Island Life Villa

Average Rating

Address: 222 S Harbor Dr Location: Holmes Beach Type: House
5 Bedrooms 4 Bathrooms Sleeps 10 No

*During high season, we currently rent Saturday – Saturday. Please adjust your date range or contact our reservations office for additional assistance, questions, or rental stays longer than 7 nights.*

Relax. Recharge. Reconnect. Come live the Island Life at one of Anna Maria’s finest rentals designed for making magical memories! Check out past guests ' experiences:

Key features: Oversized double lot property within walking distance of the beach and direct bay access, stunning views of the bay and Skyview Bridge, heated pool with jet spas and built-in table, tiki bar, large dock with green lights, boat slip next door with ability park trailer second driveway, putting green, outdoor grill, eight ft. giant Adirondack chair, hanging hammock, fire pit, outdoor games, outdoor shower, two kitchens and two living rooms for privacy and space, large balcony with magical views 1-minute walk to the bus stop for the free Island Trolley and so much more!

Entertainment amenities: Adult and children kayaks, beach wagons, beach chairs and umbrellas, toys, outdoor ping pong, cornhole, PS4, Sonos, and much more!

Overlooking the bay where you can watch Manatees and catch fish, paddleboard, or kayak! Want to visit the beach? No problems, this is just a 4 min walk away. Come enjoy Island life in this very unique five bed, four baths, 3,338 sq. ft. This home is only ever rented out as a single property. Still, it offers a unique set-up for privacy for its guests as the property is composed of a double lot boasting a three bedroom/3 bath main residence and an attached guest residence with a separate entrance that has two bedrooms and one bath, its own full kitchen, living room, and its view of the pool and bay, the perfect combination designed for multi-family or groups to visit comfortable in the large common-spaces while providing privacy when needed. The home is also unique as it was built at an angle, so you have unobstructed views of the bay and Skyview Bridge.

The outdoor space was truly built for entertaining with a 1,300 sq. ft. deck, a heated pool with a built-in table with jets, a BBQ, a putting green, a dock, a fire pit, ample seating, and even its own custom tiki bar! There is a 100' long seawall with an oversized cap and dock, plus a boat slip next door, perfect for mooring a boat. The property also has ample parking with two oversized driveways. Enjoy the home's impressive location with the best of both worlds being on the bay but a close walk to the beach;
• Drop off the boat, kayak, paddleboard.... all in your private "backyard"
• 4-minute walk to the amazing sugar sand beach
• Unobstructed views of Skyway Bridge
• Second-floor balcony with table seating for 8 and luxury hanging hammock
• 1-minute walk to the bus stop for the free Island Trolley

As you walk into this home, you are greeted by the impressive 30' high glass entryway that opens into the kitchen and dining table that seats 8. Also on the first floor is a bedroom with a king bed and an en-suite bathroom. Adjoining this is a queen-over-full custom bunk bed that adjoins the family bathroom with tub/shower.

As you go to the second floor via the entrance or side staircase you will be impressed with the open space and 10' high ceilings. The main living room has a wet bar and seating for 5 with fantastic views, perfect for entertaining. There is also a card table that seats 8 and a leather sofa with electrical recliners. Sonos sound and an 85-Inch SMART TV, Apple TV, and a PS4 will keep your group entertained. Open the balcony doors to your large balcony with fantastic views, high-top seating for 6, and a daybed. Also on the second floor is the main master boasting amazing views, open space, and a luxurious walk-in bathroom with his and hers vanity sinks, a walk-in shower with multi jets, and an impressive oversized walk-in closet.

Via a side entrance or the rear patio deck, you can access the guest suite, boasting its own dedicated living room, 82-Inch SMART TV, Sonos, full kitchen, and 1 bedroom with King and a second bedroom with two twin/twin bunk beds both with adjoining access to the bathroom. There is also a dedicated laundry room with a washer and dryer.

Treat yourself to this unique property today, and get ready to start living the Island Life!

• 1,300 Sq. Ft space
• 100' seawall with docking space for boat
• Large dock with washing and cutting
station, snook light, plenty of bumpers, and room for up
to a 35' boat
• 4 rocking chairs and 2 double seating chairs on the dock
• Heated pool with a built-in table with spa jets
• Webber BBQ grill
• 4 rocking Adirondack chairs + 2, 2 seater chairs on the dock
• 8 ft giant Adirondack chair + chairs around the firepit
• 4 sun loungers
• Tiki bar seating for 6
• Patio table seating for 8
• Daybed
• Mini golf putting green that lights up at night
• Outdoor shower
• Beach cart, chairs, and umbrellas for guest use

Living Room - Main House
• 85-Inch SMART TV
• Sony PS4
• Xbox One
• Apple TV
• Sonos
• Wet bar seating for 5 and ice maker
• Sofa with electrical recliners
• Cards table seats 8

Living Room - Duplex
• 82-Inch SMART TV
• Sonos
• Apple TV
• Sofa

• View Sunshine Skyview Bridge
• 6 bar stools and hanging hammock
• Daybed

Bed Configuration;
• Main Home
• King - First floor
• Queen/Full Bunkbed - First floor
• King - Second Floor

• Duplex:
• King - First floor
• Two Twin/Twin Bunk beds- First floor

Please note:
• This property is for general vacation rental use only. Vacation rentals may not be used for events or group gatherings that exceed occupancy. The property is located in a residential area, please be a good neighbor and keep the noise to a respectful level. For security
• We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details.
• Due to family allergies, no pets are allowed
• 4 car maximum, please plan accordingly and coordinate with your group. No overnight parking for additional vehicles
• Boatlift and 2 car garage for owner use only
• Property managed by AMI Locals, an Anna Maria Island property management company

Please Remember:

"You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property."
*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.


SwipeDrag for Availability
  • Air Conditioning
  • Beach Towels Included
  • Bed Linens
  • Clothes Hangers
  • Guest Essentials
  • Hair Dryer
  • Heating
  • Hot Water
  • Private Entrance
  • Towels
  • Wireless Internet

  • BBQ Area
  • Grill
  • Heated Pool
  • Patio
  • Private Pool

Fun & Entertainment
  • TV with Cable or Satellite channels
  • Television

Home Safety
  • Carbon Monoxide Detector
  • Deadbolt Lock
  • Fire Extinguisher
  • Security Camera
  • Smoke Detector

  • Full Kitchen
  • Living Room

  • Coffee Maker
  • Dishes & Silverware
  • Microwave
  • Oven
  • Refrigerator
  • Stove

  • Anna Maria Island
  • Canal Front
  • Less than a 10-minute walk to the beach
  • On Anna Maria Island
  • Residential Street
  • Water Views
  • Waterfront
(9) Reviews
SwipeDrag for Reviews
Questions And Answers
Want to know specifics? Ask anything about this specific property that you would like to know...
Example: “Is the Balcony screened in?” or “Is there a toaster oven?”
Want to know specifics? Ask anything in reference to vacationing at this property that you would like to know...
Example: “Are fresh linens Provided?”
Leave this field empty

Select your Arrival and Departure dates to see Detailed Pricing


Find Available Dates For this Property