Tripletail, Beachfront, Pool, Hot Tub

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.

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

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.

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.

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.