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1,618 Pensacola Beach 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 Beach holiday rentals from 10 rental sites including HomeAway, Expedia, TripAdvisor and more, from $25 a night.

Pensacola Beach Information

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

Looking for a vacation rental in Pensacola Beach? Tripping.com has 1608 vacation rental homes available in Pensacola Beach. You'll find 12 studios, 285 1-bedroom, 617 2-bedroom and 694 rentals with 3 or more bedrooms ranging from $25 a night. For extra convenience, many of these vacation homes can be booked directly online.

The average price of a nightly rental in Pensacola Beach is $348 while the average price of a weekly rental is $2940. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Pensacola Beach home is $25.

Wondering if you can bring your dog or cat along with you? There are 216 pet-friendly vacation rentals available in Pensacola Beach. In addition to accommodating pets, Pensacola Beach rentals offer a variety of amenities. In particular, 1395 rentals have Internet and WiFi, 1451 have TV and/or cable and 971 have a pool or hot tub.

Search properties from 10 vacation rental sites in Pensacola Beach where the top providers in that area are HomeAway, Expedia, and TripAdvisor. There are 1298 HomeAway rentals, 116 Expedia short term rentals and 115 TripAdvisor vacation rentals.