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

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323 Vacation rentals

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 - $991 / week

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from $128 / 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

$1091 - $1580 / week

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from $200 / 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

$1091 - $1580 / week

Book View

from $200 / 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

$1091 - $1580 / week

Book View

from $200 / 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 - $2200 / week

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from $162 / 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

$1091 - $1606 / week

Book View

from $200 / 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

$885 - $1285 / week

Book View

from $165 / 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

$1091 - $1580 / week

Book View

from $200 / 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

16

Anna Maria Island / Holmes Beach

1 4 Min stay varies

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

 …see more

from $130 / night

$720 - $935 / week

Book View

from $130 / night

(1) Excellent 

18

Anna Maria Island / Holmes Beach

2 6 Min stay varies

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

 …see more

from $130 / night

$900 / week

Book View

from $130 / 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

 …see more

from $130 / night

$720 - $996 / week

Book View

from $130 / 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

 …see more

from $150 / night

$825 - $1231 / week

Book View

from $150 / 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

 …see more

from $150 / night

$825 - $1231 / week

Book View

from $150 / 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 $150 / night

$825 - $1231 / week

Book View

from $150 / 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

 …see more

from $165 / night

$885 - $1285 / week

Book View

from $165 / 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

$1091 - $1606 / week

Book View

from $200 / 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

$725 - $1101 / week

Book View

from $120 / night

(3) Very Good 

14

Anna Maria Island / Holmes Beach

3 6 7 nights min

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

 …see more

from $300 / night

$2100 / week

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from $300 / night

(9) Excellent 

28

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

 …see more

from $136 / night

$950 - $1601 / week

Book View

from $136 / 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

(1) Excellent 

24

Anna Maria Island / Holmes Beach

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $143 / night

$996 - $1400 / week

Book View

from $143 / night

(4) Excellent 

9

Anna Maria Island / Holmes Beach

2 6 7 nights min

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

 …see more

from $108 / night

$750 - $1201 / week

Book View

from $108 / night

25

Anna Maria Island / Holmes Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children

 …see more

from $137 / night

$950 - $1400 / week

Inquire View

from $137 / 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

 …see more

from $125 / night

$700 - $996 / week

Book View

from $125 / 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

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

31

Anna Maria Island / Holmes Beach

2 6 Min stay varies

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

 …see more

from $122 / night

$850 - $1601 / week

Book View

from $122 / night

23

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Air conditioning

 …see more

from $129 / night

$900 / week

Book View

from $129 / 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 $145 / night

$795 - $1325 / week

Book View

from $145 / night

12

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 $140 / night

$835 - $1211 / week

Book View

from $140 / 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

 …see more

from $479 / night

$2906 - $3353 / week

Book View

from $479 / night

(1)  

57

Anna Maria Island / Holmes Beach

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $120 / night

$834 - $1051 / week

Book View

from $120 / night

(5) Excellent 

27

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly

 …see more

from $200 / night

$1350 - $1781 / week

Book View

from $200 / night

(2) Excellent 

24

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

$800 - $1425 / week

Book View

from $200 / 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

 …see more

from $150 / night

$825 - $1580 / week

Book View

from $150 / night

36

Anna Maria Island / Holmes Beach

2 4 Min stay varies

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

 …see more

from $108 / night

$750 - $1500 / week

Book View

from $108 / night

(1) Excellent 

27

Anna Maria Island / Holmes Beach

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $165 / night

$1151 - $1801 / week

Inquire View

from $165 / 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

 …see more

from $120 / night

$680 - $920 / week

Book View

from $120 / night

(4) Very Good 

24

Anna Maria Island / Holmes Beach

2 4 Min stay varies

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

 …see more

from $115 / night

$725 - $1051 / week

Book View

from $115 / night