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Vacation Rentals & Apartments in Longboat Key

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2,346 apartments

LaPlaya 109A

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$311

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. 2 hours 37 minutes

Price per night from

$272

Condo by the Bay: Pool Access, Beach Gear & Grill!

Longboat Key apartment

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 5 minutes

Price per night from

$182

Longboat Key Retreat

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$151

Renovated Beachfront Condo with Spectacular Ocean View unit 403

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 21 minutes

Price per night from

$216

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!!

Responds fast! avg. 2 hours 37 minutes

Price per night from

$245

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. 2 hours 37 minutes

Price per night from

$275

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!

Responds fast! avg. 2 hours 37 minutes

Price per night from

$211

Two Story Condo on the Gulf of Mexico

Longboat Key condo

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$636

55+ Community with pool and club house

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$82

~ BEACH FRONT APARTMENT ~

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 36 minutes

Price per night from

$161

LaPlaya 201C

Longboat Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 51 minutes

Price per night from

$414

LaPlaya 104E

Longboat Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$220

~ The Beach on Longboat Key ~ * 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. 3 hours 36 minutes

Price per night from

$115

~ STUDIO - DIRECT BEACH FRONT CONDO ~

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 36 minutes

Price per night from

$114

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$340

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 21 minutes

Price per night from

$228

Florida Ocean Front Condo March 21- March 28 or April 11 -21, 2020

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 14 minutes

Price per night from

$502

Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$164

Zilli Ocean Front 101

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$171

ZILLI VILLA

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$409

GORGEOUS gated Multi-level LONGBOAT KEY HOME with DOCK ~ Near beach & private!

Longboat Key house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 32 minutes

Price per night from

$153

LaPlaya 108B

Longboat Key condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$350

LaPlaya 101A

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$320

Beach front condo in Longboat Key

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 39 minutes

Price per night from

$363

BBB on Marbury lane-Beach, boating, BBQ!

Longboat Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$293

Lovely Tropical Longboat Town house

Longboat Key townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 54 minutes

Price per night from

$150

2 bedroom poolside condo steps from ocean beach and dock on bay 4-11to 4-18

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 14 minutes

Price per night from

$317

LaPlaya 105B

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$350

LaPlaya 101E

Longboat Key condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$227

Longboat Key Cosy 1bed/1bath between white sand beach and Sarasota bay.

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$78

1 bedroom single story family friendly resort March 21 - March 28, 2020

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 14 minutes

Price per night from

$234

Tropical Waterfront Home in Historic Village

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$753

LaPlaya 107A

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$311

LaPlaya 205D

Longboat Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 51 minutes

Price per night from

$414

LaPlaya 102E

Longboat Key condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$220

Holiday Home Directly by Sea - Self Catering

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$218

Viewing 38 of 2,346
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

~ 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
Longboat Key Retreat
Beach house

We really enjoyed our stay at the beach house The owners were friendly and available for questions. The access to the beach is a little tricky but they do provide a map with instructions to show you how to reach the access, which is actually very easy. We really enjoyed the restaurant, Harry’s which is just down the block and served excellent food and had an excellent delisee 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
Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent
Got all u need

Fine place from patio you can see the gulf. Good King size bed, felt good. Had all utensils you need , new appliances. 2 bath 2 bed rooms. Comcast Cable Works good. 50 yards from beach. Great swimming pool. … see more
~ The Beach on Longboat Key ~ * 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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