Vacation Rentals & Apartments in Longboat Key

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1,163 apartments

Price per night from

$311

Price per night from

$414

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key studio

  • Studio
  • 1 bathroom
  • sleeps 3

“Nice Beachfront Location” We stayed there in late June and found it very suitable for our needs. The beach was very accessible. View was awesome. The unit was clean and comfortable for 2 adults.

Responds fast! avg. 1 hour 56 minutes

Price per night from

$194

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 56 minutes

Price per night from

$194

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$435

Zilli Ocean Front 101

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$320

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$622

ZILLI VILLA

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$453

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$430

Price per night from

$376

LaPlaya 101A - Step out to the beach from your screened lanai. Light and bright

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$376

2 bedroom poolside condo steps from ocean beach and dock on bay

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$425

LaPlaya 101E-Relax on your private lanai under the palms!

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$275

LaPlaya 107A-Soak up the sun or float in the warm Gulf waters.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$311

LaPlaya 205D-Spectacular sunsets from your private Gulf-front lanai or sundeck.

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$414

LaPlaya 206C-Gorgeous vistas of the Gulf

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$414

1 bedroom single story ocean view

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$360

Unit #205 Sand Cay Beach Resort Gulf View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$305

Unit #113 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$278

Unit #310 Sand Cay Beach Resort Pool and Garden

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$278

Unit #312 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$278

Unit #104 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$342

Unit #307 Sand Cay Beach Resort Pool and Garden

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$278

Unit #204 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$342

Unit #217 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$342

Unit #105 Sand Cay Beach Resort Gulf View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$305

Unit #309 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$278

Unit #112 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$278

Unit #316 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$342

Unit #218 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$342

Unit #211 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$278

Unit #120 Sand Cay Beach Resort Gulf View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$305

Unit #320 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$342

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$745

Unit #103 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$342

Unit #110 Sand Cay Beach Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$278

Unit #315 Sand Cay Beach Resort Gulf View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$305

180 Panoramic beach View and amazing Sunset.

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$457

Viewing 38 of 1,163
rentals in Longboat Key

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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.

Top Destination reviews

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO
Ms

Nice efficiency with a beautiful ocean front view. Conveniently located between each end of the Island. … see more

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