. 403

3.5 star property
9.8 out of 10, Exceptional, (23)
"Plenty of space and clean room. Really enjoyed my time!"
The price is €207
includes taxes & fees
27 Feb - 28 Feb
424-Apt. 403

Industrial Loft 3 min to Hillman Cancer Center Sleeps 6

10.0 out of 10, Exceptional, (27)
"Quick stay in Pittsburgh for graduation. Great location and great hosts. Beds were very comfortable. Easy to access building and great communication with hosts. Recommend this place. "
The price is €233
includes taxes & fees
16 Feb - 17 Feb
Industrial Loft 3 min to Hillman Cancer Center Sleeps 6

Reimagined 1915 Heritage House

10.0 out of 10, Exceptional, (20)
"My husband and I needed a place to stay near family for Christmas, along with our (adult) niece and nephew, and our dog. Clark's house had plenty of room for all of us! We so appreciated the warm welcome we found when we arrived: bacon, eggs and bread for breakfast, and a local liquor to unwind after the drive! There was even a cute Christmas tree to get us in the holiday mood. Thank you, Clark! We will definitely be back! "
Reimagined 1915 Heritage House

Pittsburgh Townhome ~ 5 Miles to Market Square

9.8 out of 10, Exceptional, (31)
"This property is as advertised: Very Clean and spacious. 4 bedrooms, and 1 has a bunk bed for kids, it was perfect. Owner was easy to contact and check in, wi-fi and 4 TV's wwe great! Highly recommend!"
Pittsburgh Townhome ~ 5 Miles to Market Square

Modern All-New, Near Downtown, Private Parking - walking to Children Hospital

10.0 out of 10, Exceptional, (44)
"We had a family gathering and I wanted to stay closer to town so I lucked up on this property. My grandchildren came to visit me in between time and we had a blast catching up. The house was clean and pretty much close to anything we wanted to do. I actually thought the pictures may have stretched the actual room size but the place was very spacious. I really didn't need that much space but I totally enjoyed it. I will definitely book again."
The price is €315
includes taxes & fees
17 Feb - 18 Feb
Modern All-New, Near Downtown, Private Parking - walking to Children Hospital

Comfortable and clean whole apartment, great for couples and friends getaways.

9.6 out of 10, Exceptional, (14)
"Nice place, accurate listing, all amenities you may need for a nice visit. Would stay again for sure!"
Comfortable and clean whole apartment, great for couples and friends getaways.

Pittsburgh Home w/ Pool, Fire Pit + Game Room

7.6 out of 10, Good, (4)
"Loved it nice and quiet area"
Pittsburgh Home w/ Pool, Fire Pit + Game Room

Family-Friendly Shadyside Gem Near Dtwn Pittsburgh

10.0 out of 10, Exceptional, (15)
"We travel at least one week a month and stay in bnbs from Maine coast to California vineyards. The home was the highest quality, and the host was the most responsive and helpful I have ever experienced. The home perfectly accommodated three adult families and a toddler. We all had privacy and beautiful spaces to be alone or together. Everything we needed was included. Comfortable, perfectly clean, and the best location in Pittsburgh…we have visited here for years. Walk to restaurants,...
Family-Friendly Shadyside Gem Near Dtwn Pittsburgh

Home away from home!!!

8.4 out of 10, Very good, (23)
"Wonderful house, very spacious and comfortable. "
The price is €422
includes taxes & fees
17 Feb - 18 Feb
Home away from home!!!

Pet-Friendly Apollo Home w/ Furnished Deck!

9.0 out of 10, Wonderful, (8)
"Traveling for a wedding, our family decided to be together. It was wonderful. This was a perfect home for the 10 of us. The home is very spacious w everything you need. Communication w the owner was simple and prompt. Location was peaceful & the neighborhood appeared safe. Thank you for contributing to some wonderful memories! . "
Pet-Friendly Apollo Home w/ Furnished Deck!

*New* Huge! Spacious 3 Bedroom in Oakland that sleeps 12! over 3000+ sq ft

9.8 out of 10, Exceptional, (40)
"The place was very nice. Lots of room. Very open. Very clean. Parking kind of sucked if you didn’t get a pass for the garage. But everything else was perfect"
The price is €418
includes taxes & fees
16 Feb - 17 Feb
*New* Huge! Spacious 3 Bedroom in Oakland that sleeps 12! over 3000+ sq ft

Pet-Friendly Home - 100 Feet to Walnut Street

10.0 out of 10, Exceptional, (27)
"Perfect spot for me and my daughter (HS senior) to stay while visiting colleges in Pittsburgh. Location was amazing. Literal steps from Shadyside neighborhood, restaurants, and shopping. Property was clean and neat. Road noise in the front was a bit loud at night, but white noise helped. We felt very safe in the neighborhood and secure in the property. Would stay here again."
Pet-Friendly Home - 100 Feet to Walnut Street
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Penn
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Penn you may be interested in

Hampton Inn Pittsburgh University/Medical Center

2.5 star property
8.0 out of 10, Very good, (1003)
"I stayed three nights and then returned for another night while my husband was having extensive surgery. Everyone was extremely nice. I liked my first room, but loved the second room!"
The price is €111
includes taxes & fees
20 Feb - 21 Feb
Hampton Inn Pittsburgh University/Medical Center

Hampton Inn Pittsburgh/Monroeville

2.5 star property
8.2 out of 10, Very good, (1002)
"Location! Location! Location!"
The price is €111
includes taxes & fees
9 Mar - 10 Mar
Hampton Inn Pittsburgh/Monroeville

The Maverick by Kasa

3.0 star property
8.8 out of 10, Excellent, (553)
"Very cool artistic style "
The price is €78
includes taxes & fees
19 Feb - 20 Feb
The Maverick by Kasa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a holiday rental in Penn?

Yes, there are holiday rentals close to the most popular sights in Penn, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Penn has to offer?

Not so tiny house with full kitchen & patio swing: This holiday home rental outside of Penn is located in the city centre, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and an oven.

What’s there to see and do in Penn?

Explore the area and family-friendly sights such as Kennywood, or get out into nature at a spot like Presque Isle State Park. Seton Hill University and The Palace Theatre are a couple of places you'll find in the wider area.

What’s a holiday rental in Penn like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Penn. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips.