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

Close

View larger map

Also consider

Vacation rentals Holmes Beach
325 properties
Vacation rentals Bradenton Beach
194 properties
Vacation rentals Anna Maria
134 properties

Anna Maria Island

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

667 Vacation rentals

(4) Excellent 

28

Vacation condo in Florida Gulf Coast

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 $86 / night

$599 - $1340 / week

Book View

from $86 / night

(3) Very Good 

15

Florida Gulf Coast 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 $136 / night

$945 - $1400 / week

Inquire View

from $136 / night

24

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 $242 / night

$1700 - $2900 / week

Book View

from $242 / night

(1) Good 

11

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning

 …see more

from $120 / night

$726 - $1101 / week

Book View

from $120 / night

15

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $200 / night

$1090 - $1580 / week

Book View

from $200 / night

(1) Good 

15

Vacation home in Florida Gulf Coast

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 $140 / night

$981 - $1331 / week

Inquire View

from $140 / night

(1) Excellent 

14

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $151 / night

$826 - $1230 / week

Book View

from $151 / night

20

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $200 / night

$1090 - $1580 / week

Book View

from $200 / night

(1) Excellent 

12

Florida Gulf Coast 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

Inquire View

from $285 / night

(17) Very Good 

42

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

 …see more

from $114 / night

$801 - $1101 / week

Book View

from $114 / night

(10) Very Good 

25

Florida / Anna Maria Island

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

 …see more

from $200 / night

$1400 - $1626 / week

Book View

from $200 / night

12

Florida / Anna Maria Island

2 6 7 nights min

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

 …see more

from $129 / night

$901 - $1600 / week

Book View

from $129 / night

(1) Excellent 

21

Anna Maria Island / Anna Maria

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children

 …see more

from $229 / night

$1600 - $1901 / week

Book View

from $229 / night

16

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Air conditioning

 …see more

from $131 / night

$721 - $935 / week

Book View

from $131 / night

25

Anna Maria Island / Anna Maria

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly

 …see more

from $600 / night

$3799 - $9400 / week

Book View

from $600 / night

(5) Very Good 

17

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $200 / night

$1090 - $1580 / week

Book View

from $200 / night

(10) 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 - $3250 / week

Book View

from $225 / night

23

Anna Maria Island / Holmes Beach

1 8 Min stay varies

  • 1 bedroom
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

 …see more

from $200 / night

$1090 - $1606 / week

Book View

from $200 / 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 $116 / night

$775 - $895 / week

Book View

from $116 / night

(2) Very Good 

18

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $200 / night

$1090 - $1580 / week

Book View

from $200 / night

(29) 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 $115 / night

$801 - $1800 / week

Inquire View

from $115 / night

7

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $162 / night

$852 - $2201 / week

Book View

from $162 / night

(1) 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 $170 / night

$1351 - $1551 / week

Book View

from $170 / night

16

Anna Maria Island / Bradenton Beach

2 4 7 nights min

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

 …see more

from $216 / night

$1500 / week

Book View

from $216 / night

4

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $162 / night

$852 - $1863 / week

Book View

from $162 / night

29

Anna Maria Island / Holmes Beach

2 6 7 nights min

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

 …see more

from $128 / night

$890 - $990 / week

Book View

from $128 / night

(2) Excellent 

21

Anna Maria Island / Bradenton Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $139 / night

$973 / week

Book View

from $139 / night

(4) Very Good 

13

Anna Maria Island / Holmes Beach

2 6 Min stay varies

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

 …see more

from $206 / night

$1351 - $2201 / week

Book View

from $206 / night

17

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $165 / night

$886 - $1285 / week

Book View

from $165 / night

14

Anna Maria Island / Anna Maria

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly

 …see more

from $145 / night

$1001 - $1351 / week

Book View

from $145 / night

21

Florida / Anna Maria Island

2 6 Min stay varies

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

 …see more

from $191 / night

$2030 - $2556 / week

Book View

from $191 / night

(1) Very Good 

37

Anna Maria Island / Bradenton Beach

Studio 4 2 nights min

  • Studio
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

 …see more

from $128 / night

$800 - $1451 / week

Book View

from $128 / 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 $249 / night

$1743 / week

Book View

from $249 / night

(1) Excellent 

19

Anna Maria Island / Holmes Beach

2 4 7 nights min

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

 …see more

from $128 / night

$895 / week

Book View

from $128 / night

(4) 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

 …see more

from $216 / night

$1505 - $2444 / week

Book View

from $216 / night

(16) Excellent 

32

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool

 …see more

from $172 / night

$1201 - $2150 / week

Book View

from $172 / night

(1) 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

$801 - $1201 / week

Book View

from $120 / night

(4) Very Good 

19

Anna Maria Island / Bradenton Beach

2 4 7 nights min

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

 …see more

from $136 / night

$950 - $1250 / week

Book View

from $136 / night

23

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

 …see more

from $200 / night

$1090 - $1606 / week

Book View

from $200 / night

(1) Very Good 

20

Anna Maria Island / Bradenton Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

 …see more

from $136 / night

$826 - $1201 / week

Book View

from $136 / 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