1,404 Pensacola Beach Holiday Rentals

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Compare Pensacola Beach holiday rentals from 7 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $40 to $1542 a night.

Information about Pensacola Beach

About Pensacola Beach

Pensacola Beach is a small Florida beach town of about 8 square miles on Santa Rosa Island that is primarily known for its beautiful white sand beaches. Pensacola Beach weather is more stable than mainland Florida, and the island town enjoys a soothing sea breeze in the afternoons that the mainland does not usually experience. The best time to visit is the summer when the weather is at its warmest and the Pensacola Beach Air Show is live. The Santa Rosa Sound is to the north of Pensacola Beach and the Gulf of Mexico is to the south, while the Gulf Islands National Seashore property is to both the east and west. Although small, Pensacola Beach has some of the tallest buildings between Mobile and Tallahassee, all of which are hotels or condos. Most are surprised to learn that Pensacola Beach was settled before better-known Jamestown and St. Augustine, making the town over 450 years old. Pensacola Beach is the perfect place for some quiet relaxation when you need it, but is close enough to other beach towns to offer all of the exciting Floridian vacation activities of a bigger destination. Pensacola Beach produces great memories time after time, which manifests in the hundreds of glowing vacation reviews online.

Things to do in Pensacola Beach

Visitors are drawn to Pensacola Beach for none other than the exquisite beaches! Casino Beach is the most frequented and most lively, providing beach volleyball courts, changing rooms, surfing, and the fishing-friendly Gulf Pier for its visitors. Another favorite is Quietwater Beach, which not only boasts calm, clear, shallow water, but also has the Portofino Boardwalk! The boardwalk, also referred to as the Quietwater Beach Boardwalk, attracts both locals and visitors alike with its shopping, dining, and entertainment options. The picturesque Portofino Boardwalk Amphitheatre overlooks the beach, which makes the live concerts especially impressive during sunset. Major events like the Lobster Fest, Bushwacker Music Fest, and DeLuna Fest, also happen in the Amphitheatre, which can be recognized by its iconic shell. Other beaches in Pensacola Beach include Fort Pickens Gate Park, Park East, and Langdon Beach. Chartered sailing or fishing trips, paddle boarding, scuba diving, parasailing, and other water sports are an adventurous way to see the island and get the most out of a Pensacola Beach vacation. For a break from the beach scene, check out Pensacola Beach’s local sightseeing stops, which include Fort Pickens, the Flintstone House, the Spaceship House “Futuro," and the dome house.

Pensacola Beach Accommodations

Even though Pensacola Beach is surrounded by water on all sides, getting to this island paradise is still relatively easy. The Pensacola Bay Bridge connects the island to mainland Pensacola, and two other bridges, the Bob Sikes Bridge and Garcon Point Road, connect Pensacola Beach to Gulf Breeze. If you are coming from afar, the Pensacola International Airport, Destin-Fort Walton Beach Airport, and Northwest Florida Beaches International Airport are all closeby. On the island, most attractions can be reached by foot, although the beach trolley, boat rentals, and bike rentals are also common modes of transportation. You’ll have no trouble finding a spacious rental with a view in Pensacola Beach on Tripping.com!

Vacation Rentals in Pensacola Beach

Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Pensacola Beach offers 922 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $341 a night, or a long-term rental for an average price of $2460 a month.

These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 838 of Pensacola Beach’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 628 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 726 cozy homes.

Traveling with pets? Choose from 119 pet-friendly rentals in Pensacola Beach for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

Search properties from 7 rental sites in Pensacola Beach where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 770 HomeAway rentals, 80 TripAdvisor short term rentals and 40 Booking.com vacation rentals.