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Anna Maria Island

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Vacation Rentals in Anna Maria Island, FL

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • 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
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.

 
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
Florida, Anna Maria Island, Bradenton Beach Holiday Rentals
Condo 2 BR / 2 BA, Heated Pool, Tennis Court
Slideshow
4 of 5 stars 2 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 5
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
88 AUD
Week:
616 AUD - 1,334 AUD
Month:
2,053 AUD - 3,489 AUD
Minimum rental - 1 week
Check availability
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Florida, Anna Maria Island, Holmes Beach Holiday Rentals
AVAILABLITY FOR MARCH! Close to Beach  Anna Maria
Slideshow
4.5 of 5 stars 4 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
272 AUD
Week:
1,437 AUD - 1,899 AUD
Month:
3,028 AUD - 3,900 AUD
Minimum rental - 1 night
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The Shady Mango, Anna Maria
Florida, Anna Maria Island, Anna Maria Holiday Rentals
The Shady Mango
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Check availability
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Also consider
Feel like in...
718 AUD - 924 AUD / week
2 Bedrooms, sleeps 4
2 Bathrooms
Condo steps to...
821 AUD - 924 AUD / week
3 Bedrooms, sleeps 8
2 Bathrooms
Gulf Sounds...
180 AUD - 251 AUD / night
2 Bedrooms, sleeps 6
1 Bathroom
Stunning...
718 AUD / night
4 Bedrooms, sleeps 9
5 Bathrooms
Waterfront...
5,901 AUD / month
4 Bedrooms, sleeps 8
3 Bathrooms
Florida, Anna Maria Island, Holmes Beach Holiday Rentals
Gulf Front - Shady Pines
Slideshow
4.5 of 5 stars 9 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
265 AUD
Week:
1,693 AUD - 2,053 AUD
Minimum rental - 1 week
Check availability
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Palm Haven, 2 Bedroom, Holmes Beach
Florida, Anna Maria Island, Holmes Beach Holiday Rentals
Palm Haven, 2 Bedroom
4 of 5 stars 1 review
  • Villa
  • 2 Bedrooms, sleeps 7
  • 1 Bathroom
  • Professional
EMAIL AGENT
Week:
718 AUD - 975 AUD
Month:
2,443 AUD - 3,315 AUD
Minimum rental - 1 week
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Florida, Anna Maria Island, Bradenton Beach Holiday Rentals
Island Resort Condo; Relaxed Old Florida Lifestyle
Slideshow
4 of 5 stars 3 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
175 AUD
Week:
744 AUD - 1,232 AUD
Month:
2,463 AUD - 3,746 AUD
Minimum rental - 1 week
Check availability
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Florida, Anna Maria Island, Anna Maria Holiday Rentals
Blue Dolphin Inn - Flamingo Up
Slideshow
4.5 of 5 stars 3 reviews
  • Condo/Apartment
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
193 AUD - 257 AUD
Week:
1,078 AUD - 1,437 AUD
Minimum rental - 3 nights
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Sunbow Bay 305, Holmes Beach
Florida, Anna Maria Island, Holmes Beach Holiday Rentals
Sunbow Bay 305
Slideshow
4 of 5 stars 3 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Week:
718 AUD - 1,006 AUD
Minimum rental - 1 week
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Florida, Anna Maria Island, Bradenton Beach Holiday Rentals
A Lime Cottage Pool beach house..ahhh this is it!!
Slideshow
5 of 5 stars 18 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
200 AUD
Week:
1,016 AUD - 1,360 AUD
Minimum rental - 1 week
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United States, Florida, Anna Maria Island Holiday Rentals
Plumfish, a luxurious home, beautiful water views
Slideshow
4.5 of 5 stars 18 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
1,642 AUD - 1,847 AUD
Minimum rental - 1 week
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Sunbow Bay 310, Holmes Beach
Florida, Anna Maria Island, Holmes Beach Holiday Rentals
Sunbow Bay 310
Slideshow
4 of 5 stars 2 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Week:
718 AUD - 1,006 AUD
Minimum rental - 1 week
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Florida, Anna Maria Island, Anna Maria Holiday Rentals
C-view: Idyllic Canal Home, Heated Pool, Nr Beach
Slideshow
4 of 5 stars 4 reviews
  • Holiday Rental House
  • 5 Bedrooms, sleeps 8
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
308 AUD - 513 AUD
Week:
2,463 AUD - 2,874 AUD
Month:
7,697 AUD
Minimum rental - 3 nights
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Graham's Getaway, Holmes Beach
Florida, Anna Maria Island, Holmes Beach Holiday Rentals
Graham's Getaway
Slideshow
4 of 5 stars 4 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
821 AUD
Minimum rental - 1 week
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Bermuda Bay 1421, Bradenton Beach
Florida, Anna Maria Island, Bradenton Beach Holiday Rentals
Bermuda Bay 1421
Slideshow
4 of 5 stars 10 reviews
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Week:
1,006 AUD - 1,580 AUD
Minimum rental - 1 week
Check availability
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Florida, Anna Maria Island, Holmes Beach Holiday Rentals
Beautiful Home 1 Block to the Gulf on Spring Lake.
Slideshow
4.5 of 5 stars 7 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
144 AUD
Week:
924 AUD - 1,232 AUD
Month:
3,695 AUD - 4,618 AUD
Minimum rental - 1 week
Check availability
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Florida, Anna Maria Island, Holmes Beach Holiday Rentals
North Beach Village 58
Slideshow
4.5 of 5 stars 2 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Week:
872 AUD - 1,232 AUD
Month:
2,791 AUD - 3,920 AUD
Minimum rental - 1 week
Check availability
Show on map

Anna Maria Island Holiday Rental Advice

Gulf Drive traffic query
Posted by ukmummy, 2 May 2008
... place for us I'd not like to have to change. Realise no-one knows what'll happen tomorrow but I'm keeping everything crossed! Perhaps this is normal with holiday rentals on AMI.....). Anyhow have saved Casa Sierra info...just in case I need it later on! Thanks again ... more
starfish cottage holmes beach
Posted by suzer58, 11 Feb 2008
Has anyone stayed at the Starfish Cottage run by Idyllic Holiday rentals in Holmes Beach? They look nice and reaonably priced. If anyone has stayed there let me know. ... more
Lots of questions
Posted by zen_journeyman, 15 Apr 2012
... Googling on 'anna maria island vacation rental real estate companies' should get you started, then you can cross-reference your choices against as many sites & forums' ratings as you desire to help narrow it down. The AMI destination expert here should be able to help considerably more than I, and ... more
Help me pick a house!
Posted by amomslove, 9 Jan 2012
Berryfish looks very nice. We ended up renting Bean Point Beach Shack.. on the beach. http://www.satorealestate.com/Vacation-Rentals-details-view.aspx?PropID=388#images/houses/XUMCMBLJNS.jpg ... more
Stand Up Paddle
Posted by FunandMoreRentals, 22 Mar 2012
Hi, Yes we have paddle boards and have been renting them for years. We deliver to the beach or to your vacation rental. Here is a link http://www.funandmorerentals.com/pages/products/?cat=paddle Have FUN ... more
Help!!! 18 people!
Posted by chambrick, 10 Mar 2012
Help! I'm drowning in vacation rental search engines. We have 18 people (10 adult and 8 kids) for a family week that is very important due to an illness. We really want to stay on the beach and realize that doing that in 1 house will be impossible. However ... more
Duncan Real Estate
Posted by sunluvinislandgirl, 20 Feb 2012
... the forum topic below called Vacation rental agency. Someone else was asking for info last night on this subject. Good luck with your hunt I am sure your wife will be pleased with anything that you find, you almost can't go wrong on Anna Maria Island. I have traveled ... more
Wedding places/suggestions?
Posted by Becka2121, 8 Feb 2012
We are looking to get married in March or April of next year. We are just looking for some suggestions on places? Which route would be the best to go vacation rental or hotels? Thank you! ... more
private chef?
Posted by peeky, 24 Oct 2011
Can anyone recommend a private chef who could prepare an anniversary dinner at our vacation rental? Also any idea of how much this would cost?Any recommendations would be much appreciated. ... more
gulfcoastrentals.com?
Posted by Hello-FL, 18 Aug 2011
... are owners that advertise their vacation rental. While most of the time this works out fine if you want to lower your risk choose a rental management company that is located directly on Anna Maria Island. If you want to go a step further call the AMI Chamber of commerce ... more