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Anna Maria Island Rentals with Pools

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1153 rentals in Anna Maria Island.
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This is the one! 9 bd, Waterslide, Pool, Spa, Rooftop Deck - Island Sol!
9 bedrooms
7 bathrooms
Sleeps 22
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Skip to Beach & Shops in New Stunning Home, Pool/Spa, Beach Gear, Pets OK
4 bedrooms
5 bathrooms
Sleeps 8
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Beautiful Anna Maria Island
2 bedrooms
2 bathrooms
Sleeps 4
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Anna Maria The Pink Flamingo
2 bedrooms
2 bathrooms
Sleeps 6
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Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453
3 bedrooms
3 bathrooms
Sleeps 6
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Beach Haven #204 of Holmes Beach FL
1 bedroom
1 bathroom
Sleeps 4
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Roof Top deck plus outside bar and 1 min to the beach!
6 bedrooms
5 bathrooms
Sleeps 12
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BAY FRONT HOUSE WITH PRIVATE DOCK
2 bedrooms
2 bathrooms
Sleeps 4
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Family-friendly vacation home w/ private, heated pool & furnished patio
4 bedrooms
3 bathrooms
Sleeps 8
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It's my Dream - private heated pool, 2 minute walk to the beach! Pet friendly
3 bedrooms
2 bathrooms
Sleeps 6
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Coconut Bayou - a gem with heated pool on a fantastic location in Anna Maria
3 bedrooms
3 bathrooms
Sleeps 6
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Sea Pearl - on the Canal in Anna Maria with heated pool. Pet friendly!
3 bedrooms
2 bathrooms
Sleeps 8
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PRIVATE POOL, WALK TO BEACH
3 bedrooms
3 bathrooms
Sleeps 8
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' Sweet dream'Beautiful ground level Beach front rental walk to bridge street
2 bedrooms
2 bathrooms
Sleeps 5
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RUNAWAY BAY #230 - 2 BED/2 BATH CONDO - STEPS TO BRADENTON BEACH ON ANNA MARIA
2 bedrooms
2 bathrooms
Sleeps 4
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8 bd luxury home with private pool + spa! Close to the beach, great location!
8 bedrooms
8 bathrooms
Sleeps 16
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Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches
2 bedrooms
2 bathrooms
Sleeps 4
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HISTORIC WATERFRONT COTTAGES..DOCK...BEACH...Couples, Families, Reunions!
4 bedrooms
4 bathrooms
Sleeps 15
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'Serendipity’ PEACEFUL, Newly renovated, steps to beach & fishing dock on bay
1 bedroom
1 bathroom
Sleeps 2
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Newly built home w/ heated private pool only a few blocks away from Gulf beaches
3 bedrooms
2 bathrooms
Sleeps 6
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ISLAND TOWNHOUSE - 200 Steps to the BEACH
2 bedrooms
2 bathrooms
Sleeps 4
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Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier
3 bedrooms
2 bathrooms
Sleeps 8
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Angie's Place! 2br/2ba, heated pool and a view of the Gulf!
2 bedrooms
2 bathrooms
Sleeps 4
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Relaxing Beach Getaway
2 bedrooms
1 bathroom
Sleeps 6
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1 BR / 1 BA, Anna Maria Island,Holmes Beach Florida, Gulf Coast, Beach Condo
1 bedroom
1 bathroom
Sleeps 4
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Sweet Melissa's Beach House, 3 bedrooms, Great Location close to beach! Pool!
3 bedrooms
3 bathrooms
Sleeps 8
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Mintfish, beautiful views across Bimini Bay! 4-Bed
4 bedrooms
4 bathrooms
Sleeps 8
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Plumfish, located on the Hammock Bayou. Beautiful!
3 bedrooms
2 bathrooms
Sleeps 8
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Honeyfish, stunning views across Bimimi Bay!
4 bedrooms
4 bathrooms
Sleeps 8
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Poolside Ocean View Beach Front Apartment
1 bedroom
1 bathroom
Sleeps 4
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Gulf view condo w/ WiFi, AC, full kitchen, furnished balcony, & more!
1 bedroom
1 bathroom
Sleeps 4
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Best Little Beach House on Anna Maria Island...With a pool
1 bedroom
1 bathroom
Sleeps 2
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Beautiful, Gulf-Front Home on Bean Point--Halcyon House
4 bedrooms
4 bathrooms
Sleeps 8
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Dragonfly - Southern charm on the North end of Anna Maria Island
5 bedrooms
4 bathrooms
Sleeps 10
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Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl
2 bedrooms
2 bathrooms
Sleeps 6
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Luxury Suite Near The Beach
2 bedrooms
2 bathrooms
Sleeps 4
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Gulf View Retreat, Beach Views, Pool, Firepit, 2 Kayaks, PaddleBoard, 3BR/2Ba
3 bedrooms
4 bathrooms
Sleeps 8
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Elevator! Luxury Home, Pool, Spa, 3 min. walk to Beach, Office and Monitor!
5 bedrooms
5 bathrooms
Sleeps 12
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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
2 bedrooms
1 bathroom
Sleeps 6
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Surfside AMI, LOADED FOR FUN! Golf Cart, Heated Pool, SUP, Kayak, Beach Gear...
4 bedrooms
4 bathrooms
Sleeps 12
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Family Fun Close to Beach, Pool Slide Spa & Elevator
4 bedrooms
5 bathrooms
Sleeps 12
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Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool
2 bedrooms
2 bathrooms
Sleeps 6
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North Island Beach Escape
3 bedrooms
2 bathrooms
Sleeps 6
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Anna Maria, Prive Heated Pool, Lanai
2 bedrooms
2 bathrooms
Sleeps 6
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Luxury Spacious Waterfront Pool, Spa, Bar, Dock, Near Beaches, Fall $380/n
4 bedrooms
3 bathrooms
Sleeps 8
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Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!
4 bedrooms
4 bathrooms
Sleeps 8
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Dream Lover Boat & Breakfast on Anna Maria Island
2 bedrooms
2 bathrooms
Sleeps 4
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Fabulous One/Two Bedroom Apartments On Anna Maria Island Special Rates 4/15-5/6
2 bedrooms
2 bathrooms
Sleeps 4
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$200 towards a private fishing charter with Captain Josh with 2020 reservation
3 bedrooms
2 bathrooms
Sleeps 8
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Anna Maria Beach Condo 1/1
1 bedroom
1 bathroom
Sleeps 4
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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.