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1,644 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
$312
Charming Beach House in Longboat Key/ pool/pet/dock
Longboat Key house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$264
Las Hermanas/Starfish #3 Beach front Longboat Key
Longboat Key apartment
1 bedroom / 1 bathroom / sleeps 4
“Little Piece Of Paradise” Everything you could want in a vacation rental. We wanted to be right on the beach and this place offers that and more. Great kitchen,stocked with everything you need. Beach views from almost every room. We really enjoyed eating on the porch. We will be returning soon.
Responds fast! avg. 3 hours 40 minutes
Price per night from
$186
Renovated Beachfront Condo with Spectacular Ocean View unit 403
Longboat Key apartment
1 bedroom / 1 bathroom / sleeps 6
Responds fast! avg. 1 hour 18 minutes
Price per night from
$224
“Location! Location! Location!” The listing description and photos were accurate, this rental property is amazing. Studio #1 was tastefully decorated and very clean. We had beautiful views of the ocean from the living area. It was very spacious with plenty of room for three of us to spread out comfortably. It had lots of storage for our belongings, roomy bathroom with an extra open closet area and a wonderful kitchen area. 5 steps and your toes are in the sand and 40 more steps and you're in the water. A beautiful beach to walk, crystal clear water for swimming, the wildlife was awesome and sunsets were spectacular. James unfortunately had to come twice to let us in because we locked ourselves out, but he did so each time with a smile and friendly conversation. Right out front is an amazing wide sidewalk for bike rides to Bradenton Beach , St. Armand's Circle and to wonderful restaurants. Definitely found a great spot to settle in for a few weeks of relaxing fun in the sun. Thank you so much James and Cindy!!
Responds fast! avg. 3 hours 40 minutes
Price per night from
$163
Las Hermanas/Starfish #2 Beachfront Longboat Key
Longboat Key apartment
1 bedroom / 1 bathroom / sleeps 4
“Paradice on the beach” We really enjoyed our stay at Las Hermanas/ Starfish, right on the beach, nice sand and great view of the ocean and sunsets. Very clean and well appointed rooms. Good parking. Handy laundry room.
Responds fast! avg. 3 hours 40 minutes
Price per night from
$186
“Relaxing Beachfront Studio” My wife and I stayed here over Spring Break, and had a wonderful time. The unit was clean, updated, and had all the amenities we needed. The beach, which was just steps out the back door, was quiet and away from the crowds (we go on vacation to relax, not fight over beach chairs and get trampled by people). And the building's location is close to St Armand's Circle, great for dining and shopping. We will definitely be back, thank you Jim and Cindy for a great stay!
Responds fast! avg. 3 hours 50 minutes
Travelers’ Choice award
Price per night from
$140
Responds fast! avg. 2 hours 27 minutes
Price per night from
$183
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
~ OCEAN FRONT DLX STUDIO ~ SPECIAL $142/night , Feb 6-13
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 27 minutes
Price per night from
$149
~ OCEAN FRONT DLX STUDIO ~ SPECIAL $142/night , Feb 6-13
Longboat Key apartment
1 bedroom / 1 bathroom / sleeps 3
Responds fast! avg. 2 hours 27 minutes
Price per night from
$149
Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$380
Amazing views of the Gulf and beach from your own balcony unit 301
Longboat Key apartment
1 bedroom / 1 bathroom / sleeps 6
Responds fast! avg. 1 hour 18 minutes
Price per night from
$226
Price per night from
$529
Responds fast! avg. 3 hours 42 minutes
Price per night from
$241
Responds fast! avg. 3 hours 42 minutes
Price per night from
$421
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
$361
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
$330
Responds fast! avg. 41 minutes
Price per night from
$289
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
$362
LaPlaya 101E-Relax on your private lanai under the palms!
Longboat Key condo
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$234
Price per night from
$264
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
$312
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
$416
Holiday Home Directly by Sea - Self Catering
Longboat Key apartment
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$225
Price per night from
$416
Responds fast! avg. 2 hours 34 minutes
Price per night from
$236
Unit #109 Sand Cay Beach Resort Pool and Garden View
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 34 minutes
Price per night from
$215
Responds fast! avg. 2 hours 34 minutes
Price per night from
$271
Responds fast! avg. 2 hours 34 minutes
Price per night from
$271
Price per night from
$115
Responds fast! avg. 2 hours 34 minutes
Price per night from
$236
Unit #111 Sand Cay Beach Resort Pool and Garden View
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 34 minutes
Price per night from
$215
Unit #307 Sand Cay Beach Resort Pool and Garden
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 34 minutes
Price per night from
$215
Unit #311 Sand Cay Beach Resort Pool and Garden View
Longboat Key condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 34 minutes
Price per night from
$215
Responds fast! avg. 2 hours 34 minutes
Price per night from
$236
Responds fast! avg. 2 hours 34 minutes
Price per night from
$236
Price per night from
$98
Viewing 38 of 1,644
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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