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Anna Maria Island Vacation Rentals

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1132 rentals in Anna Maria Island.
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Anna Maria Island Absolute Anna Maria-Private Beach Access-Heated Pool
2 bedrooms
2 bathrooms
Sleeps 5
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4 other travelers have booked this property
Anna Maria Island Private Tropical Garden Home
3 bedrooms
2 bathrooms
Sleeps 6
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25 other travelers have booked this property
C-viewFlorida, Canal/Dock/Heated Pool/Near Gulf - A Hidden Gem
5 bedrooms
4 bathrooms
Sleeps 10
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Lemonfish, stunning and spacious 4-bed rental!
4 bedrooms
3 bathrooms
Sleeps 8
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Relaxed Old Florida Lifestyle: Apt 162 Runaway Bay
2 bedrooms
2 bathrooms
Sleeps 6
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2 other travelers have booked this property
Ohana Hale North 2 Bedroom on Anna Maria
2 bedrooms
1 bathroom
Sleeps 6
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35 other travelers have booked this property
Blue Bayou
2 bedrooms
2 bathrooms
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16 other travelers have booked this property
$300 OFF MARCH PARADISIAC ENCLAVE 5* Waterfront Canal Pool Home-Dock/Kayak/BikeS
2 bedrooms
2 bathrooms
Sleeps 6
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9 other travelers have booked this property
Dream Lover Boat & Breakfast on Anna Maria Island
2 bedrooms
2 bathrooms
Sleeps 4
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2 other travelers have booked this property
Mintfish, beautiful views across Bimini Bay! 4-Bed
4 bedrooms
4 bathrooms
Sleeps 8
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OakView - Anna Maria Island - Old World Florida
4 bedrooms
3 bathrooms
Sleeps 12
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Ohana Hale South West Suite
2 bedrooms
1 bathroom
Sleeps 6
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48 other travelers have booked this property
CURRENT SPECIAL: ANNA MARIA : BEAUTIFUL BEACHFRONT CONDO, 2+ BR. 2 bath
3 bedrooms
2 bathrooms
Sleeps 4
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43 other travelers have booked this property
Bermuda Bay Club betwn the Beach and Bay , elevator, nicely furnished
3 bedrooms
3 bathrooms
Sleeps 6
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11 other travelers have booked this property
Stunning luxury beachfront house with pool and spa
4 bedrooms
5 bathrooms
Sleeps 8
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Gulf Beach Place, miles of whites sandy beach
2 bedrooms
2 bathrooms
Sleeps 6
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11 other travelers have booked this property
Coquina Sands, view beach from balcony, priv pool
2 bedrooms
3 bathrooms
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13 other travelers have booked this property
2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!
3 bedrooms
2 bathrooms
Sleeps 8
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10 other travelers have booked this property
ISLAND TOWNHOUSE - 200 Steps to the BEACH
2 bedrooms
2 bathrooms
Sleeps 4
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64 other travelers have booked this property
Ocean View 3 bedroom, pool, North Shore Drive
3 bedrooms
2 bathrooms
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41 other travelers have booked this property
Lovely oceanview house, steps to the beach
3 bedrooms
3 bathrooms
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2 other travelers have booked this property
New 'Paradise Cove' Steps to beach & fishing Dock incl pole beach cart umbrella
1 bedroom
1 bathroom
Sleeps 3
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15 other travelers have booked this property
Sublime Interlude
2 bedrooms
2 bathrooms
Sleeps 5
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AMI Island Living -Walk to Beach-Ground Level Unit
2 bedrooms
1 bathroom
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12 other travelers have booked this property
Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches
2 bedrooms
2 bathrooms
Sleeps 4
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23 other travelers have booked this property
Steps to Beach, Gulf View, Footprints in the Sand
2 bedrooms
1 bathroom
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51 other travelers have booked this property
Luxury 3 Bedrooms/3 Full Baths, Private Heated Pool with Waterfall, Beach
3 bedrooms
3 bathrooms
Sleeps 6
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7 other travelers have booked this property
Cherryfish, a spectacular spacious 4-bed home!
4 bedrooms
3 bathrooms
Sleeps 8
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Anna Maria Island Beach Sands
2 bedrooms
2 bathrooms
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1 other traveler has booked this property
Anna Maria Island Stunning Waterfront home
3 bedrooms
2 bathrooms
Sleeps 7
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Las Brisas, Cottage on bay side of Island.
2 bedrooms
2 bathrooms
Sleeps 7
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3 other travelers have booked this property
Anna Maria Island Beach Palms 6B
2 bedrooms
2 bathrooms
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2 other travelers have booked this property
Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453
3 bedrooms
3 bathrooms
Sleeps 6
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47 other travelers have booked this property
A Pearl of a Beach Home - with luxury private heated pool and hot tub
3 bedrooms
3 bathrooms
Sleeps 6
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32 other travelers have booked this property
Island Vacation Rental
2 bedrooms
2 bathrooms
Sleeps 4
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9 other travelers have booked this property
Spectacular Beach House With GulfView Only Steps to a Pristine Beach
3 bedrooms
3 bathrooms
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6 other travelers have booked this property
Jacaranda Artist Retreat
3 bedrooms
2 bathrooms
Sleeps 6
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8 other travelers have booked this property
Gorgeous views,spectacular home!
5 bedrooms
3 bathrooms
Sleeps 12
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90 other travelers have booked this property
Fully Remodeled Vacation Rental Anna Maria Island
2 bedrooms
1 bathroom
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9 other travelers have booked this property
Anna Maria Island Beach Palms 5B
2 bedrooms
2 bathrooms
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6 other travelers have booked this property
Anna Maria Island Beach Breeze
2 bedrooms
1 bathroom
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Lifestyle on the island
2 bedrooms
2 bathrooms
Sleeps 4
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6 other travelers have booked this property
Anna Maria The Pink Flamingo
2 bedrooms
2 bathrooms
Sleeps 6
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7 other travelers have booked this property
Ohana Hale Beachside Suite D 2 Bedroom with Gulf View
2 bedrooms
1 bathroom
Sleeps 6
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25 other travelers have booked this property
Ohana Hale Beachside Suite B One Bedroom
1 bedroom
1 bathroom
Sleeps 4
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16 other travelers have booked this property
Coconuts Courtyard 119 Upstairs
1 bedroom
1 bathroom
Sleeps 4
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31 other travelers have booked this property
Coconuts Poolside Unit 102
1 bedroom
1 bathroom
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4 other travelers have booked this property
Coconuts Beach Front 112 Upstairs
1 bedroom
1 bathroom
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Coconuts Tahitian 207
1 bedroom
2 bathrooms
Sleeps 2
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27 other travelers have booked this property
Coconuts Beach Front 109 Upstairs
1 bedroom
1 bathroom
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9 other travelers have booked this property
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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.
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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.