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Vacation Rentals in Anna Maria Island, FL

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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 821 Rentals in Anna Maria Island
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From
$154
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
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From
$215
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
17 photos Details
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From
$243
Per Night
Anna Maria
5 Bedrooms, 3 Bathrooms, Sleeps 16
31 photos Details
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Also consider
ISLAND TOWNHOUSE - 200 Steps to the BEACH
2 Bedrooms, sleeps 4
$105 - $125 / night
Island Time Inn on Bridge St  - 1 Bdrm w/Kitchen
1 Bedroom, sleeps 2
$90 - $135 / night
Luxurious beach Villa in North Anna maria 6bed 4ba
6 Bedrooms, sleeps 16
$448 - $614 / night
AMI Island Living -Walk to Beach-Ground Level Unit
2 Bedrooms, sleeps 6
$650 - $750 / week
From
$429
Per Night
Anna Maria
5 Bedrooms, 4 Bathrooms, Sleeps 12
28 photos Details
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From
$154
Per Night
Holmes Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
24 photos Details
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From
$300
Per Night
Anna Maria
4 Bedrooms, 3 Bathrooms, Sleeps 10
25 photos Details
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From
$129
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
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From
$159
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
33 photos Details
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From
$79
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details
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From
$111
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
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From
$171
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
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From
$274
Per Night
Holmes Beach
4 Bedrooms, 3 Bathrooms, Sleeps 12
40 photos Details
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From
$231
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
15 photos Details
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From
$184
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details
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From
$50
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
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From
$215
Per Night
Holmes Beach
3 Bedrooms, 7 Bathrooms, Sleeps 6
14 photos Details
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From
$146
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
29 photos Details
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From
$215
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
25 photos Details
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From
$96
Per Night
Anna Maria
4 Bedrooms, 3 Bathrooms, Sleeps 10
23 photos Details
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From
$93
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
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From
$100
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
18 photos Details
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From
$245
Per Night
Holmes Beach
3 Bedrooms, 4 Bathrooms, Sleeps 6
20 photos Details
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From
$155
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
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From
$300
Per Night
Anna Maria
5 Bedrooms, 8 Bathrooms, Sleeps 10
27 photos Details
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From
$116
Per Night
Holmes Beach
2 Bedrooms, 6 Bathrooms, Sleeps 5
22 photos Details
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From
$78
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
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From
$209
Per Night
Anna Maria
4 Bedrooms, 4 Bathrooms, Sleeps 8
17 photos Details
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From
$1,350
Per Week
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
10 photos Details
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From
$600
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 7
5 photos Details
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From
$243
Per Night
Holmes Beach
4 Bedrooms, 4 Bathrooms, Sleeps 8
24 photos Details
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From
$154
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 10
37 photos Details
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From
$110
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
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From
$120
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details
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From
$189
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
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From
$98
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
11 photos Details
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From
$111
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
31 photos Details
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From
$231
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
24 photos Details
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From
$175
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
12 photos Details
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From
$130
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
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From
$171
Per Night
Holmes Beach
3 Bedrooms, 7 Bathrooms, Sleeps 6
14 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 (514)
  • Parking (480)
  • Grill (418)
  • Other outdoor space (377)
  • View all amenities
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Filter search results by:
Book Online(130)

Suitability

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

Amenities

  • Internet (737)
  • All pools (514)
  • Parking (480)
  • Grill (418)
  • Other outdoor space (377)
  • View all amenities
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.