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Cottage Rentals in Anna Maria Island, Florida

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

DEAL!! Seagrape II-charming & steps to the beach
Anna Maria Island Cottage Rental Picture
  • Cottage Rental Deals and Discounts $40 off = $600 per week
  • bedrooms 1
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $85 - $110 /nt
    $560 - $700 /wk
    $2,100 - $2,700 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Songbird
Anna Maria Island Cottage Rental Picture
  • Cottage Rental Deals and Discounts $85 off = $490 per week
  • bedrooms 2
  • community Holmes Beach
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $525 - $1,000 /wk
    $1,650 - $3,000 /mth
 
 
 
 
 

52 reviews write a review

Coconut Vacations - 104 N. 23rd - Bradenton Beach, FL
Anna Maria Island Cottage Rental Picture
  • bedrooms 5
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 18
  • baths 4
  • rates (USD) $90 - $143 /nt
    $700 - $910 /wk
    $2,520 - $3,276 /mth
 
 
 
 
 

5 reviews write a review

Anna Maria Beach Cottage
Anna Maria Island Cottage Rental Picture
  • bedrooms 3
  • community
  • rental type Cottage
  • sleeps 8
  • baths 2
  • rates (USD) $1,250 - $2,050 /wk
    $4,000 - $8,200 /mth
 
 
 
 
 

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Tradewinds Resort-Vacation Cottage Rental-Daily/ Wkly Specal
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • community Tradewinds Resort
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $155 - $265 /nt
    $867 - $1,364 /wk
    $3,500 - $4,640 /mth
 
 
 
 
 

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Summer Breeze: Dont Miss This Price $750/wk Between July 23 - August 8, 2014
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $700 - $975 /wk
 
 
 
 
 

2 reviews write a review

Luxury finishes, private backyard with heated pool! Steps to the beach!
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 5
  • baths
  • rates (USD) $158 - $275 /nt
    $1,225 - $1,925 /wk
    $3,675 - $5,775 /mth
 
 
 
 
 

1 reviews write a review

Newly Remodeled with specatacular outdoor pool space! Near new construction, 10% discount!
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 5
  • baths 2
  • rates (USD) $180 - $293 /nt
    $1,400 - $2,050 /wk
    $4,200 - $6,150 /mth
 
 
 
 
 

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Newly Remodeled Duplex! Steps to the beach, luxury finishes!
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 4
  • baths 2
  • rates (USD) $170 - $279 /nt
    $1,325 - $1,950 /wk
    $3,975 - $5,850 /mth
 
 
 
 
 

1 reviews write a review

Pineapple Cottage: 2BR/1BA Quaint Family- and Pet-Friendly Cottage
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $157 - $186 /nt
    $1,100 - $1,300 /wk
 
 
 
 
 

31 reviews write a review

Island Place Cottage: 1BR/1BA Quaint Pet-Friendly Cottage
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $121 - $143 /nt
    $850 - $1,000 /wk
 
 
 
 
 

21 reviews write a review

LABOR DAY WEEKEND AVAILABLE!!! 3 NIGHTS FOR $600
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $150 - $175 /nt
    $750 - $850 /wk
    $2,800 - $3,200 /mth
 
 
 
 
 

32 reviews write a review

Swim Up Tiki Bar Pool Exclusively for your use
Anna Maria Island Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 8
  • baths 2
  • rates (USD) $193 - $275 /nt
    $1,350 - $1,925 /wk
 
 
 
 
 

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Spoil yourself! Pool-spa-dock-sea+only steps to sugar-white-sand. GEM!
Anna Maria Island Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $357 - $729 /nt
    $5,100 /wk
 
 
 
 
 

26 reviews write a review

Plum Cottage 324 with Beautiful & Peaceful Tropical Garden ~ RA43477
Anna Maria Island Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $145 - $325 /nt
    $1,000 - $2,245 /wk
 
 
 
 
 

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BoatHouse Cottage - N. end Anna Maria- steps to beach - Private Pool
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $200 - $225 /nt
    $1,050 - $1,225 /wk
    $3,920 /mth
 
 
 
 
 

17 reviews write a review

The Shady Mango - Anna Maria's Most Charming Coastal Cottage!
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,750 - $2,450 /wk
 
 
 
 
 

6 reviews write a review

Seaglass Cottage, 3 houses from Bean Point beach, Heated Pool
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 5
  • baths 2
  • rates (USD) $1,300 - $1,750 /wk
 
 
 
 
 

11 reviews write a review

Unexpected Blessings One house from beach
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $175 /nt
    $1,095 /wk
 
 
 
 
 

11 reviews write a review

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