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Holiday Rentals in Anna Maria Island, FL

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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 836 Rentals in Anna Maria Island
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From
₹8,246
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
15 photos Details
Reviews (13) Make Enquiry
From
₹5,176
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (4) Make Enquiry
From
₹7,283
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (2) Make Enquiry
Also consider
Holmes Beach Condo
1 Bedroom, sleeps 4
₹6,922 - ₹11,135 / night
Anna Maria Island Gulf-View Retreat
3 Bedrooms, sleeps 8
₹8,126 - ₹14,205 / night
Sun Porch - Florida Island Beach House
2 Bedrooms, sleeps 4
₹8,427 / night
NEW LISTING! Gulf View Getaway steps from beach!!!
4 Bedrooms, sleeps 9
₹18,599 - ₹29,493 / night
From
₹14,566
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (12) Make Enquiry
From
₹11,376
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (1) Make Enquiry
From
₹10,293
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (1) Make Enquiry
From
₹63,200
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (8) Make Enquiry
From
₹8,968
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (10) Make Enquiry
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From
₹9,029
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (4) Make Enquiry
From
₹37,920
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
10 photos Details
Reviews (3) Make Enquiry
From
₹7,223
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (2) Make Enquiry
From
₹34,188
Per Night
Anna Maria
5 Bedrooms, 6 Bathrooms, Sleeps 10
24 photos Details
Reviews (5) Make Enquiry
From
₹12,881
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
26 photos Details
Reviews (7) Make Enquiry
From
₹8,246
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
18 photos Details
Reviews (4) Make Enquiry
From
₹12,881
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details
Reviews (2) Make Enquiry
From
₹13,543
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (15) Make Enquiry
From
₹6,260
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 10
53 photos Details
Reviews (6) Make Enquiry
From
₹105,333
Per Week
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Reviews (6) Make Enquiry
From
₹21,067
Per Night
Holmes Beach
3 Bedrooms, 4 Bathrooms, Sleeps 6
22 photos Details
Reviews (2) Make Enquiry
From
₹15,469
Per Night
Anna Maria
4 Bedrooms, 3 Bathrooms, Sleeps 10
24 photos Details
Reviews (4) Make Enquiry
From
₹53,870
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (121) Make Enquiry
From
₹24,076
Per Night
Anna Maria
4 Bedrooms, 2 Bathrooms, Sleeps 8
23 photos Details
Reviews (2) Make Enquiry
From
₹10,834
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
31 photos Details
Reviews (2) Make Enquiry
From
₹10,834
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
44 photos Details
Reviews (7) Make Enquiry
From
₹8,246
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (1) Make Enquiry
From
₹16,312
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (76) Make Enquiry
From
₹180,571
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 12
12 photos Details
Reviews (28) Make Enquiry
From
₹9,029
Per Night
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
24 photos Details
Reviews (8) Make Enquiry
From
₹25,822
Per Night
Anna Maria
5 Bedrooms, 4 Bathrooms, Sleeps 12
28 photos Details
Reviews (2) Make Enquiry
From
₹7,825
Per Night
Bradenton Beach
Studio, 1 Bathroom, Sleeps 4
47 photos Details
Reviews (13) Make Enquiry
From
₹18,057
Per Night
Anna Maria
4 Bedrooms, 4 Bathrooms, Sleeps 8
34 photos Details
Reviews (5) Make Enquiry
From
₹37,920
Per Week
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
13 photos Details
Reviews (14) Make Enquiry
From
₹7,524
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (3) Make Enquiry
From
₹37,920
Per Week
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details
Reviews (10) Make Enquiry
From
₹18,057
Per Night
Anna Maria
3 Bedrooms, 7 Bathrooms, Sleeps 9
26 photos Details
Reviews (1) Make Enquiry
From
₹5,959
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 4
14 photos Details
Reviews (7) Make Enquiry
From
₹10,232
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
52 photos Details
Reviews (7) Make Enquiry
From
₹11,195
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
36 photos Details
Reviews (25) Make Enquiry
From
₹32,683
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
16 photos Details
Reviews (9) Make Enquiry
From
₹45,143
Per Week
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (1) Make Enquiry
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Suitability

  • Wheelchair access (39)
  • Elder access (213)
  • Suitable for children (258)
  • Pet friendly (178)
  • Smoking allowed (2)

Amenities

  • Internet (754)
  • Parking (532)
  • All pools (526)
  • Grill (426)
  • Other outdoor space (391)
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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.