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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. 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

  3. 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 $490/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
    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

  6. 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 $274/night

  7. 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

  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

    $493 to $995/night

  9. 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

    $356 to $1,781/night

  10. 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

    $145 to $1,781/night

  11. 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 $333/night

  12. 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

  13. HOUSE
    Gladiolus House

    Gladiolus House

    Anna Maria, FL

    Welcome to Gladiolus House and what a location, north of Pine Avenue! An old style florida two bedroom/two bathroom cottage on the north end of the Island! Not enough room for all the family, Gladiolus House is right behind Hibiscus House so why...

    $128 to $271/night

  14. 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

  15. HOUSE
    Manatee Cottage

    Manatee Cottage

    Anna Maria, FL

    Manatee Cottage is a newly remodeled two bedroom, two bathroom private home with a pool and spa. This fabulous house is only a short walk to the white sand beaches of Anna Maria and also a short walk to Bay Front park.  Stroll down to Pine Avenue...

    Pool

    $274 to $411/night

  16. HOUSE
    Bodacious Oasis

    Bodacious Oasis

    Anna Maria, FL

    Welcome to Bodacious Oasis! This beautiful 4 bedroom 2 and 1/2 bath property can accommodate 8 guests very comfortably inside and out.  Larger families will enjoy the open floor plan, providing plenty of room to spread out and enjoy comfortable...

    Pool

    $314 to $686/night

  17. 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

  18. 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

  19. HOUSE
    Pier To Pier Paradise

    Pier To Pier Paradise

    Anna Maria, FL

    Welcome to Pier to Pier Paradise! This beautiful brand new luxury home is one of a kind!  Three stories high and ideally situated on Anna Maria's North end, the property is tucked into a quiet little neighborhood across the street from the beach...

    Pool

    $392 to $1,176/night

  20. HOUSE
    The Lady Fish

    The Lady Fish

    Anna Maria, FL

    Nestled on the far north end of Anna Maria Island, three houses from beach access, is The Lady Fish, a newly remodeled three bedroom, two bathroom vacation home. Guests will enjoy a full gourmet kitchen with gas oven, cook top and ice maker,...

    Pets OK

    $216 to $460/night

  21. HOUSE
    Tarpon Pointe

    Tarpon Pointe

    Anna Maria, FL

    Tarpon Pointe is a gorgeous newly remodeled 2 bedroom 2 bath island home located on the north end of Anna Maria Island. You’ll enter the home from a large front deck with sliding glass doors into the living area. The living area features a large...

    Pool

    $235 to $465/night

  22. TOWNHOUSE
    Blue Dolphin Inn- Ibis

    Blue Dolphin Inn- Ibis

    Anna Maria, FL

    The Ibis unit at the Blue Dolphin Inn, located at 780 Jacaranda 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 free...

    Pool
    FREE CANCELLATION

    $137 to $1,781/night

  23. HOUSE
    White Shell House 225

    White Shell House 225

    Anna Maria, FL

    Beds2 King2 QueenAmenitiesDeck - 1Parking Spaces - 2Stories - 2View - Canal FrontLaundry - In UnitParkingJacuzziPoolAir ConditioningDishwasherGrill/BBQBoat DockHot...

    Pool Hot Tub
    FREE CANCELLATION

    $374 to $1,781/night

  24. HOUSE
    Anna Maria Escape

    Anna Maria Escape

    Anna Maria, FL

    The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home!...

    Pets OK
    FREE CANCELLATION

    $251 to $1,781/night

  25. 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 $321/night

  26. 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

    $588 to $1,781/night

  27. 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

  28. 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

  29. 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

  30. 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