Photo by Cody Trimm

Southeast Pensacola holiday rentals

We found 321 holiday rentals — enter your dates for availability
Discover a selection of 82 homes, 20 apartments and other holiday rentals in Southeast Pensacola that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for spending time at your holiday home, which might include a garden and hot tub. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Southeast Pensacola

Showing deals for:25 Dec - 1 Jan

Room
Property grounds
Living area
Interior
Exceptional
(30 reviews)

Beautiful French Creole Historical studio in downtown Pensacola.. one of a kind!

Pensacola

8% off
S$1,534
for 7 nights, 1 cottage
S$219 per night
includes taxes & fees
Beautiful French Creole Historical studio in downtown Pensacola.. one of a kind!
Interior
Private kitchen
Living area
Dining
Exceptional
(52 reviews)

Java the Hut: Cozy Retreat in Downtown Pensacola

Pensacola

7% off
S$2,014
for 7 nights, 1 cottage
S$288 per night
includes taxes & fees
Java the Hut: Cozy Retreat in Downtown Pensacola
Master Bath / Master Bedroom
Private kitchen
Family Room/Kitchen
Living area
Exceptional
(35 reviews)

Beautiful Victorian-style home - 15 min from beach

Pensacola

8% off
S$6,409
for 7 nights, 1 home
S$916 per night
includes taxes & fees
Beautiful Victorian-style home - 15 min from beach
Living area
Interior
Room
Exterior
Exceptional
(47 reviews)

Pet Friendly 2/1.5 in the Heart of Historic Pensacola

Pensacola

8% off
S$2,315
for 7 nights, 1 home
S$331 per night
includes taxes & fees
Pet Friendly 2/1.5 in the Heart of Historic Pensacola
Room
Private kitchen
Interior
Interior
Excellent
(7 reviews)

Cozy tiny home in downtown Pensacola

Pensacola

8% off
S$1,696
for 7 nights, 1 apartment
S$242 per night
includes taxes & fees
Cozy tiny home in downtown Pensacola
Interior
Dining
Exterior
Property grounds
Exceptional
(174 reviews)

Historic Downtown Bayfront New Home - Mins to Beach, Walk Downtown, Pool, Bikes

Pensacola

8% off
S$2,961
for 7 nights, 1 home
S$423 per night
includes taxes & fees
Historic Downtown Bayfront New Home - Mins to Beach, Walk Downtown, Pool, Bikes
Dining area
Modern Kitchen
Front Porch
Private kitchen
Exceptional
(53 reviews)

One of a Kind Cottage Close to Downtown Pensacola & Bay Center ~15 min to Beach!

Pensacola

7% off
S$1,520
for 7 nights, 1 home
S$217 per night
includes taxes & fees
One of a Kind Cottage Close to Downtown Pensacola & Bay Center ~15 min to Beach!
Enjoy this great kitchen.
Open living room.
You will have the whole house to yourself.
Enjoy the private outdoor space.
Exceptional
(27 reviews)

Historic Pensacola, a new warehouse inspired home.

Pensacola

8% off
S$2,773
for 7 nights, 1 home
S$396 per night
includes taxes & fees
Historic Pensacola, a new warehouse inspired home.
Room
Private kitchen
Private kitchen
Bathroom
Wonderful
(16 reviews)

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

Pensacola

8% off
S$1,696
for 7 nights, 1 cottage
S$242 per night
includes taxes & fees
Cute little cottage located 2 blocks from the heart of Downtown Pensacola.
Dining
Unit offers plenty of space to gather with your group in a meaningful way.
View Across Great Room
View of from kitchen looking toward light-filled living space
Wonderful
(14 reviews)

Amazing Loft in Historic Waterworks Building, near Downtown Pensacola

Pensacola

8% off
S$3,195
for 7 nights, 1 apartment
S$456 per night
includes taxes & fees
Amazing Loft in Historic Waterworks Building, near Downtown Pensacola
Consider sleeping in a little longer this morning!
Wake up to a fresh pot at our coffee bar.
Get comfy here for a movie.
Enjoy our cozy kitchen fully stocked for your enjoyment.
Very good
(6 reviews)

Your dog gets a fenced yard. You get a quiet East Hill home base minutes from downtown, the beach, and everything you came to Pensacola to enjoy.

Pensacola

14% off
S$1,435
for 7 nights, 1 apartment
S$205 per night
includes taxes & fees
Your dog gets a fenced yard. You get a quiet East Hill home base minutes from downtown, the beach, and everything you came to Pensacola to enjoy.
Room
Private kitchen
Outdoor dining
Exterior
Exceptional
(96 reviews)

Beautiful 3bdr 2bath , 5 min to Pensacola beach / downtown, close to

Pensacola

7% off
S$1,926
for 7 nights, 1 home
S$275 per night
includes taxes & fees
Beautiful 3bdr 2bath , 5 min to Pensacola beach / downtown, close to
Dining for two
Our self-check-in process is a breeze
Experience clean!
Don't forget to brew a cup at our coffee bar!
Excellent
(8 reviews)

The stay guests remember because everything—from the location to the fenced yard—simply makes the trip easier.

Pensacola

14% off
S$1,572
for 7 nights, 1 apartment
S$225 per night
includes taxes & fees
The stay guests remember because everything—from the location to the fenced yard—simply makes the trip easier.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Southeast Pensacola?
According to our data, houses are the most sought-after type of holiday rental in Southeast Pensacola. But having said that, everyone's idea of an epic stay isn't going to be the same. Vrbo has holiday homes with every size, shape and budget in mind, so you're sure to discover the perfect match.
How much does it cost to rent a holiday rental in Southeast Pensacola?
The average price for a holiday rental in Southeast Pensacola can vary based on factors such as season, property type and length of stay. Whether you're looking for a sprawling villa with a pool or a quaint cabin just enough for two, just enter your travel dates to view some great-value stays.
How much does it cost to rent a beach house in Southeast Pensacola?
Prices for beach houses in Southeast Pensacola can differ depending on the size and type of the property and time of year you're travelling. All you need to do is enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use our filters to tailor your search by ratings, amenities, nearby activities and more.
Are there pet-friendly holiday rentals in Southeast Pensacola?
Pack a bone and a squeezy toy for your puppy dog because Southeast Pensacola has 123 properties that open their doors to pets. Let your furriest pal get in on the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and dates, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Southeast Pensacola?
Add an extra layer of fun to your getaway by booking your family into one of the 13 houses with a private pool in Southeast Pensacola. Use our search filter to find properties with pools on Vrbo, then spend your days splashing around in a swimming pool that's for your use only.
What are popular rental amenities in Southeast Pensacola?
When it comes to rental amenities that guests are looking for in Southeast Pensacola, a nearby waterfront, nearby museums and a nearby river rank the highest. With Vrbo holiday rentals, you'll enjoy options to fit your style and taste, whether you're going on a trip with your partner, family members or even pets.
Are there large group holiday rentals in Southeast Pensacola?
Southeast Pensacola has four holiday properties that can cater to 10 or more people. These properties come with all the space you need to enjoy good times with your nearest and dearest.
Are there holiday rentals in Southeast Pensacola that welcome kids?
With 122 family-friendly holiday properties to select from in Southeast Pensacola, there's never been a better time to introduce the kids to the magic of travel. Simply check our "Properties good for families" filter box to look for stays packed with amenities perfect for families on the move, such as living rooms, swimming pools, hot tubs and entertainment areas.
What are the top attractions for families in Southeast Pensacola?
Keeping the kiddos entertained during your stay in Southeast Pensacola is simple with these fabulous family-friendly attractions:
  • Splash City Adventures
  • Pensacola Childrens Museum
  • Fast Eddies Fun Centre
Are there one-bedroom holiday rentals in Southeast Pensacola?
Yes, Southeast Pensacola has 34 one-bedroom rentals available. Typically situated in well-regarded areas due to their compact size, a one-bedroom rental is great if you're travelling with your partner or a pal. And with home comforts such as wireless internet and more privacy than a standard hotel, you'll be able to chill out while enjoying this fantastic destination.
Can I find two-bedroom holiday rentals in Southeast Pensacola?
You can pick from 38 two-bedroom holiday rentals in Southeast Pensacola. Give your little ones the second room or maybe fill it with a couple of your besties. There's a comfy spot for whoever's fortunate enough to be coming along for the ride.
Are there holiday rentals with WiFi in Southeast Pensacola?
Whether you want to stay in touch with world events, make a video call or surf social networks, there are 64 holiday homes with WiFi in Southeast Pensacola. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Southeast Pensacola?
Pick your dates and then use our filter tool to see holiday rentals with ac in Southeast Pensacola on Vrbo. With 117 air-conditioned properties to choose from here, you can enjoy a comfortable and cool stay.
How old do you have to be to rent a holiday rental in Southeast Pensacola?
We advise checking with the Southeast Pensacola holiday rental you're looking at on Vrbo as the minimum age varies. However, normally it's 16, 18 or 21.
How long can I rent a holiday rental in Southeast Pensacola for?
The length of time you can rent a holiday rental in Southeast Pensacola depends on the property. Simply enter your desired travel dates to look at a list of options offering extended stays. With a range of features such as air conditioning and laundries, as well as some offering weekly or monthly discounts, you're sure to discover the perfect place to call your home away from home in Southeast Pensacola.

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