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312 vacation rentals
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

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

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

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

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

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

23

Blue Dolphin Inn - Flamingo Up

Anna Maria Island / Anna Maria

Anna Maria house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$201

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$201

28

Blue Dolphin Inn - Heron Up

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

$187

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$187

(23) Very Good 

29

Anna Maria Island Nantucket

Anna Maria Island / Anna Maria

Anna Maria house

4 8 28 nights min

  • 4 bedrooms
  • sleeps 8
  • 28 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“"Great vacation home"” open, spacious, comfy home. very clean, beautifully decorated. everything you need was there( paper products, spices, dishes, etc.). great for families with children. game room, pool, bikes, all beach necessities.
…see more

Price per night from

$175

Responds fast!
avg. 2 hours 3 minutes

Price per night from

$175

Great rentals within 20 miles that match your search

Distance approx 19.69 km from Anna Maria

(53) Excellent 

28

The best guest rated condos at Madeira Beach area!

Florida / Madeira Beach

Madeira Beach apartment

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“Wonderful apartment” Me and my family spent a week in apartment #310 and had a magnificent time. The apartment is fully equipt with everything you possibly could want for your vacation. Nice locaion. Beautiful view from the balcony. The information fr
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Price per night from

$134

Price per night from

$134

Distance approx 12.7 km from Anna Maria

(16) Excellent 

11

bring A Boat, 12 Minutes To Sarasota Bay

Southwest Gulf Coast / Sarasota

Sarasota house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 4 mi
  • Swimming pool
  • Air conditioning
“Great Spot: Helpful Host, Attractive Accommodations, Relaxing Hot Tub” Nestled within the first golfing/housing development in Florida (c. 1924),Whitfield Estates, Jim's renovated1960s house is an especially easy place to stay. It has a very large liv
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Price per night from

$123

Responds fast!
avg. 2 hours 32 minutes

Price per night from

$123

Distance approx 18.33 km from Anna Maria

(14) Excellent 

34

Late SALE Sep/Oct only -Lakeside villa Uni. Park,golf,cycles,pool, beach

Southwest Gulf Coast / Sarasota

Sarasota villa

3 4 30 nights min

  • 3 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool
“A perfect setting and location” Everything about this vacation is perfect from start to finish. Joyce guides you through the pre vacation procedure seamlessly. All relevant information is sent concerning local amenities and events occurring duri
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Price per night from

$180

Responds fast!
avg. 1 hour 23 minutes

Price per night from

$180

Distance approx 9.18 km from Anna Maria

24

SHOREWALK VACATION VILLA

Southwest Gulf Coast / Bradenton

Bradenton apartment

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Price per night from

$125

Price per night from

$125

Distance approx 4.98 km from Anna Maria

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

Distance approx 15.55 km from Anna Maria

22

Beautiful Island Sanctuary Best Location in South Longboat Key!

Florida / Longboat Key

Longboat Key house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$422

Price per night from

$422

Distance approx 18 km from Anna Maria

14

#309 Beach Place Condos

Florida / Treasure Island

Treasure Island house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$194

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$194

Distance approx 15.07 km from Anna Maria

24

Sabal Harbour 17

Southwest Gulf Coast / Bradenton

Bradenton house

3 6 min stay varies

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

Price per night from

$194

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$194

Distance approx 17.05 km from Anna Maria

(1) Excellent 

8

Pet Friendly Heritage Harbour Beauty

Southwest Gulf Coast / Bradenton

Bradenton villa

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$107

Price per night from

$107

Distance approx 5.07 km from Anna Maria

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

Distance approx 2.77 km from Anna Maria Show on Map

11

Anna Maria Beach Place, Unit 6

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

$154

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$154

Distance approx 18 km from Anna Maria

27

#407 Beach Place Condos

Florida / Treasure Island

Treasure Island house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$262

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$262

Distance approx 18.1 km from Anna Maria

16

North Madeira # 205

Florida / Treasure Island

Treasure Island house

2 6 min stay varies

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

Price per night from

$180

Responds fast!
avg. 1 hour 55 minutes

Price per night from

$180

Distance approx 3.18 km from Anna Maria Show on Map

21

Four Beach Lovers 1

Anna Maria Island / Holmes Beach

Holmes Beach house

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Car not necessary
  • Air conditioning
  • Pet Friendly

Price per night from

$220

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$220

Distance approx 4.71 km from Anna Maria

16

Good Times Upstairs A

Anna Maria Island / Bradenton Beach

Bradenton Beach house

2 4 7 nights min

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

Price per night from

$174

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$174

Distance approx 5.4 km from Anna Maria

17

Coquina Moorings 106

Anna Maria Island / Bradenton Beach

Bradenton 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

$234

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$234

Distance approx 2.9 km from Anna Maria Show on Map

17

Cove At Sandy Pointe 208a

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. 1 hour 58 minutes

Price per night from

$126

Distance approx 2.77 km from Anna Maria Show on Map

18

Anna Maria Beach Place, Unit 4

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 6 min stay varies

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

Price per night from

$172

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$172

Distance approx 4.92 km from Anna Maria

22

Anna's Cottage

Anna Maria Island / Bradenton Beach

Bradenton Beach house

3 8 7 nights min

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

Price per night from

$248

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$248

Distance approx 18.1 km from Anna Maria

18

Wood # 513 North

Florida / Treasure Island

Treasure Island house

2 6 min stay varies

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

Price per night from

$180

Responds fast!
avg. 1 hour 40 minutes

Price per night from

$180

Distance approx 18 km from Anna Maria

14

#200 Beach Place Condos

Florida / Treasure Island

Treasure Island house

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$136

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$136

Distance approx 16 km from Anna Maria

53

Kings Treasure

Florida / Treasure Island

Treasure Island house

4 13 min stay varies

  • 4 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$892

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$892

Distance approx 2.51 km from Anna Maria Show on Map

11

Cast Away 1

Anna Maria Island / Holmes Beach

Holmes Beach house

2 6 min stay varies

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

Price per night from

$216

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$216

Distance approx 18.11 km from Anna Maria

13

Sandy Shores Condos #304

Florida / Madeira Beach

Madeira Beach condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$194

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$194

Distance approx 3.12 km from Anna Maria Show on Map

14

Palm Cay 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

$147

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$147

Distance approx 9.76 km from Anna Maria

28

Haagen's Turtle Nest

Southwest Gulf Coast / Bradenton

Bradenton apartment

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Price per night from

$110

Price per night from

$110

Distance approx 19.85 km from Anna Maria

21

AAA Accommodation in The Meadows - Sarasota

Florida / Fruitville

Fruitville condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 14 mi
  • Swimming pool
  • Child Friendly

Price per night from

$86

Responds fast!
avg. 1 hour 0 minutes

Price per night from

$86

Distance approx 17.38 km from Anna Maria

(1) Excellent 

26

GULF VIEW, TWO x 2BR SUITES, BEACHFRONT BLDG, POOLS, HOT TUB, GYM, FREE PARKING

Florida / Treasure Island

Treasure Island apartment

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$417

Price per night from

$417

Distance approx 11.76 km from Anna Maria

26

22-2 BeachHouse Sleeps6 Beauty&Redone w/WiFI&Bikes

St. Pete Beach / Pass-a-Grille

St. Pete Beach cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$194

Price per night from

$194