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Vacation Rentals & Apartments in Longboat Key

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1,573 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

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.

Price per night from

$183

Renovated Beachfront Condo with Spectacular Ocean View unit 403

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 3 minutes

Price per night from

$235

Beachfront Studio #1 Longboat Key

Longboat Key studio

Studio / 1 bathroom / sleeps 4

“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!!

Price per night from

$161

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.

Price per night from

$184

Beachfront Unit 4, Cozy Getaway for two

Longboat Key studio

Studio / 1 bathroom / sleeps 2

“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!

Price per night from

$140

~ BEACH FRONT APARTMENT ~

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 14 minutes

Price per night from

$160

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 14 minutes

Price per night from

$148

~ OCEAN FRONT DLX STUDIO ~ SPECIAL $142/night , Feb 6-13

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 14 minutes

Price per night from

$148

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. 3 hours 3 minutes

Price per night from

$234

Florida Ocean Front Condo

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$528

Zilli Ocean Front 101

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 51 minutes

Price per night from

$240

ZILLI VILLA

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 51 minutes

Price per night from

$417

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

$359

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

$328

Beach front condo in Longboat Key

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 19 minutes

Price per night from

$286

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

$233

1 bedroom single story

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

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

$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

Price per night from

$225

LaPlaya 206C-Gorgeous vistas of the Gulf

Longboat Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$414

Unit #106 Sand Cay Beach Resort Gulf View

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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

Unit #116 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 34 minutes

Price per night from

$271

Unit #217 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$271

Seaplace Condo - 1975 GMD 104

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$115

Unit #105 Sand Cay Beach Resort Gulf View

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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

Unit #206 Sand Cay Beach Resort Gulf View

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$236

Unit #201 Sand Cay Beach Resort Gulf View

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$236

Longboat Key Waterfront Condo

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$98

SEAPLACE 2BR2BA condo on Longboat Key near SARASOTA !!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 36 minutes

Price per night from

$171

Viewing 38 of 1,573
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

Beachfront Unit 4, Cozy Getaway for two
Perfect getaway

Excellent location right on the beach. A true gem we were lucky to find! Updated unit. Kitchen could use a few utensils like hot pads but overall everything else was perfect. … see more
~ 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
Beachfront Studio #1 Longboat Key
Studio on the beach

Lovely, very accommodating unit and location. On the beach and easy access to grocery and restaurants. We … 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
~ OCEAN FRONT DLX STUDIO ~ SPECIAL $142/night , Feb 6-13
Ms

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

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