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Vacation rentals in Anna Maria Island, FL

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  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 822 Rentals in Anna Maria Island
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From
$195
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 8
29 photos Details
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From
$114
Per Night
Holmes Beach
1 Bedroom, 2 Bathrooms, Sleeps 2
10 photos Details
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From
$96
Per Night
Holmes Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details
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Also consider
Get Away to Anna Maria Island, Holmes Beach
2 Bedrooms, sleeps 4
$1,175 - $1,709 / week
Casa Rosa! Canal Front Home With Pool And Dock
2 Bedrooms, sleeps 6
$230 - $260 / night
The Shady Mango ~ Anna Maria Island's Most Charming Coastal Cottage!
2 Bedrooms, sleeps 4
$267 - $374 / night
Anna Maria Island Beach Palace
4 Bedrooms, sleeps 8
$427 - $534 / night
From
$118
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
13 photos Details
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From
$641
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 7
5 photos Details
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From
$150
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
9 photos Details
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From
$134
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details
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From
$160
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
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From
$214
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details
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From
$107
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
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From
$1,509
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
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From
$167
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 4
16 photos Details
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From
$139
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
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From
$153
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 7
16 photos Details
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From
$1,763
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
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From
$166
Per Night
Holmes Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
22 photos Details
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From
$2,243
Per Week
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
14 photos Details
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From
$187
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
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From
$503
Per Night
Holmes Beach
4 Bedrooms, 3 Bathrooms, Sleeps 8
34 photos Details
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From
$107
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
11 photos Details
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From
$101
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 5
15 photos Details
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From
$517
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 16
18 photos Details
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From
$210
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
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From
$160
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
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From
$96
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 2
8 photos Details
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From
$118
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
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From
$801
Per Week
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
15 photos Details
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From
$123
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 5
14 photos Details
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From
$288
Per Night
Holmes Beach
4 Bedrooms, 2 Bathrooms, Sleeps 10
29 photos Details
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From
$160
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
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From
$176
Per Night
Holmes Beach
1 Bedroom, 2 Bathrooms, Sleeps 2
8 photos Details
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From
$176
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
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From
$160
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
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From
$214
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
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From
$176
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details
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From
$139
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
5 photos Details
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From
$176
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details
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From
$214
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
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From
$160
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
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From
$214
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
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Suitability

  • Wheelchair access (41)
  • Elder access (220)
  • Suitable for children (267)
  • Pet friendly (166)
  • Smoking allowed (2)

Amenities

  • Internet (737)
  • All pools (515)
  • Parking (479)
  • Grill (419)
  • Other outdoor space (376)
  • View all amenities
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Waterfront vacation rentals on Anna Maria Island

Whether an experienced or a first-time vacation home renter, you’ll enjoy the many choices for beachside getaways on Anna Maria Island. Luxury gulf side villas, quaint beach cottages and canal front condos offer breathing-room space and countless amenities that traditional hotel stays can’t match. Beyond the advantage of preparing some meals at home, your beach rental allows you to slide right into islander life and feel very much at home.

“Old Florida” charm and easy island living

Three small communities share Anna Maria Island – Bradenton Beach, Holmes Beach and Anna Maria. Each gathers along 7 miles of silky white beach overlooking the Gulf of Mexico. The island offers the village feel of Old Florida, with simple beach cottages and sandy lanes dipping under lazy Florida oaks and beachfront villas overlooking turquoise bays. There’s plenty to do on the family-friendly island, but nothing quite as important as simple relaxation. Rent a bike to roam the island or a kayak to explore the waterways. Fish, sail, comb the beaches for shells, and pack a little picnic for a sunset meal.

One-of-a-kind dining and shopping

Shop names reveal that island boutiques are anything but ordinary. The Painted Gate, Egret’s Landing, Paper Panache and other local establishments offer everything from resort wear to arts and crafts. The free island trolley runs North and South, as a convenient way to explore. Ginny's and Jane E's at the old IGA is a popular spot, where vintage furniture mixes with home-baked quiches and brioches in an internet café setting. One restaurant you can’t miss is Rod & Reel located at the end of a wooden pier jutting out into the bay. Kick back, fish, eat and let that tropical seascape deliver complete relaxation.

Take a side trip south to “Shangri-la”

Don your best resort wear and head south along Highway 789 that links Anna Maria Island to Longboat and St. Armand Keys. The gulf front drive leads you to famous St. Armand’s Circle, where elite shopping and pampered dining venues merge in an elegant European atmosphere. After a gourmet lunch, venture over to Sarasota for a visit to the cherished Ringling enclave, home to the Museum of Art and Ca d’Zan Mansion. Set in a lush 20-acre garden overlooking the water, the Venetian mansion is considered “the last of the Gilded Age mansions” built in America.

Vacation rental homes, a superb value for families and friends

Spacious living areas, plenty of baths and bedrooms and every imaginable amenity explain why vacation homes are today’s most popular travel choices. From the comfort of your own island getaway, you’ll enjoy every pleasure Anna Maria Island offers.