176 Pensacola Holiday Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Pensacola holiday rentals from 8 rental sites including HomeAway, Booking.com, TripAdvisor and more, ranging from $38 to $1200 a night.

Information about Pensacola

About Pensacola

Pensacola, not to be confused with nearby Pensacola Beach, is an Emerald Coast city in Escambia County located on Pensacola Bay. This beach city is referred to by many nicknames, which explain a great deal about Pensacola. As the westernmost city on the Florida Panhandle, the "Western Gate to the Sunshine Gate" has a rich and celebrated history that is alluded to in another common Pensacola nickname, the "City of Five Flags." With the help of Pensacola’s consistently warm weather, the pristine white sand draw thousands of vacationers to the coastal city all year, earning Pensacola the title, "World’s Whitest Beaches." Aside from being a popular Florida destination, the "Cradle of Naval Aviation" is famous for the Pensacola Naval Air Station, which is the oldest in the US and the part-time home to the Blue Angels. The locals and the lucky students of Pensacola State College and University of West Florida know that there is never a bad time to visit "The Upside of Florida" for a vacation!

Things to do in Pensacola

The free live music and entertainment options offered in Pensacola are what really set it apart from the other nearby beach communities. Free evening concerts and events, like the Great Gulfcoast Arts Festival, are most frequently held in Old Seville Square, where you can park your lawn chairs and dance along with the band on the gazebo. The 10,000 seat Pensacola Bay Center, historic Saenger Theatre, and Gulfside Pavillion in nearby Pensacola Beach are other popular entertainment venues. Pensacola is locally renowned for several of its annual festivals, the Pensacola Crawfish Festival (April-May), Fiesta of Five Flags (May-June), and Pensacola Seafood Festival (September), which are all free and open to the public. One of Pensacola’s biggest attractions, the National Naval Aviation Museum is the world’s largest naval aviation museum, and admission is free. Every Wednesday, you can meet the famous Blue Angels, the US Navy’s elite fighter jet demonstration team. Attend a Blue Wahoos minor league baseball game at the Pensacola Bayfront Stadium, or one of the many other sporting events that take place there, for a some classic American fun with a truly unbeatable view. Visit Historic Pensacola Village, where you will find a charming collection of historic buildings operated by the University of West Florida and the Pensacola Children’s Museum. Experience Pensacola’s arts, history, and culture at the Pensacola Museum of Art, the T.T. Wentworth Jr. Florida State Museum, Civil War Soldiers Memorial, and Fort Barrancas. Outdoor and bird watching enthusiasts will be delighted to discover Big Lagoon State Park, Uncle Sandy’s Macaw Bird Park, and the Edward Ball Nature Trail. Johnson Beach, Bayview Dog Beach, and Perdido Key State Park are the main beach spots in town, and there are countless others within ten minutes of Pensacola in vacation destinations like Pensacola Beach, Gulf Breeze, and Santa Rosa Island. Fishing and paddle boarding are a fun and unique way to enhance the beach experience, and there are plenty of rental shops in town that make finding gear easy. Finish off the day of lounging and shopping at the Palafox Market by watching a beautiful sunset from bayside DeLuna Park. Just sit back, relax, and enjoy the laidback Florida vibe.

Pensacola Accommodations

Located just a matter of minutes outside of the downtown area, the Pensacola International Airport makes coming to Pensacola from any homebase easy. Driving into town on the major state highways is also common, and it is by far the best way to get around Pensacola during your stay. In addition, there is Greyhound service to Pensacola and bike lanes all over town if you would prefer not to use a car. Tripping.com will help you find the perfect vacation rental for your needs, whether it be a luxury home with a boat dock or a cozy condo close to downtown. Happy travels!

Vacation Rentals in Pensacola

Looking for the perfect vacation rental for your Pensacola getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Pensacola offers 927 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 525 properties with high-speed internet, 351 full with jacuzzi and pool, and homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $5538 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Pensacola has 927 gorgeous homes with 78 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

Search properties from 8 rental sites in Pensacola where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 459 HomeAway rentals, 321 Booking.com short term rentals and 55 TripAdvisor vacation rentals.
How likely would you be to recommend Tripping.com to a friend?
Not At All
  • 0
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
Extremely Likely
Thank you for your response!
Why?