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Vacation Rentals & Apartments in Longboat Key

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Vacation Rentals & Apartments in Longboat Key

About Longboat Key

3,119 apartments

Spacious Gulf Front beach condo on Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$198

1 / 17

Longboat Key Condo w/ Pool Access- Walk to Bay!

Longboat Key apartment

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 28 minutes

Price per night from

$185

1 / 24

Beautiful Private condo on the beach

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 14 minutes

Price per night from

$200

1 / 21

LaPlaya 109A

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$258

1 / 31

Charming Beach House in Longboat Key/ pool/pet/dock

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

1 / 18

Beachfront Condo on the Beautiful Gulf of Mexico

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Great place to Relax!” This is my 2nt time renting this property and I highly recommend it. It is the perfect place to relax & unwind. Beach is great & Ramona makes the whole renting process easy & painless. Looking forward to staying here again soon!

Responds fast! avg. 1 hour 59 minutes

Price per night from

$300

1 / 38

Beachfront Longboat Key Studio #1

Longboat Key apartment

/ 1 bathroom / sleeps 4

“If you are looking for a quiet and quaint place stay here” Very clean and nicely decorated. Beautiful kitchen, comfortable bathroom and the views and the beach are amazing!! Great service by Jimand Cindy

Responds fast! avg. 2 hours 56 minutes

Price per night from

$125

1 / 6

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 ea

Responds fast! avg. 2 hours 56 minutes

Price per night from

$142

1 / 7

Longboat Key: Dolphins & Sunsets

Longboat Key house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 45 minutes

Price per night from

$286

1 / 111

Longboat Key Retreat

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$129

1 / 8

Two Story Condo on the Gulf of Mexico

Longboat Key condo

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$514

1 / 5

Renovated Beachfront Condo with Spectacular Ocean View

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$179

1 / 28

Longboat Key Gulf-front 2 BR/2 BA, amazing views

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$272

1 / 12

Beachfront Unit 4, Cozy Getaway for two

Longboat Key apartment

/ 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 crowd

Responds fast! avg. 2 hours 56 minutes

Price per night from

$113

1 / 11

Little Gull Cottages

Longboat Key cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$126

1 / 13

Steps to the Sand! Longboat Key 2 Bed 2 & 1/2 Bath Gulf Front Condo with Den.

Longboat Key apartment

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 56 minutes

Price per night from

$268

1 / 28

Gulf of Mexico Paradise

Longboat Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$142

1 / 13

Outrigger Resort unit #3

Longboat Key apartment

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$214

1 / 29

761 Penfield

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$233

1 / 54

Beautiful Gulf Front Apartment #319 at Sand Cay on Longboat Key

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$245

1 / 15

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 56 minutes

Price per night from

$142

1 / 7

Private Bungalow on Canal a block from Beach

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 34 minutes

Price per night from

$115

1 / 15

LaPlaya 201C

Longboat Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$344

1 / 23

July SPECIAL Designer Villa on canal next to secluded beach

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$145

1 / 18

55+ Community with pool and club house

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$70

1 / 12

** DIRECT OCEAN FRONT SPECIAL MONDAY TO FRIDAY **

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 6 minutes

Price per night from

$159

1 / 29

LUXURIOUS 1 BEDROOM ON THE BEACH , $150.00 PER NIGHT FOR NOVEMBER AND DECEMBER

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

“beautiful condo & wonderful stay” My wife & I just returned from a 4 night stay at this property in Longboat Key and had a wonderful vacation. The condo is beautifully and tastefully decorated, making us feel at home immediately. Everything we needed

Price per night from

$151

1 / 29

LaPlaya 104E

Longboat Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$183

1 / 19

Newly renovated 2/2 w/ private beach access!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 55 minutes

Price per night from

$106

1 / 12

Amazing views of the Gulf and beach from your own balcony

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$178

1 / 35

~OCEAN FRONT SPECIAL ~ Please inquire about special rates

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 6 minutes

Price per night from

$167

1 / 16

** OCEAN FRONT DLX STUDIO - SPECIAL FROM $99/NIGHT **

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 6 minutes

Price per night from

$110

1 / 27

Florida Ocean Front Condo April 13-20, 2019

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$430

1 / 12

Honeysuckle Cottage in North Village of Longboat Key, Fla

Longboat Key cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$101

1 / 17

Beach Front 1 Bedroom Condo on Gulf of Mexico #10

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$158

1 / 6

Village of Longboat Key, 1 BR & 1 BA Comfortable Cottage Very Clean

Longboat Key house

1 bedroom / 1 bathroom / sleeps 4

“VERY Pretty” When they say Luxury Log Cabin, that is exactly what you get. This home was beautiful!! Everything you need to stay all night or a week. Living room with couch chair tv, kitchen with everything. 1 bed and full bath upstairs, wrap arou

Price per night from

$101

1 / 15

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$290

1 / 22

Gorgeous Multi-level Private Home LONGBOAT KEY w/elevator. Short walk to beach!

Longboat Key house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 41 minutes

Price per night from

$133

1 / 28
Viewing 38 of 3,119

About Longboat Key

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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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