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Anna Maria Island Vacation Rentals

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2255 rentals in Anna Maria Island.
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Close to beach, gorgeous 5 bd luxury home! Private Pool, Spa, and Putting Green!

Rental Home
5 bedrooms
7 bathrooms
Sleeps 8
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Anna Maria The Pink Flamingo

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2 bedrooms
2 bathrooms
Sleeps 6
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BAY FRONT HOUSE WITH PRIVATE DOCK

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2 bedrooms
2 bathrooms
Sleeps 4
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Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Beach+Dock+Pool+2 SUPs+2 Kayaks+Fishing+Water Views,duplex,140 steps to Beach

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3 bedrooms
2 bathrooms
Sleeps 7
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Coastal Cottage - NORTH END 3 bedroom, 2 bath pet friendly pool home!

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3 bedrooms
2 bathrooms
Sleeps 6
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AMI Beach Shack

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Ocean View Villa

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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50 Steps to Beach�. Hot Tub! 1bd modern cottage�

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
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Songbird Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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ISLAND TOWNHOUSE - 200 Steps to the BEACH

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Isle Haven B - steps to the beach and many other conveniences - pet friendly!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Beach Club at Anna Maria #2: 1 BR / 1 BA Resort on Anna Maria by RVA, Sleeps 4

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Best Little Beach House on Anna Maria Island...With a pool

Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Beautiful, Gulf-Front Home on Bean Point--Halcyon House

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Dragonfly - Southern charm on the North end of Anna Maria Island

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Elevator! Luxury Home, Pool, Spa, 3 min. walk to Beach, Office and Monitor!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
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Luxury Suite Near The Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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PRIVATE POOL, WALK TO BEACH

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3 bedrooms
3 bathrooms
Sleeps 6
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Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Gulf View Retreat, Beach Views, Pool, Firepit, 2 Kayaks, PaddleBoard, 3BR/2Ba

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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Surfside AMI, LOADED FOR FUN! Golf Cart, Heated Pool, SUP, Kayak, Beach Gear...

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Serendipity - Beach Front Home on Bean Point , Anna Maria

Rental Home
4 bedrooms
8 bathrooms
Sleeps 8
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Fabulous One/Two Bedroom Apartments On Anna Maria Island Special Rates 4/15-5/6

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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1 BR / 1 BA, Anna Maria Island,Holmes Beach Florida, Gulf Coast, Beach Condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Coquina Reef! 1 Block From Beautiful Bradenton Beach!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 8
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Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Anna Maria, Prive Heated Pool, Lanai

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Pricing Specials! 2 BR 2 Full BA on Anna Maria Island just steps to Beach!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Bungalow On The Bayou (Best Location on the Island)

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
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Spectacular Beachfront House with Pool

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
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New 2019 - 90sec. to beach - all day sun - big pool - quite - clean - safe - fun

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Family Fun Close to Beach, Pool Slide Spa & Elevator

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
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Seaside Sanctuary #1 - World's Greatest Sunsets!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Anna Maria Beach Condo 1/1

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Salty Snapper Beach House, Steps to Beach, Pool Table, Tropical Yard w/Fire Pit

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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$200 towards a private fishing charter with Captain Josh with 2020 reservation

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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2BR/2BA Bayfront Retreat! Watch Sunrise Over Water with Bay Views & Free WIFI

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Blue Water Beach House: 5+ bdrm, 4.5 bath, Heated Pool/spa, 1.5 blocks to beach

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
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Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Beach View Retreat - 180-degree Beach/Gulf Views, beach 30 feet away, Bridge Str

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
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Tranquil Anna Maria Island Resort, Unit 1... Only 4 units, all amenities!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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250 Foot Steps To The Gulf Of Mexico AND a low chlorine pool!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Frequently Asked Questions about Anna Maria Island





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.