Photo by Cody Trimm

Southeast Pensacola holiday lettings

We found 318 holiday rentals — enter your dates for availability
Discover a selection of 83 homes, 19 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:1 Jan - 8 Jan

Dining
Unit offers plenty of space to gather with your group in a meaningful way.
View of from kitchen looking toward light-filled living space
View Across Great Room
Wonderful
(14 reviews)

Amazing Loft in Historic Waterworks Building, near Downtown Pensacola

Pensacola

7% off
£1,957
for 7 nights, 1 apartment
£280 per night
includes taxes & fees
Amazing Loft in Historic Waterworks Building, near Downtown Pensacola
Living area
Private kitchen
Interior
Living area
Exceptional
(52 reviews)

Java the Hut: Cozy Retreat in Downtown Pensacola

Pensacola

7% off
£1,059
for 7 nights, 1 cottage
£151 per night
includes taxes & fees
Java the Hut: Cozy Retreat in Downtown Pensacola
Room
Property grounds
Living area
Living area
Exceptional
(31 reviews)

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

Pensacola

8% off
£752
for 7 nights, 1 cottage
£107 per night
includes taxes & fees
Beautiful French Creole Historical studio in downtown Pensacola.. one of a kind!
Private kitchen
Modern Kitchen
Dining area
Stock tank pool
Exceptional
(53 reviews)

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

Pensacola

7% off
£916
for 7 nights, 1 home
£131 per night
includes taxes & fees
One of a Kind Cottage Close to Downtown Pensacola & Bay Center ~15 min to Beach!
Master Bath / Master Bedroom
Private kitchen
Living area
Family Room/Kitchen
Exceptional
(35 reviews)

Beautiful Victorian-style home - 15 min from beach

Pensacola

7% off
£3,967
for 7 nights, 1 home
£567 per night
includes taxes & fees
Beautiful Victorian-style home - 15 min from beach
Bathroom
Private kitchen
Room
Private kitchen
Wonderful
(16 reviews)

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

Pensacola

8% off
£1,024
for 7 nights, 1 cottage
£146 per night
includes taxes & fees
Cute little cottage located 2 blocks from the heart of Downtown Pensacola.
Interior
Private kitchen
Room
Interior
Excellent
(7 reviews)

Cozy tiny home in downtown Pensacola

Pensacola

8% off
£1,024
for 7 nights, 1 apartment
£146 per night
includes taxes & fees
Cozy tiny home in downtown Pensacola
Room
Interior
Living area
Exterior
Exceptional
(47 reviews)

Pet Friendly 2/1.5 in the Heart of Historic Pensacola

Pensacola

7% off
£1,313
for 7 nights, 1 home
£188 per night
includes taxes & fees
Pet Friendly 2/1.5 in the Heart of Historic Pensacola
Living area
Room
Private kitchen
Exterior detail
Exceptional
(44 reviews)

Historic Pensacola 2BR townhouse open now for Spring and Summer.Walk everywhere!

Pensacola

8% off
£1,443
for 7 nights, 1 home
£206 per night
includes taxes & fees
Historic Pensacola 2BR townhouse open now for Spring and Summer.Walk everywhere!
Gather the friends around the fire pit!
Our self-check-in process is a breeze
Dining for two
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

13% off
£759
for 7 nights, 1 apartment
£108 per night
includes taxes & fees
The stay guests remember because everything—from the location to the fenced yard—simply makes the trip easier.
Bespoke bar area
Interior
Large dining table seats 8 with additional seating available in the drawing room
Living area
Exceptional
(65 reviews)

Huge Historical Mansion for Groups Downtown Pensacola 1 Block from Palafox St

Pensacola

9% off
£2,590
for 7 nights, 1 home
£370 per night
includes taxes & fees
Huge Historical Mansion for Groups Downtown Pensacola 1 Block from Palafox St
Enjoy our cozy kitchen fully stocked for your enjoyment.
Wake up to a fresh pot at our coffee bar.
Get comfy here for a movie.
Consider sleeping in a little longer this morning!
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
£691
for 7 nights, 1 apartment
£99 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.
  • 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, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Southeast Pensacola?
Prices for holiday rentals in Southeast Pensacola vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Southeast Pensacola to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Southeast Pensacola holiday house rentals?
You can find great discounts on house rentals in Southeast Pensacola on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Southeast Pensacola holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Southeast Pensacola with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Southeast Pensacola?
A long-stay holiday rental in Southeast Pensacola is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Southeast Pensacola for a holiday rental?
The best time to visit Southeast Pensacola for a holiday rental is during the peak season from May to July. This vibrant period draws many visitors eager to enjoy the beautiful beaches, warm weather, and a variety of outdoor activities. July, in particular, is the most popular month, as families flock to the area for sun-soaked holidays filled with beach fun and local festivities.During these summer months, you can expect average temperatures ranging from 24 to 32 degrees Celsius, making it great for water sports, beach lounging, and exploring the charming local attractions. The warm climate invites you to partake in activities like paddleboarding, fishing, and sightseeing along the stunning coastline, ensuring plenty of opportunities for relaxation and adventure.For those seeking a more budget-friendly visit, consider planning your trip in November. This month offers a quieter experience, with fewer tourists and a chance to enjoy the natural beauty of the area at a more leisurely pace. November temperatures are still mild, generally between 15 to 23 degrees Celsius, allowing for pleasant outdoor exploration without the summer crowds.
How early should I book a Southeast Pensacola holiday rental?
Book your Southeast Pensacola holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Southeast Pensacola, Florida, United States of America?
In Southeast Pensacola, visitors can enjoy a variety of attractions that showcase the area's natural beauty and historical significance. One of the highlights is the stunning Gulf Islands National Seashore, which offers pristine beaches, hiking trails, and opportunities for water sports. Holiday rentals in nearby areas provide easy access to the beach, making it ideal for sunbathing and swimming.The Pensacola Lighthouse and Museum, located on the grounds of the Naval Air Station Pensacola, is another top attraction, offering panoramic views from the top and insight into the area's maritime history. Visitors can also explore the historic district of Pensacola, where charming historic architecture and local shops can be found.For those interested in culture, the Saenger Theatre hosts a variety of performances and events throughout the year, while the Pensacola Museum of Art showcases both contemporary and historical works.
Can I change or cancel my Southeast Pensacola home rental booking on Vrbo?
To find Southeast Pensacola holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Southeast Pensacola holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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