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Holiday Villas Anna Maria Island, FL

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All 694 Rentals in Anna Maria Island
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$342
Per Night
Anna Maria
4 Bedrooms, 3 Bathrooms, Sleeps 8
23 photos Details
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From
$138
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Reviews (1) Make Enquiry
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$221
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details
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3 Bedrooms, sleeps 6
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2 Bedrooms, sleeps 4
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2 Bedrooms, sleeps 4
$466 / night
From
$105
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
32 photos Details
Reviews (2) Make Enquiry
From
$342
Per Night
Holmes Beach
5 Bedrooms, 4 Bathrooms, Sleeps 10
40 photos Details
Reviews (1) Make Enquiry
From
$170
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
18 photos Details
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From
$277
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 4
30 photos Details
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From
$351
Per Night
Anna Maria
4 Bedrooms, 3 Bathrooms, Sleeps 9
24 photos Details
Reviews (1) Make Enquiry
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From
$929
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
21 photos Details
Reviews (4) Make Enquiry
From
$166
Per Night
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
11 photos Details
Reviews (1) Make Enquiry
From
$127
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 5
Bookings
10 photos Details
Reviews (2) Make Enquiry
From
$221
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details
Reviews (7) Make Enquiry
From
$152
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
18 photos Details
Reviews (4) Make Enquiry
From
$852
Per Week
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
18 photos Details
Reviews (4) Make Enquiry
From
$237
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details
Reviews (2) Make Enquiry
From
$258
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
33 photos Details
Reviews (8) Make Enquiry
From
$174
Per Night
Holmes Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
24 photos Details
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From
$189
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
24 photos Details
Reviews (1) Make Enquiry
From
$232
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
25 photos Details
Reviews (5) Make Enquiry
From
$213
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
28 photos Details
Reviews (4) Make Enquiry
From
$158
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (2) Make Enquiry
From
$142
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (24) Make Enquiry
From
$355
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
24 photos Details
Reviews (26) Make Enquiry
From
$221
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
21 photos Details
Reviews (7) Make Enquiry
From
$126
Per Night
Bradenton Beach
Studio, 1 Bathroom, Sleeps 4
47 photos Details
Reviews (16) Make Enquiry
From
$569
Per Night
Bradenton Beach
6 Bedrooms, 5 Bathrooms, Sleeps 14
43 photos Details
Reviews (1) Make Enquiry
From
$181
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
64 photos Details
Reviews (1) Make Enquiry
From
$189
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
12 photos Details
Reviews (1) Make Enquiry
From
$111
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
33 photos Details
Reviews (10) Make Enquiry
From
$183
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
9 photos Details
Reviews (1) Make Enquiry
From
$1,820
Per Week
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
22 photos Details
Reviews (24) Make Enquiry
From
$1,278
Per Week
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
22 photos Details
Reviews (1) Make Enquiry
From
$206
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
40 photos Details
Reviews (25) Make Enquiry
From
$221
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
32 photos Details
Reviews (19) Make Enquiry
From
$158
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (1) Make Enquiry
From
$166
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (4) Make Enquiry
From
$205
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
24 photos Details
Reviews (3) Make Enquiry
From
$119
Per Night
Holmes Beach
2 Bedrooms, 1 Bathroom, Sleeps 5
12 photos Details
Reviews (2) Make Enquiry
From
$387
Per Night
Holmes Beach
3 Bedrooms, 4 Bathrooms, Sleeps 6
Booking
22 photos Details
Reviews (2) Make Enquiry
From
$118
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (5) Make Enquiry
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Suitability

  • Wheelchair access (44)
  • Elder access (241)
  • Suitable for children (310)
  • Pet friendly (140)
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Amenities

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  • All pools (456)
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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.