50 Best Holmes Beach Vacation rentals on Holiday Lettings - House rentals

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459 Vacation rentals

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

Book View

from $94 / 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

Book View

from $100 / night

(4) Very Good 

24

Anna Maria Island / Holmes Beach

2 4 7 nights min

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

from $115 / night

$730 - $1155 / week

Book View

from $115 / 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

from $125 / night

$700 - $1200 / week

Book View

from $125 / night

31

Anna Maria Island / Holmes Beach

2 6 7 nights min

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

from $122 / night

$850 - $1760 / week

Book View

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

from $200 / night

$1000 - $1425 / week

Book View

from $200 / 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

Book View

from $129 / 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

Book View

from $258 / 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

Book View

from $519 / night

(5) Very Good 

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

from $150 / night

$825 - $1350 / week

Book View

from $150 / 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

Book View

from $125 / night

(2) Good 

11

Anna Maria Island / Holmes Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Car not necessary
  • Air conditioning

from $130 / night

$720 - $995 / week

Book View

from $130 / 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

Book View

from $159 / night

(2) Very Good 

10

Anna Maria Island / Holmes Beach

2 4 7 nights min

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

from $186 / night

$1300 - $2500 / week

Book View

from $186 / night

16

Anna Maria Island / Holmes Beach

1 4 Min stay varies

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

from $130 / night

$720 - $995 / week

Book View

from $130 / 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

from $150 / night

$852 - $2375 / week

Book View

from $150 / night

(2) Excellent 

15

Anna Maria Island / Holmes Beach

2 6 Min stay varies

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

from $99 / night

$630 - $1800 / week

Book View

from $99 / night

(3) Very Good 

14

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly

from $300 / night

$2100 / week

Book View

from $300 / night

(1) Very Good 

19

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

from $150 / night

$825 - $1350 / week

Book View

from $150 / night

(2) Excellent 

22

Anna Maria Island / Holmes Beach

2 6 Min stay varies

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

from $199 / night

$900 - $1600 / week

Book View

from $199 / 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

Book View

from $125 / 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

from $136 / night

$950 - $1600 / week

Book View

from $136 / 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

from $150 / night

$825 - $1350 / week

Book View

from $150 / 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

from $143 / night

$999 - $1900 / week

Book View

from $143 / 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

Book View

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

Book View

from $472 / night

13

Anna Maria Island / Holmes Beach

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $180 / night

$1140 / week

Book View

from $180 / 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

from $200 / night

$1090 - $1750 / week

Book View

from $200 / night

(1) Excellent 

4

Anna Maria Island / Holmes Beach

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning

from $125 / night

$875 / week

Book View

from $125 / night

21

Anna Maria Island / Holmes Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool

from $250 / night

$1600 - $2400 / week

Book View

from $250 / night

(5) Excellent 

24

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

from $165 / night

$825 - $1390 / week

Book View

from $165 / night

24

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly

from $165 / night

$1155 - $2065 / week

Book View

from $165 / 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

Book View

from $193 / night

(1) Excellent 

18

Anna Maria Island / Holmes Beach

2 4 7 nights min

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

from $143 / night

$1000 - $1540 / week

Book View

from $143 / night

(2) Excellent 

20

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Ask about children

from $86 / night

$600 - $900 / week

Book View

from $86 / night

(3) Very Good 

19

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

from $200 / night

$1095 - $1695 / week

Book View

from $200 / night

(4) Very Good 

23

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

from $150 / night

$825 - $1350 / week

Book View

from $150 / night

(2) 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

from $128 / night

$895 / week

Book View

from $128 / night

36

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

from $143 / night

$1000 - $1500 / week

Book View

from $143 / night

(4) Very Good 

27

Anna Maria Island / Holmes Beach

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $300 / night

$1665 - $2265 / week

Book View

from $300 / night

1