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Longboat Key Rentals

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Longboat Key Rentals

About Longboat Key

93 apartments

NEW! 2BR Longboat Key Condo - Walk to Bay!

Longboat Key apartment

2 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 14 minutes

$115

1 / 24

Spacious Gulf Front beach condo on Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / Sleeps 4

$199

1 / 17

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. 3 hours 52 minutes

$113

1 / 11

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

Longboat Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$272

1 / 12

Florida Ocean Front Condo April 13-20, 2019

Longboat Key condo

2 bedrooms / 2 bathrooms / Sleeps 6

$429

1 / 12

Gulf Breezes, Soft Sand! Your Place on the beach!

Longboat Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Brillant” This was the best place I ever stayed in - it was just on the beech and even though the water was chilly the pool is heated- the grounds are a delight for plant lovers , and included an orchid garden- the staff are top class - always there

$171

1 / 55

~OCEAN FRONT SPECIAL ~ Please inquire about special rates

Longboat Key apartment

1 bedroom / 1 bathroom / Sleeps 4

$186

1 / 16

Beach Front 1 Bedroom Condo on Gulf of Mexico #10

Longboat Key apartment

1 bedroom / 1 bathroom / Sleeps 4

$158

1 / 6

Longboat Key Retreat

Longboat Key house

2 bedrooms / 2 bathrooms / Sleeps 4

$129

1 / 8

The perfect vacation spot on Longboat Key

Longboat Key condo

1 bedroom / 1 bathroom / Sleeps 2

$128

1 / 28

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. 3 hours 52 minutes

$124

1 / 6

Sand Cay #310 Luxurious 2/2 on the Beach

Longboat Key condo

2 bedrooms / 2 bathrooms / Sleeps 6

$185

1 / 27

Outrigger Resort unit #3

Longboat Key apartment

3 bedrooms / 4 bathrooms / Sleeps 8

$214

1 / 29

** 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.

$109

1 / 17

Newly renovated 2/2 w/ private beach access!

Longboat Key condo

2 bedrooms / 2 bathrooms / Sleeps 5

$106

1 / 12

55+ Community with pool and club house

Longboat Key villa

2 bedrooms / 2 bathrooms / Sleeps 6

$70

1 / 12

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. 3 hours 52 minutes

$142

1 / 7

** DIRECT OCEAN FRONT SPECIAL MONDAY TO FRIDAY **

Longboat Key apartment

1 bedroom / 1 bathroom / Sleeps 3

$139

1 / 28

Little Gull Cottages

Longboat Key cottage

1 bedroom / 1 bathroom / Sleeps 4

$125

1 / 9

LaPlaya 109A

Longboat Key condo

2 bedrooms / 2 bathrooms / Sleeps 4

$258

1 / 31

Gulf of Mexico Paradise

Longboat Key apartment

2 bedrooms / 1 bathroom / Sleeps 4

$142

1 / 13

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

Longboat Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$67

1 / 24

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

$300

1 / 38

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

Longboat Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$214

1 / 18

Longboat Key: Dolphins & Sunsets

Longboat Key house

3 bedrooms / 4 bathrooms / Sleeps 6

Responds fast! avg. 53 minutes

$286

1 / 111

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 52 minutes

$142

1 / 7

Whitney Beach 145

Longboat Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$83

1 / 28

Sunshine Cottage, Historic Longbeach Village

Longboat Key cottage

2 bedrooms / 2 bathrooms / Sleeps 4

Responds fast! avg. 3 hours 7 minutes

$157

1 / 10

Waterfront 4 BR Home with Private Dock and Screened Pool!

Longboat Key house

4 bedrooms / 2 bathrooms / Sleeps 10

$299

1 / 96

Lovely Tropical Longboat Town house

Longboat Key townhouse

2 bedrooms / 3 bathrooms / Sleeps 6

$128

1 / 24

Tropical Waterfront Home in Historic Village

Longboat Key house

2 bedrooms / 2 bathrooms / Sleeps 5

$350

1 / 23

Private Bungalow on Canal a block from Beach

Longboat Key house

2 bedrooms / 2 bathrooms / Sleeps 4

$175

1 / 15

761 Penfield

Longboat Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$233

1 / 54

Holiday Home Directly by Sea - Self Catering

Longboat Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$186

1 / 28

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

Responds fast! avg. 2 hours 31 minutes

$100

1 / 14

BBB on Marbury lane-Beach, boating, BBQ!

Longboat Key house

3 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 2 hours 6 minutes

$195

1 / 19

Renovated Beachfront Condo with Spectacular Ocean View

Longboat Key apartment

1 bedroom / 1 bathroom / Sleeps 6

$138

1 / 28

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / Sleeps 6

$290

1 / 22
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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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