5 Bedroom House Rental in Anna Maria Island, FL (2024)

Welcome to A Pirate’s Dream, a stunning canal-front vacation home with a private swimming pool and a private dock that is also just a five-minute walk to the warm sands of Holmes Beach! This four-bedroom, three-and-a-half-bathroom rental sleeps up to twelve guests. The open living area has large windows that let in the bright Florida sun and gives guests a relaxing place to connect with friends and family or have a movie night. Additionally, the living space opens up to the balcony with stunning views of the canal for guests to enjoy while relaxing and discussing Anna Maria Island activities. The fully equipped kitchen is a chef's dream, with stainless steel appliances, ample counter space, and a wine fridge! Enjoy a quick snack at the kitchen island and a cup of coffee on the balcony in the morning. There is an indoor dining area and a dining area on the balcony, which are perfect for delighting in homemade island-inspired meals or the best Anna Maria Island take-out. Additionally, there is an outdoor kitche
Avast ye! This grand, waterfront 5BR/3.5BA Spanish Colonial Revival style contemporary private home on Holmes Beach house is A Pirate’s Dream! Immerse yourself in the lore of piracy and the island history of Anna Maria. Relax by the dock (accommodates vessels up to 35 ft), drop your kayak, paddleboard, and fishing line, set sail, or look into boat rentals! Swim in your private pool or dine alfresco while savoring enchanting water views, vibrant sunrises, and sunsets. Holmes Beach and Manatee Public Beach are a five-minute stroll, and the free Island trolley stop is a three-minute walk from your doorstep.

The bedrooms have magnificent water views; the primary suite has a balcony. The main (2nd) floor living/kitchen/dining has a wrap-around deck with covered alfresco dining. The first floor has a game room/lounge, bonus kitchen, and an outdoor kitchen with a BBQ grill beside the pool, stone pool deck, tiki bar, and firepit.

A wide paver driveway leads to the elegant, Mediterranean-style front loggia, boasting columns, arches, and decorative details such as traditional lantern-style chandeliers and Spanish wrought iron railings. Pirate’s Dream is an architectural delight! Royal palms shade this sophisticated dream home and beautifully landscaped yard. Ideal for families, large groups, multi-family vacations, reunions, corporate retreats, guys/girls boating/fishing getaways, etc., A Pirate’s Dream is spacious, comfortable, fully appointed, and sleeps 10 guests. Welcome pirates, privateers, buccaneers, wenches, and scurvy dogs!

Highlights:
Private Dock up to 35 feet
Private Pool (Heated Between Nov. 1-May 1)
5-minute walk to the beach
Ping Pong Table
Bonus Room

Living:
The elegant interior of A Pirate’s Dream has a soft, soothing palette of whites, neutrals, and dune grass. No detail has been overlooked; all the fixtures are elegant, ceilings have recessed lighting and fans, and every room in the home features beautiful crown molding, trim, and baseboards.

The bright, airy, open-design second-floor living area has large windows that bathe the space in sunlight and honey-hued hardwood floors. Relax on cream-colored suede sofas, play family board games, cozy up with a good book, or stream your favorite shows or movies on the large wall-mounted SmartTV. This living space has a soothing coastal ambiance with nautical blues, greens, and maritime accents.

Additionally, the living space has sliding glass doors that open out to the balcony with stunning canal views for guests to enjoy while relaxing and discussing Anna Maria Island activities.
The home's 1st (ground floor level) has a game room with a living area/lounge area with a sofa, table, and chairs beside the ping pong table. Enjoy family games such as Giant Connect Four or corn hole. This game room/lounge space is a great spot to escape the heat or play indoors on a rainy day.

Kitchen/Dining:
The bright and sunny gourmet chef’s kitchen is an entertainer’s dream! Prepare a pirate feast after a day at the beach. This main-level (2nd floor) kitchen has abundant custom cabinetry, gorgeous granite countertops offering plenty of meal prep space, and stainless steel appliances, including a gas stove with hood, convection oven, microwave, French door fridge with icemaker, dishwasher, and double basin sink. The kitchen is fully equipped with pots, pans, cookware, utensils, cutlery, dishware, glassware, a coffee maker, a kettle, a toaster, a blender, a chef’s caliber knife block, and more.

The granite kitchen breakfast bar has stool seating for four. The open design of the kitchen/dining area ensures that a chef is never isolated from the group. This breakfast bar is a sublime spot to sip your morning cappuccino or fresh-squeezed citrus juice. Or, sit at the breakfast bar and share a glass of wine with the chef during meal prep.

Just off the main floor kitchen is a grand dining table with seating for six, illuminated by a modern geometric chandelier. A huge picture window offers spectacular canal views right from the kitchen table. Prefer alfresco dining? Serve your home-cooked meal on the covered balcony just off the kitchen. A dining table on the balcony offers cushioned seating for six. A ceiling fan with a lamp keeps the breeze moving. Enjoy views of aquamarine water that stretch to the horizon.

Additionally, there’s an outdoor, poolside kitchen with a full grill set up perfect for grilling fresh caught seafood, steaks, burgers, or veggie kabobs. This gorgeous stone and white granite outdoor kitchen features a large, wall-mounted SmartTV to watch the game while you BBQ! After dinner, gather your group for evening co*cktails at the tiki bar. Hoist the Jolly Roger! Drink rum and sing shanties with your crew!

Bedrooms/Baths:
A Pirate’s Dream has four bedrooms and three-and-a-half baths. These water-view bedrooms have luxurious mattresses and sumptuous bedding. Dream of mysterious lost treasures and sunken pirate ships in the deep, dark seas.

The primary bedroom radiates luxury and accesses the second-level balcony with dazzling canal views. The primary ensuite bathroom has ample storage space and a grand, marble-tile walk-in shower.

The second bedroom has calming beach decor to make guests smile and an ensuite bathroom with a bright walk-in shower. The third bedroom has access to the private third-floor balcony with breathtaking views and shares a jack-n-jill bathroom with the fourth bedroom.

Bedrooms all have wall-mounted SmartTVs, ceiling fans, and bedside tables with reading lamps. Plush bath towels, toiletries, and hair dryers are provided. There’s a laundry room with a state-of-the-art washer and dryer and a granite vanity laundry room sink.

Sleeping Arrangement Overview (Sleeps 10)
Primary Bedroom, 2nd floor: King bed, TV, balcony access, and an ensuite bathroom with walk-in shower.
Second bedroom, 3rd floor: King bed, TV, and an ensuite bathroom with walk-in shower.
Third bedroom, 3rd floor: King bed, TV, and jack-n-jill bathroom with walk-in shower.
Fourth Bedroom, 3rd floor: King bed, TV, and jack-n-jill bathroom with walk-in shower.
Fifth Bedroom, 3rd floor: four twin bunk beds.

Outdoor Amenities:
The canalside location and private dock at A Pirate’s Dream make this home ideal for boating, fishing, and water sports enthusiasts. The dock can accommodate vessels up to thirty-five feet. The neighborhood boat launch at Sportsman’s Harbor is just minutes away. Convenience to beaches, dining, and great seafood is another highlight. Stroll to Holmes Beach and Manatee Public Beach in less than five minutes. The free island trolley stop is a three-minute walk from your doorstep.

Bright sunshine and ocean breezes make Florida one of the best places for coastal living. Relax and sip your morning coffee or evening co*cktail on a balcony overlooking the sparkling waters of the Intracoastal and Jones Bayou. The three levels, with balconies and views in every direction, highlight A Pirate’s Dream. Palm fronds rustle in the sea breeze, pelicans and cormorants dive for fish, and a roseate spoonbill hunts for shrimp in shallow water.

Multiple alfresco dining spaces and a tiki bar are additional highlights of this home. These outdoor dining spaces provide tranquil spots for serene Florida sunsets in pink, violet, orange, and gold hues.

The private free-form swimming pool will delight families, children, the very young, and the young at heart. The pool has a sun shelf and a built-in picnic table. Bring out games from the game room! Play corn hole on the pool deck while grilling grouper or sipping margaritas at the tiki bar. After dinner, stargaze and watch the moonrise over the water.

The Neighborhood:
The white sand beaches of Anna Maria flaunt the prettiest seashells in Florida! Anna Maria is also a top US location for rare seashells. Swim in the turquoise Gulf of Mexico, where dolphins play daily. Bring your fishing gear to cast a line off the pier, or rent a boat to get out on deep water and fish.

The Shoppes of Paradise Bay Plaza is just about .5 miles away and offers grocery shopping, restaurants, a Starbucks coffee shop, and a Dollar Tree store. The Sarasota/Bradenton airport is a 19-minute drive (10.1 miles) south. Downtown Sarasota and St Armands Circle are about a 30-minute drive south, which is a great place for watching a sunset from a rooftop bar and casual and upscale dining and shopping.

Longboat Key, Bradenton Beach, and Anna Maria Island have fantastic restaurants and beachside activities such as boat rentals, sunset cruises, jet ski, bike, paddleboard, scooter, and kayak rentals. Don't forget a trip to downtown Bradenton on the Manatee River with bars, dining, and Village of the Arts. The Village of the Arts is an eclectic live-work community of colorful historic cottages that house everything from award-winning restaurants to specialty shops, studios, healing arts, bakeries, and Bradenton’s best art galleries.

Proximity to Anna Maria Island is a highlight of the Perico Bay Club Community. There’s a saying here; “When you're on Anna Maria Island, you don’t go to the beach… because on Anna Maria Island, you’re already at the beach.” With Gulf temperatures averaging 84 degrees and 360 days of sunshine per year, the surrounding waters of AMI are known as “the nursery” because of the many dolphins that raise their young here.

This area, surrounded by water and interlaced with canals, hosts many amazing sea creatures, including Loggerhead Turtles, Manatees, and dolphins. Loggerhead turtles are a protected species. A Turtle Watch group of wonderful folks search the beaches for nests and protect those nests until the eggs hatch (it is illegal for anyone to tamper with the nests). Manatees are also protected here in Florida - they are commonly seen in the summer when they leave their winter-warm waters and migrate south.

Unique Benefits
Grand, contemporary Spanish Revival style, 3-story, 5BR/3.5BA canal-front Anna Maria Island dream home! Private dock (up to 35 feet), private pool, sunrise/set vistas over Intracoastal/Jones Bayou/Gulf. Waterview bedrooms/balconies, chef’s kitchen, covered alfresco Waterview dining, poolside granite kitchen w/ BBQ/Tiki Bar, game room w/ ping pong. Bright, airy, spacious. Hardwood/marble floors. 4-minute stroll to Holmes Beach/dining/pier/Sportsman's Harbor boat launch. WiFi/Laundry. Sleeps 12.

5 Bedroom House Rental in Anna Maria Island, FL (2024)

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