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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
₹281,420
Per Week
Holmes Beach
4 Bedrooms, 4 Bathrooms, Sleeps 10
22 photos Details
Reviews (9) Make Enquiry
From
₹7,724
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (9) Make Enquiry
From
₹6,826
Per Night
Holmes Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
20 photos Details
Reviews (8) Make Enquiry
Also consider
Happy Island Cottage with heated private Pool
3 Bedrooms, sleeps 8
₹10,179 - ₹25,567 / night
ISLAND TOWNHOUSE - 200 Steps to the BEACH
2 Bedrooms, sleeps 4
₹6,287 - ₹7,485 / night
Becker's Beach Bungalow!
2 Bedrooms, sleeps 6
₹7,485 / night
Gulf Front - Shady Pines
2 Bedrooms, sleeps 6
₹14,490 - ₹17,963 / night
From
₹85,923
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (14) Make Enquiry
From
₹22,214
Per Night
Bradenton Beach
4 Bedrooms, 3 Bathrooms, Sleeps 8
24 photos Details
Reviews (1) Make Enquiry
From
₹11,915
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details
Reviews (7) Make Enquiry
From
₹94,306
Per Week
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 6
126 photos Details
Reviews (11) Make Enquiry
From
₹35,926
Per Night
Anna Maria
4 Bedrooms, 5 Bathrooms, Sleeps 8
21 photos Details
Reviews (13) Make Enquiry
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From
₹11,077
Per Night
Holmes Beach
2 Bedrooms, 3 Bathrooms, Sleeps 6
12 photos Details
Reviews (2) Make Enquiry
From
₹14,550
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (4) Make Enquiry
From
₹11,137
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (2) Make Enquiry
From
₹7,724
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 4
23 photos Details
Reviews (2) Make Enquiry
From
₹7,724
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (2) Make Enquiry
From
₹52,392
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (7) Make Enquiry
From
₹9,999
Per Night
Holmes Beach
4 Bedrooms, 2 Bathrooms, Sleeps 8
17 photos Details
Reviews (9) Make Enquiry
From
₹10,957
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details
Reviews (7) Make Enquiry
From
₹117,358
Per Week
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (17) Make Enquiry
From
₹12,574
Per Night
Anna Maria
4 Bedrooms, 2 Bathrooms, Sleeps 14
22 photos Details
Reviews (10) Make Enquiry
From
₹83,827
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (11) Make Enquiry
From
₹69,158
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
Reviews (10) Make Enquiry
From
₹15,209
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
12 photos Details
Reviews (2) Make Enquiry
From
₹10,059
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (1) Make Enquiry
From
₹6,826
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (4) Make Enquiry
From
₹8,622
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
15 photos Details
Reviews (25) Make Enquiry
From
₹7,485
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
14 photos Details
Reviews (13) Make Enquiry
From
₹8,981
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
24 photos Details
Reviews (2) Make Enquiry
From
₹67,062
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (4) Make Enquiry
From
₹39,818
Per Week
Holmes Beach
2 Bedrooms, 3 Bathrooms, Sleeps 8
16 photos Details
Reviews (9) Make Enquiry
From
₹12,814
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (1) Make Enquiry
From
₹10,359
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (3) Make Enquiry
From
₹39,818
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (6) Make Enquiry
From
₹5,988
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
16 photos Details
Reviews (4) Make Enquiry
From
₹34,190
Per Night
Holmes Beach
6 Bedrooms, 4 Bathrooms, Sleeps 16
59 photos Details
Reviews (2) Make Enquiry
From
₹8,981
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 5
4 photos Details
Reviews (1) Make Enquiry
From
₹113,167
Per Week
Bradenton Beach
4 Bedrooms, 4 Bathrooms, Sleeps 10
22 photos Details
Reviews (1) Make Enquiry
From
₹7,544
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details
Reviews (6) Make Enquiry
From
₹37,722
Per Week
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
22 photos Details
Reviews (6) Make Enquiry
From
₹41,914
Per Week
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
17 photos Details
Reviews (14) Make Enquiry
From
₹7,724
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (1) Make Enquiry
From
₹26,944
Per Night
Holmes Beach
6 Bedrooms, 9 Bathrooms, Sleeps 14
39 photos Details
Reviews (3) Make Enquiry
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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)
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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.