- Casa del Mar View all rentals (103)
- The Beach View all rentals (1473)
- Privateer View all rentals (796)
- Longboat Key Club View all rentals (23)
- Sand Cay Beach View all rentals (12)
- Whitney Beach View all rentals (5)
Rentals Near Longboat Key Attractions
Featured Longboat Key Properties
1 / 27
Longboat Key condo
1 BR / 1 BA / Sleeps 3
Longboat Key condo
- Min stay varies
About Longboat Key
With warm weather year-round and some of the best beaches in the region, Longboat Key has become one of the premiere vacation destinations in the Florida area. Longboat Key has several major festivals and events held throughout the year, so try to plan your trip around one of them. Some of the major events in the area include the St. Armand's Circle Art Festival, held in late January; the Say I Do Again Festival on Valentine's Day, where couples can renew their vows on Siesta Public Beach; and the Siesta Fiesta, an annual arts and crafts fair held in early May.
While you're on vacation in the Longboat Key area, be sure to make time for some of these main attractions and destinations:
- Sarasota Jungle Gardens: There are five shows at the gardens that feature both animals and rare plants.
- Historic Palm Avenue: This is known as downtown Sarasota's "Best Walk in Town."
- Bolletieri Tennis Academy: Located in nearby Bradenton, see the academy where champions like Andre Agassi and Monica Seles got their start.
- Go shopping: St. Armand's Circle has a huge selection of unique shops and fine dining.
- Catch a baseball game: If you're in the area during the spring, the Baltimore Orioles train in nearby Sarasota.
- Historic Spanish Point: Take a guided tour here and learn more about the history of Southwest Florida.
No matter what time of year you visit, you'll be able to find a vacation rental in Longboat Key to suit your needs. In addition to villa rentals with all the amenities and comforts of home, you can also book a beachfront condo rental with white sand beaches right outside your door.
There are also several excellent day-trip options from Longboat Key. Tampa is a short drive via I-75 North. Disney World is also a short distance by car and offers an unforgettable experience for the whole family.