Tripletail | Beachfront | Pool | Hot Tub

Anna Maria, Florida
$1502 avg/night Minimum Stay 1 Nights
Bed 4

Bed

Bath 5

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 1 nights

Min Stay

Summary:

Experience the ultimate Anna Maria Island getaway at Tripletail! This stunning 4-bedroom, 4-bath bayfront home offers breathtaking waterfront views and is perfectly located near Pine Avenue and the City Pier. Enjoy mornings watching dolphins, afternoons by the private pool, and evenings relaxing in the hot tub. With beach access and a host of amenities, Tripletail promises an unforgettable vacation.



The Space:

Designed for both gathering and privacy, Tripletail’s layout is ideal for families and couples traveling together:



Main Level:



King bedroom with waterfront access



Second king bedroom



Fully equipped kitchen, dining area, and family room with water views



Upper Level:



Two additional king bedrooms, each with private bathrooms



Cozy sitting area perfect for reading, games, or relaxing after beach days



Guest Access:

You'll have exclusive access to the entire house, including all four bedrooms, four bathrooms, the living room, kitchen, dining room, laundry room, balconies, and front yard. Enjoy the convenience of a private entrance and amenities like the outdoor pool, hot tub, and BBQ grill. A personalized smart lock code ensures easy, keyless entry anytime after 4 PM.



The Neighborhood:

Explore the best of Anna Maria Island's Beaches from our prime location! Our home is perfectly situated near Pine Avenue, a charming hub just around the corner, offering a delightful array of boutique shops, cozy cafes, and diverse dining options. You're also just moments away from the historic City Pier, perfect for a leisurely stroll or enjoying the sunset. For those seeking adventure, we provide adult bikes for exploring the island's scenic streets and paddleboards and a kayak for enjoying the calm bay waters.



Getting Around:

Getting around is easy! Tripletail is conveniently located near Pine Avenue, just a short walk from the beach, shops, and restaurants. The free island trolley has a stop on Pine Avenue, offering easy access to explore the island. You'll find free parking both on the property and on the street. For those arriving by air, the closest major airport is about an hour's drive away.



Other Things to Note:

Heated Pool, hot tub and fenced yard with turf.



Four adult bikes, paddle boards, kayak, beach chairs all included.



Please review and agree to the Reservation Agreement. Rates and Availability are subject to change until reservation is completed. A deposit must be received in order to reserve the dates you desire.



Pets- Non-Aggressive breeds, vaccinated & current on a flea prevention program allowed only with prior approval. Pet Fee and Pet Waiver Required. $300 per pet

Any unauthorized pets= 25% surcharge



Traveler must provide photo ID and guest list

If for some reason the property you booked is unavailable, we may offer to rebook the Traveler at another property, if a substantially similar property is available for the same period and under a new reservation. Owner is not responsible for events beyond our control, ie: inclement weather, storms, evacuations, etc. Travel Insurance is recommended and may be purchased independently from several sites (Red Sky Travel Insurance, Square Mouth, etc.)



Due to the extensive equipment provided at the home, there are additional documents required. The use of the bikes, SUP and Kayak require a signed Equipment Waiver for anyone 18+



All Drivers of the property's Golf Cart must be 25, and provide a copy of a valid U.S. Driver's License and Insurance.



Interaction with Guests:

We give our guests space to relax but are always available if needed! You’ll receive a personal smart lock code before check-in, and we’re just a message, call, or email away if you have any questions or need anything during your stay.



For direct support, contact our office phone.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    2 Total Pets Pet Friendly Welcoming Dogs Only
  • BEACH

    On The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Double-glazed Windows Energy-saving Switches Locally-owned & Organized Tours & Activities Recycling Unit Size: 2231 Sq Ft (207 Sq M) Uses Some LED Lighting
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Garden Yard
  • POOL/SPA

    Heated Pool Hot Tub Outdoor Pool Private Pool Shared/communal Pool
  • BATHROOMS

    5 Bathrooms Hair Dryer Shampoo Shower Towels Provided
  • WORKSPACES

    Office
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Cycling Nearby Fishing Nearby Golf Privileges Horse Riding Nearby Kayak On Site Paddleboard On Site Water Park Nearby
  • ENTERTAINMENT

    Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Dinnerware Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near The Ocean Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Change Of Bedsheets (on Request) Change Of Towels (on Request) Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Stair-free Path To Entrance Tile Flooring In Public Areas Upper Floors Accessible By Stairs Only Well-lit Path To Entrance

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Sarah M.

    Submitted Jan 23, 2026

    Stayed Jan 2, 2026

    This property was great. The view is exceptional from the first floor and second floor. The house is great, comfortable and clean. It is right on the gulf coast, only about 6ft from your back porch. We saw dolphins swim by every day of our 7 day trip. The rental company was great to deal with and work hard for you. Loved the kayak and paddle boards.

  • Jill G.

    Submitted Nov 15, 2025

    Stayed Nov 12, 2025

    We had the best time, this house was so nice, clean, well-stocked and convenient. Great for adults and would be great for kids! I can’t wait to return to AMI and stay here again.

  • Sylvia H.

    Submitted Mar 21, 2025

    Stayed Mar 18, 2025

    Wow, what an incredible property! Super clean, beds comfortable, great location being able to walk to the main street with all shops and restaurants, and being off the water was amazing (saw dolphins every day). The owners were super great to work with from start to finish. Looking forward to coming back!!

  • Chris M.

    Submitted Dec 23, 2024

    Stayed Nov 26, 2024

    Great house in a great location. Rick (the owner) was great about communicating and getting us anything we needed. The house is comfortable and all the furniture and appliances were new due to water damage. There were a few minor issues that were easily addressed and Rick was always willing to help whenever we needed anything.The house was very comfortable for our family of 7 adults and we were able to comfortably cook and eat Thanksgiving dinner at the house. The location is walking distance to many restaurants and other attractions and for anything else it is a short drive or golf cart ride. Recommended.

  • Sheri M.

    Submitted Apr 17, 2024

    Stayed Apr 4, 2024

    Everything was perfect. The location, the checkin in and check out process, the beds, the towels, all of the fully stocked kitchen. I can’t say enough positive things about Tripletail. It was simply amazing and magical!!! My 4 year old Grand daughter asks daily when can we go back to our “other house.”

  • J.P. B.

    Submitted Mar 29, 2024

    Stayed Mar 23, 2024

    It's rare when a property exceeds your expectation based on description and photos provided online, but I'm happy to report that in this case it does! This was perfect for my family and I, including my 5 1/2 year old daughter and 2 year old son. We loved that the patio opened right onto the beach, and the front pool area was really fun as well. The provided golf cart is a huge plus for getting around the area. 5 stars, 2 thumbs up. Rick was a big help, and very nice to deal with. Hoping to be back!

  • Anthony C.

    Submitted Aug 11, 2023

    Stayed Jul 25, 2023

    Beautiful house and amazing location. Rick was the best host.

  • Marissa C.

    Submitted Jun 25, 2023

    Stayed Jun 22, 2023

    My friends and I celebrated a special birthday weekend- the home is amazing, well stocked, meticulously clean and decorated. Cannot say enough great things! Looking forward to another stay in the future!

  • jackeline r.

    Submitted May 18, 2023

    Stayed May 12, 2023

    amazing house I love the house

Your dates are Available!

Total

Includes taxes and fees
$1,502+
View details