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Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP

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Exterior
Smart TV, books
Smart TV, books
Interior
4 bedrooms, desk, iron/ironing board, travel crib

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 82231 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Pet friendly
  • Hot Tub
  • Air conditioning

Explore the area

View in a map
Anna Maria, FL
  • Place, Anna Maria City Pier
    ‪3 min walk‬
  • Place, Bean Point Beach
    ‪20 min walk‬
  • Place, Anna Maria Beach
    ‪20 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪40 min drive‬

Room options

About the neighborhood

Anna Maria

On the beach.With a stay at this Anna Maria vacation home, you'll be steps from Bay Boulevard Beach and a 5-minute walk from Anna Maria City Pier. Bayfront Park and Historic Green Village are also within half a mile (1 km).
View more Vacation Homes in Anna MariaOpens in a new window

What's nearby

  • Anna Maria City Pier - 3 min walk - 0.2 miles
  • Anna Maria Island Museum and Historical Park - 8 min walk - 0.4 miles
  • Bean Point Beach - 20 min walk - 1.1 miles
  • Anna Maria Beach - 20 min walk - 1.1 miles
  • Bradenton Beach - 4 min drive - 1.3 miles

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 47 min drive

Restaurants

  • ‪The Sandbar Restaurant - ‬14 min walk
  • ‪The Ugly Grouper - ‬6 min drive
  • ‪The Waterfront Restaurant - ‬2 min walk
  • ‪Ginny's & Jane E's - ‬11 min walk
  • ‪North Shore Cafe - ‬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.

Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP

Tripletail @ 308 S Bay Blvd – Private Beachfront Luxury Home

4 King Bedrooms | 4 Bathrooms | Heated Pool + Hot Tub | Golf Cart Included

Welcome to Tripletail, your private beachfront escape on Anna Maria Island. Perfectly located just one block from Pine Avenue and the historic City Pier, this luxury home combines stunning Gulf views with walkable access to shops, dining, and local attractions.

From your back deck, watch dolphins and manatees swim by, or take the bikes and complimentary golf cart to explore the island at your own pace.

⸻

Home Highlights
• Beachfront Location – Step directly onto the sand from your backyard.
• Heated Pool & Hot Tub – Relax after a day in the sun.
• Spacious Layout – Perfect for families and groups, with an open floor plan.
• Gulf Views – Panoramic water views from multiple rooms and decks.
• Golf Cart Included – Easy island transportation.
_________
Layout

Ground Floor
• Beachfront King Bedroom with en-suite bathroom
• Second King Bedroom with bathroom access
• Open-concept kitchen, dining, and living room overlooking the Gulf

Upstairs
• Two additional King Bedrooms with private bathrooms
• Comfortable sitting area for relaxing or reading

⸻

Why Guests Love Tripletail
• Private beachfront home – no crowded condos or shared spaces
• Short stroll to Pine Avenue boutiques, cafes, and restaurants
• Watch breathtaking sunrises over Tampa Bay and walk to the pier for fishing or ice cream
• Fully stocked kitchen for home-cooked meals
• Luxurious touches throughout with plenty of space for everyone

⸻

This is more than a vacation rental – it’s your island sanctuary. Whether you’re relaxing by the heated pool, soaking in the hot tub, or enjoying cocktails on the deck as dolphins pass by, Tripletail offers the quintessential Anna Maria Island experience.

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Exterior

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4.8 out of 5, Exceptional, 42 reviews
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Property amenities

Beach

  • On the beach
  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Hot tub
  • Outdoor pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car recommended
  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Chef service
  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 4 private bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Yard

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • 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
  • Smoking not allowed

Services and conveniences

  • Change of bedsheets (on request)
  • Change of towels on request
  • Housekeeping (on request)
  • Iron/ironing board
  • Meal delivery service

Location highlights

  • In a village
  • Near a health/beauty spa
  • Near a hospital
  • Near a zoo
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Bicycles
  • Golf
  • Heated pool
  • Kayak
  • Paddleboard
  • Water park
  • Basketball nearby
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Theme park nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours 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
  • Deadbolt lock

General

  • At least 80% lighting from LEDs
  • Bed sheets changed on request
  • Bicycles
  • Double-glazed windows
  • Energy-saving switches in guestrooms
  • Garden
  • Housekeeping (on request)
  • Locally-owned and organized 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 available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Check-out instructions

The host requires you 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 trash
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.

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

No 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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 accepts cash. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each 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
138874

Frequently asked questions

How close is Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP to the airport?

This vacation home is 19.8 mi (47-min drive) away from the Sarasota-Bradenton Intl. Airport (SRQ) airport, the closest popular airport to the property.

Does Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP to the beach?

This vacation home is on the beach. Don't forget your sunscreen!

Does Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP?

No, there is no casino at this vacation home.

What time is check-in at Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP?

Check-in begins at 4:00 PM.

Is there free parking at Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP?

Free parking is not available at this vacation home.

Does Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP have a pool?

This vacation home features an outdoor pool.

Does Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP have a spa?

There are no spa services available at this vacation home.

How close is Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP to downtown Anna Maria?

This vacation home is 0.2 mi away from Anna Maria.

Reviews

Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP Reviews

9.8

Exceptional

10/10

Cleanliness
Rating 10 - Excellent. 7 out of 8 reviews
Rating 8 - Good. 1 out of 8 reviews
Rating 6 - Okay. 0 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

Reviews

8/10 Good

Sandi S., Cincinnati

Stayed 9 nights in Jul 2025

10/10 Excellent

Sylvia H.

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!!
Stayed 3 nights in Mar 2025

10/10 Excellent

Chris M.

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.
Stayed 3 nights in Nov 2024

10/10 Excellent

Sheri M.

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.”
Stayed 3 nights in Apr 2024

10/10 Excellent

J.P. B.

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!
Stayed 5 nights in Mar 2024

10/10 Excellent

Anthony C.

Liked: Cleanliness

Anna Maria

Beautiful house and amazing location. Rick was the best host.
Stayed 6 nights in Jul 2023

10/10 Excellent

Marissa C.

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!
Stayed 3 nights in Jun 2023

10/10 Excellent

jackeline r.

Liked: Cleanliness

is beautifull and George house

amazing house I love the house
Stayed 3 nights in May 2023