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

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2,041 Holiday homes

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

from £255 / night

£1,786 - £2,214 / week

Home rental in Longboat Key with swimming pool

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

3

from £215 / night

£1,504 / week

Holiday apartment in Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

15

Responds fast! avg. 2 hours 37 minutes

from £222 / night

£1,549 - £1,681 / week

Longboat Key holiday apartment rental

Longboat Key apartment

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 8 minutes

from £149 / night

£1,041 / week

Holiday home rental

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

2

from £121 / night

£848 / week

Holiday studio in Longboat Key

Longboat Key studio

Studio / 1 bathroom / sleeps 4

10

Responds fast! avg. 2 hours 37 minutes

from £200 / night

£1,395 - £1,526 / week

Apartment rental in Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 6

1

Responds fast! avg. 3 hours 21 minutes

from £177 / night

£1,220 - £1,417 / week

Holiday studio in Longboat Key

Longboat Key studio

Studio / 1 bathroom / sleeps 2

13

Responds fast! avg. 2 hours 37 minutes

from £170 / night

£1,184 / week

Holiday villa rental

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 6

from £66 / night

£462 / week

Longboat Key holiday condo rental

Longboat Key condo

4 bedrooms / 4 bathrooms / sleeps 10

from £510 / night

£3,571 / week

Holiday apartment in Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

11

Responds fast! avg. 2 hours 37 minutes

from £222 / night

£1,549 - £1,681 / week

Holiday apartment in Longboat Key

Longboat Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 51 minutes

from £181 / night

£1,265 - £1,621 / week

Apartment rental in Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

6

Responds fast! avg. 3 hours 36 minutes

from £131 / night

£822 - £1,579 / week

Holiday condo in Longboat Key

Longboat Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 51 minutes

from £340 / night

£2,379 - £2,886 / week

Holiday studio in Longboat Key

Longboat Key studio

Studio / 1 bathroom / sleeps 3

5

Responds fast! avg. 3 hours 36 minutes

from £94 / night

£612 - £1,252 / week

Holiday apartment in Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 21 minutes

from £184 / night

£1,203 - £1,418 / week

Holiday apartment in Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 36 minutes

from £94 / night

£612 - £1,252 / week

Longboat Key holiday villa accommodation

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 10

8

from £329 / night

£3,262 - £4,645 / week

Holiday condo rental

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 14 minutes

from £404 / night

£2,824 / week

Holiday apartment in Longboat Key

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

1

from £132 / night

£921 / week

Longboat Key holiday condo rental

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 6

4

from £159 / night

£1,114 / week

Holiday condo with golf nearby in Longboat Key

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

from £273 / night

£1,911 / week

Holiday home in Longboat Key

Longboat Key house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 31 minutes

from £126 / night

£882 / week

Holiday condo in Longboat Key

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

1

Responds fast! avg. 39 minutes

from £292 / night

£2,354 / week

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 51 minutes

from £287 / night

£2,010 - £2,405 / week

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

from £263 / night

£1,839 - £2,214 / week

Longboat Key holiday townhouse rental

Longboat Key townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 54 minutes

from £121 / night

£841 - £1,715 / week

Longboat Key holiday home rental

Longboat Key house

3 bedrooms / 3 bathrooms / sleeps 8

from £236 / night

£1,648 / week

Longboat Key holiday condo rental

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 14 minutes

from £255 / night

£1,785 / week

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 51 minutes

from £187 / night

£1,305 - £1,621 / week

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

from £287 / night

£2,010 - £2,405 / week

Longboat Key holiday apartment rental

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

from £63 / night

£442 / week

Longboat Key holiday apartment rental

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

from £175 / night

£1,224 / week

Longboat Key holiday home rental

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 5

from £605 / night

£4,236 / week

Holiday condo in Longboat Key

Longboat Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 51 minutes

from £340 / night

£2,379 - £2,886 / week

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

from £255 / night

£1,786 - £2,214 / week

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 51 minutes

from £181 / night

£1,265 - £1,621 / week

Holiday condo in Longboat Key

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 14 minutes

from £188 / night

£1,316 / week

Longboat Key holiday condo rental

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 14 minutes

from £256 / night

£1,789 / week

Holiday condo with shared pool in Longboat Key

Longboat Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 7 minutes

from £203 / night

£1,200 - £1,430 / week

Viewing 40 of 2,041
rentals in Longboat Key

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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.

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