50 Best Anna Maria Island Vacation rentals on Holiday Lettings - Beach rentals

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105 properties

Anna Maria Island

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634 Vacation rentals

Travelers going to Anna Maria Island are booking April dates now. Secure your vacation rental today and have the perfect trip.

(4) Excellent 

28

Vacation condo in Anna Maria Island

Florida / Anna Maria Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in the heart of Anna Maria Island in the sun-drenched community of Holmes Beach is 'Seacrest' where you can enjoy island living at its best in this stunning destination.Our light & roomy 2 bedroom condo (one of only four in a quiet location being i  …see more

from $106 / night

$738 - $1725 / week

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from $106 / night

(5) Excellent 

15

Anna Maria Island Vacation cottage rental

Florida / Anna Maria Island

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Shell Cottage is situated just 200ft away from the beautiful white sandy beach of Anna Maria which is 7 miles long. Set in a quiet leafy lane Shell shares our heated pool with our other 2 cottages and can be rented together or separately. Shell Cottage has a small sofa-  …see more

from $135 / night

$945 - $1400 / week

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from $135 / night

(31) Excellent 

39

Townhouse rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Anna Maria Island is situated on Florida's beautiful Gulf Coast and offers many varied activities for the discerning holiday maker - stunning beaches, fine restaurants and many outdoor activities such as fishing, sailing, water sports, golfing, shopping and cultura  …see more

from $186 / night

$1300 - $1900 / week

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from $186 / night

(1) Excellent 

11

Anna Maria Island Vacation home rental

Florida / Anna Maria Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
The Beach House is situated on one of the quietest areas of the beautiful white sandy beach, that stretches from one end of the island to the other. A nature lovers paradise where you can sit on the balcony with a glass of chilled wine and watch the dolphins play in the  …see more

from $285 / night

$1995 - $2978 / week

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from $285 / night

(1) Good 

15

Vacation home in Anna Maria Island

Florida / Anna Maria Island

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
BEACHCOMBER, just 200ft from 7 miles of white sandy beach, is a beautifully furnished cottage with 2 bedrooms, 1 double and 1 twin. The master bedroom has an en-suite bathroom. There is also a 2nd bathroom with shower, WC and basin only. A large open plan living room  …see more

from $145 / night

$1015 - $1330 / week

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from $145 / night

(1) Excellent 

8

Florida / Anna Maria Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $108 / night

$751 - $1200 / week

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from $108 / night

11

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 60 nights min

  • 2 bedrooms
  • Sleeps 6
  • 60 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This beautiful island condo is newly refurbished and redecorated for a perfect get-away. This quiet, 55+ community is a paradise. Situated in Anna Maria Island, Florida, the island has quiet, old-Florida charm with numerous restaurants, shops, and conveniences. A fre  …see more

from $94 / night

$654 / week

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from $94 / night

(2) Excellent 

75

Anna Maria Island / Bradenton Beach

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $107 / night

$1260 - $2450 / week

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from $107 / night

26

Anna Maria Island / Holmes Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $258 / night

$2500 - $3500 / week

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from $258 / night

(24) Excellent 

17

Anna Maria Island / Bradenton Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $120 / night

$795 - $895 / week

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from $120 / night

(1) Excellent 

13

Anna Maria Island / Bradenton Beach

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $42 / night

$294 / week

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from $42 / night

(2) Excellent 

29

Florida / Anna Maria Island

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $120 / night

$800 - $1200 / week

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from $120 / night

(1) Excellent 

21

Anna Maria Island / Anna Maria

Studio 7 7 nights min

  • Studio
  • Sleeps 7
  • 7 nights min
  • Ask about children

 …see more

from $229 / night

$1600 - $1900 / week

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from $229 / night

(1) Excellent 

44

Anna Maria Island / Anna Maria

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $357 / night

$2500 - $2900 / week

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from $357 / night

33

Anna Maria Island / Anna Maria

Studio 10 7 nights min

  • Studio
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children

 …see more

from $465 / night

$3250 - $3650 / week

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from $465 / night

6

Anna Maria Island / Bradenton Beach

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children

 …see more

from $115 / night

$800 - $1000 / week

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from $115 / night

(29) Excellent 

24

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $135 / night

$850 - $1350 / week

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from $135 / night

20

Anna Maria Island / Bradenton Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $115 / night

$800 - $1400 / week

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from $115 / night

(12) Excellent 

44

Anna Maria Island / Anna Maria

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $225 / night

$1400 - $3500 / week

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from $225 / night

25

Anna Maria Island / Anna Maria

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

 …see more

from $249 / night

$1743 / week

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from $249 / night

(4) Very Good 

24

Anna Maria Island / Holmes Beach

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Ask about children

 …see more

from $115 / night

$730 - $1050 / week

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from $115 / night

(4) Excellent 

39

Anna Maria Island / Anna Maria

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

 …see more

from $243 / night

$1699 - $2449 / week

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from $243 / night

24

Anna Maria Island / Bradenton Beach

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children

 …see more

from $136 / night

$950 - $1250 / week

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from $136 / night

18

Florida / Anna Maria Island

Studio 5 Min stay varies

  • Studio
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $190 / night

$1200 - $1600 / week

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from $190 / night

(9) Excellent 

28

Anna Maria Island / Holmes Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

 …see more

from $136 / night

$950 - $1600 / week

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from $136 / night

(10) Excellent 

23

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $220 / night

$1800 - $2450 / week

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from $220 / night

(4) Excellent 

23

Anna Maria Island / Anna Maria

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $239 / night

$1673 / week

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from $239 / night

69

Anna Maria Island / Bradenton Beach

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning

 …see more

from $107 / night

$1260 - $2450 / week

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from $107 / night

(2) Excellent 

16

Anna Maria Island / Anna Maria

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $169 / night

$1400 - $1550 / week

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from $169 / night

24

Anna Maria Island / Bradenton Beach

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children

 …see more

from $115 / night

$800 - $1250 / week

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from $115 / night

31

Anna Maria Island / Holmes Beach

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children

 …see more

from $122 / night

$850 - $1600 / week

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from $122 / night

11

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Swimming pool

 …see more

from $125 / night

$700 - $1200 / week

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from $125 / night

55

Anna Maria Island / Bradenton Beach

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $150 / night

$1050 - $2450 / week

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from $150 / night

(8) Excellent 

21

Anna Maria Island / Bradenton Beach

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $250 / night

$1250 - $1950 / week

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from $250 / night

(2) Excellent 

27

Anna Maria Island / Bradenton Beach

Studio 5 7 nights min

  • Studio
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Ask about children

 …see more

from $190 / night

$1200 - $1600 / week

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from $190 / night

(9) Excellent 

14

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

 …see more

from $135 / night

$850 - $1350 / week

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from $135 / night

(12) Excellent 

35

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

 …see more

from $143 / night

$999 - $2150 / week

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from $143 / night

29

Anna Maria Island / Holmes Beach

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Ask about children

 …see more

from $128 / night

$890 - $990 / week

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from $128 / night

24

Anna Maria Island / Holmes Beach

Studio 5 7 nights min

  • Studio
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Ask about children

 …see more

from $122 / night

$850 - $1300 / week

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from $122 / night

(2) Excellent 

31

Anna Maria Island / Holmes Beach

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $200 / night

$1000 - $1425 / week

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from $200 / night

1