The Jolly Fortune

United States / Florida / Anna Maria Island

This grand, waterfront, four-bedroom, and four-and-a-half bathroom vacation home is a dream!

up to 4
Bedrooms
up to 8
Guests
4.5
Bathrooms
Min. Nights Upon Request

Overview

Immerse yourself in the lore of piracy and the island history of Anna Maria. You can relax by the dock, which can accommodate vessels up to 38 ft, drop your kayak, paddleboard, and fishing line, set sail, or even look into boat rentals! You can also swim in the private pool or dine alfresco while savoring enchanting water views of the bay, vibrant sunrises, and sunsets. 

A broad paver driveway leads to the graceful, Mediterranean-style front loggia, featuring columns, arches, and elaborate accents such as classic lantern-style chandeliers and Spanish wrought iron railings. The opulent interior spares no details; there are sizable picture windows framing canal and bay views for our guests to enjoy. Unwind on the plush cream-colored leather couches, engage in family board games, curl up with a good book, or stream your preferred shows or movies on the large wall-mounted Smart TV. 

The spacious and bright gourmet chef's kitchen is perfect for entertaining guests. It features custom cabinetry, beautiful granite countertops, a breakfast bar with four stools, 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 also comes fully equipped with pots, pans, cookware, utensils, cutlery, dishware, glassware, a coffee maker, a kettle, a toaster, a blender, and a chef's knife block, among other things. 

Just adjacent is a large dining table that can seat six people comfortably. The modern geometric chandelier illuminates the dining area, while the outdoor dining table on the balcony provides cushioned seating for another six people. 

Each bedroom has luxurious mattresses, sumptuous bedding, wall-mounted Smart TVs, ceiling fans, and bedside tables with reading lamps. The primary bedroom, located on the second floor, is particularly lavish with premium bedding and breathtaking water views from the balcony. Its attached bathroom boasts ample storage space and a grand walk-in shower adorned with marble tiles. 

The second bedroom features calming beach decor and a spacious ensuite bathroom with a walk-in closet and a gorgeous walk-in shower. The third and fourth bedrooms share a jack-n-jill bathroom with a walk-in shower, and the third bedroom also has a private balcony. The loft area is perfect for children, with two bunk beds and fun bean bag chairs to create a cozy oasis. 

There’s even a convenient laundry room with a state-of-the-art washer and dryer and a granite vanity laundry room sink. On the first floor is a game room with a lounge area with a sofa, a table, and chairs beside the ping pong table. It also features fun family games such as Connect Four and Corn Hole and a fridge and counter space that can be used as an extra space when using the poolside kitchen. 

This backyard boasts outstanding amenities, is surrounded by water and interlaced with canals, and host to many amazing sea creatures, including Loggerhead Turtles, Manatees, and dolphins. There is a free-form swimming pool, a sun shelf and a built-in picnic table, which is great for all ages, and the dock can accommodate vessels up to 38 feet. 

The outdoor kitchen is made of gorgeous stone and features a high-end grill and a large wall-mounted Smart TV. After dinner, you can gather your group for evening cocktails at the tiki bar, hoist the Jolly Roger, and drink some rum! 

The beautiful white sand beaches of Anna Maria Island are less than a 5-minute walk away, and they are home to some of the most stunning seashells in all of Florida. It's quite common to see dolphins swimming and tourists enjoying a swim in the Gulf of Mexico. If you enjoy fishing, you can bring your gear and cast a line off the pier, or rent a boat and venture out into deeper waters to reel in some fish. 

The free island trolley stop is also just a two-minute walk from your doorstep. 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.


Amenities

4 Bedrooms, 4.5 Bathrooms

Sleeps 8 Guests

  • Golf Nearby
  • Heated between Nov 1st- May 1st
  • Freeform Swimming Pool with Sun Shelf and Built-In Picnic Table
  • Tennis Nearby
  • Washer/Dryer
  • Sink
  • Bar Stools - 4
  • Gas Stove with Hood
  • Convection Oven
  • Microwave
  • French Door Fridge with Icemaker
  • Dishwasher
  • Double Basin Sink
  • Pots / Pans / Cookware / Utensils / Cutlery / Dishware / Glassware
  • Coffee Maker
  • Kettle
  • Toaster
  • Blender
  • Chef's Knife Block
  • Ceiling Fans
  • Indoor and Outdoor Dining Areas
  • Private Dock
  • Outdoor Kitchen with BBQ / Smart TV / 3 Bar Stools
  • Ping Pong
  • Game Room
  • Smart TV
  • Connect Four
  • Cornhole
  • Desk

Details

Bedroom Details

Bedroom 1 (2nd floor): King Bed, Smart TV, Ceiling Fan, Ensuite Bathroom with Walk-In Shower, Balcony Access, Water Views

Bedroom 2 (3rd floor): King Bed, Smart TV, Ceiling Fan, Ensuite Bathroom with Walk-In Shower

Bedroom 3 (3rd floor): King Bed, Smart TV, Ceiling Fan, Jack n Jill Bathroom with Walk-In Shower, Balcony Access

Bedroom 4 (3rd floor): King Bed, Smart TV, Ceiling Fan, Jack n Jill Bathroom with Walk-In Shower

Loft (3rd floor): Two Sets of Twin/Twin Bunk Beds, Smart TV, Desk, Ceiling Fan, Balcony Access

Beach Details

Manatee County Beach: 5 minute walk
Cortez Beach: 10 minute drive
Coquina Beach: 10 minute drive
Bean Point Beach: 10 minute drive
Bayfront Park: 10 minute drive
Bradenton Beach: 10 minute drive

Pool Details

Private Freeform Swimming Pool with Sun Shelf and Built-In Picnic Table (Heated between Nov 1st - May 1st)

Location Details

Sarasota Bradenton International Airport: 35 minute drive
Tampa International Airport: 1 hour drive
Key Royale Golf Club: 10 minute drive
Manatee County Golf Course: 20 minute drive
Holmes Beach Tennis Courts: 5 minute drive
Holmes Beach Skate Park: 5 minute drive

Villa Notes

Dock can accommodate vessels up to 38 ft.


Exclusive Offers

Executive Owners now receive up to $100 Destination Dollars when booking a Villas of Distinction property with Club Points. Number of Nights = Destination Dollar Amount 1-4 Nights = $50 5+ Nights = $100 You can use your Destination Dollars to enhance your stay. Once the property of your choice is booked, your personal Concierge will coordinate and schedule eligible experiences for your stay, giving you more time to spend with family.

4-night minimum stay required. Subject to availability. Offer open to book from August 20, 2020 at 12:00 AM EST to December 30, 2028 at 11:59 PM EST. Travel between August 20, 2020 and December 30, 2028. May not be combinable with other offers. Additional restrictions may apply; please call for full details. Applies to new bookings only. Access to the Vacation Homes is made available through the Abound by Marriott Vacations® exchange program and is subject to the terms and conditions as outlined in the applicable Abound by Marriott Vacations® exchange program documents. Actual experiences will be provided via contractual arrangements with third-party providers and may require the payment of additional fees. The experiences described herein are examples of potential vacation opportunities and are subject to change.

Chairman's Club Owners now receive up to $250 Destination Dollars when booking a Villas of Distinction property with Club Points. Destination Dollar Amount: 1-4 Nights = $150 5+ Nights = $250 You can use your Destination Dollars to enhance your stay. Once the property of your choice is booked, your personal Concierge will coordinate and schedule eligible experiences for your stay, giving you more time to spend with family.

4-night minimum stay required. Subject to availability. Offer open to book from August 20, 2020 at 12:00 AM EST to December 30, 2028 at 11:59 PM EST. Travel between August 20, 2020 and December 30, 2028. Additional restrictions may apply; please call for full details. Applies to new bookings only. Destination Dollars are Valid for select prepaid services only. Minimum night stay requirement may apply. Service offered is subject to availability. No cash value. The value of any unused Destination Dollars is nonrefundable. Destination Dollars cannot be applied toward booking value. Destination Dollars may not be combined with other offers. All offers are subject to availability and may not apply to all villas or travel dates. Other restrictions may apply. Access to the Vacation Homes is made available through the Abound by Marriot Vacations™ exchange program and is subject to the terms and conditions as outlined in the applicable Abound by Marriot Vacations™ exchange program documents. Actual experiences will be provided via contractual arrangements with third-party providers and may require the payment of additional fees. The experiences described herein are examples of potential vacation opportunities and are subject to change.

Presidential Owners now receive up to $175 Destination Dollars when booking a Villas of Distinction property with Club Points. Destination Dollar Amount: 1-4 Nights = $100 5+ Nights = $175 You can use your Destination Dollars to enhance your stay. Once the property of your choice is booked, your personal Concierge will coordinate and schedule eligible experiences for your stay, giving you more time to spend with family.

4-night minimum stay required. Subject to availability. Offer open to book from August 20, 2020 at 12:00 AM EST to December 30, 2028 at 11:59 PM EST. Travel between July 1, 2026 and December 31, 2028. Additional restrictions may apply; please call for full details. Applies to new bookings only. Destination Dollars are Valid for select prepaid services only. Minimum night stay requirement may apply. Service offered is subject to availability. No cash value. The value of any unused Destination Dollars is nonrefundable. Destination Dollars cannot be applied toward booking value. Destination Dollars may not be combined with other offers. All offers are subject to availability and may not apply to all villas or travel dates. Other restrictions may apply. Access to the Vacation Homes is made available through the Abound by Marriot Vacations™ exchange program and is subject to the terms and conditions as outlined in the applicable Abound by Marriot Vacations™ exchange program documents. Actual experiences will be provided via contractual arrangements with third-party providers and may require the payment of additional fees. The experiences described herein are examples of potential vacation opportunities and are subject to change.


Rates and Availability


Accidental Damage Waiver
A $299 Accidental Damage Waiver applies to every reservation.
Minimum Stay Details
Minimum night stay may vary. Please contact a villa specialist to confirm.

Location

Villa information may change without notice and should be confirmed with our villa rental specialists.