50 Best Anna Maria Island Villas and Holiday rentals – Holiday Lettings - Holiday Rentals Anna Maria Island

Close

View larger map

Also consider

Villas Holmes Beach
288 properties
Villas Bradenton Beach
150 properties
Holiday rentals Anna Maria
85 properties
Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

537 Holiday homes

Travellers going to Anna Maria Island are booking July dates now. Secure your holiday home today and have the perfect trip.

(13) Excellent 

1 / 32

Holiday home accommodation

Anna Maria Island / Holmes Beach

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $200 / night

$1401 - $2150 / week

Book Book View

from $200 / night

(14) Very Good 

1 / 45

Holiday home in Anna Maria

Anna Maria Island / Anna Maria

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from $286 / night

$1776 - $5198 / week

Book Book View

from $286 / night

(5) Excellent 

1 / 24

Holiday home in Anna Maria

Anna Maria Island / Anna Maria

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $225 / night

$1401 - $3250 / week

Book Book View

from $225 / night

(3) Excellent 

1 / 41

Holiday home with swimming pool in Anna Maria

Anna Maria Island / Anna Maria

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $200 / night

$1400 - $2400 / week

Book Book View

from $200 / night

(5) Excellent 

1 / 21

Holiday apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay

from $200 / night

$1201 - $1951 / week

Book Book View

from $200 / night

(19) Excellent 

1 / 21

Holiday cottage in Bradenton Beach

Anna Maria Island / Bradenton Beach

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $130 / night

$825 - $875 / week

Book Book View

from $130 / night

(3) Good 

1 / 23

Holmes Beach holiday home rental

Anna Maria Island / Holmes Beach

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $301 / night

$1761 - $2201 / week

Book Book View

from $301 / night

(2) Excellent 

1 / 23

Holiday home in Anna Maria

Anna Maria Island / Anna Maria

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $309 / night

$2100 - $3495 / week

Book Book View

from $309 / night

(4) Very Good 

1 / 13

Holiday apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $206 / night

$1350 - $2201 / week

Book Book View

from $206 / night

(7) Excellent 

1 / 25

Anna Maria Island holiday home rental

Florida / Anna Maria Island

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $200 / night

$1401 - $1750 / week

Book Book View

from $200 / night

(9) Excellent 

1 / 23

Apartment rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $221 / night

$1500 - $2451 / week

Book Book View

from $221 / night

(1) Excellent 

1 / 25

Holiday home in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $216 / night

$1506 - $2444 / week

Book Book View

from $216 / night

(3) Very Good 

1 / 24

Holmes Beach holiday apartment rental

Anna Maria Island / Holmes Beach

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $166 / night

$886 - $1286 / week

Book Book View

from $166 / night

(3) Good 

1 / 35

Holiday home in Anna Maria

Anna Maria Island / Anna Maria

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $358 / night

$2500 - $3500 / week

Book Book View

from $358 / night

(11) Excellent 

1 / 35

Holiday apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $143 / night

$996 - $1900 / week

Book Book View

from $143 / night

(10) Excellent 

1 / 33

Bradenton Beach holiday apartment rental

Anna Maria Island / Bradenton Beach

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from $151 / night

$1000 / week

Book Book View

from $151 / night

(9) Excellent 

1 / 28

Holiday home in Holmes Beach

Anna Maria Island / Holmes Beach

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $136 / night

$951 - $1600 / week

Book Book View

from $136 / night

(7) Very Good 

1 / 10

Bradenton Beach holiday studio rental

Anna Maria Island / Bradenton Beach

Sleeps 52 nights min stay

  • Sleeps 5
  • 2 nights min stay

from $145 / night

$985 - $1451 / week

Book Book View

from $145 / night

1 / 29

Holiday condo in Anna Maria Island

Florida / Anna Maria Island

2 bedroomsSleeps 51 night min stay

  • 2 bedrooms
  • Sleeps 5
  • 1 night min stay

from $121 / night

$801 - $1500 / week

Book Book View

from $121 / night

1 / 44

Cottage rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $144 / night

$1007 - $1628 / week

Book Book View

from $144 / night

(5) Very Good 

1 / 10

Home rental in Holmes Beach with shared pool

Anna Maria Island / Holmes Beach

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from $486 / night

$3400 - $4101 / week

Book Book View

from $486 / night

(2) Very Good 

1 / 14

Holmes Beach holiday home rental

Anna Maria Island / Holmes Beach

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $301 / night

$2100 / week

Book Book View

from $301 / night

1 / 16

Apartment rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $225 / night

$1551 - $2555 / week

Book Book View

from $225 / night

(1) Excellent 

1 / 16

Bradenton Beach holiday apartment rental

Anna Maria Island / Bradenton Beach

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $195 / night

$1100 - $1951 / week

Book Book View

from $195 / night

(8) Excellent 

1 / 33

Home rental in Anna Maria Island

Florida / Anna Maria Island

3 bedroomsSleeps 730 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 30 nights min stay

from $233 / night

$1632 / week

Book Book View

from $233 / night

(9) Very Good 

1 / 88

Holiday home in Holmes Beach

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $154 / night

$1076 - $1375 / week

Book Book View

from $154 / night

(1) Excellent 

1 / 20

Holmes Beach holiday cottage let

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $199 / night

$967 - $1653 / week

Book Book View

from $199 / night

(3) Excellent 

1 / 10

Holiday home with shared pool in Holmes Beach

Anna Maria Island / Holmes Beach

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $465 / night

$3250 - $3701 / week

Book Book View

from $465 / night

(17) Very Good 

1 / 41

Holiday apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $114 / night

$801 - $1100 / week

Book Book View

from $114 / night

1 / 18

Anna Maria holiday home rental

Anna Maria Island / Anna Maria

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $200 / night

$1401 - $1750 / week

Book Book View

from $200 / night

(1) Very Good 

1 / 19

Bradenton Beach holiday condo rental

Anna Maria Island / Bradenton Beach

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $151 / night

$963 - $1532 / week

Book Book View

from $151 / night

(5) Very Good 

1 / 17

Holmes Beach holiday apartment rental

Anna Maria Island / Holmes Beach

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $200 / night

$1091 - $1581 / week

Book Book View

from $200 / night

(1) Excellent 

1 / 9

Holmes Beach holiday home rental

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $122 / night

$850 - $1201 / week

Book Book View

from $122 / night

(1) Excellent 

1 / 24

Holiday cottage with swimming pool in Holmes Beach

Anna Maria Island / Holmes Beach

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $200 / night

$1100 - $1420 / week

Book Book View

from $200 / night

(1) Excellent 

1 / 39

Holiday home in Anna Maria

Anna Maria Island / Anna Maria

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from $270 / night

$1850 - $2000 / week

Book Book View

from $270 / night

(1) Excellent 

1 / 33

Holmes Beach holiday condo rental

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $100 / night

$651 - $1401 / week

Book Book View

from $100 / night

(5) Excellent 

1 / 27

Holiday apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $200 / night

$1301 - $1631 / week

Book Book View

from $200 / night

(1) Good 

1 / 13

Holmes Beach holiday apartment rental

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $166 / night

$1000 - $1490 / week

Book Book View

from $166 / night

1 / 18

Holmes Beach holiday condo rental

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $121 / night

$850 - $901 / week

Book Book View

from $121 / night

(1) Excellent 

1 / 19

Holiday apartment rental

Anna Maria Island / Holmes Beach

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $128 / night

$896 / week

Book Book View

from $128 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page