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Holiday Villas 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 819 Rentals in Anna Maria Island
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From
$146
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
15 photos Details
Reviews (13) Make Enquiry
From
$164
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (2) Make Enquiry
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$182
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (1) Make Enquiry
Also consider
Anna Maria Island Stunning Waterfront home
3 Bedrooms, sleeps 7
$248 / night
Mintfish an exclusive waterfront home
4 Bedrooms, sleeps 10
$532 - $578 / night
Dream Lover Boat & Breakfast on Anna Maria Island
2 Bedrooms, sleeps 4
$212 - $240 / night
Beautiful Home 1 Block to the Gulf on Spring Lake.
3 Bedrooms, sleeps 6
$167 / night
From
$258
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (11) Make Enquiry
From
$365
Per Night
Anna Maria
4 Bedrooms, 4 Bathrooms, Sleeps 11
37 photos Details
Reviews (2) Make Enquiry
From
$671
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
10 photos Details
Reviews (3) Make Enquiry
From
$228
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
24 photos Details
Reviews (1) Make Enquiry
From
$212
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (10) Make Enquiry
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From
$1,118
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (8) Make Enquiry
From
$121
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 7
9 photos Details
Reviews (1) Make Enquiry
From
$289
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (76) Make Enquiry
From
$228
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details
Reviews (2) Make Enquiry
From
$112
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
36 photos Details
Reviews (11) Make Enquiry
From
$1,864
Per Week
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Reviews (6) Make Enquiry
From
$605
Per Night
Anna Maria
5 Bedrooms, 6 Bathrooms, Sleeps 10
24 photos Details
Reviews (4) Make Enquiry
From
$160
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (4) Make Enquiry
From
$240
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (15) Make Enquiry
From
$426
Per Night
Anna Maria
4 Bedrooms, 2 Bathrooms, Sleeps 8
23 photos Details
Reviews (2) Make Enquiry
From
$953
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (121) Make Enquiry
From
$91
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (1) Make Enquiry
From
$251
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 10
30 photos Details
Reviews (2) Make Enquiry
From
$146
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
18 photos Details
Reviews (4) Make Enquiry
From
$128
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (2) Make Enquiry
From
$160
Per Night
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
24 photos Details
Reviews (8) Make Enquiry
From
$373
Per Night
Holmes Beach
3 Bedrooms, 4 Bathrooms, Sleeps 6
22 photos Details
Reviews (2) Make Enquiry
From
$111
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 10
53 photos Details
Reviews (6) Make Enquiry
From
$198
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (3) Make Enquiry
From
$105
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 4
14 photos Details
Reviews (7) Make Enquiry
From
$136
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (2) Make Enquiry
From
$133
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (3) Make Enquiry
From
$235
Per Night
Anna Maria
3 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details
Reviews (1) Make Enquiry
From
$905
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (1) Make Enquiry
From
$198
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
36 photos Details
Reviews (25) Make Enquiry
From
$160
Per Night
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
11 photos Details
Reviews (1) Make Enquiry
From
$671
Per Week
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details
Reviews (10) Make Enquiry
From
$154
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (2) Make Enquiry
From
$326
Per Night
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Reviews (18) Make Enquiry
From
$114
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (5) Make Enquiry
From
$3,195
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 12
12 photos Details
Reviews (28) Make Enquiry
From
$201
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (1) Make Enquiry
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Suitability

  • Wheelchair access (41)
  • Elder access (215)
  • Suitable for children (262)
  • Pet friendly (165)
  • Smoking allowed (2)

Amenities

  • Internet (735)
  • All pools (514)
  • Parking (474)
  • Grill (415)
  • Other outdoor space (374)
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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.