A family-friendly stay in Anna Maria awaits you at this holiday home. Within steps you'll find Bay Boulevard Beach and Anna Maria City Pier within a short 5-minute stroll. Highlights at this beachfront holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 5 bathrooms and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a dining area and a private garden are also available. Change of towels is available on request .Spend the day at the beach and enjoy the on-site outdoor swimming pool and Hot tub. Additionally, you'll find laundry facilities, a garden and barbecues. .Attractions within a 30-minute walk of this Anna Maria holiday home include Anna Maria Beach and Bean Point Beach.
Anna Maria Island Museum and Historical Park - 11 min walk - 0.9 km
Bradenton Beach - 14 min walk - 1.2 km
Bean Point Beach - 2 min drive - 1.7 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 47 min drive
Restaurants
Anna Maria Island Beach Cafe - 9 min drive
The Ugly Grouper - 6 min drive
The Sandbar Restaurant - 14 min walk
The Waterfront Restaurant - 2 min walk
Ginny's & Jane E's - 11 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Tripletail | Beachfront | Pool | Hot Tub
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.
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Stair-free path to entrance
Tile flooring in public areas
Upper floors accessible by stairs only
Well-lit path to entrance
Smoke-free property
Services and conveniences
Change of bedsheets (on request)
Change of towels on request
Iron/ironing board
Location highlights
Near a health/beauty spa
Near the ocean
On the waterfront
Things to do
Bicycles
Heated pool
Kayak
Optional golf privileges
Paddleboard
Cycling nearby
Fishing nearby
Horseback riding nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
General
At least 80% lighting from LEDs
Bed sheets changed on request
Bicycles
Double-glazed windows
Energy-saving switches in guestrooms
Garden
Locally-owned and organised tours and activities
Recycling
Towels (changed on request)
Unit size: 2,231 square feet
Water-efficient showers
Water-efficient toilets
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 21
Check-out
Check-out before 10:00 AM
Contactless check-out
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Check-out instructions
The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.
Rules
Anna Maria Island Parking – Strictly Enforced for all Vehicles/Golf Carts
All tires must be off the pavement where permitted
Obey all posted sign...
Pets
Pets are welcome
Only dogs are allowed
Maximum 2 pets
Service animals are exempt from fees.
Note from host: Pre-Approval, signed waiver and pet fee required
Children and extra beds
Children are welcome.
Events
Events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
Parties and events are allowed on site
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. This property accepts cash. Parties and events are allowed on site. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a first aid kit in all accommodation.
Property is also known as
Vrbo Property
Tripletail Anna Maria
Tripletail Private vacation home
Tripletail Private vacation home Anna Maria
4 bed/4 bath beach front/ golf cart included
69b975e6b028b000140e7d59
Frequently asked questions
Are there any beaches close to Tripletail | Beachfront | Pool | Hot Tub?
Yep, Tripletail | Beachfront | Pool | Hot Tub is a short 17-minute walk from Anna Maria Beach.
Fun beach activities include fishing.
Does Tripletail | Beachfront | Pool | Hot Tub have a pool?
Take your pick from a heated pool, a pool and a communal pool.
What luxury perks are available at Tripletail | Beachfront | Pool | Hot Tub?
This property features a heated pool, as well as a private pool and a private yard.
What makes Tripletail | Beachfront | Pool | Hot Tub a romantic place to stay?
1 hot tub, private pools, and private balconies all help set the scene for a sizzling getaway at Tripletail | Beachfront | Pool | Hot Tub.
Is Tripletail | Beachfront | Pool | Hot Tub family-friendly?
You bet! With amenities such as laundry facilities and a BBQ, as well as highchairs and children's dinnerware, it's no surprise that Tripletail | Beachfront | Pool | Hot Tub is a winner with our family travellers.
Is there a private hot tub at Tripletail | Beachfront | Pool | Hot Tub?
Yep, there is a hot tub.
Is there a free airport shuttle available at Tripletail | Beachfront | Pool | Hot Tub?
No, Tripletail | Beachfront | Pool | Hot Tub does not offer an airport shuttle service.
What time are check-in & check-out at Tripletail | Beachfront | Pool | Hot Tub?
Check-in begins at 4:00 PM. Check-out time is 10:00 AM.
Tripletail | Beachfront | Pool | Hot Tub Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 10 out of 11 reviews
10 - Excellent
10
Rating 8 - Good. 1 out of 11 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 11 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 11 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 11 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Sinan T.
7 Mar 2026
Liked: Cleanliness
Our room was right on the beach. Excellent view. The owners were very responsive.
Sinan T.
Stayed 4 nights in Mar 2026
10/10 Excellent
Sarah M.
23 Jan 2026
Liked: Cleanliness
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.
Sarah M.
Stayed 7 nights in Jan 2026
10/10 Excellent
Jill G.
15 Nov 2025
Liked: Cleanliness
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.
Jill G.
Stayed 3 nights in Nov 2025
8/10 Good
Sandi S., Cincinnati
16 Aug 2025
Sandi S.
Stayed 9 nights in Jul 2025
10/10 Excellent
Sylvia H.
21 Mar 2025
Liked: Cleanliness
Incredible stay!
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!!
Sylvia H.
Stayed 3 nights in Mar 2025
10/10 Excellent
Chris M.
23 Dec 2024
Liked: Cleanliness
Great Thanksgiving stay in Anna Maria
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.
Chris M.
Stayed 3 nights in Nov 2024
10/10 Excellent
Sheri M.
17 Apr 2024
Liked: Cleanliness
Perfect Stay!
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.”
Sheri M.
Stayed 3 nights in Apr 2024
10/10 Excellent
J.P. B.
29 Mar 2024
Liked: Cleanliness
Awesome rental, great host
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!
J.P. B.
Stayed 5 nights in Mar 2024
10/10 Excellent
Anthony C.
11 Aug 2023
Liked: Cleanliness
Anna Maria
Beautiful house and amazing location. Rick was the best host.
Anthony C.
Stayed 6 nights in Jul 2023
10/10 Excellent
Marissa C.
25 Jun 2023
Liked: Cleanliness
Birthday Heaven!
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!