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Holiday Lettings
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> 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

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  • 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.
Property type
  • Townhouse (1)
  • Apartment (19)
  • Villa (2)
  • Cottage (4)
  • House (25)
  • Manor House (1)
  • Bungalow (1)
  • Studio (3)
  • Condo (39)
  • Guest house (1)
  • Hotel apartment (1)

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1 Holiday homes

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Great rentals within 20 miles that match your search

Holiday townhouse in Siesta Key

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6
1 review

from £344 / night

£2,382 / week

1 / 38

Great rentals within 20 miles that match your search

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St. Petersburg holiday home rental

St. Petersburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £206 / night

£1,443 / 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: Property type

1 review

from £916 / night

£6,412 / 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: Property type

2 reviews

from £240 / night

£1,680 / 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: Property type

1 review

from £92 / night

£2,290 / week

1 / 24

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: Property type

25 reviews

from £218 / night

£1,520 - £2,080 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday bungalow in Treasure Island

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

10 reviews

from £174 / night

£1,077 - £1,718 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday condo in Treasure Island

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

4 reviews

from £277 / night

£1,799 - £1,992 / week

1 / 28

Great rentals within 20 miles that match your search

Apartment rental in St. Petersburg

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

3 reviews

from £106 / night

£710 / week

1 / 19

Great rentals within 20 miles that match your search

Siesta Key holiday condo rental

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

29 reviews

from £227 / night

£1,588 - £3,199 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday condo rental

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

1 review

from £129 / night

£898 / week

1 / 52

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: Property type

18 reviews

from £133 / night

£926 - £1,596 / week

1 / 41

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: Walking holidays

7 reviews

from £218 / night

£2,640 / week

1 / 50

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: Property type

1 review

from £182 / night

£1,270 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday apartment in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Property type

2 reviews

from £81 / night

£567 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday home in Siesta Key

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 filter does not match: Property type

2 reviews

from £321 / night

£2,290 / week

1 / 22

Great rentals within 20 miles that match your search

Madeira Beach holiday condo rental

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

4 reviews

from £266 / night

£2,016 - £2,290 / week

1 / 14

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: Property type

44 reviews

from £159 / night

£1,209 - £2,290 / week

1 / 43

Great rentals within 20 miles that match your search

Bradenton holiday home rental

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

11 reviews

from £294 / night

£2,052 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday condo in St. Petersburg

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

20 reviews

from £344 / night

£2,405 / week

1 / 120

Great rentals within 20 miles that match your search

Holiday condo in Bradenton

Bradenton condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

1 review

from £86 / night

£599 / week

1 / 16

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: Property type

7 reviews

from £164 / night

£1,145 / week

1 / 28

Great rentals within 20 miles that match your search

Siesta Key holiday condo rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

8 reviews

from £152 / night

£1,100 - £1,924 / week

1 / 22

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: Property type

35 reviews

from £126 / night

£859 - £1,684 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday condo with swimming pool in Madeira Beach

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

25 reviews

from £458 / night

£1,237 - £2,382 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday villa in Bradenton Beach

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Property type

from £458 / night

£3,206 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday townhouse in Bradenton Beach

Bradenton Beach townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Walking holidays

from £229 / night

£1,603 / week

1 / 16

Great rentals within 20 miles that match your search

Townhouse rental in Tierra Verde

Tierra Verde townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Walking holidays

from £229 / night

£1,603 / week

1 / 4

Great rentals within 20 miles that match your search

Siesta Key holiday condo rental

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

1 review

from £393 / night

£2,748 / week

1 / 23

Great rentals within 20 miles that match your search

Townhouse rental in Siesta Key

Siesta Key townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Walking holidays

from £190 / night

£1,329 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday home in Cortez

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £1,200 / night

£6,964 / week

1 / 60

Great rentals within 20 miles that match your search

Holiday hotel apartment in Treasure Island

Treasure Island hotel apartment

  • 12 bedrooms
  • 11 bathrooms
  • sleeps 49

1 filter does not match: Property type

from £2,474 / night

£17,312 / week

1 / 53

Great rentals within 20 miles that match your search

Studio rental in St. Pete Beach

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 1

1 filter does not match: Property type

from £138 / night

£1,374 / week

1 / 9

Great rentals within 20 miles that match your search

Condo accommodation in Holmes Beach with golf nearby

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £623 / night

£4,360 / week

1 / 55

Great rentals within 20 miles that match your search

Madeira Beach ski guest house to rent.

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

1 review

from £138 / night

£962 / week

1 / 100

Great rentals within 20 miles that match your search

Holiday cottage in Anna Maria Island

Anna Maria Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

35 reviews

from £88 / night

£616 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday townhouse with shared pool in Tierra Verde

Tierra Verde townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Walking holidays

from £330 / night

£2,309 / week

1 / 54

Great rentals within 20 miles that match your search

Holiday home with golf nearby in St. Pete Beach

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

22 reviews

from £174 / night

£916 / week

1 / 31

Great rentals within 20 miles that match your search

Apartment letting in Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Property type

from £110 / night

£770 / week

1 / 75

Great rentals within 20 miles that match your search

Sarasota holiday apartment rental

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Property type

from £110 / night

£770 / week

1 / 72

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