South Pensacola holiday rentals
We found 302 holiday rentals — enter your dates for availability
Discover a selection of 128 homes, 12 apartments and other holiday rentals in South Pensacola that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. Whatever you're looking for, you'll find a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - South Pensacola
Showing deals for:1 Aug - 8 Aug
Image gallery for Coastal Getaway near Pensacola beach, Downtown & NAS + walk to bayou & marinas
1010 out of 10 rating
Exceptional
(13 reviews)
Coastal Getaway near Pensacola beach, Downtown & NAS + walk to bayou & marinas
Pensacola, FL
8% off
Price is S$2,543
S$2,543
S$363 per night
includes taxes & fees
Image gallery for Amazing Loft in Historic Waterworks Building, near Downtown Pensacola
8.88.8 out of 10 rating
Excellent
(13 reviews)
Amazing Loft in Historic Waterworks Building, near Downtown Pensacola
Pensacola, FL
8% off
Price is S$3,168
S$3,168
S$453 per night
includes taxes & fees
Image gallery for Historic Loft near Downtown Pensacola
9.29.2 out of 10 rating
Wonderful
(14 reviews)
Historic Loft near Downtown Pensacola
Pensacola, FL
7% off
Price is S$2,656
S$2,656
S$379 per night
includes taxes & fees
Image gallery for New home close to NAS and Corey Station
9.69.6 out of 10 rating
Exceptional
(7 reviews)
New home close to NAS and Corey Station
Pensacola, FL
7% off
Price is S$1,624
S$1,624
S$232 per night
includes taxes & fees
Image gallery for Spacious & Bright DWTN 3BR/2B, By Beach, W/ Kayaks
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Spacious & Bright DWTN 3BR/2B, By Beach, W/ Kayaks
Pensacola, FL
7% off
Price is S$2,279
S$2,279
S$326 per night
includes taxes & fees
Image gallery for NEW-The Bayou Bungalow in Downtown Pensacola. Come join us on the Bayou!
1010 out of 10 rating
Exceptional
(5 reviews)
NEW-The Bayou Bungalow in Downtown Pensacola. Come join us on the Bayou!
Pensacola, FL
7% off
Price is S$1,025
S$1,025
S$146 per night
includes taxes & fees
Image gallery for Little Blue Osprey - Heart of downtown Pensacola
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Little Blue Osprey - Heart of downtown Pensacola
Pensacola, FL
7% off
Price is S$1,731
S$1,731
S$247 per night
includes taxes & fees
Image gallery for Summer Fun Awaits! Cozy Downtown Cottage!
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Summer Fun Awaits! Cozy Downtown Cottage!
Pensacola, FL
7% off
Price is S$1,779
S$1,779
S$254 per night
includes taxes & fees
Image gallery for Olivers Oasis
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Olivers Oasis
Pensacola, FL
8% off
Price is S$3,025
S$3,025
S$432 per night
includes taxes & fees
Image gallery for Huge Historical Victorian Mansion in Downtown Pensacola
1010 out of 10 rating
Exceptional
(51 reviews)
Huge Historical Victorian Mansion in Downtown Pensacola
Pensacola, FL
12% off
Price is S$5,952
S$5,952
S$850 per night
includes taxes & fees
Image gallery for Beautiful Remodel Close to Bases
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Beautiful Remodel Close to Bases
Pensacola, FL
7% off
Price is S$1,775
S$1,775
S$254 per night
includes taxes & fees
Image gallery for Awesome Historical Cottage Near Bay Center & Downtown Pensacola 15 min to Beach!
9.69.6 out of 10 rating
Exceptional
(29 reviews)
Awesome Historical Cottage Near Bay Center & Downtown Pensacola 15 min to Beach!
Pensacola, FL
8% off
Price is S$2,205
S$2,205
S$315 per night
includes taxes & fees
Image gallery for Cute, Peaceful Home, Centrally Located in Pensacola
1010 out of 10 rating
Exceptional
(57 reviews)
Cute, Peaceful Home, Centrally Located in Pensacola
Pensacola, FL
11% off
Price is S$1,597
S$1,597
S$228 per night
includes taxes & fees
Image gallery for Cozy vintage airstream downtown Pensacola, pet friendly
8.08.0 out of 10 rating
Very good
(12 reviews)
Cozy vintage airstream downtown Pensacola, pet friendly
Pensacola, FL
8% off
Price is S$1,008
S$1,008
S$144 per night
includes taxes & fees
Image gallery for Charming 1 bedroom cottage with free parking
8.88.8 out of 10 rating
Excellent
(10 reviews)
Charming 1 bedroom cottage with free parking
Pensacola, FL
7% off
Price is S$1,050
S$1,050
S$150 per night
includes taxes & fees
Image gallery for The Pensacola Retreat- Spacious, Pet-friendly home
1010 out of 10 rating
Exceptional
(5 reviews)
The Pensacola Retreat- Spacious, Pet-friendly home
Pensacola, FL
7% off
Price is S$2,262
S$2,262
S$323 per night
includes taxes & fees
Image gallery for The Bayou Front Home
8.48.4 out of 10 rating
Very good
(19 reviews)
The Bayou Front Home
Pensacola, FL
7% off
Price is S$2,024
S$2,024
S$289 per night
includes taxes & fees
Image gallery for Palm House in Pensacola
1010 out of 10 rating
Exceptional
(7 reviews)
Palm House in Pensacola
Pensacola, FL
7% off
Price is S$1,559
S$1,559
S$223 per night
includes taxes & fees
Image gallery for **Coastal Luxury & Comfort** Best location
9.49.4 out of 10 rating
Exceptional
(45 reviews)
**Coastal Luxury & Comfort** Best location
Pensacola, FL
11% off
Price is S$2,557
S$2,557
S$365 per night
includes taxes & fees
Image gallery for Pensacola Breeze/ Downtown
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Pensacola Breeze/ Downtown
Pensacola, FL
7% off
Price is S$2,352
S$2,352
S$336 per night
includes taxes & fees
Image gallery for Spacious downtown, modern cottage perfect for family, pups & catching the Blues!
1010 out of 10 rating
Exceptional
(51 reviews)
Spacious downtown, modern cottage perfect for family, pups & catching the Blues!
Pensacola, FL
7% off
Price is S$1,949
S$1,949
S$278 per night
includes taxes & fees
Image gallery for Historic Pensacola, a new warehouse inspired home.
1010 out of 10 rating
Exceptional
(18 reviews)
Historic Pensacola, a new warehouse inspired home.
Pensacola, FL
8% off
Price is S$3,898
S$3,898
S$557 per night
includes taxes & fees
Image gallery for Relaxing Historic Suite Downtown | 12 min to Beach
1010 out of 10 rating
Exceptional
(18 reviews)
Relaxing Historic Suite Downtown | 12 min to Beach
Pensacola, Florida
8% off
Price is S$2,297
S$2,297
S$328 per night
includes taxes & fees
Image gallery for Java the Hut: Cozy Retreat in Downtown Pensacola
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Java the Hut: Cozy Retreat in Downtown Pensacola
Pensacola, FL
7% off
Price is S$1,760
S$1,760
S$251 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - South Pensacola
Cozy Coastal Retreat - 3BR Townhome in Pensacola - Near Beaches & Downtown
Sleeps 8 · 3 bedrooms · 1+ bathroom
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Stylish Modern Retreat in Downtown w/ Pool, 3 Bedroom, 2.5 bath, free parking
Sleeps 7 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
NEW-The Bayou Bungalow in Downtown Pensacola. Come join us on the Bayou!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
1 Mi to Dtwn: Home w/ Furnished Patio in Pensacola
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Bright & open/walk to downtown!
Sleeps 6 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Luna Bungalow - Downtown Pensacola
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
5 reviews(5 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in South Pensacola?
The most desirable types of holiday rentals in South Pensacola are houses. Prefer something different? Vrbo has many options to match our guests’ unique requirements, so you’ll see holiday properties in all shapes and sizes, and for all budgets. The ideal home away from home is waiting for you — discover yours today.
How much does it cost to rent a holiday rental in South Pensacola?
A number of things can determine how much you pay for a holiday rental in South Pensacola, such as the time of year, property type and length of stay. Still, all our holiday homes have one thing in common — unbeatable value. Simply add your travel dates to find your ideal match.
How much does it cost to rent a beach house in South Pensacola?
When you travel and the style and size of the property will determine the cost of your beachside holiday rental. Put in your South Pensacola travel dates to see your options on Vrbo. Did someone just say “hot tub”? Use our filters to pick the amenities and features you want in your rental.
Are there pet-friendly holiday rentals in South Pensacola?
Yes. You’ll have your pick of 128 holiday rentals that allow pets in South Pensacola. Lots of our pet-friendly holiday rentals even have space outdoors for your four-legged pal to run around in, dog beds, complimentary treats and proximity to parks. Apply the “Pets allowed” filter to find your place on Vrbo.
Can I rent a house with a pool in South Pensacola?
Pack your swimwear and inflatable swan, because there are 13 houses with a private pool in South Pensacola. Book one of these popular holiday rentals and every day can be a pool day. Simply enter your dates into Vrbo, then use the “pool” filter to find a place to make a splash!
What are popular rental amenities in South Pensacola?
A chef, an electric car charging station and a barbecue grill rank as the most popular rental amenities in South Pensacola. Whether you’re taking to the road as a party of one, with your spouse or a bunch of friends, Vrbo will help you find a holiday home that suits your style with all the features you need.
Are there large group holiday rentals in South Pensacola?
With two holiday rentals that can sleep 10 or more people in South Pensacola, you won’t have to cross anyone off the invite list. From extended family holidays to special events like birthday parties and weddings, Vrbo will help you find a large group rental to match the occasion.
Are there holiday rentals in South Pensacola that welcome kids?
South Pensacola has 126 family-friendly holiday rentals to pick from. And securing a stay that welcomes kids is simple with Vrbo’s “Properties good for families” filter. Besides having the whole place to yourselves, you’ll enjoy access to conveniences and perks such as bunk beds, kitchens and private pools.
What are the top attractions for families in South Pensacola?
Keep the kids amused at these top family-friendly attractions in South Pensacola:
- Perdido Key Beach
- Johnson Beach
- Splash City Adventures
Are there one-bedroom holiday rentals in South Pensacola?
There are 40 one-bedroom properties in South Pensacola to choose from. A one-bedroom holiday property is a great option if it’s only two of you or if you’re holidaying alone. Throw in more space, convenience and privacy compared to a standard hotel, and you’ve got the makings of a memorable trip.
Can I find two-bedroom holiday rentals in South Pensacola?
South Pensacola has 23 two-bedroom properties to choose from. Book a holiday home with all the comfort and privacy you want at a price that’s hard to resist on Vrbo.
Are there holiday rentals with WiFi in South Pensacola?
South Pensacola has 69 holiday rentals with WiFi, so you’ll be able to stay connected during your trip. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to catching up on social media, these Vrbo homes make it easy to go online.
How can I find holiday rentals with air conditioning in South Pensacola?
You’ll find 124 Vrbo holiday rentals with air conditioning in South Pensacola offering that gentle, cool breeze and extra element of comfort. Enter your chosen travel dates and then take advantage of our filters to search for stays with air conditioning.
How old do you have to be to rent a holiday rental in South Pensacola?
The minimum age requirements can differ across properties on Vrbo, so look at the rules of the holiday home in South Pensacola you want. But in general, it’s 16, 18 or 21.
How long can I rent a holiday rental in South Pensacola for?
It’s really down to the South Pensacola property. To see a list of options offering extended stays, simply type your dates and number of people into Vrbo. Enjoy having the property to yourself, along with home comforts such as a fully-equipped kitchen and a backyard where the kids can run around and play. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.