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Holiday Rentals in Anna Maria Island, FL

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  • Flexible dates & rates
  • 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 820 Rentals in Anna Maria Island
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From
₹9,341
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
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From
₹12,873
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
20 photos Details
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From
₹10,718
Per Night
Holmes Beach
4 Bedrooms, 4 Bathrooms, Sleeps 11
25 photos Details
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Also consider
Anna Maria Island Private Tropical Garden Home
3 Bedrooms, sleeps 6
₹16,227 - ₹22,214 / night
Holiday Beach Townhouses
2 Bedrooms, sleeps 4
₹11,796 - ₹17,783 / night
2 Bedroom Beach Front Condo, Anna Maria Island Fl.
2 Bedrooms, sleeps 4
₹11,975 - ₹13,472 / night
Bay rest
2 Bedrooms, sleeps 6
₹98,796 - ₹119,753 / week
From
₹21,436
Per Night
Holmes Beach
8 Bedrooms, 7 Bathrooms, Sleeps 23
17 photos Details
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From
₹17,963
Per Night
Anna Maria
4 Bedrooms, 3 Bathrooms, Sleeps 10
25 photos Details
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From
₹52,392
Per Week
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 10
9 photos Details
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From
₹11,257
Per Night
Bradenton Beach
4 Bedrooms, 2 Bathrooms, Sleeps 8
27 photos Details
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From
₹90,354
Per Week
Bradenton Beach
5 Bedrooms, 3 Bathrooms, Sleeps 10
17 photos Details
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From
₹10,239
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
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From
₹8,981
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
11 photos Details
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From
₹6,586
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
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From
₹11,796
Per Night
Anna Maria
4 Bedrooms, 2 Bathrooms, Sleeps 8
15 photos Details
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From
₹4,730
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 6
10 photos Details
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From
₹14,969
Per Night
Holmes Beach
6 Bedrooms, 8 Bathrooms, Sleeps 12
25 photos Details
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From
₹7,245
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
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From
₹6,586
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
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From
₹52,392
Per Week
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
14 photos Details
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From
₹26,944
Per Night
Holmes Beach
6 Bedrooms, 9 Bathrooms, Sleeps 14
40 photos Details
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From
₹21,556
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
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From
₹6,586
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details
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From
₹16,466
Per Night
Bradenton Beach
4 Bedrooms, 5 Bathrooms, Sleeps 10
28 photos Details
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From
₹17,963
Per Night
Anna Maria
5 Bedrooms, 8 Bathrooms, Sleeps 10
27 photos Details
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From
₹8,981
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
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From
₹9,880
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
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From
₹17,963
Per Night
Bradenton Beach
5 Bedrooms, 9 Bathrooms, Sleeps 12
6 photos Details
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From
₹6,946
Per Night
Holmes Beach
2 Bedrooms, 6 Bathrooms, Sleeps 5
22 photos Details
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From
₹10,059
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
12 photos Details
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From
₹15,388
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
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From
₹6,646
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
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From
₹11,017
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details
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From
₹10,478
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
11 photos Details
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From
₹11,975
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
8 photos Details
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From
₹10,239
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
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From
₹8,263
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
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From
₹8,682
Per Night
Holmes Beach
3 Bedrooms, 7 Bathrooms, Sleeps 8
25 photos Details
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From
₹8,981
Per Night
Bradenton Beach
3 Bedrooms, 7 Bathrooms, Sleeps 6
22 photos Details
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From
₹5,628
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
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From
₹8,263
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
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From
₹6,646
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
31 photos Details
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From
₹9,520
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
33 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 (736)
  • All pools (513)
  • Parking (479)
  • Grill (418)
  • Other outdoor space (377)
  • 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.