Anna Maria Island Vacation Rentals
977 rentals with 11,251 photos.Most Popular
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Bradenton Beach
Lazy Liv'n Condo #5, located at 2312 Avenue C is just that! Lazy Living at it's best. Relax on tranquil Anna Maria Island, stroll to the beach is less than a minute, jump in the pool to cool off or jump on the Free Trol...
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per night
2 beds
1 bath
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Holmes Beach
Meticously maintained 3 bed/3 bath home with two master suites. Gourmet kitchen with breakfast bar overlooking the pool. Over sized lot with large open pool area overlooking Bimini Bay with lush landscaping. Great cover...
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per night
3 beds
3 baths
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Anna Maria
The Anna Maria Island Inn is a direct Beachfront Resort facing the white sands of the Gulf of Mexico. We feature 14 distinct Apartments; Direct Beachfront, Beachside, or Poolside units within four different buildings. T...
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per night
2 beds
2 baths
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Listings
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Holmes Beach
Meticously maintained 3 bed/3 bath home with two master suites. Gourmet kitchen with breakfast bar overlooking the pool. Over sized lot with large open pool area overlooking Bimini Bay with lush landscaping. Great cover...
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per night
3 beds
3 baths
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Holmes Beach
On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked. But at this house, it might not even take you that long. With ...
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per night
3 beds
2 baths
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Holmes Beach
A lovely, two bedroom/two bathroom, modern, Gulf front penthouse apartment on Holmes Beach! This unit has a king bedroom with flat screen television and another bedroom with two twin beds. This great apartment has views...
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per night
2 beds
2 baths
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Anna Maria
Time spent on Anna Maria Island should be savored. We islanders move through our day with a slower, mellower attitude. And being able to do that comes from having a sanctuary to eat, sleep, and daydream in. This is just...
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per night
3 beds
2 baths
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Holmes Beach
On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked. But when you pull up the east side of this elevated vacation h...
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per night
2 beds
2 baths
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Holmes Beach
Just what you're looking for - a ground level villa value priced for vacationing in Florida for a month or more! Fabulous two bedroom and two bath Island vacation rental recently updated with new tile floors and new pai...
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per night
2 beds
2 baths
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Anna Maria
This charming two bedroom two bathroom direct Gulf view property is located within a Four Unit Complex sleeps 6.
The property is beautifully furnished, covered parking, phone, cable, microwave, dishwasher, and washing ...
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per night
2 beds
2 baths
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Holmes Beach
Fabulous and gulf front, this vacation condo is located at 2700 Gulf Drive in Holmes Beach, right in the heart of Anna Maria Island. This two bedroom, two bathroom rental sits nestled in one of the island's most coveted...
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per night
2 beds
2 baths
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Anna Maria
Recently updated direct gulf front 2 bedroom, 2 bathroom unit. This Anna Maria vacation rental is located in a four unit complex. Located on the lower level, up just 1 flight of stairs. This property is cheery, bright d...
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per night
2 beds
2 baths
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Anna Maria
This Anna Maria vacation community. Unit is a 2 bedroom/2bathroom property that sleeps 4 guests. Master bedroom has a king bed. Full kitchen.
Amenities Include:
Oven
Ice maker
Dishwasher
Microwave
Blender
Toaster
Coff...
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2 beds
2 baths
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Anna Maria Island
This well-furnished luxury condo is two blocks from the beach, near a quiet nature reserve, overlooking the Sarasota Bay and the Sandy Pointe swimming pool. Visit "Cafe at the Beach", and the Anna Maria fishing pier for...
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per night
2 beds
2 baths
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Holmes Beach
This Beach Cottage is in the preferred, northern end of Holmes Beach is an elegant, Gulf front, ground level home on a pristine beach. Walk for miles in either direction on the white, sugar sand and explore the island s...
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per night
2 beds
2 baths
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Anna Maria
What a charmer! Enjoy all that this 2 bedroom 2 bath cottage-style vacation home has to offer from it's tropical beachy interior to it's private and peaceful exterior and pool. Delight in the island's balmy, sun-filled ...
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per night
2 beds
2 baths
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Anna Maria
Located in the Beautiful Northern End of Anna Maria Island, this Direct bayfront home offers endless water views! Just a short stroll to the Gulf beaches via Bean Point. While staying here, enjoy the shopping, restauran...
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per night
3 beds
3 baths
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Anna Maria
An appealing blend of comfort and Florida casual in this pretty, four bedroom, Anna Maria vacation rental home which is spacious and airy and extremely family friendly. Located directly across from the bay with views of...
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per night
4 beds
3 baths
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Anna Maria
(3+Den) Bed: (2) Bath: Accommodates up to (8) people: 1 King, 1 Full & 2 Twins: Internet - Highspeed: No smoking: No Pets.
What a special place! Remember days gone by in this Key West style island getaway with sparklin...
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per night
3 beds
2 baths
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Anna Maria
Located on the highly desirable North-end of Anna Maria, this 2 bedroom, 2 bath vacation pool home has a view of a natural bayou right in your backyard! The kitchen with it's white bead-board kitchen cabinetry, granite ...
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per night
2 beds
2 baths
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Anna Maria
This 3 bedroom 2 bath ground level Anna Maria vacation home is just 30 feet from the water! Breathtaking views of Tampa Bay and Egmont Key. Direct water views from master bedroom, dining room and kitchen.
Outdoor firep...
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per night
3 beds
2 baths
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Anna Maria
Sparkling new Village Center residence with private Heated pool located in the heart of Anna Maria. Just a short walk or bike ride from everything that makes Anna Maria special. From sunrise at the City Pier to Sunset o...
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per night
2 beds
2 baths
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Holmes Beach
This Holmes Beach Vacation Rental, located in Holmes Beach is an extremely popular three bedroom, two bath home with a private heated pool, tropical landscaping, a double car garage and gulf views from the open deck. Th...
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per night
3 beds
2 baths
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Blog Posts
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January 08, 2013
The advertising brochure claims this is "the fifth most bizarre restaurant in the country". No arguments from us! This little guy stood on the counter to greet us as we entered. On the one side of th...
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September 14, 2012
Yesterday, I did something I have sadly never done in my home state…my husband and I went out to Anna Maria Island, rented bikes, and explored a place that I thought was familiar....
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August 29, 2012
Here are some images from our trip to Anna Maria Island, of course I am in none of them but some of my favorite people in the world are in them so that’s ok. It took me awhile to decompress and fully...
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August 29, 2012
I guess if there was anywhere I'd want to be without a car, it would be on Anna Maria Island. But, if someone happens to find a Dodge Caravan key, remote fob and 4 condo keys, could you please let me ...
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August 24, 2012
Yesterday on the beach of Anna Maria Island, I observed a young family. There was a mother in an adorable red and white polka dotted bikini, a daughter of about four, and a father. The father had what...
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August 24, 2012
The Colors & Fun of Anna Maria Island...My hubby & I have been walking every evening while on vacation. There is a trail along the beach that is mostly shaded by trees. With the breeze off of the Gulf...
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August 22, 2012
I had been to Hawaii and California plenty of times before, but I had not been any where near Florida or to a place like Anna Maria Island. One of the things I loved about the Island is that it did no...
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August 16, 2012
The pic below is Anna Maria Island on the Gulf Side, south of Tampa near Sarasota. Stumbled upon a little beach bar and grill at Manatee Beach and had incredible fish tacos, coconut shrimp Caesar sala...
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August 01, 2012
I went a little MIA for a few days because John and I were busy soaking up the sun in beautiful Anna Maria Island, FL (Bradenton Beach, specifically) with my family. This island is becoming a quick fa...
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July 19, 2012
It was Bradenton Beach. The area we drove to was also going into Anna Maria Island. Too bad our time was cut short, so we had to leave a little over an hour later. It was just so very nice to take a w...
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