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

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Vacation rentals Holmes Beach
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243 properties
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104 properties

Anna Maria Island

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822 Vacation rentals

(5) 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 in a little cul …see more

from $108 / night

$756 - $1767 / week

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from $108 / 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 cultural att …see more

from $172 / night

$1200 - $1800 / week

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from $172 / 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

(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

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

(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) 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

from $108 / night

$751 - $1200 / week

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from $108 / night

(1) Excellent 

21

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $100 / night

$650 - $1450 / week

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from $100 / night

13

Anna Maria Island / Holmes Beach

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $129 / night

$903 / week

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from $129 / night

24

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children

from $136 / night

$950 - $1375 / week

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from $136 / night

19

Anna Maria Island / Anna Maria

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

from $219 / night

$1423 - $1795 / week

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from $219 / night

(19) Very Good 

45

Anna Maria Island / Anna Maria

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $290 / night

$1695 - $4750 / week

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from $290 / night

30

Anna Maria Island / Anna Maria

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children

from $325 / night

$1400 - $2310 / week

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from $325 / night

(1) Very Good 

11

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Swimming pool

from $125 / night

$700 - $995 / week

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from $125 / night

22

Anna Maria Island / Anna Maria

3 8 Min stay varies

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

from $250 / night

$2000 - $3500 / week

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from $250 / 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

from $250 / night

$1250 - $1950 / week

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from $250 / 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

from $135 / night

$850 - $1350 / week

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from $135 / 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

from $258 / night

$2300 - $3500 / week

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from $258 / 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

from $269 / night

$1883 / week

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from $269 / night

(2) Excellent 

25

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets

from $125 / night

$875 / week

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from $125 / night

(3) Excellent 

10

Anna Maria Island / Holmes Beach

5 10 30 nights min

  • 5 bedrooms
  • Sleeps 10
  • 30 nights min
  • Swimming pool
  • Ask about children

from $472 / night

$3300 - $4070 / week

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from $472 / night

23

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Air conditioning

from $159 / night

$950 / week

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from $159 / night

(7) Excellent 

31

Anna Maria Island / Holmes Beach

2 6 7 nights min

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

from $125 / night

$720 / week

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from $125 / night

18

Anna Maria Island / Anna Maria

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $145 / night

$895 - $1600 / week

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from $145 / night

(2) Excellent 

75

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

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

from $107 / night

$749 / week

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from $107 / night

(5) Excellent 

27

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly

from $193 / night

$1200 - $1780 / week

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from $193 / 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

from $135 / night

$850 - $1350 / week

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from $135 / night

(7) Excellent 

42

Anna Maria Island / Bradenton Beach

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $225 / night

$1590 / week

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from $225 / 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

from $120 / night

$795 - $895 / week

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from $120 / night

(1) Excellent 

16

Anna Maria Island / Bradenton Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.02 mi
  • Swimming pool

from $195 / night

$1150 - $1950 / week

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from $195 / night

(4) Very Good 

30

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children

from $136 / night

$950 - $1375 / week

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from $136 / night

21

Anna Maria Island / Bradenton Beach

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $89 / night

$525 / week

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from $89 / 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

from $289 / night

$2023 / week

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from $289 / 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

from $200 / night

$1000 - $1425 / week

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from $200 / night

10

Anna Maria Island / Bradenton Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children

from $189 / night

$1320 - $1815 / week

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from $189 / night

(23) Very Good 

17

Anna Maria Island / Holmes Beach

2 6 Min stay varies

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

from $125 / night

$850 - $1350 / week

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from $125 / night

33

Anna Maria Island / Anna Maria

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children

from $465 / night

$3250 - $4015 / week

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from $465 / night

(3) Excellent 

22

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly

from $125 / night

$875 / week

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from $125 / night

(5) Excellent 

25

Anna Maria Island / Bradenton Beach

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

from $259 / night

$1813 - $2205 / week

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from $259 / night

(1) Excellent 

21

Anna Maria Island / Holmes Beach

3 6 Min stay varies

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

from $519 / night

$3213 - $3353 / week

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from $519 / night

1