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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, (388 reviews)
"Definitely recommend staying here .I will be back"
United States
Giselle
The price is NZ$195
includes taxes & fees
27 Sept - 28 Sept
stayAPT Suites Pensacola-UWF/West Florida Hospital Area

2. The Kitchen | Historic East Hill Studio Near Downtown Pensacola

The Kitchen | Historic East Hill Studio Near Downtown Pensacola
Downtown Pensacola
10.0 out of 10, Exceptional, (21 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$235
includes taxes & fees
28 Sept - 29 Sept
The Kitchen | Historic East Hill Studio Near Downtown Pensacola

3. Hide-Away | Historic North Hill Studio Near Downtown Pensacola

Hide-Away | Historic North Hill Studio Near Downtown Pensacola
Downtown Pensacola
9.2 out of 10, Wonderful, (57 reviews)
"We had a great anniversary stay here! Great location."
United States
The Yarbroughs
The price is NZ$227
includes taxes & fees
4 Oct - 5 Oct
Hide-Away | Historic North Hill Studio Near Downtown Pensacola

4. Quiet. Private. Perfect. Courtyard Suite for Two

Quiet. Private. Perfect. Courtyard Suite for Two
Downtown Pensacola
9.6 out of 10, Exceptional, (29 reviews)
"Brother Fox and Sister Hen almost directly acrossed the street. Downtown within walking distance. Plenty of restaurants and bars. The guest suite is perfect for two."
United States
Greg D.
The price is NZ$609
includes taxes & fees
27 Sept - 28 Sept
Quiet. Private. Perfect. Courtyard Suite for Two

5. The Kelley House Fall Getaway | Suite 2

The Kelley House Fall Getaway | Suite 2
Downtown Pensacola
10.0 out of 10, Exceptional, (33 reviews)
"It was wonderfully decorated & stay. Highly recommend. "
United States
Bryan C.
The price is NZ$383
includes taxes & fees
27 Sept - 28 Sept
The Kelley House Fall Getaway | Suite 2

6. Historic Downtown Studio

Historic Downtown Studio
Downtown Pensacola
10.0 out of 10, Exceptional, (18 reviews)
"Always our favorite place to stay in Pensacola! Will definitely be back!!!"
United States
Carmen R.
The price is NZ$343
includes taxes & fees
27 Sept - 28 Sept
Historic Downtown Studio

7. Historic Downtown Pensacola Retreat

Historic Downtown Pensacola Retreat
Seville Historic District
9.4 out of 10, Exceptional, (45 reviews)
"Good location to downtown"
United States
Brooke M.
The price is NZ$385
includes taxes & fees
27 Oct - 28 Oct
Historic Downtown Pensacola Retreat

8. East side cottage✨10 min to Downtown✨15 min to NAS✨20 min to Pensacola Beach

East side cottage✨10 min to Downtown✨15 min to NAS✨20 min to Pensacola Beach
Southeast Pensacola
9.4 out of 10, Exceptional, (18 reviews)
"Great place to stay. Plenty of restaurants nezrby and things to do."
United States
Sandra B.
The price is NZ$330
includes taxes & fees
6 Oct - 7 Oct
East side cottage✨10 min to Downtown✨15 min to NAS✨20 min to Pensacola Beach

9. The Gadsden Hideaway | Historic East Hill Rental Near Downtown Pensacola

The Gadsden Hideaway | Historic East Hill Rental Near Downtown Pensacola
Downtown Pensacola
10.0 out of 10, Exceptional, (46 reviews)
"Great place in a great neighborhood! We enjoyed our stay here and would stay again."
United States
marshall n.
The price is NZ$341
includes taxes & fees
27 Oct - 28 Oct
The Gadsden Hideaway | Historic East Hill Rental Near Downtown Pensacola

10. Cypress Cottage, Zen Garden, Hot Tub, Dog Welcome

Cypress Cottage, Zen Garden, Hot Tub, Dog Welcome
Southeast Pensacola
10.0 out of 10, Exceptional, (73 reviews)
"The cottage was wonderful and exactly the relaxation I needed. It was great being so close to all the things I wanted to do!"
United States
Garrett R.
The price is NZ$642
includes taxes & fees
28 Sept - 29 Sept
Cypress Cottage, Zen Garden, Hot Tub, Dog Welcome

11. Walk to D-Town Restaurants Seafood Festival & Havana Nights Close to Beach & NAS

Walk to D-Town Restaurants Seafood Festival & Havana Nights Close to Beach & NAS
Downtown Pensacola
9.2 out of 10, Wonderful, (16 reviews)
"great place to stay!"
United States
Lydia H.
The price is NZ$379
includes taxes & fees
27 Sept - 28 Sept
Walk to D-Town Restaurants Seafood Festival & Havana Nights Close to Beach & NAS

12. Groovy Downtown Cottage — Free Bikes + Private Yard + Pet Friendly

Groovy Downtown Cottage — Free Bikes + Private Yard + Pet Friendly
South Pensacola
10.0 out of 10, Exceptional, (7 reviews)
"Easy to find , quick simple check in , nice hosts ,"
United States
Anonymous traveller
The price is NZ$327
includes taxes & fees
26 Oct - 27 Oct
Groovy Downtown Cottage — Free Bikes + Private Yard + Pet Friendly

13. Downtown cottage 7 miles to beach. Coastal w/out luxury resort prices

Downtown cottage 7 miles to beach. Coastal w/out luxury resort prices
Southeast Pensacola
9.8 out of 10, Exceptional, (11 reviews)
"This cozy cottage was absolutely outstanding! Perfect distance to all our events in the area. Our hosts were super sweet and there if we needed anything. We enjoyed our stay! "
United States
Badge L.
The price is NZ$345
includes taxes & fees
30 Sept - 1 Oct
Downtown cottage 7 miles to beach. Coastal w/out luxury resort prices

14. Charming cottage in Pensacola

Charming cottage in Pensacola
Southeast Pensacola
9.8 out of 10, Exceptional, (33 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$293
includes taxes & fees
28 Sept - 29 Sept
Charming cottage in Pensacola

15. Bee Our Guest | East Pensacola Heights Rental Near Downtown Pensacola Beach

Bee Our Guest | East Pensacola Heights Rental Near Downtown Pensacola Beach
Southeast Pensacola
9.6 out of 10, Exceptional, (48 reviews)
"Cute little home away from home!"
United States
Diana O.
The price is NZ$282
includes taxes & fees
26 Oct - 27 Oct
Bee Our Guest | East Pensacola Heights Rental Near Downtown Pensacola Beach

16. 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, (51 reviews)
"Convenient to a number of great restaurants. Would definitely stay there again."
United States
Cynthia V.
The price is NZ$563
includes taxes & fees
28 Sept - 29 Sept
Stylish Downtown Home: steps away from all downtown hotspots

17. The Wave is private, cozy, comfortable and super chill!!..

The Wave is private, cozy, comfortable and super chill!!..
Southeast Pensacola
9.8 out of 10, Exceptional, (9 reviews)
"Very comfortable, clean"
United States
Thomas D.
The price is NZ$200
includes taxes & fees
30 Sept - 1 Oct
The Wave is private, cozy, comfortable and super chill!!..

18. The Jesse: Cottage in Historic Downtown Pensacola

The Jesse: Cottage in Historic Downtown Pensacola
Seville Historic District
9.2 out of 10, Wonderful, (39 reviews)
"Great stay and I plan to be back. Love the place, I could live there."
United States
Edmund D.
The price is NZ$385
includes taxes & fees
7 Oct - 8 Oct
The Jesse: Cottage in Historic Downtown Pensacola

19. 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$477
includes taxes & fees
27 Sept - 28 Sept
Cute little cottage located 2 blocks from the heart of Downtown Pensacola.

20. Pensacola FL | King Bed

Pensacola FL | King Bed
Northwest Pensacola
10.0 out of 10, Exceptional, (62 reviews)
"Accommodations are snug, really enjoyed my time there."
United States
Anonymous traveller
The price is NZ$204
includes taxes & fees
27 Sept - 28 Sept
Pensacola FL | King Bed
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 Pensacola Children's Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Pensacola like the popular beaches and acclaimed theatre scene this destination is known for. The great live music and fascinating museums 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?

Beach Bungalow: This highly rated holiday home rental in Pensacola is located on the beach, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of books in this rental home to help you unwind. Other favourite homes for rent in Pensacola are Blue Angel Beach House-2 king suites+Fire pit+air hockey🌴 and The Dory Is A Gulf Front Treasure Your Family Will Love!.

How many holiday rentals are there in Pensacola?

Choose from 224 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.