Skip to main content
Naples Florida Vacation Homes
Rentals
Collections
Locations
Neighborhoods
Select by Name
About
Support
Contact
Sign up for our newsletter
Naples Florida Vacation Homes
Neighborhoods
Select by Name
Our Properties
Dates
Guests
Age 13 and above
-
+
Age 2-12
-
+
Bringing a pet?
Filters

-
+
-
+
Types of Place


Features & Amenities

5th Avenue South: A Destination Within a Destination

Dine, shop, explore art galleries, and attend theatrical performances all in one iconic location. Fifth Avenue South rivals the sophistication of the world’s great cultural districts.

About 5th Avenue South

The Heart of Naples’ Cultural Scene

What makes Fifth Avenue South such an iconic attraction? It’s the diversity and sophistication found nowhere else in Naples—rivaled only by Waterside Shops and the Mercato. Here you’ll find everything from cozy cafes to four-star luxury dining, from specialized boutiques to high-end art galleries. At its heart sits Cambier Park, hosting concerts by the Naples Philharmonic Orchestra and major community events like Art in the Park, the Naples Jazz Society concerts, and the Annual Christmas lighting ceremony. Two premier playhouses—Gulf Shore Playhouse and the Naples Players—anchor the city’s drama scene, while the von Liebig Art Center offers art lessons and sponsors professional shows through the Naples Art Association.

Life on Fifth Avenue

World-Class Dining

From cozy cafes like Café on Fifth to premier restaurants like Truluck’s, Osteria Tulia, and Bistro 821—every palate finds its perfect match.

Art & Theater

Home to Gulf Shore Playhouse, Naples Players, and the von Liebig Art Center—plus year-round festivals celebrating fine art and crafts.

Sophisticated Shopping

High-end boutiques like Fifth Avenue Design Gallery and Sheldon Fine Art sit alongside national favorites like Chico’s and White House Black Market.
Fifth Avenue South is where culture, cuisine, and elegance converge in the heart of Naples.

Signature Dining Experiences

Truluck’s

One of Naples’ most premiere restaurants, offering an exceptional fine dining experience with a focus on fresh seafood and an elegant ambiance.

Osteria Tulia

A celebrated Italian restaurant bringing authentic flavors and rustic charm to Fifth Avenue’s sophisticated dining scene.

Bistro 821

Contemporary American cuisine in an upscale-casual setting, known for seasonal menus and impeccable service.

Bha! Bha!

A unique Persian bistro offering exotic flavors and an intimate atmosphere that sets it apart from typical Fifth Avenue fare.

Beaches Near 5th Avenue South

Naples Pier

The iconic Naples landmark offering stunning Gulf views, fishing opportunities, and unforgettable sunsets just minutes from Fifth Avenue.

Lowdermilk Beach

A family-friendly beach with excellent amenities, playground, and volleyball courts—perfect for a full day of sun and sand.

Gordon Pass

A scenic inlet where Naples Bay meets the Gulf of Mexico, ideal for watching boats and enjoying pristine coastal beauty.

Attractions Next to 5th Avenue South

Cambier Park

Tin City

Naples Botanical Garden

Naples Historical Society’s Historic Palm Cottage

Rookery Bay

Naples Depot Museum


    Stay Near 5th Avenue South

    Experience Naples’ most iconic cultural district from your luxury vacation rental.