Anna Maria Island
 
 
 

Wet your appetite at one of the countless fine dinning establishments within walking distance from many of the accommodations. Sharky's Steak and Sea Grill offers fine dinning in a casual atmosphere, as award-winning European Chef Anton prepares a feast you will not soon forget. For a culinary experience unlike any other, venture over to the world-renowned Beach Bistro. The Bistro boasts the highest Zagat food rating in the state, and is included in Zagat's "Best Restaurants in America", where it is said to be "as good as any food in New York or Paris". Its wine list has received a Wine Spectator Award of Excellence for having one of the best wine lists in the world. When you're not feasting on some of the finest cuisine around, you can take part in the many activities that the island has to offer. Almost Heaven Kayak Adventures offers a variety of kayak eco-tours, while Sun Coast Kayak Fishing Tours will be your guide to some of the finest charter fishing around. Take a walk through Marie Selby Botanical Gardens and view over 20,000 types of plant life in the 11-acre open air museum. For those with children, Disney World, Adventure Island, Busch Gardens, and Universal Studios are all just a short drive away.

 
 
 
Browse the listings near Anna Maria Island or filter by a nearby city from the list below.

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Featured Listings
 
Sugar Plum Hideaway West
3 bedroom Anna Maria Home Vacation Rental Home
3 BR/ 2.00 BA Sleeps 6
More Info
Anna Maria Island Club Unit 18
2 bedroom Bradenton Beach Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
Open and Airy Holmes Beach ...
2 bedroom Holmes Beach Home Vacation Rental Home
2 BR/ 2.00 BA Sleeps 6
More Info
 
 
 
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Florida Gulf side condo steps from fishing dock Mint clean!!

Bradenton Beach
Beach Access, Golf nearby
Our new ground level, 2 bedroom cottage (2 queen beds, 1 sleeper couch) is nothing like any other be...

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Condo 2 / 1 / 4

$100 - $300
Per Night

$700 - $1900
Per Week

 
 

Carissa Beach House - Anna Maria Island, Florida

Holmes Beach Anna Maria Island
Beach Access, Ocean nearby
Cozy, cute and clean, just like home. 1 bedroom, 1 bath apartment / Sleeps 2 adults - Queen bed Abo...

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Apartment 1 / 1 / 2

$90 - $90
Per Night

$630 - $630
Per Week

 
 

Mangrove Cottage

Anna Maria
Staying at Mangrove Cottage, known to some as simply “Mangrove Cottage”, is less about vacationing a...

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Cottage 2 / 2 / 5

Online Booking

$180 - $335
Per Night

$1260 - $2345
Per Week

 
 

Grant's View

Anna Maria
Grant's View is a private bay front home is located on the Tampa Bay where you will enjoy the amazin...

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Cottage 2 / 2 / 6

Online Booking

$180 - $385
Per Night

$1260 - $2695
Per Week

 
 

Alamanda by the Gulf 620 N Bay

Anna Maria
Located on the coveted northern end of Anna Maria Island, “Alamanda by the Gulf” is a charming beach...

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Home 3 / 2 / 6

Online Booking

$170 - $265
Per Night

$1190 - $1855
Per Week

 
 

Anna Maria Island Club Unit 17

Bradenton Beach
2 Bedroom, 2 Bath (sleeps 4) - "Anna Maria Island Club" - 2600 Gulf Drive N. Unit #17, Bradenton Bea...

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Condo 2 / 2 / 4

Online Booking

$240 - $425
Per Night

$1680 - $2975
Per Week

 
 

All Decked Out

Anna Maria
Beach Access
“All Decked Out" Welcomes you to beautiful Anna Maria Island Florida! This private single family hom...

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Home 5 / 3 / 12

Online Booking

$330 - $805
Per Night

$2310 - $5635
Per Week

 
 

2 bedrooms - 2 baths Holmes Beach Condo Rental

Holmes Beach
The large heated pool and nestled right in the sands of the Gulf of Mexico beaches. Enjoy a sunset r...

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Home 2 / 2 / 4

Online Booking

$205 - $240
Per Night

$1435 - $1680
Per Week

 
 

2 Bedroom 2 Bath Holmes Beach Holiday Rental Villa

Holmes Beach
Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in r...

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Home 2 / 2 / 5

Online Booking

$155 - $250
Per Night

$1085 - $1750
Per Week

 
 

River Strand 25

Bradenton
Enjoy the nearby Sarasota cultural venues, shopping and world-class beaches. Checkout the Boardwak a...

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Home 3 / 2 / 6

Online Booking

$140 - $190
Per Night

$980 - $1330
Per Week

 
 

Gulf Shores Unit 205

Holmes Beach
Welcome to Gulf Shores Condominiums! We more than know how to live a life of luxury, but simplicity ...

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Condo 3 / 2 / 6

Online Booking

$230 - $385
Per Night

$1610 - $2695
Per Week

 
 

2 Bedroom 2 Bath Holmes Beach Holiday Villa

Holmes Beach
Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in r...

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Home 2 / 2 / 6

Online Booking

$190 - $295
Per Night

$1330 - $2065
Per Week

 
 

Tiffany Place 213

Holmes Beach
It was Holly Golightly, as played by the immortal Audrey Hepburn, that once looked off into the dist...

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Condo 2 / 2 / 4

Online Booking

$140 - $240
Per Night

$980 - $1680
Per Week

 
 

Sun Ray

Holmes Beach
Welcome to Sun Ray just a short walk to the Gulf of Mexico and the sugar sand beaches of Holmes Beac...

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Home 2 / 2 / 4

Online Booking

$145 - $250
Per Night

$1015 - $1750
Per Week

 
 

Holly Jewel

Anna Maria
3 Bedroom, 2.5 Bathroom (Sleeps 6) – “Holley Jewel” – 727 Holly Road in the city of Anna Maria. Fal...

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Home 3 / 2.5 / 6

Online Booking

$215 - $290
Per Night

$1505 - $2030
Per Week

 
 

The Anna Maria Island Beach Castaway 1

Holmes Beach
The Anna Maria Island Beach Castaway 1 is locateddirectly in the middle of Anna Maria Island and is ...

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Condo 2 / 1 / 6

Online Booking

$165 - $420
Per Night

$1155 - $2940
Per Week

 
 

Casa Varadero

Holmes Beach
Welcome to Casa Varadero a new ground level vacation rental home on Anna Maria Island in the quiet u...

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Home 4 / 3 / 8

Online Booking

$400 - $550
Per Night

$2800 - $3885
Per Week

 
 

Palm Isle 3210

Holmes Beach
Welcome to Palm Isle 3210, a one bedroom and one bathroom villa in the heart of quiet, friendly Holm...

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Cottage 1 / 1 / 4

Online Booking

$130 - $240
Per Night

$910 - $1680
Per Week

 
 

Water's Edge 106 North

Holmes Beach
Direct gulf front two bedroom and two bath condo in desirable Water's Edge complex which is the best...

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Condo 2 / 1.5 / 6

Online Booking

$145 - $275
Per Night

$1015 - $1925
Per Week

 
 

Old Florida Charm

Anna Maria
Welcome to the "Old Florida" charm of this well cared for ground level cottage located at 215 Fir Av...

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Home 2 / 2 / 4

Online Booking

$190 - $340
Per Night

$1330 - $2380
Per Week

 
 

River Pointe 01

Bradenton
Lake View
River Pointe is a boating community along the Manatee River with nearby River Isles Golf Course.Grea...

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Home 4 / 2 / 8

Online Booking

$140 - $200
Per Night

$980 - $1400
Per Week

 
 

River Strand 46

Bradenton
Nearby about 20 minutes you`ll find the white sandy beaches of the Florida Gulf Coast.A beautiful 3 ...

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Home 3 / 2 / 6

Online Booking

$150 - $205
Per Night

$1050 - $1435
Per Week

 
 

Island Pearl

Holmes Beach
Beautiful light, bright and beachy relaxing seasonal rental. (4) Bedroom, (4) Bathroom, accomodates ...

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Home 4 / 4 / 8

Online Booking

$290 - $550
Per Night

$2030 - $3885
Per Week

 
 

SeaShell-Sunsets

Holmes Beach
A luxury Anna Maria Island vacation destination perfect for the entire family, you and your loved on...

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Home 4 / 4.5 / 8

Online Booking

$715 - $890
Per Night

$5005 - $6230
Per Week

 
 

West Winds 6828 Gulf Drive

Holmes Beach
The quintessential Florida beach side condo, you’ll love your Anna Maria Island vacation when you st...

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Condo 2 / 2 / 4

Online Booking

$215 - $360
Per Night

$1505 - $2520
Per Week

 
           
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