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Anna Maria Island Romantic Vacation Rentals

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2243 rentals in Anna Maria Island.
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Songbird Cottage
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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View of beach side of home from waters edge at dusk.
Aerial view of home.
Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Island House - Funboard
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Ocean View Villa
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Condo overlooking the private pool
Living room
Free Trolley Bus around the Island
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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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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Luxury Suite Near The Beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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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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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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Seaside Sanctuary #1 - World's Greatest Sunsets!
Rental Home
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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Spectacular Beachfront House with Pool
Rental Home
4 bedrooms
5 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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PRIVATE POOL, WALK TO BEACH
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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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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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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Serendipity - Beach Front Home on Bean Point , Anna Maria
Rental Home
4 bedrooms
8 bathrooms
Sleeps 8
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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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North Island Beach Escape
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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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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Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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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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Gulf View Retreat, Beach Views, Pool, Firepit, 2 Kayaks, PaddleBoard, 3BR/2Ba
Rental Home
0 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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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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Coquina Reef! 1 Block From Beautiful Bradenton Beach!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Anna Maria, Prive Heated Pool, Lanai
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
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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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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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Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach
Rental Home
3 bedrooms
2 bathrooms
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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Family Fun Close to Beach, Pool Slide Spa & Elevator
Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
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Anna Maria Beach Condo 1/1
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Sea Pirate #8, Family Friendly Cottage By The Sea on Anna Maria Island
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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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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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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*VERY CLEAN !!!*ANNA MARIA ISLAND*2BED/2BATH*COMPLETELY UPDATED/WELL MAINTAINED*
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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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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Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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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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Stella Marina on Anna Maria Island
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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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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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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Spacious canal front home with private heated pool on Anna Maria Island
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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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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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.