Destination guide

Be the latest in a long line of invaders

Pensacola isn't the sort of place you only visit once. It's known as "the city of the 5 flags," thanks to the number of different colonial and domestic powers that have conquered it over the years—and now it's your turn, with a Pensacola vacation rental. Pensacola's full of history and grand colonial architecture, and many vacationers will want to lose themselves in its old historic streets or spend hours nosing round its many museums. But it's also a lively, modern city with plenty of dining and nightlife options. And don't even get us started on those white sand beaches.

Things to do

Take a ride into the danger zone, Maverick

Fancy seeing how those flyboys did things back in the day? Pay a visit to the National Naval Aviation Museum, where you can also pose in front of an F-14 in your Ray Bans like you're Tom Cruise in Top Gun. If you're more artistically minded, you might want to spend some time in the Pensacola Museum of Art, set in the old city jail. And to really get to grips with Pensacola's past, head to the Historic Pensacola Village in the Downtown area, with museums covering local history, commerce, and industry.


The beaches round here are like white sugar

Like your beaches wide and your sand pearly white? Well, you're in luck—Pensacola Beach is just outside city limits, and is popular with locals and tourists alike. For somewhere a bit quieter, you might want to try Perdido Key, a little farther out. Apart from that, Pensacola is a handsome city with several historic districts, and is great for sightseeing, especially if you book yourself onto one of the guided walking tours. Another feature of a Pensacola vacation rental is the full program of festivals and events, covering everything from seafood and live music to art and comics.


Hold up! Step away from that heavy parka!

Whatever time of year you book your Pensacola vacation rental, you're unlikely to need more than a light jacket. Summers are long, hot, and wonderfully lazy. The coastal location means the heat rarely gets too much, but it can be humid, and you can expect the air to clear itself out with fairly frequent thunderstorms. Winters are mild and comparatively drier, while spring and fall can be great times to book a Pensacola vacation rental. And the one item that needs to go in your suitcase before anything else? An umbrella. Pensacola can see rain at any time of year.

Natural features

Panhandling for awesome vacations in Pensacola

Your Pensacola vacation rental will stick you right out on the end of the Florida Panhandle, with the Alabama border just a 20-minute drive from downtown Pensacola. It's on the Gulf Coast, but set between the city and the Gulf of Mexico is Santa Rosa Island, home to the Pensacola Beach community. This natural barrier gives beachgoers some interesting options, with fresher breezes and sea views on one side of the island, and safer, more sheltered waters on the other. Whatever beach you pick, you can bank on white sand and warm waters.

How to get there

Traveling to and around Pensacola

Fly into Pensacola, FL (PNS-Pensacola Intl.), the closest airport, located 4.7 mi (7.6 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Fort Walton Beach, FL (VPS-Northwest Florida Regional), which is 40.1 mi (64.5 km) away.

If you prefer train travel, the main station serving the city is Pensacola Station.

Where to stay around Pensacola?

Our 2019 property listings offer a large selection of 1,562 vacation rentals near Pensacola. From 358 Houses to 1,037 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Pensacola for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Pensacola?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Pensacola:

  • Downtown: 44 vacation rentals
  • East Hill: 27 vacation rentals
  • Southeast Pensacola: 47 vacation rentals
  • South Pensacola: 42 vacation rentals
  • Northeast Pensacola: 19 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Pensacola?

HomeAway offers a large selection of vacation rentals near lovely places in Pensacola. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Pensacola Bayfront Stadium: 2,727 vacation rentals
  • Wayside Park: 2,600 vacation rentals
  • Bayview Beach Park: 2,585 vacation rentals
  • Destination Archaeology Resource Center: 2,707 vacation rentals
  • Pensacola Station: 2,310 vacation rentals

But there are many other points of interest around Pensacola listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Pensacola?

Yes, of course. HomeAway has 358 Houses in Pensacola. Our other popular types of vacation rentals in Pensacola include:

  • Condos/Apartments: 1,037 rentals available
  • Cottages: 11 rentals available
  • Townhouses: 122 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Pensacola?

Yes, you can select your preferred vacation rental with pool among our 1,187 vacation rentals with pool available in Pensacola. Please use our search bar to access the selection of vacation rentals available.

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