Downtown Pensacola holiday rentals

We found 266 holiday rentals — enter your dates for availability

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August 2025

September 2025

Select from 59 houses, 17 flats and other holiday rentals to find the perfect place for your stay in Downtown Pensacola. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and Wi-Fi. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Downtown Pensacola

Showing deals for:31 Oct - 7 Nov

Enjoy open concept living, dining, and kitchen areas

Exceptional

(16 reviews)

Downtown Townhome l Community Pool l Great for Families l 10 Minutes to NAS Pensacola l Fast WiFi

Pensacola, FL

10% off

AU$392 per night

includes taxes & fees

Exceptional

(60 reviews)

BAY HOUSE - Steps to its own Private Beach - Amazing Sunsets on the Water

Pensacola, FL

8% off

AU$622 per night

includes taxes & fees

Exceptional

(9 reviews)

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

Pensacola, FL

7% off

AU$162 per night

includes taxes & fees

Exceptional

(66 reviews)

East Hill Coastal Cottage, prefect for couples and families, pet friendly.

Pensacola, FL

8% off

AU$333 per night

includes taxes & fees

"This is the place! Henry’s Hideaway was an absolute GEM! Our family takes an annual vacation to Pensacola Beach every summer & we always look for places that are clean, accessible to everything, & kid-friendly."

Exceptional

(12 reviews)

Close to Beach & Downtown ~ Fenced Yard

Pensacola, FL

6% off

AU$351 per night

includes taxes & fees

Exceptional

(10 reviews)

Downtown bungalow, pet friendly, fenced yrd, walk to restaurants, parades & bay!

Pensacola, FL

18% off

AU$293 per night

includes taxes & fees

Exceptional

(37 reviews)

Dog Friendly - Charming Downtown Cottage - Handicap Accessible - Fast WiFi - Off Street Parking

Pensacola, FL

16% off

AU$269 per night

includes taxes & fees

Excellent

(5 reviews)

Close to Wahoos, Palafox Restaurants and Events.Visit Beaches and Blue Angels.

Pensacola, FL

8% off

AU$404 per night

includes taxes & fees

Unit offers plenty of space to gather with your group in a meaningful way.

Wonderful

(14 reviews)

Amazing Loft in Historic Waterworks Building, near Downtown Pensacola

Pensacola, FL

9% off

AU$450 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Downtown Pensacola

Saenger Theatre

Find the best place to stay - Downtown Pensacola

Showing deals for: 31 Oct - 3 Nov

Great spot for your morning coffee or viewing the sunset with a cocktail

Zen! Refreshing! Spotless! Relaxing! Welcoming! Well-appointed! Dock your boat!

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 houseboat

AU$506 per night

includes taxes & fees

Seville Harbour/Houseboats 1-2-3/Pensacola Bay

Tranquil! Amazing! Immaculate! Unique! Downtown!10 stars! Dock your boat!!

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 houseboat

AU$506 per night

includes taxes & fees

The first Houseboat you see when entering Seville Harbour!

The View! Hidden Gem! Pristine! Quiet Retreat! Charming! Go fish! Dock a boat!

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 houseboat

AU$523 per night

includes taxes & fees

Peaceful! Inviting! Clean! Perfect! Heavenly floating getaway! Dock your boat!!

Sleeps 6 · 1 bedroom · 1 bathroom

for 3 nights, 1 houseboat

AU$506 per night

includes taxes & fees

Gadsden Hideaway: Historic Downtown Luxury in East Hill Preservation District

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 cottage

AU$214 per night

includes taxes & fees

Cozy vintage airstream downtown Pensacola, pet friendly

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

AU$220 per night

includes taxes & fees

Top rated rentals - Downtown Pensacola

Premier Host

Basketball friends

The house is very lovely and walking distance to the Pensacola Bay Center. It was extremely clean. The Communications before and during the stay with Bill and Mindy was great.

Marcia A.

Stayed Mar 2025

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 home accommodation in Downtown Pensacola?

Houses are the most popular style of holiday home in Downtown Pensacola, according to our data. Even if you've got something different in mind, Stayz has holiday homes in many shapes and sizes. Browse our many options to find your perfect match.

How much does it cost to rent a holiday home in Downtown Pensacola?

A range of things influence what you'll pay for your holiday home in Downtown Pensacola, like the type of property, length of stay and season. But, all Stayz homes have something in common — incredible value. Just add your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Downtown Pensacola?

The average price for a holiday home close to the beach in Downtown Pensacola depends on when you're visiting the area and the size and style of property you're looking for. You can find prices easily and quickly on Stayz by entering your preferred travel dates and destination. Then use our filters to choose the number of bedrooms and amenities important to you, such as a pool, WiFi and air conditioning.

Are there pet-friendly holiday homes in Downtown Pensacola?

Yes. You'll have your pick of 105 stays that allow pets in Downtown Pensacola on Stayz. Our furry best friends need a break too, so simply use our search function for pet-friendly holiday homes to book a property where your puppy dog can be near his favourite humans.

Can I rent a house with a pool in Downtown Pensacola?

Grab your swimwear and goggles, because there are six houses with a private pool in Downtown Pensacola. Book one of these superb holiday homes and enjoy a pool day every day. Simply enter your dates into Stayz, then use the "pool" filter to find the perfect place for a splashing good time!

What are popular home amenities in Downtown Pensacola?

A fireplace, a garden and a water view are rated the most popular home amenities in Downtown Pensacola. Whether you're heading away solo, with your better half or as a family, Stayz will help you find a holiday home that fits your tastes with all the features you need.

Are there large group holiday homes in Downtown Pensacola?

Downtown Pensacola has five holiday properties that can fit 10 or more people. These properties come with the space you need to share good times with your nearest and dearest.

Are there holiday homes in Downtown Pensacola that welcome kids?

With 104 family-friendly holiday properties to select from in Downtown Pensacola, now is a great time to introduce your children to the wonders of travel. Simply check our "Properties good for families" filter box to look for stays that come with conveniences ideal for holidaying families, such as living rooms, swimming pools, bunk beds and entertainment units.

What are the top attractions for families in Downtown Pensacola?

Keeping the kiddos entertained during your holiday in Downtown Pensacola is a snap with these awesome family-friendly attractions:

Perdido Key Beach
Johnson Beach
Splash City Adventures

Are there one-bedroom holiday homes in Downtown Pensacola?

You'll find 30 one-bedroom properties in Downtown Pensacola to pick from. A one-bedroom holiday home is a great option if it's only you and your partner or if you're flying solo. Throw in more space, privacy and convenience compared to a regular hotel, and you're bound to have an unforgettable break.

Can I find two-bedroom holiday homes in Downtown Pensacola?

Take your pick of 35 two-bedroom homes in Downtown Pensacola. Give your little ones the second room or fill it with a couple of your nearest and dearest friends. There's a comfy spot for whoever's lucky enough to be joining in on the fun.

Are there holiday homes with WiFi in Downtown Pensacola?

Whether you want to keep up with the news, check emails or surf your social networks, there are 51 holiday homes with WiFi in Downtown Pensacola. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.

How can I find holiday homes with air conditioning in Downtown Pensacola?

Pick your dates and then make use of the filters to search for holiday homes with ac in Downtown Pensacola on Stayz. With 104 air-conditioned properties available, you can enjoy a comfortable and cool stay.

How old do you have to be to rent a holiday home in Downtown Pensacola?

The minimum age permitted can differ across properties on Stayz, so be sure to look at the rules of the holiday home in Downtown Pensacola you're interested in. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Downtown Pensacola for?

The amount of time you can stay in a Downtown Pensacola holiday home for is up to each property. Simply put in your preferred travel dates to see options offering longer term stays. They come with everything you need to make your extended break more enjoyable like kitchens and yards. Some properties might also offer weekly or monthly discounted prices, so you can stay longer for less money.