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

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1,439 Holiday homes

Holiday studio in Longboat Key

Longboat Key studio

Studio • 1 bathroom • sleeps 2

from £101 / night

£704 - £1,047 / week

1 / 11

Condo rental in Longboat Key

Longboat Key condo

1 bedroom • 1 bathroom • sleeps 2

from £66 / night

£463 / week

1 / 18

Apartment rental in Longboat Key

Longboat Key apartment

1 bedroom • 1 bathroom • sleeps 3

from £141 / night

£872 - £1,404 / week

1 / 21

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms • 2 bathrooms • sleeps 4

from £226 / night

£1,580 / week

1 / 17

Holiday condo with shared pool in Longboat Key

Longboat Key condo

2 bedrooms • 2 bathrooms • sleeps 4

from £226 / night

£1,580 / week

1 / 25

Longboat Key holiday condo rental

Longboat Key condo

3 bedrooms • 3 bathrooms • sleeps 6

from £372 / night

£2,605 / week

1 / 21

Holiday home in Longboat Key

Longboat Key house

3 bedrooms • 2 bathrooms • sleeps 5

from £187 / night

£1,305 / week

1 / 31

Holiday cottage in Longboat Key

Longboat Key cottage

1 bedroom • 1 bathroom • sleeps 4

from £77 / night

£535 / week

1 / 15

Longboat Key holiday condo rental

Longboat Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from £262 / night

£1,832 / week

1 / 11

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms • 2 bathrooms • sleeps 5

from £125 / night

£875 / week

1 / 20

Longboat Key holiday condo rental

Longboat Key condo

1 bedroom • 1 bathroom • sleeps 4

from £166 / night

£1,160 / week

1 / 39

Holiday guest house in Longboat Key

Longboat Key guest house

1 bedroom • 1 bathroom • sleeps 2

from £85 / night

£590 / week

1 / 19

Holiday condo in Longboat Key

Longboat Key condo

1 bedroom • 1 bathroom • sleeps 4

from £190 / night

£1,330 / week

1 / 10

Longboat Key holiday home rental

Longboat Key house

3 bedrooms • 2 bathrooms • sleeps 6

from £147 / night

£1,026 / week

1 / 15

Holiday condo with shared pool in Longboat Key

Longboat Key condo

3 bedrooms • 2 bathrooms • sleeps 6

from £152 / night

£775 / week

1 / 56

Longboat Key holiday apartment rental

Longboat Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £162 / night

£1,081 / week

1 / 28

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms • 2 bathrooms • sleeps 4

from £238 / night

£1,908 / week

1 / 7

Holiday condo with shared pool in Longboat Key

Longboat Key condo

3 bedrooms • 2 bathrooms • sleeps 6

from £301 / night

£2,104 / week

1 / 24

Holiday condo with shared pool in Longboat Key

Longboat Key condo

3 bedrooms • 2 bathrooms • sleeps 6

from £301 / night

£2,104 / week

1 / 18

Holiday condo with shared pool in Longboat Key

Longboat Key condo

3 bedrooms • 2 bathrooms • sleeps 6

from £301 / night

£2,104 / week

1 / 20

Holiday condo with shared pool in Longboat Key

Longboat Key condo

3 bedrooms • 2 bathrooms • sleeps 6

from £301 / night

£2,104 / week

1 / 6

Holiday condo with shared pool in Longboat Key

Longboat Key condo

3 bedrooms • 2 bathrooms • sleeps 6

from £301 / night

£2,104 / week

1 / 34

Holiday condo with shared pool in Longboat Key

Longboat Key condo

2 bedrooms • 1 bathroom • sleeps 4

from £261 / night

£1,908 / week

1 / 15

Holiday condo with shared pool in Longboat Key

Longboat Key condo

2 bedrooms • 1 bathroom • sleeps 4

from £160 / night

£1,119 / week

1 / 12

Holiday condo with shared pool in Longboat Key

Longboat Key condo

2 bedrooms • 2 bathrooms • sleeps 4

from £238 / night

£1,908 / week

1 / 12

Holiday condo with shared pool in Longboat Key

Longboat Key condo

2 bedrooms • 2 bathrooms • sleeps 4

from £226 / night

£1,580 / week

1 / 9

Holiday condo with shared pool in Longboat Key

Longboat Key condo

2 bedrooms • 2 bathrooms • sleeps 4

from £247 / night

£1,908 / week

1 / 22

Holiday condo with shared pool in Longboat Key

Longboat Key condo

2 bedrooms • 1 bathroom • sleeps 4

from £169 / night

£1,394 / week

1 / 5

Holiday studio in Longboat Key

Longboat Key studio

Studio • 1 bathroom • sleeps 3

from £141 / night

£874 - £1,108 / week

1 / 29

Holiday apartment in Longboat Key

Longboat Key apartment

1 bedroom • 1 bathroom • sleeps 3

from £141 / night

£875 - £1,108 / week

1 / 23

Holiday bungalow accommodation

Longboat Key bungalow

2 bedrooms • 2 bathrooms • sleeps 6

from £178 / night

£1,246 / week

1 / 34

Holiday studio in Longboat Key

Longboat Key studio

Studio • 1 bathroom • sleeps 4

from £119 / night

£829 - £1,432 / week

1 / 6

Longboat Key holiday condo rental

Longboat Key condo

1 bedroom • 1 bathroom • sleeps 4

from £158 / night

£1,102 / week

1 / 41

Holiday villa with shared pool in Longboat Key

Longboat Key villa

2 bedrooms • 1 bathroom • sleeps 6

from £115 / night

£805 / week

1 / 24

Holiday apartment in Longboat Key

Longboat Key apartment

1 bedroom • 1 bathroom • sleeps 6

from £171 / night

£1,195 / week

1 / 35

Holiday cottage with shared pool in Longboat Key

Longboat Key cottage

2 bedrooms • 2 bathrooms • sleeps 4

from £98 / night

£682 / week

1 / 12

Holiday condo in Longboat Key

Longboat Key condo

2 bedrooms • 1 bathroom • sleeps 4

from £70 / night

£489 / week

1 / 30

Holiday condo in Longboat Key

Longboat Key condo

1 bedroom • 1 bathroom • sleeps 4

from £96 / night

£670 / week

1 / 25

Holiday condo with golf nearby in Longboat Key

Longboat Key condo

3 bedrooms • 2 bathrooms • sleeps 6

from £184 / night

£1,249 - £1,749 / week

1 / 40

Longboat Key holiday villa accommodation

Longboat Key villa

2 bedrooms • 2 bathrooms • sleeps 10

from £304 / night

£2,127 / week

1 / 41

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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.

Top Destination reviews

LaPlaya 109A-Enjoy the balmy Gulf breezes in this corner end unit right on the b
Fantasy!

Unforgettable visit! Well-appointed condo. Full view of ocean from kitchen and den. Lanai off of den. Walk out onto beach. Great location. … see more

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