COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Vacation Rentals & Apartments in Longboat Key

Updating...

age 0-16
1347 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

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

~ BEACH FRONT APARTMENT ~

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

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

Zilli Ocean Front 101

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 50 minutes

Price per night from

$274

Florida Ocean Front Condo

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 4 minutes

Price per night from

$524

ZILLI VILLA

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 50 minutes

Price per night from

$453

Beach front condo in Longboat Key

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

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

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

Responds fast! avg. 3 hours 4 minutes

Price per night from

$315

Unit #205 Sand Cay Beach Resort Gulf View

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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

Unit #104 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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

Unit #204 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 30 minutes

Price per night from

$336

Unit #217 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 30 minutes

Price per night from

$336

Unit #105 Sand Cay Beach Resort Gulf View

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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

Unit #316 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 30 minutes

Price per night from

$336

Unit #218 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 30 minutes

Price per night from

$336

Unit #318 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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

GULF FRONT 2 BR 2 BATHROOM CONDO

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$192

Unit #120 Sand Cay Beach Resort Gulf View

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 30 minutes

Price per night from

$299

Unit #320 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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.

Top Destination reviews

~ BEACH FRONT APARTMENT ~
Perfect.

We're from Sarasota so this was close and convenient. Great time! We will DEFINITELY be looking to come back … see more
Castle in the Sky Near Beach and Tennis
Awesome stay

We had a great stay! Our Family of 9 people fit very comfortable, all the rooms were equipped with all the essentials, although is an older home it was very clean and had lots of space. We had Good communication with the owner. … see more
Fabulous Longboat Key - A Mermaids' Oasis 4 minute walk to beach!
Wonderful location

We absolutely loved our time at the Mermaids Oasis. The quiet beach was a quick walk and the quiet street was great. The house was laid out wonderfully for the 8 people we had. It didn’t feel like anyone was on top of the other person. The house was stocked with lots of towels, cookware, linens, beach chairs, and other items which came of great use. The only concerns we had were the amount of mosquitoes and the driveway flooding with the rain. To be fair, we had a few hour thunderstorm everyday of our stay, so as soon as the water would recede, it’d fill back up. The driveway is huge so if you have multiple families coming, there’s no worry over parking. We fit a mini van, a large truck, and a midsize SUV and could’ve fit a few more cars. Overall the place was lovely and the owner’s communication was great. We’d go back for sure!see more
~ SUPER SPECIAL from $139/night ~ OCEAN FRONT DLX STUDIO
Ms

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

Also consider