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Holiday Villas Anna Maria Island, FL

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All 869 Rentals in Anna Maria Island
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From
$74
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
17 photos Details
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$166
Per Night
Holmes Beach
3 Bedrooms, 7 Bathrooms, Sleeps 8
35 photos Details
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$106
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
22 photos Details
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Also consider
Happy Island Cottage with heated private Pool
3 Bedrooms, sleeps 8
$183 - $459 / night
Fully Remodeled Vacation Rental Anna Maria Island
2 Bedrooms, sleeps 6
$140 - $161 / night
Bermuda Bay Townhome(19) miles of white sand beach
3 Bedrooms, sleeps 8
$161 - $242 / night
Ditch the Crowds – Quiet Gulf-View Condo with Rooftop Deck, Heated Pool!
2 Bedrooms, sleeps 6
$153 - $298 / night
From
$139
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (1) Make Enquiry
From
$146
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 9
21 photos Details
Reviews (1) Make Enquiry
From
$186
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
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From
$254
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
30 photos Details
Reviews (1) Make Enquiry
From
$286
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
38 photos Details
Reviews (1) Make Enquiry
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From
$1,119
Per Week
Holmes Beach
3 Bedrooms, 4 Bathrooms, Sleeps 12
21 photos Details
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From
$1,252
Per Week
Bradenton Beach
2 Bedrooms, 3 Bathrooms, Sleeps 5
23 photos Details
Reviews (15) Make Enquiry
From
$166
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
18 photos Details
Reviews (1) Make Enquiry
From
$1,129
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (8) Make Enquiry
From
$138
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
24 photos Details
Reviews (29) Make Enquiry
From
$139
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (2) Make Enquiry
From
$313
Per Night
Anna Maria
4 Bedrooms, 3 Bathrooms, Sleeps 8
23 photos Details
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From
$124
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 5
Bookings
10 photos Details
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From
$199
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
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24 photos Details
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From
$251
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
33 photos Details
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From
$123
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
33 photos Details
Reviews (9) Make Enquiry
From
$341
Per Night
Anna Maria
4 Bedrooms, 3 Bathrooms, Sleeps 9
24 photos Details
Reviews (1) Make Enquiry
From
$204
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
25 photos Details
Reviews (4) Make Enquiry
From
$184
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (1) Make Enquiry
From
$93
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
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From
$145
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
16 photos Details
Reviews (1) Make Enquiry
From
$176
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
64 photos Details
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From
$215
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
21 photos Details
Reviews (7) Make Enquiry
From
$484
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
20 photos Details
Reviews (1) Make Enquiry
From
$169
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (11) Make Enquiry
From
$161
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
11 photos Details
Reviews (1) Make Enquiry
From
$269
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 4
30 photos Details
Reviews (2) Make Enquiry
From
$215
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details
Reviews (23) Make Enquiry
From
$188
Per Night
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
21 photos Details
Reviews (2) Make Enquiry
From
$140
Per Night
Bradenton Beach
Studio, 1 Bathroom, Sleeps 4
47 photos Details
Reviews (16) Make Enquiry
From
$1,183
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
18 photos Details
Reviews (2) Make Enquiry
From
$834
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
18 photos Details
Reviews (5) Make Enquiry
From
$156
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
12 photos Details
Reviews (6) Make Enquiry
From
$188
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 3
22 photos Details
Reviews (1) Make Enquiry
From
$941
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (4) Make Enquiry
From
$376
Per Night
Holmes Beach
3 Bedrooms, 4 Bathrooms, Sleeps 6
Booking
22 photos Details
Reviews (2) Make Enquiry
From
$118
Per Night
Bradenton Beach
1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
21 photos Details
Reviews (13) Make Enquiry
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Suitability

  • Wheelchair access (43)
  • Elder access (242)
  • Suitable for children (305)
  • Pet friendly (187)
  • Smoking allowed (2)

Amenities

  • Internet (773)
  • All pools (604)
  • Parking (539)
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  • Other outdoor space (415)
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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.