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1,347 apartments
LaPlaya 109A-Enjoy the balmy Gulf breezes in this corner end unit right on the b
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$311
LaPlaya 201C-Breathtaking Gulf panorama from this corner end unit with a private
Longboat Key condo
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$414
~ SUPER SPECIAL from $139/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. 2 hours 25 minutes
Price per night from
$160
Responds fast! avg. 2 hours 25 minutes
Price per night from
$183
~ SUPER SPECIAL from $129/night ~ OCEAN FRONT DLX STUDIO , Dec 8 - Jan 9
Longboat Key apartment
1 bedroom / 1 bathroom / sleeps 3
Responds fast! avg. 2 hours 25 minutes
Price per night from
$160
Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$333
Responds fast! avg. 3 hours 50 minutes
Price per night from
$274
Responds fast! avg. 3 hours 4 minutes
Price per night from
$524
Responds fast! avg. 3 hours 50 minutes
Price per night from
$453
Responds fast! avg. 24 minutes
Price per night from
$321
LaPlaya 108B-Dream views of the Gulf from your private balcony or screened lanai
Longboat Key condo
2 bedrooms / 1 bathroom / sleeps 4
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
$370
2 bedroom poolside condo steps from ocean beach and dock on bay
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 4 minutes
Price per night from
$328
LaPlaya 101E-Relax on your private lanai under the palms!
Longboat Key condo
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$265
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
Holiday Home Directly by Sea - Self Catering
Longboat Key apartment
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 59 minutes
Price per night from
$224
Price per night from
$414
Responds fast! avg. 3 hours 4 minutes
Price per night from
$315
Responds fast! avg. 3 hours 30 minutes
Price per night from
$299
Unit #113 Sand Cay Beach Resort Pool and Garden View
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 30 minutes
Price per night from
$273
Unit #310 Sand Cay Beach Resort Pool and Garden
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 30 minutes
Price per night from
$273
Unit #312 Sand Cay Beach Resort Pool and Garden View
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 30 minutes
Price per night from
$273
Responds fast! avg. 3 hours 30 minutes
Price per night from
$336
Unit #307 Sand Cay Beach Resort Pool and Garden
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 30 minutes
Price per night from
$273
Responds fast! avg. 3 hours 30 minutes
Price per night from
$336
Responds fast! avg. 3 hours 30 minutes
Price per night from
$336
Responds fast! avg. 3 hours 30 minutes
Price per night from
$299
Unit #309 Sand Cay Beach Resort Pool and Garden View
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 5
Responds fast! avg. 3 hours 30 minutes
Price per night from
$273
Unit #112 Sand Cay Beach Resort Pool and Garden View
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 30 minutes
Price per night from
$273
Responds fast! avg. 3 hours 30 minutes
Price per night from
$336
Responds fast! avg. 3 hours 30 minutes
Price per night from
$336
Responds fast! avg. 3 hours 30 minutes
Price per night from
$336
Unit #211 Sand Cay Beach Resort Pool and Garden View
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 30 minutes
Price per night from
$273
Price per night from
$192
Responds fast! avg. 3 hours 30 minutes
Price per night from
$299
Responds fast! avg. 3 hours 30 minutes
Price per night from
$336
March 19-26, 2022 Springbreak 3bdr on the beach Longboat key
Longboat Key cottage
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$688
Viewing 38 of 1,347
rentals in Longboat Key
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.
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