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Viewing 40 of 706 rentals in Anna Maria Island

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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 -

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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.
Property type
  • Apartment (1)
  • Bungalow (1)
  • Private room (1)

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3 Holiday homes

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Private pool
City breaks

Great rentals within 20 miles that match your search

Holiday bungalow with swimming pool in St. Petersburg

St. Petersburg bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £83 / night

£486 - £1,777 / week

1 / 42

Great rentals within 20 miles that match your search

Holiday private room in St. Petersburg

St. Petersburg private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2
1 review

from £115 / night

£685 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday apartment in Siesta Key

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10
23 reviews

from £388 / night

£2,712 - £6,302 / week

1 / 24

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Holiday condo with shared pool in Redington Shores

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Private pool

from £274 / night

£1,918 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday apartment in Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Private pool

from £186 / night

£1,302 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday apartment in St. Petersburg

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Private pool

5 reviews

from £115 / night

£772 / week

1 / 17

Great rentals within 20 miles that match your search

St. Petersburg holiday home rental

St. Petersburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: City breaks

from £206 / night

£1,439 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday manor house in St. Petersburg

St. Petersburg manor house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

1 filter does not match: City breaks

1 review

from £914 / night

£6,394 / 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 3

1 filter does not match: Private pool

from £165 / night

£914 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday apartment with golf nearby in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: City breaks

1 review

from £229 / night

£1,285 - £4,499 / week

1 / 59

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: City breaks

2 reviews

from £411 / night

£2,877 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Sarasota

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 filter does not match: City breaks

2 reviews

from £183 / night

£1,279 / week

1 / 21

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: City breaks

1 review

from £797 / night

£5,575 / week

1 / 23

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: Private pool

1 review

from £343 / night

£2,375 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Treasure Island

Treasure Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

1 filter does not match: City breaks

5 reviews

from £1,576 / night

£11,029 / week

1 / 99

Great rentals within 20 miles that match your search

Holiday home in Sarasota

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Private pool

19 reviews

from £151 / night

£1,055 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday cottage with swimming pool in Sarasota

Sarasota cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: City breaks

1 review

from £424 / night

£2,969 / week

1 / 32

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: City breaks

9 reviews

from £320 / night

£2,238 / 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: City breaks

40 reviews

from £379 / night

£2,654 / week

1 / 36

Great rentals within 20 miles that match your search

Gulfport holiday home rental

Gulfport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: City breaks

6 reviews

from £293 / night

£2,046 / week

1 / 21

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: City breaks

1 review

from £157 / night

£1,096 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday apartment with golf nearby in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: City breaks

5 reviews

from £188 / night

£1,023 - £3,749 / week

1 / 60

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: City breaks

37 reviews

from £503 / night

£1,804 - £9,042 / week

1 / 49

Great rentals within 20 miles that match your search

Holiday apartment with swimming pool, golf nearby in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: City breaks

2 reviews

from £151 / night

£852 - £2,999 / week

1 / 91

Great rentals within 20 miles that match your search

Holiday apartment with golf nearby in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: City breaks

12 reviews

from £265 / night

£1,486 - £5,163 / week

1 / 48

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: City breaks

63 reviews

from £399 / night

£2,792 - £5,584 / week

1 / 47

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: City breaks

45 reviews

from £547 / night

£4,469 / 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: Private pool

34 reviews

from £406 / night

£2,839 / week

1 / 52

Great rentals within 20 miles that match your search

Holmes Beach holiday home rental

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: City breaks

from £183 / night

£1,279 / week

1 / 45

Great rentals within 20 miles that match your search

Apartment rental in Indian Shores

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: City breaks

18 reviews

from £305 / night

£2,129 - £3,408 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday apartment in Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Private pool

11 reviews

from £83 / night

£576 / week

1 / 8

Great rentals within 20 miles that match your search

Apartment rental in Anna Maria Island with golf nearby

Anna Maria Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: City breaks

21 reviews

from £210 / night

£1,159 - £4,111 / week

1 / 70

Great rentals within 20 miles that match your search

St. Pete Beach holiday cottage rental

St. Pete Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Private pool

from £256 / night

£1,608 - £5,010 / week

1 / 67

Great rentals within 20 miles that match your search

Holiday studio with golf nearby in Holmes Beach

Holmes Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 filter does not match: City breaks

1 review

from £181 / night

£1,266 / week

1 / 36

Great rentals within 20 miles that match your search

Indian Shores holiday condo accommodation

Indian Shores condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: City breaks

44 reviews

from £158 / night

£1,206 - £2,284 / week

1 / 43

Great rentals within 20 miles that match your search

Condo accommodation in Treasure Island with swimming pool

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: City breaks

7 reviews

from £164 / night

£1,142 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday condo in Treasure Island

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Private pool

80 reviews

from £176 / night

£1,106 - £4,091 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday apartment rental

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: City breaks

from £137 / night

£959 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday condo rental

St. Pete Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: City breaks

1 review

from £320 / night

£2,238 / week

1 / 13

Great rentals within 20 miles that match your search

Longboat Key holiday villa accommodation

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Private pool

16 reviews

from £389 / night

£2,718 / week

1 / 41

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