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311 vacation rentals
48

Beach Side Oasis W/ Pool and Short Walk to Restaurants and Bars on Bridge St.

Anna Maria Island / Bradenton Beach

Bradenton Beach condo

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$117

Price per night from

$117

32

Villa Marisol

Anna Maria Island / Anna Maria

Anna Maria house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Car not necessary
  • Air conditioning

Price per night from

$988

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$988

(3) Very Good 

45

PARADISAICAL ENCLAVE 5*Waterfront Canal Pool Home-Dock/Kayak/Bikes/FamilyFun/Pet

Anna Maria Island / Holmes Beach

Holmes Beach house

2 6 7 nights min

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

Price per night from

$194

Price per night from

$194

13

Alamanda Villas 3

Anna Maria Island / Holmes Beach

Holmes Beach apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$207

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$207

12

Bollinger Duplex, B

Anna Maria Island / Holmes Beach

Holmes Beach house

1 6 7 nights min

  • 1 bedroom
  • sleeps 6
  • 7 nights min
  • Car not necessary
  • Air conditioning

Price per night from

$113

Responds fast!
avg. 3 hours 36 minutes

Price per night from

$113

33

Blue Dolphin Inn - All Units

Anna Maria Island / Anna Maria

Anna Maria house

9 26 min stay varies

  • 9 bedrooms
  • sleeps 26
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$489

Responds fast!
avg. 3 hours 36 minutes

Price per night from

$489

29

Walk to the Beach and More from this Renovated Anna Maria Island Rental

Anna Maria Island / Holmes Beach

Holmes Beach condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$101

Price per night from

$101

100

Ss Salamander Both Units

Anna Maria Island / Holmes Beach

Holmes Beach house

4 11 7 nights min

  • 4 bedrooms
  • sleeps 11
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$412

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$412

13

MI Happy Place Sand Castle 1

Anna Maria Island / Holmes Beach

Holmes Beach house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$167

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$167

29

Updated and within Walking Distance to Uncrowded Beach Stores and Restaurants

Anna Maria Island / Holmes Beach

Holmes Beach condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$101

Price per night from

$101

19

Seaside Beach House 205

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$220

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$220

21

Blue Dolphin Inn - Skimmer Dow

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$146

Responds fast!
avg. 3 hours 36 minutes

Price per night from

$146

22

A Wright Place

Anna Maria Island / Holmes Beach

Holmes Beach house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$161

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$161

21

Valhalla Up And Down

Anna Maria Island / Holmes Beach

Holmes Beach house

5 13 7 nights min

  • 5 bedrooms
  • sleeps 13
  • 7 nights min
  • Car not necessary
  • Air conditioning
  • Pet Friendly

Price per night from

$614

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$614

21

Holiday Beach Townhouses

Florida / Anna Maria Island

Anna Maria Island apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$224

Responds fast!
avg. 1 hour 51 minutes

Price per night from

$224

12

Alamanda Villas 7

Anna Maria Island / Holmes Beach

Holmes Beach apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$206

Responds fast!
avg. 3 hours 36 minutes

Price per night from

$206

17

Blue Dolphin Inn - Ibis

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$146

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$146

28

Anna Cabana Beach House

Anna Maria Island / Holmes Beach

Holmes Beach house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$211

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$211

13

MI Happy Place Sand Dollar 2

Anna Maria Island / Holmes Beach

Holmes Beach house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$167

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$167

31

Dolphin Dance, Both Units

Anna Maria Island / Bradenton Beach

Bradenton Beach house

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Car not necessary
  • Air conditioning

Price per night from

$360

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$360

21

Cove At Sandy Pointe 111

Anna Maria Island / Holmes Beach

Holmes Beach apartment

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$146

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$146

23

Azure Seas

Anna Maria Island / Anna Maria

Anna Maria house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Car not necessary
  • Air conditioning
  • Pet Friendly

Price per night from

$392

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$392

24

Ocean Park Terrace 202

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 5 14 nights min

  • 2 bedrooms
  • sleeps 5
  • 14 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$227

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$227

17

Shell Cove 9

Anna Maria Island / Bradenton Beach

Bradenton Beach apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Car not necessary
  • Air conditioning

Price per night from

$214

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$214

17

Waters Edge 210s

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$234

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$234

46

Four Beach Lovers All Units

Anna Maria Island / Holmes Beach

Holmes Beach house

4 16 7 nights min

  • 4 bedrooms
  • sleeps 16
  • 7 nights min
  • Car not necessary
  • Air conditioning
  • Pet Friendly

Price per night from

$758

Responds fast!
avg. 3 hours 36 minutes

Price per night from

$758

16

Sunset View

Anna Maria Island / Bradenton Beach

Bradenton Beach house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$334

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$334

18

Anna Maria Escape

Anna Maria Island / Anna Maria

Anna Maria house

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Car not necessary
  • Air conditioning
  • Pet Friendly

Price per night from

$274

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$274

39

Fountainhead Condo 3

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$141

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$141

32

Expansive Views, Walk to Beach and Grocer, Anna Maria Island Vacation Rental

Anna Maria Island / Holmes Beach

Holmes Beach condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$90

Price per night from

$90

13

Terrace Condo 2

Anna Maria Island / Holmes Beach

Holmes Beach house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$133

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$133

22

Fountainhead Condo 4

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$141

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$141

39

Bollinger Duplex Both Sides

Anna Maria Island / Holmes Beach

Holmes Beach house

3 14 7 nights min

  • 3 bedrooms
  • sleeps 14
  • 7 nights min
  • Car not necessary
  • Air conditioning

Price per night from

$259

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$259

17

Sandy Pointe 210

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$126

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$126

15

Cyndy's Beach House

Anna Maria Island / Holmes Beach

Holmes Beach house

2 4 28 nights min

  • 2 bedrooms
  • sleeps 4
  • 28 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$153

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$153

(1) Excellent 

18

Gulf Sands 201

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$266

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$266

43

Absolutely Perfect

Anna Maria Island / Holmes Beach

Holmes Beach house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$989

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$989

19

Sunset Terrace 109

Anna Maria Island / Bradenton Beach

Bradenton Beach apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$267

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$267