South Pensacola holiday homes
We found 302 holiday rentals — enter your dates for availability
Discover a selection of 123 homes, 14 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:14 Nov - 21 Nov
Image gallery for Java the Hut: Cozy Retreat in Downtown Pensacola
9.29.2 out of 10 rating
Wonderful
(21 reviews)
Java the Hut: Cozy Retreat in Downtown Pensacola
Pensacola, FL
5% off
Price is NZ$1,698
NZ$1,698
NZ$243 nightly
Includes taxes & fees
Image gallery for Spacious 4-bedroom house in enjoyable Pensacola with AC, WiFi
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Spacious 4-bedroom house in enjoyable Pensacola with AC, WiFi
Pensacola, FL
7% off
Price is NZ$2,671
NZ$2,671
NZ$382 nightly
Includes taxes & fees
Image gallery for Renovated Bungalow near Downtown Pensacola with King Bed!
1010 out of 10 rating
Exceptional
(25 reviews)
Renovated Bungalow near Downtown Pensacola with King Bed!
Pensacola, FL
11% off
Price is NZ$1,876
NZ$1,876
NZ$268 nightly
Includes taxes & fees
Image gallery for Palm House in Pensacola
1010 out of 10 rating
Exceptional
(9 reviews)
Palm House in Pensacola
Pensacola, FL
7% off
Price is NZ$1,940
NZ$1,940
NZ$277 nightly
Includes taxes & fees
Image gallery for Little Gem |Reduced Rates |Extended Stays Accepted |5 Min to NAS & Downtown Pensacola |Fenced Yard
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Little Gem |Reduced Rates |Extended Stays Accepted |5 Min to NAS & Downtown Pensacola |Fenced Yard
Pensacola, FL
20% off
Price is NZ$1,914
NZ$1,914
NZ$273 nightly
Includes taxes & fees
Image gallery for Downtown-Garden District-Boho Steampunk Farmhouse. Comforts of home . New HVAC.
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Downtown-Garden District-Boho Steampunk Farmhouse. Comforts of home . New HVAC.
Pensacola, FL
7% off
Price is NZ$1,589
NZ$1,589
NZ$227 nightly
Includes taxes & fees
Image gallery for Pet-Friendly Pensacola Home w/ Patio & Yard!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Pet-Friendly Pensacola Home w/ Patio & Yard!
Pensacola, FL
7% off
Price is NZ$2,663
NZ$2,663
NZ$380 nightly
Includes taxes & fees
Image gallery for Charming 1 bedroom cottage with free parking
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Charming 1 bedroom cottage with free parking
Pensacola, FL
7% off
Price is NZ$1,111
NZ$1,111
NZ$159 nightly
Includes taxes & fees
Image gallery for **Coastal Luxury & Comfort** Best location
9.49.4 out of 10 rating
Exceptional
(47 reviews)
**Coastal Luxury & Comfort** Best location
Pensacola, FL
11% off
Price is NZ$3,209
NZ$3,209
NZ$458 nightly
Includes taxes & fees
Image gallery for ~Gem on G Street~Downtown Pensacola~Summer Getaway Time!
1010 out of 10 rating
Exceptional
(14 reviews)
~Gem on G Street~Downtown Pensacola~Summer Getaway Time!
Pensacola, FL
7% off
Price is NZ$2,137
NZ$2,137
NZ$305 nightly
Includes taxes & fees
Image gallery for Coastal Getaway near Pensacola beach, Downtown & NAS + walk to bayou & marinas
1010 out of 10 rating
Exceptional
(16 reviews)
Coastal Getaway near Pensacola beach, Downtown & NAS + walk to bayou & marinas
Pensacola, FL
8% off
Price is NZ$2,757
NZ$2,757
NZ$394 nightly
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 NZ$2,922
NZ$2,922
NZ$417 nightly
Includes taxes & fees
Image gallery for Olivers Oasis
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Olivers Oasis
Pensacola, FL
7% off
Price is NZ$2,386
NZ$2,386
NZ$341 nightly
Includes taxes & fees
Image gallery for Cute little cottage located 2 blocks from the heart of Downtown Pensacola.
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Cute little cottage located 2 blocks from the heart of Downtown Pensacola.
Pensacola, FL
7% off
Price is NZ$1,259
NZ$1,259
NZ$180 nightly
Includes taxes & fees
Image gallery for Awesome Tiny Home with Stock Tank Pool Near Downtown Pensacola
9.49.4 out of 10 rating
Exceptional
(33 reviews)
Awesome Tiny Home with Stock Tank Pool Near Downtown Pensacola
Pensacola, FL
8% off
Price is NZ$1,786
NZ$1,786
NZ$255 nightly
Includes taxes & fees
Image gallery for Private Suite in Historic Home
9.89.8 out of 10 rating
Exceptional
(190 reviews)
Private Suite in Historic Home
Pensacola, FL
12% off
Price is NZ$1,262
NZ$1,262
NZ$180 nightly
Includes taxes & fees
Image gallery for Close to Beach & Downtown ~ Fenced Yard
9.49.4 out of 10 rating
Exceptional
(12 reviews)
Close to Beach & Downtown ~ Fenced Yard
Pensacola, FL
6% off
Price is NZ$2,165
NZ$2,165
NZ$309 nightly
Includes taxes & fees
Image gallery for Cozy tiny home in downtown Pensacola
8.88.8 out of 10 rating
Excellent
(5 reviews)
Cozy tiny home in downtown Pensacola
Pensacola, FL
7% off
Price is NZ$1,259
NZ$1,259
NZ$180 nightly
Includes taxes & fees
Image gallery for Walk to Downtown Fun, Short Drive to Beach & NAS
1010 out of 10 rating
Exceptional
(26 reviews)
Walk to Downtown Fun, Short Drive to Beach & NAS
Pensacola, FL
7% off
Price is NZ$2,228
NZ$2,228
NZ$318 nightly
Includes taxes & fees
Image gallery for Pensacola Breeze/ Downtown
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Pensacola Breeze/ Downtown
Pensacola, FL
7% off
Price is NZ$3,016
NZ$3,016
NZ$431 nightly
Includes taxes & fees
Image gallery for Cute, Peaceful Home, Centrally Located in West Pensacola
1010 out of 10 rating
Exceptional
(60 reviews)
Cute, Peaceful Home, Centrally Located in West Pensacola
Pensacola, FL
11% off
Price is NZ$2,044
NZ$2,044
NZ$292 nightly
Includes taxes & fees
Image gallery for NEW-The Bayou Bungalow in Downtown Pensacola. Come join us on the Bayou!
9.69.6 out of 10 rating
Exceptional
(13 reviews)
NEW-The Bayou Bungalow in Downtown Pensacola. Come join us on the Bayou!
Pensacola, FL
7% off
Price is NZ$1,325
NZ$1,325
NZ$189 nightly
Includes taxes & fees
Image gallery for Beautiful Remodel Close to Bases
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Beautiful Remodel Close to Bases
Pensacola, FL
7% off
Price is NZ$2,081
NZ$2,081
NZ$297 nightly
Includes taxes & fees
Image gallery for Bright & Cozy Historic Getaway | Suite 2 - 1st floor
1010 out of 10 rating
Exceptional
(15 reviews)
Bright & Cozy Historic Getaway | Suite 2 - 1st floor
Pensacola, FL
8% off
Price is NZ$2,802
NZ$2,802
NZ$400 nightly
Includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - South Pensacola
Baylen House/Pensacola Downtown Historic District~walk downtown
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Seabird Shack: Dog Friendly, Downtown Pensacola!
Sleeps 6 · 3 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
77 reviews(77 reviews)
1 Mi to Dtwn: Home w/ Furnished Patio in Pensacola
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
10 reviews(10 reviews)
1 Mi to Dtwn: Pet-Friendly Pensacola Getaway!
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Ms. Jackson Bungalow
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Luna Bungalow - Downtown Pensacola
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
9 reviews(9 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