Pirate Cove Cottages - Vacation Rentals in Anna Maria Beach

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From US $485

         

9.8 (297 Reviews)

Cottage

Charming cottage in quiet area, close to beach & bay.

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $1,026

         

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10.0 (2 Reviews)

House

Coconut Lagoon - Lovely Historic Renovated Cottage wHuge Heated Pool Backyard OasisCabanaBar

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $300

         

9.8 (47 Reviews)

Cottage

Tropical Landscaped Beach Cottage with Heated Jetted Pool

• Air Conditioner
• Pet Friendly
• Pool

• Sarasota
• Anna Maria

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From US $446

         

9.6 (120 Reviews)

Cottage

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

• Air Conditioner
• Parking
• TV

• Sarasota
• Anna Maria

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From US $811

         

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10.0 (1 Review)

House

Buttonwood Cottage

• Parking
• Pet Friendly
• Pool

• Sarasota
• Anna Maria

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From US $384

         

|

New

Cottage

Serenity Cottage

• Air Conditioner
• Pool
• Balcony/Terrace

• Sarasota
• Anna Maria

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From US $446

         

10.0 (10 Reviews)

Cottage

Ground Floor Cottage with 2 Master Suites and Private Heated Pool - Close to Beach!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $662

         

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9.8 (4 Reviews)

House

The Cottage on Pine - Luxury Boho Beach Cottage wPvt Heated Pool On Pine Ave

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $519

         

10.0 (15 Reviews)

Cottage

Holmes Beach Cottage Steps to the Beach with Heated Pool!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $458

         

10.0 (17 Reviews)

Cottage

Two Bedroom Cottage with Tropical Landscaping Surrounding Private Heated Pool!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $479

         

10.0 (13 Reviews)

Cottage

Ground Floor Two Bedroom Island Styled Home on Beautiful Anna Maria. Close to Beaches!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $422

         

10.0 (14 Reviews)

Cottage

Beautiful cottage just around the corner from the beach with Private Pool!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $469

         

10.0 (8 Reviews)

Cottage

Two Bedroom Ground Floor Island Home Sleeps 5 and Includes Heated Pool.

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $381

         

10.0 (2 Reviews)

Cottage

Ground Floor home for 5, short walk to beach and private heated pool! Lovely open living area

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $697

         

10.0 (2 Reviews)

Cottage

Recently Renovated Luxury Ground Floor Island Home Close to Beach!o Sleeps 4

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $634

         

9.8 (47 Reviews)

Cottage

Prices cut by 20% for stays up to 31.01.26 - Starfish Cottage

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $284

         

9.8 (41 Reviews)

Cottage

Prices cut by 20% for stays up to 31.01.26 - Shell Cottage

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $568

         

10.0 (127 Reviews)

Cottage

Private Pool - Seaglass Cottage by SeaBreeze Vacation

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $523

         

10.0 (293 Reviews)

Cottage

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $237

         

10.0 (71 Reviews)

Cottage

Quiet Nights of Quiet Stars on Anna Maria Island

• Air Conditioner
• Parking
• TV

• Sarasota
• Holmes Beach

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From US $617

         

10.0 (48 Reviews)

Cottage

Beach Basket Cottage: Cute Old Florida Style Beach Cottage just steps to the Beach!

• Air Conditioner
• Pet Friendly
• Pool

• Sarasota
• Anna Maria

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From US $315

         

10.0 (31 Reviews)

Cottage

Coastal Home with Heated Pool, Close to Beach!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Holmes Beach

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From US $507

         

10.0 (26 Reviews)

Cottage

Home with Private Pool, Two Blocks from the Beach! - Queen Palms

• Air Conditioner
• Parking
• Pool

• Sarasota
• Holmes Beach

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From US $374

         

10.0 (26 Reviews)

Cottage

Charming Ground Level Resort Style 3 units Condo of a TRIPLEX- unit A

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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