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Pensacola Holiday Rentals

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Our top choices for Pensacola holiday rentals

1. The Brent Lofts

The Brent Lofts
4.0 star property
Downtown Pensacola
9.8 out of 10, Exceptional, (8 reviews)
"Location"
United States
April
The price is NZ$563
includes taxes & fees
15 Nov - 16 Nov
The Brent Lofts

2. Shore Break Cottage | Stylish Downtown Pensacola Getaway Near NAS

Shore Break Cottage | Stylish Downtown Pensacola Getaway Near NAS
Downtown Pensacola
9.0 out of 10, Wonderful, (64 reviews)
"Location is just perfect close to downtown nice stores and restaurants"
United States
Amalia
The price is NZ$272
includes taxes & fees
16 Nov - 17 Nov
Shore Break Cottage | Stylish Downtown Pensacola Getaway Near NAS

3. 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, (22 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$224
includes taxes & fees
15 Nov - 16 Nov
The Kitchen | Historic East Hill Studio Near Downtown Pensacola

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

stayAPT Suites Pensacola-UWF/West Florida Hospital Area
3.5 star property
Pensacola
9.0 out of 10, Wonderful, (419 reviews)
"Very convenient and comfortable stay in Pensacola."
United States
Blaise
The price is NZ$238
includes taxes & fees
12 Nov - 13 Nov
stayAPT Suites Pensacola-UWF/West Florida Hospital Area

5. Historic Downtown Pensacola Retreat

Historic Downtown Pensacola Retreat
Seville Historic District
9.4 out of 10, Exceptional, (46 reviews)
"Second time here and loved it all over again! Best location to downtown Pensacola for date night!"
United States
Mike L.
The price is NZ$365
includes taxes & fees
13 Nov - 14 Nov
Historic Downtown Pensacola Retreat

6. 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)
"Our stay there was great, would book this again!"
United States
Allison B.
The price is NZ$272
includes taxes & fees
17 Nov - 18 Nov
Bee Our Guest | East Pensacola Heights Rental Near Downtown Pensacola Beach

7. The Kelley House | Cozy Fall Suite 3 w/Balcony

The Kelley House | Cozy Fall Suite 3 w/Balcony
Downtown Pensacola
10.0 out of 10, Exceptional, (18 reviews)
"Excellent location, walking distance to restaurants (Brother Fox was excellent!) and shopping.Beautiful property. Our second time with this host and we will definitely stay here again."
United States
michael r.
The price is NZ$380
includes taxes & fees
30 Nov - 1 Dec
The Kelley House | Cozy Fall Suite 3 w/Balcony

8. 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, (48 reviews)
"Fantastic place, would definitely stay again. Clean and spacious. AC worked Great. Fantastic location. Houe is also supplied nicely with essentials and comforts."
United States
J R.
The price is NZ$330
includes taxes & fees
15 Nov - 16 Nov
The Gadsden Hideaway | Historic East Hill Rental Near Downtown Pensacola

9. 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, (13 reviews)
"Perfect spot close to downtown for cheap Ubers."
United States
Amir
The price is NZ$187
includes taxes & fees
15 Nov - 16 Nov
The Wave is private, cozy, comfortable and super chill!!..

10. Pensacola Paradise - Apartment

Pensacola Paradise - Apartment
South Pensacola
The price is NZ$443
includes taxes & fees
12 Nov - 13 Nov
Pensacola Paradise - Apartment

11. Charming cottage in Pensacola

Charming cottage in Pensacola
Southeast Pensacola
9.8 out of 10, Exceptional, (39 reviews)
"Great little cottage and the owners are great"
United States
George N.
The price is NZ$281
includes taxes & fees
13 Nov - 14 Nov
Charming cottage in Pensacola

12. 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)
"The property was was very clean and very convenient to nearby places. The host was very friendly and checked to make sure we had everything we needed. We enjoyed our stay!!"
United States
Shawna K.
The price is NZ$384
includes taxes & fees
15 Nov - 16 Nov
East side cottage✨10 min to Downtown✨15 min to NAS✨20 min to Pensacola Beach

13. The Jesse: Cottage in Historic Downtown Pensacola

The Jesse: Cottage in Historic Downtown Pensacola
Seville Historic District
9.2 out of 10, Wonderful, (40 reviews)
"This was a wonderfully located cottage. Walking distance to so many great sites, shopping, and restaurants. Would definitely stay here again the next time I come to Pensacola."
United States
Danny S.
The price is NZ$376
includes taxes & fees
17 Nov - 18 Nov
The Jesse: Cottage in Historic Downtown Pensacola

14. Historic Downtown Studio

Historic Downtown Studio
Downtown Pensacola
9.8 out of 10, Exceptional, (25 reviews)
"Always our favorite place to stay in Pensacola! Will definitely be back!!!"
United States
Carmen R.
The price is NZ$371
includes taxes & fees
12 Nov - 13 Nov
Historic Downtown Studio

15. 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)
"Really enjoyed our stay! Just what we were looking for, will be booking again. Loved how close it was to downtown and the beach, made everything really convenient!"
United States
Haley B.
The price is NZ$317
includes taxes & fees
17 Nov - 18 Nov
Groovy Downtown Cottage — Free Bikes + Private Yard + Pet Friendly

16. 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, (12 reviews)
"Cute little cottage, clean and well maintained, easy street parking, well lit at night and quiet. The host was very communicative and nice. We really enjoyed our quick stay and very close to downtown and Fish House restaurant which was amazing!"
United States
Sara N.
The price is NZ$351
includes taxes & fees
9 Dec - 10 Dec
Downtown cottage 7 miles to beach. Coastal w/out luxury resort prices

17. Pensacola FL | 2 Full Bed

Pensacola FL | 2 Full Bed
Northwest Pensacola
10.0 out of 10, Exceptional, (65 reviews)
"Friendly staff and good amenities kept us smiling."
United States
Anonymous traveller
The price is NZ$148
includes taxes & fees
1 Dec - 2 Dec
Pensacola FL | 2 Full Bed

18. Spectacular Beach Front Views! Free Lazy Days Beach Chairs & Umbrella Included!

Spectacular Beach Front Views! Free Lazy Days Beach Chairs & Umbrella Included!
Pensacola Beach
9.6 out of 10, Exceptional, (392 reviews)
"This was our 2nd time staying at this property and it did not disappoint! The view, the view, the view. Comfortable bed and great communication. Would not hesitate to rent for your vacation!"
United States
Debbie D.
Spectacular Beach Front Views! Free Lazy Days Beach Chairs & Umbrella Included!

19. Festival weekend !! Art, Greek, Foofoo. Walk to D-Town!Close to Beaches & NAS!

Festival weekend !! Art, Greek, Foofoo. Walk to D-Town!Close to Beaches & NAS!
Downtown Pensacola
9.2 out of 10, Wonderful, (16 reviews)
"great place to stay!"
United States
Lydia H.
The price is NZ$389
includes taxes & fees
7 Dec - 8 Dec
Festival weekend !! Art, Greek, Foofoo. Walk to D-Town!Close to Beaches & NAS!

20. Charming villa steps from the water in beautiful Pensacola

Charming villa steps from the water in beautiful Pensacola
Southeast Pensacola
10.0 out of 10, Exceptional, (35 reviews)
"Great stay!"
United States
Ivan V.
The price is NZ$273
includes taxes & fees
15 Nov - 16 Nov
Charming villa steps from the water in beautiful Pensacola
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 Fast Eddies Fun 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 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 222 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.