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Pensacola Holiday Rentals

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Our top choices for Pensacola holiday rentals

1. stayAPT Suites Pensacola-UWF/West Florida Hospital Area

stayAPT Suites Pensacola-UWF/West Florida Hospital Area
4.0 star property
Pensacola
9.0 out of 10, Wonderful, (342 reviews)
"Great place to stay, room very clean. Bed was very comfortable. Loved my stay"
United States
Wanda
The price is NZ$188
includes taxes & fees
1 Sept - 2 Sept
stayAPT Suites Pensacola-UWF/West Florida Hospital Area

2. The Kitchen: Cozy Historic Retreat in East Hill Preservation District!

The Kitchen: Cozy Historic Retreat in East Hill Preservation District!
Downtown Pensacola
9.8 out of 10, Exceptional, (19 reviews)
"The property is clean and the air conditioning was very good and the value is very good. Check in and out were easy. "
United States
Derek
The price is NZ$220
includes taxes & fees
13 Aug - 14 Aug
The Kitchen: Cozy Historic Retreat in East Hill Preservation District!

3. Historic Downtown Pensacola Retreat

Historic Downtown Pensacola Retreat
Seville Historic District
9.4 out of 10, Exceptional, (44 reviews)
"Perfect size for a couple in an ideal location for people who enjoy a stroll. "
United States
Scott P.
The price is NZ$372
includes taxes & fees
24 Aug - 25 Aug
Historic Downtown Pensacola Retreat

4. Hide-Away: Downtown Pensacola, North Hill Studio

Hide-Away: Downtown Pensacola, North Hill Studio
Downtown Pensacola
9.2 out of 10, Wonderful, (54 reviews)
"We had a great anniversary stay here! Great location."
United States
The Yarbroughs
The price is NZ$212
includes taxes & fees
13 Aug - 14 Aug
Hide-Away: Downtown Pensacola, North Hill Studio

5. The Kelley House | Suite 1 - 1st Floor

The Kelley House | Suite 1 - 1st Floor
Downtown Pensacola
10.0 out of 10, Exceptional, (29 reviews)
"Location is awesome - if you live to have fun! (Great place to stay!"
United States
Max L.
The price is NZ$584
includes taxes & fees
1 Sept - 2 Sept
The Kelley House | Suite 1 - 1st Floor

6. Sunny Pensacola Studio Near Beach & Downtown

Sunny Pensacola Studio Near Beach & Downtown
South Pensacola
9.8 out of 10, Exceptional, (19 reviews)
"Very clean and the host were very friendly we had an amazing stay thank you. "
United States
Cecilia
The price is NZ$354
includes taxes & fees
14 Aug - 15 Aug
Sunny Pensacola Studio Near Beach & Downtown

7. Groovy Cottage in Downtown Pensacola, Pet Friendly

Groovy Cottage in Downtown Pensacola, Pet Friendly
South Pensacola
10.0 out of 10, Exceptional, (6 reviews)
"Easy to find , quick simple check in , nice hosts ,"
United States
Anonymous traveller
The price is NZ$330
includes taxes & fees
24 Aug - 25 Aug
Groovy Cottage in Downtown Pensacola, Pet Friendly

8. Charming cottage in Pensacola

Charming cottage in Pensacola
Southeast Pensacola
9.8 out of 10, Exceptional, (31 reviews)
"Great spot right off the Bay bridge to get you quickly to Gulf Breeze and Pensacola beach! Also just minutes away from Palafox St. and downtown dining. Highly recommended and one I plan to re-book next year!"
United States
Nate
The price is NZ$282
includes taxes & fees
17 Aug - 18 Aug
Charming cottage in Pensacola

9. Bee Our Guest: EPH, Close to Downtown and Beach!

Bee Our Guest: EPH, Close to Downtown and Beach!
Southeast Pensacola
9.6 out of 10, Exceptional, (46 reviews)
"I was very pleased with my stay at the Bee Our Guest. The property was clean and as described, and the check-in and check-out was simple and smooth. The location was great for me - close to both the airport and downtown - and in a nice neighborhood. I would definitely stay there again."
United States
Eirikur
The price is NZ$274
includes taxes & fees
24 Aug - 25 Aug
Bee Our Guest: EPH, Close to Downtown and Beach!

10. Historic Downtown Loft B

Historic Downtown Loft B
Downtown Pensacola
9.8 out of 10, Exceptional, (8 reviews)
"Great host and location!"
United States
Dominic B.
The price is NZ$372
includes taxes & fees
13 Aug - 14 Aug
Historic Downtown Loft B

11. Gadsden Hideaway: Historic Downtown Luxury in East Hill Preservation District

Gadsden Hideaway: Historic Downtown Luxury in East Hill Preservation District
Downtown Pensacola
10.0 out of 10, Exceptional, (42 reviews)
"This was our first stay in downtown Pensacola (we normally stay on the beach) and it did not disappoint! The Gadsden is perfectly located near downtown and all that it has to offer and having Maria's just steps away is an added bonus! The property was spotless when we arrived and well stocked with all we needed. We will surely be back for another stay!"
United States
Holly K.
The price is NZ$330
includes taxes & fees
24 Aug - 25 Aug
Gadsden Hideaway: Historic Downtown Luxury in East Hill Preservation District

12. Stylish Downtown Home: steps away from all downtown hotspots

Stylish Downtown Home: steps away from all downtown hotspots
Downtown Pensacola
9.8 out of 10, Exceptional, (48 reviews)
"Convenient to a number of great restaurants. Would definitely stay there again."
United States
Cynthia V.
The price is NZ$624
includes taxes & fees
2 Sept - 3 Sept
Stylish Downtown Home: steps away from all downtown hotspots

13. Downtown home + bay views + seafood market

Downtown home + bay views + seafood market
South Pensacola
10.0 out of 10, Exceptional, (75 reviews)
"Really nice house. Location was great for downtown and restaurants. Long drive to the beach but worth it. Traffic during the day can be noisy. Overall a good place to vacation. "
United States
Robert R.
The price is NZ$583
includes taxes & fees
17 Aug - 18 Aug
Downtown home + bay views + seafood market

14. The Wild Flower

The Wild Flower
Southeast Pensacola
8.4 out of 10, Very good, (29 reviews)
"Everything was great, Apartment was Clean, stocked Everything we need, safe neighborhood, close to stores, beach, and interstate. We will deliver rent when we travel back."
United States
Veronica
The price is NZ$281
includes taxes & fees
13 Aug - 14 Aug
The Wild Flower

15. Cute little cottage located 2 blocks from the heart of Downtown Pensacola.

Cute little cottage located 2 blocks from the heart of Downtown Pensacola.
Downtown Pensacola
9.2 out of 10, Wonderful, (16 reviews)
"This property is within walking distance to downtown. "
United States
Dee P.
The price is NZ$459
includes taxes & fees
16 Aug - 17 Aug
Cute little cottage located 2 blocks from the heart of Downtown Pensacola.

16. Charming Guest House at Live Oaks on the Bayou

Charming Guest House at Live Oaks on the Bayou
Southeast Pensacola
9.8 out of 10, Exceptional, (48 reviews)
"Enjoyed my stay "
United States
Candace B.
The price is NZ$383
includes taxes & fees
13 Aug - 14 Aug
Charming Guest House at Live Oaks on the Bayou

17. Nurse-ready Rental 2 Mi to UWF Campus & Hospital!

Nurse-ready Rental 2 Mi to UWF Campus & Hospital!
3.0 star property
Pensacola
The price is NZ$568
includes taxes & fees
18 Aug - 19 Aug
Nurse-ready Rental 2 Mi to UWF Campus & Hospital!

18. Renovated 1970’s retro camper on Bayou Grande in Pensacola with walking trail.

Renovated 1970’s retro camper on Bayou Grande in Pensacola with walking trail.
Navy Point
9.6 out of 10, Exceptional, (25 reviews)
"Very cool place. Well decorated. Great location. Very sturdy."
United States
Matt
The price is NZ$351
includes taxes & fees
13 Aug - 14 Aug
Renovated 1970’s retro camper on Bayou Grande in Pensacola with walking trail.

19. The Jesse: Cottage in Historic Downtown Pensacola

The Jesse: Cottage in Historic Downtown Pensacola
Seville Historic District
9.2 out of 10, Wonderful, (36 reviews)
"Great stay and I plan to be back. Love the place, I could live there."
United States
Edmund D.
The price is NZ$361
includes taxes & fees
13 Aug - 14 Aug
The Jesse: Cottage in Historic Downtown Pensacola

20. Walk to downtown + seafood market. *Bay views*

Walk to downtown + seafood market. *Bay views*
Downtown Pensacola
10.0 out of 10, Exceptional, (38 reviews)
"Had a very pleasant stay. Loved the proximity to downtown. "
United States
Lisa G.
Walk to downtown + seafood market. *Bay views*
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.
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Top Pensacola Hotel Reviews

Find out more about Pensacola

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pensacola holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pensacola. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pensacola. Seeing all the best attractions is bound to make you fall in love with Pensacola. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pensacola short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Pensacola?

Yes, there are holiday rentals in Pensacola close to DeLuna Lanes Bowling Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Pensacola like the popular beaches and great live music this destination is known for. The fascinating museums and entertainment choices are some other things you might like to check out during your trip.

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

Gulf side, Molokai B5-steps to the beach!: This highly rated holiday home rental in Pensacola is located on the beach, and has a balcony, a selection of games and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind. Other favourite homes for rent in Pensacola are "High Tides" | Private Beachfront Home | Upgraded | My Beach Getaways and Perdido House - Your Home Away with Private Pool and Dock.

How many holiday rentals are there in Pensacola?

Choose from 214 Expedia holiday rentals in Pensacola for a memorable holiday.

What’s there to see and do in Pensacola?

Enjoy the outdoors at Johnson Beach and Perdido Key Beach, or simply take in cultural attractions like Saenger Theatre and Historic Pensacola Village. Other places in town to visit include Pensacola Naval Air Station and Pensacola Bay Center.

What’s a holiday rental in Pensacola like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pensacola. Holiday rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.