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  1. CABIN
    604 N Shore Cabin #54645

    604 N Shore Cabin #54645

    Anna Maria, FL

    604 North Shore Drive, Anna Maria FL 34216 Unit 4 Still Water". Adorable, vintage 2 bedroom cottage on Lake La Vista located at the north end of the Island . Just 250 steps to the beach and just a short stroll to historic Pine Avenue for great...

    Pets OK
    FREE CANCELLATION

    $242 to $393/night

  2. VILLA
    Minnow 2

    Minnow 2

    Anna Maria, FL

    Minnow 2  is a ground level, beautiful, tastefully decorated, polished terrazzo throughout, two bedroom, one bathroom bungalow offering a secluded and private screened in patio! It is only a short 2 minute stroll over to the beautiful white sandy...

    $118 to $293/night

  3. CABIN
    Eureka

    Eureka

    Anna Maria, FL

    Soak up the rays, play in the waves, and watch the beautiful Florida sunsets from the north end beaches of Anna Maria Island. Take an evening dip, cool drink in hand, in the refreshing blue pool surrounded by lush tropical landscaping. Eureka...

    Pool

    $293 to $539/night

  4. HOUSE
    AMI Du Soleil

    AMI Du Soleil

    Anna Maria, FL

    "AMI" Du Soleil (Anna Maria Island/Friend of the Sun) is located on the north end of the Island and has one of the largest heated pools on the Island. Enjoy the sunset view from the front porch or from the Sandbar Restaurant, which is only half a...

    Pool

    $265 to $539/night

  5. HOUSE
    Sea Mist

    Sea Mist

    Anna Maria, FL

    Welcome to Sea Mist! his beautiful 3 bedroom 2 bathroom property has 1,742 square feet of living space and the ability to accommodate 6 guests very comfortably inside and out. From the quality quilts and linens on the beds, to TV's in the living...

    Pool

    $244 to $481/night

  6. HOUSE
    Canario Cottage

    Canario Cottage

    Anna Maria, FL

    Welcome to Canario Cottage! This beautiful 3 bedroom, 2 bathroom property has 1254 square feet of elevated living space and the ability to accommodate 6 guests very comfortably inside and out. Canario Cottage is large and offers plenty of room for...

    Pool

    $244 to $588/night

  7. HOUSE
    Gladiolus on the Water

    Gladiolus on the Water

    Anna Maria, FL

    The desirable North end of Anna Maria and a peaceful canal front setting make this beautiful home a perfect vacation getaway! Gladiolus on the Water was recently updated with new furnishings and fresh paint, all tied together with a festive and...

    Pool

    $255 to $470/night

  8. HOUSE
    Coconut Breeze Estate

    Coconut Breeze Estate

    Anna Maria, FL

    Coconut Breeze is a custom home on the north end of Anna Maria in the quiet residential area in the sought after City Of Anna Maria. Offering 4 bedrooms / 4 bathrooms. You will find that this home has everything you need for your perfect Anna Maria...

    Pool
    FREE CANCELLATION

    $632 to $995/night

  9. HOUSE
    Blue Dolphin Inn- Heron Up

    Blue Dolphin Inn- Heron Up

    Anna Maria, FL

    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free...

    Pool
    FREE CANCELLATION
  10. HOUSE
    Azure Seas Home 779

    Azure Seas Home 779

    Anna Maria, FL

    The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and...

    Pets OK
    FREE CANCELLATION
  11. COTTAGE
    Still Water Cottage #54630

    Still Water Cottage #54630

    Anna Maria, FL

    604 North Shore, Anna Maria Island, Fl 34216 Unit 2 "Still Water"... Adorable, vintage 1 bedroom cottage on Lake La Vista located at the north end of the Island . Just 250 steps to the beach and just a short stroll to historic Pine Avenue for great...

    Pets OK
    FREE CANCELLATION

    $165 to $303/night

  12. HOUSE
    Pier House

    Pier House

    Anna Maria, FL

    Welcome to the Pier House! What a location and north of Pine Avenue! An old style florida three bedroom/two bathroom cottage on the north end of the Island! Pier House is right around the corner from the Rod and Reel Pier where you can enjoy the...

    $137 to $244/night

  13. HOUSE
    Sunrise Vista

    Sunrise Vista

    Anna Maria, FL

    Surrounded by water this 3 bedroom home sits on the beach with bay and intercoastal views! Relax and enjoy a cocktail while watching the dolphins on your spacious outdoor deck over looking the beach and views out to the Skyway Bridge. This ground...

    $222 to $466/night

  14. HOUSE
    Decked Out

    Decked Out

    Anna Maria, FL

    Welcome to Decked Out! Gorgeous and newly remodeled enchanted island home is a 2 bedroom/2 bath home with amazing designer touches and finishes throughout. As you enter the home you walk up the stairs onto a large front deck which has two sets of...

    Pool

    $235 to $411/night

  15. HOUSE
    Paradise Cottage

    Paradise Cottage

    Anna Maria, FL

    Come discover "Paradise Cottage" with all it's old Florida charm as well as newly updated appliances and decor.  This lovely and colorful two bedroom, two bath home feels brand new.  You'll enjoy tile floors throughout, a large eat-in kichen,...

    Pool Pets OK

    $191 to $382/night

  16. HOUSE
    Manatee Manor

    Manatee Manor

    Anna Maria, FL

    Manatee Manor is a newly remodeled two bedroom, two bathroom, pool, and canal front home in Anna Maria. Enjoy easy island life surrounded by tropical landscaping and a sailboat canal. It sleeps up to 6 guests. The open floor plan streamlines the...

    Pool

    $228 to $465/night

  17. HOUSE
    Beach To Bay Getaway

    Beach To Bay Getaway

    Anna Maria, FL

    Welcome to Beach to Bay Getaway! Anna Maria Island was a quaint historic fishing village and has become one of the top travel destinations by travelers from around the world. Known for world class beaches, top rated restaurants, fishing/boating...

    Pool

    $244 to $490/night

  18. HOUSE
    Haupia House

    Haupia House

    Anna Maria, FL

    Haupia House is a newly remodeled two bedroom, two bathroom elevated canal front home with a pool, spa and a new boat dock in the city of Anna Maria. This fabulous house is only 2 short blocks to the white sand beaches of Anna Maria Island and a...

    Pool

    $204 to $724/night

  19. HOUSE
    The Oleander House

    The Oleander House

    Anna Maria, FL

    Enjoy the crystal clear pool at Oleander House! An appealing blend of comfort and Florida casual in this pretty four bedroom vacation rental home which is spacious and airy and extremely family friendly. Located directly across from the bay with...

    Pool

    $314 to $735/night

  20. HOUSE
    Sea Haze

    Sea Haze

    Anna Maria, FL

    Brand New Rental!   Sea Haze is a mere 212 steps to the beach and the crystalline gulf! As you take your short walk to the gulf beaches, you will take in the sights of the dense banyans, spectacular homes of Park Avenue and the tropical sea...

    Pool

    $353 to $783/night

  21. HOUSE
    Seascapes

    Seascapes

    Anna Maria, FL

    Nestled on the far north end of Anna Maria right at Bean Point, is Seascapes, newly remodeled three bedroom two bathroom vacation home directly across from the Beach. This property has direct access to the gulf and is actually closer to the water...

    $216 to $460/night

  22. HOUSE
    Villa Marisol

    Villa Marisol

    Anna Maria, FL

    Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the crystal blue waters of the gulf. This is unquestionably one of Anna...

    FREE CANCELLATION

    $1 to $1,571/night

  23. HOUSE
    Blue Dolphin Inn- Skimmer Dow

    Blue Dolphin Inn- Skimmer Dow

    Anna Maria, FL

    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a...

    Pool
    FREE CANCELLATION
  24. HOUSE
    Blue Dolphin Inn- Flamingo Up

    Blue Dolphin Inn- Flamingo Up

    Anna Maria, FL

    The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units...

    Pool
    FREE CANCELLATION
  25. HOUSE
    Blue Dolphin Inn- All Units

    Blue Dolphin Inn- All Units

    Anna Maria, FL

    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own...

    Pool
    FREE CANCELLATION

    $1 to $1,158/night

  26. COTTAGE
    604 N Shore Cottage #54637

    604 N Shore Cottage #54637

    Anna Maria, FL

    Unit 1 "Still Water"... Adorable, vintage 1 bedroom cottage on Lake La Vista located at the north end of the Island . Just 250 steps to the beach and just a short stroll to historic Pine Avenue for great shopping. Exceptional, "Old Florida" charm!...

    Pets OK
    FREE CANCELLATION

    $165 to $303/night

  27. CABIN
    Minnow 1

    Minnow 1

    Anna Maria, FL

    The Minnow is a ground level, beautiful, tastefully decorated, polished terrazzo throughout, one bedroom, one bathroom bungalow offering a secluded and private screened in patio! It is only a short 2 minute stroll over to the beautiful white sandy...

    $118 to $235/night

  28. HOUSE
    Hibiscus House

    Hibiscus House

    Anna Maria, FL

    Welcome to Hibiscus House!  This is a four bedroom, three bathrom vacation rental home which is spacious and family friendly. Located directly across from the bay with views of the intercoastal and children's playground, you'll love this location....

    $235 to $460/night

  29. HOUSE
    Mermaids Watch

    Mermaids Watch

    Anna Maria, FL

    Less than a half a block from the gorgeous gulf side beaches. This 1945 built home has the original pine wood floors, and high ceilings making it feel very quaint and perfect for your family's vacation. There's also lots of windows and natural light...

    $217 to $475/night

  30. CABIN
    Latitude Adjustment

    Latitude Adjustment

    Anna Maria, FL

    Latitude Adjustment! Here it is: that stress-free attitude you've been wishing for in the "Old Florida" at Latitude Adjustment. This super-walkable villa is within steps of beach, bay, restaurants, bars, shops, piers, and more. A charming 2...

    Pets OK

    $118 to $265/night