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Holiday Lettings
> North America
> United States
> Florida
> Villas and holiday rentals in Anna Maria Island

Villas in Anna Maria Island and Holiday rentals - Holiday Lettings - Holiday Rentals Anna Maria Island

Price per night

£1 £750 -

Bedrooms

Property rating (out of 5)
  • 5
  • 4 and above
  • 3 and above
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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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  • Condo (1)

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1 Holiday homes

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Great rentals within 20 miles that match your search

Holiday condo rental

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £262 / night

£1,831 / week

1 / 20

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Holiday home in St. Pete Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Beach or lakeside relaxation

3 reviews

from £389 / night

£2,720 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday home in Bradenton Beach

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Beach or lakeside relaxation

2 reviews

from £412 / night

£2,880 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday condo in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

2 reviews

from £240 / night

£1,677 / week

1 / 16

Great rentals within 20 miles that match your search

St. Petersburg holiday condo rental

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

1 review

from £92 / night

£2,286 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday condo in Madeira Beach

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Beach or lakeside relaxation

from £275 / night

£1,920 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday condo in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

6 reviews

from £275 / night

£1,920 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday condo rental

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

25 reviews

from £217 / night

£1,518 - £2,076 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday home in Siesta Key

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 filter does not match: Beach or lakeside relaxation

1 review

from £798 / night

£5,581 / week

1 / 23

Great rentals within 20 miles that match your search

Cottage rental in Anna Maria

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

2 reviews

from £283 / night

£1,978 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday townhouse in Siesta Key

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

1 review

from £343 / night

£2,377 / week

1 / 38

Great rentals within 20 miles that match your search

Home rental in Palmetto

Palmetto house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

from £366 / night

£2,560 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday cottage in Bradenton Beach

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Beach or lakeside relaxation

10 reviews

from £196 / night

£1,372 - £3,200 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday home in Treasure Island

Treasure Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

18 reviews

from £366 / night

£2,195 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

5 reviews

from £275 / night

£1,642 - £2,647 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday condo in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

6 reviews

from £362 / night

£2,528 / week

1 / 13

Great rentals within 20 miles that match your search

Treasure Island holiday apartment rental

Treasure Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

9 reviews

from £191 / night

£1,189 / week

1 / 53

Great rentals within 20 miles that match your search

St. Pete Beach holiday apartment let

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

9 reviews

from £320 / night

£2,240 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday home accommodation

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

40 reviews

from £380 / night

£2,656 / week

1 / 36

Great rentals within 20 miles that match your search

Siesta Key holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

15 reviews

from £247 / night

£1,646 - £2,149 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday apartment in Treasure Island

Treasure Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

10 reviews

from £228 / night

£1,555 / week

1 / 72

Great rentals within 20 miles that match your search

Madeira Beach holiday apartment rental

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Beach or lakeside relaxation

9 reviews

from £197 / night

£1,376 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday apartment in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

1 review

from £157 / night

£1,098 / week

1 / 13

Great rentals within 20 miles that match your search

Holmes Beach holiday cottage let

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

8 reviews

from £366 / night

£2,286 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday apartment in Holmes Beach

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

from £138 / night

£960 - £1,646 / week

1 / 19

Great rentals within 20 miles that match your search

Madeira Beach holiday apartment rental

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

17 reviews

from £192 / night

£1,326 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday villa in Siesta Key

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

9 reviews

from £640 / night

£4,480 / week

1 / 27

Great rentals within 20 miles that match your search

Siesta Key holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Beach or lakeside relaxation

2 reviews

from £164 / night

£1,146 / week

1 / 80

Great rentals within 20 miles that match your search

Holiday home in Anna Maria

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

1 filter does not match: Beach or lakeside relaxation

37 reviews

from £503 / night

£1,806 - £9,052 / week

1 / 49

Great rentals within 20 miles that match your search

Home rental in Anna Maria

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

3 reviews

from £174 / night

£1,216 / week

1 / 16

Great rentals within 20 miles that match your search

Treasure Island holiday condo let

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

6 reviews

from £385 / night

£2,695 / week

1 / 37

Great rentals within 20 miles that match your search

Siesta Key holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

18 reviews

from £132 / night

£924 - £1,591 / week

1 / 41

Great rentals within 20 miles that match your search

Indian Shores holiday apartment rental

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Beach or lakeside relaxation

3 reviews

from £196 / night

£1,550 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday townhouse in Siesta Key

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Beach or lakeside relaxation

7 reviews

from £218 / night

£2,635 / week

1 / 50

Great rentals within 20 miles that match your search

Holiday home in Siesta Key

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 filter does not match: Beach or lakeside relaxation

63 reviews

from £400 / night

£2,795 - £5,590 / week

1 / 47

Great rentals within 20 miles that match your search

Indian Shores holiday home rental

Indian Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Beach or lakeside relaxation

from £234 / night

£1,632 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday home in Treasure Island

Treasure Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

1 filter does not match: Beach or lakeside relaxation

45 reviews

from £548 / night

£4,474 / week

1 / 56

Great rentals within 20 miles that match your search

Villa rental in Siesta Key

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Beach or lakeside relaxation

34 reviews

from £406 / night

£2,842 / week

1 / 52

Great rentals within 20 miles that match your search

Holiday apartment in Siesta Key

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 filter does not match: Beach or lakeside relaxation

23 reviews

from £388 / night

£2,715 - £6,308 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday condo in Treasure Island

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Beach or lakeside relaxation

from £138 / night

£960 / week

1 / 31

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