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Holiday Lettings
> North America
> United States
> Florida
> Villas and holiday rentals in Longboat Key

Villas in Longboat Key and Holiday rentals - Holiday Lettings - Holiday Rentals Longboat Key

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£1 £750 -

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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Ski condo to rent in Longboat Key

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £283 / night

£1,981 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £399 / night

£2,791 / week

1 / 18

Holiday condo letting

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £290 / night

£2,029 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £336 / night

£2,352 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £234 / night

£1,632 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £581 / night

£4,064 / week

1 / 26

Holiday condo in Longboat Key

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £357 / night

£2,498 / week

1 / 30

Longboat Key ski condo to rent.

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £361 / night

£2,521 / week

1 / 29

Apartment rental in Longboat Key

Longboat Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £442 / night

£3,092 / week

1 / 27

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £254 / night

£1,775 / week

1 / 30

Ski villa to rent in Longboat Key

Longboat Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £491 / night

£3,437 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £292 / night

£2,041 / week

1 / 30

Condo rental in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £356 / night

£2,487 / week

1 / 30

Longboat Key holiday condo rental

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £218 / night

£1,521 / week

1 / 19

Longboat Key holiday condo rental

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £371 / night

£2,595 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £365 / night

£2,549 / week

1 / 30

Holiday studio in Longboat Key

Longboat Key studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £81 / night

£566 / week

1 / 30

Holiday villa in Longboat Key

Longboat Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £250 / night

£1,747 / week

1 / 24

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £276 / night

£1,928 / week

1 / 20

Ski condo to rent in Longboat Key

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £392 / night

£2,741 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £259 / night

£1,812 / week

1 / 30

Ski condo to rent in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £328 / night

£2,295 / week

1 / 30

Holiday apartment in Longboat Key

Longboat Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £421 / night

£2,945 / week

1 / 23

Condo rental in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £237 / night

£1,656 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £250 / night

£1,747 / week

1 / 18

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £208 / night

£1,453 / week

1 / 30

Holiday apartment in Longboat Key

Longboat Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £246 / night

£1,722 / week

1 / 30

Longboat Key holiday condo rental

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £231 / night

£1,611 / week

1 / 15

Holiday condo rental

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £361 / night

£2,527 / week

1 / 22

Condo letting in Longboat Key

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £352 / night

£2,459 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £375 / night

£2,623 / week

1 / 30

Holiday apartment in Longboat Key

Longboat Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £186 / night

£1,300 / week

1 / 13

Holiday condo in Longboat Key

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £452 / night

£3,160 / week

1 / 30

Longboat Key holiday condo rental

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £372 / night

£2,600 / week

1 / 30

Condo rental in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £205 / night

£1,430 / week

1 / 17

Holiday condo in Longboat Key

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £243 / night

£1,702 / week

1 / 30

Holiday apartment in Longboat Key

Longboat Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £204 / night

£1,425 / week

1 / 14

Ski condo to rent in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £361 / night

£2,527 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £323 / night

£2,261 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £472 / night

£3,303 / week

1 / 29

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Longboat Key holidays

With warm weather year-round and some of the best beaches in the region, Longboat Key has become one of the premiere holiday 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 holiday 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 holiday 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.

Also consider