A romantic island in the sun, Anna Maria Island is home to gorgeous sunsets overlooking Tampa Bay, as well as sugar-white beaches and wild palmettos. Honeymooners and families alike have frequented Anna Maria Island vacation rentals to surf, sunbathe, swim and take moonlit strolls along the beach. Guests of Anna Maria Island rentals have museums and historical attractions to visit, as well as a variety of professional sporting events to experience. Anna Maria Island beach rental guests love the fine dining, delightful shopping, and nightlife the island has to offer. The activities are literally endless, offering Anna Maria Island Florida rental guests everything from sailing and boating to parasailing and eco-tours.
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Anna Maria Island Vacation Rentals
Anna Maria Island Vacation Rentals - Search Over 250,000 Listings
| Featured Rentals | Type | Beds | Baths | Sleeps | Rate | |
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Gorgeous Lakefront Spoonbill VillaAmenities:Beach, Hot Tub, TV Description:Located on Spoonbill Landings Circle, our Anna Maria, Florida vacation rental, Spoonbill Villa, overlooks a fresh water lake. Suitable for six vacationers, our 2 bedroom rental villa in Anna Maria hosts a queen-size bed in the master bedroom, two twin beds in the guest bedroom and a queen-size futon on the lanai. The living room that opens onto the enclosed lanai features flat screen TV, DVD player, cable TV and wireless Internet access. It?s eat-in kitchen comes fully equipped and overlooks |
House |
2 Beds |
2 Baths |
6 People |
$59 - $59 |
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Captain's QuartersAmenities:Beach, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Captain's Quarters, located at 2801 Gulf Drive in Holmes Beach is an extremely popular three bedroom, two bath home with private, heated pool. Very nice and newly redecorated home with double garage, microwave, whirlpool tub, washer, dryer, cable tv, phone and fenced pool area surrounded by award winning, tropical landscaping. View of Gulf from open deck, den and living room. This home sleeps six with two queen size beds and two twin beds. Book early - one doesn't last long! |
House |
3 Beds |
2 Baths |
6 People |
$170 - $205 |
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Magnificent Gulf Front Condo in Bradenton BeachAmenities:Beach, Hot Tub, Air Conditioning, TV Description:Enjoy direct views of the Gulf of Mexico and Bay from this lovely Bradenton Beach, Florida vacation rental condo, where you can't get any closer to the beach without getting your toes wet. Located at 1000 Gulf Dr.,Bradenton Beach Florida, our 1 bedroom and 1 bath rental condo is within walking distance to a variety of island restaurants including one next door. Board the free island trolley from across the street to get from one end of the island to another to enjoy beaches, fishing piers, b |
Condo |
1 Beds |
1 Baths |
4 People |
$115 - $150 |
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Charming Townhouses on Anna Maria IslandAmenities:Beach, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Bird's Nest apartments are located on Bradenton Beach, Anna Maria island, overlooking the Gulf of Mexico. It is a small modern complex completely renovated and upgraded. |
Condo |
2 Beds |
2 Baths |
4 People |
$124 - $181 |
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Anna Maria Island - Gulf Coast Island-Tradewinds Resort Cottage RentalAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Washer/Dryer, Air Conditioning, Pets OK, TV Description:Welcome to Paradise........ This property is within a small resort, just steps from a beautiful private gulf beach on Anna Maria Island in Bradenton Beach, Florida.........if you want 'clean and quiet', you've come to the right place..... Condo Cottage with Old Florida Charm.... This island cottage is: 1 bedroom with king bed (or 2 twins, upon request) 1 bath, full kitchen with open floor plan and breakfast bar, living room w/sofa sleeper, DVD, VCR and cable TV (2). |
House |
1 Beds |
1 Baths |
4 People |
$96 - $215 |
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Splendid Condo in an Ocean-dominated LandscapeAmenities:Air Conditioning, TV Description:Located on the southern half of the Island, this Anna Maria vacation rental condo, which is a part of Bermuda Bay Club, is a perfect hideaway amid a waterfront setting. From the views of desolated beaches and the expanses of ocean to level of facilities provided, this condo is definitely going to make your vacation memorable. Our spacious 3 bedroom condo rental Anna Maria features designer furnishings. It comes with two queen-size beds and two twin beds to let six vacationers enjoy a sound |
Condo |
3 Beds |
2.5 Baths |
6 People |
$128 - $171 |
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Tiffany Place 20% off Jan-AprilAmenities:Beach, Pool, Air Conditioning, TV Description:2-WEEK MINIMUM STAY. Luxurious Tiffany Place condominium sits right on the beach and overlooks the beautiful turquoise waters of the Gulf of Mexico. This anna maria island vacation rental property on Holmes Beach has beautiful white sandy beaches and breath taking views have been voted one of the top 10 beaches in the world. Our wide and serene beaches are perfect for those long walks, shell hunting and relaxing. We are located near Long Boat Key and Sarasota. This recently remodeled and rede |
Condo |
2 Beds |
2 Baths |
4 People |
$132 - $175 |
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Anchors West: Splendid Holmes Beach Retreat Next To The OceanAmenities:Beach, Air Conditioning, TV Description:If you are looking for a classic sun and sand tropical holiday with your family or friends, then Anchors West, a Holmes Beach, Florida vacation rental is perfect for you. With its convenient location, our beautifully furnished townhouse is your perfect base to indulge in just about everything. Great shopping, excellent golfing and water sports, sightseeing and many other adventures are easily accessible from this splendid getaway. Our 2 bedroom townhouse rental can comfortably accommodate u |
House |
2 Beds |
1.5 Baths |
4 People |
$85 - $85 |
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Beautiful 2 Bedroom Townhouse in Anna MariaAmenities:Beach, Pool, Air Conditioning, TV Description:Located in west central Florida between Tampa and Sarasota, Anna Maria Island is a tropical getaway that is just now being discovered! Great fishing, boating, shelling and swimming we offer it all. For the boater/fisherman: fishing piers, excursion boats, boat rentals and charter boats are available. Rent a jet ski or kayak, go for a parasail ride or scuba dive - there are so many options! Marinas are located around the island or bring your own boat - ramps are conveniently located and the fis |
House |
2 Beds |
1.5 Baths |
4 People |
$86 - $86 |
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Anna Maria Island Florida Vacation RentalsAmenities:Beach, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:This Florida beach rentals condo is located on Anna Maria Island on Florida's Gulf Coast. Our Florida beach rentals condo is an immaculate 2 BR, 2 BA, first floor condo surrounded by water with the Gulf of Mexico to the West, Tampa Bay to the North, Sarasota Bay to the South and the Intra-coastal Waterway to the East. Featured here is a gorgeous contemporary built and elegantly furnished Anna Maria Island vacation rentals beach view condo surrounded by three of the most beautiful beaches... |
Condo |
2 Beds |
2 Baths |
6 People |
$114 - $157 |
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