Entire home

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

Overview
Amenities
Policies
Location

Exceptional

4 bedrooms4 bathroomsSleeps 82231 sq ft

Popular amenities

Parking available
Dryer
Pet-friendly
Washer
Hot tub
Pool

Explore the area

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

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

4 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 4

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio

Kitchen

Balcony

Separate dining area

Garden

Dining area

About this property

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.

Add dates for prices

Amenities

Pool

Hot tub

Kitchen

Washing machine

Dryer

Pet-friendly

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Kitchen
Washer
Dryer
Pet-friendly

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 2 total)

Pre-Approval, signed waiver and pet fee required

Smoking

Smoking is not permitted

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.

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

On-site parties or group events are strictly prohibited

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, a first aid kit and a deadlock

We should mention

This property does not have any lifts

A car is recommended for transport to and from this property

About the area

Anna Maria

Located in Anna Maria, this holiday home is near theme parks and on the beach. The area's natural beauty can be seen at Anna Maria Beach and Bean Point Beach. Travelling with kids? Consider Fish Hole Adventure Golf, or check out an event or a game at LECOM Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

View more Holiday homes in Anna Maria

Anna Maria, FL

What's nearby

Anna Maria City Pier - 3 min walk - 0.3 km
Anna Maria Island Museum and Historical Park - 8 min walk - 0.7 km
Bean Point Beach - 20 min walk - 1.7 km
Anna Maria Beach - 20 min walk - 1.7 km
Bradenton Beach - 4 min drive - 2.1 km

Getting around

Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 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

Frequently asked questions

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

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP pet-friendly?

Yes, this property allows dogs (limit 2 total).

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

Check-in begins at 4:00 PM.

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

Checkout is at 10:00 AM.

Where is Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP located?

Nestled on the beach, this Anna Maria holiday home is within 1 mi (2 km) of Bay Boulevard Beach, Anna Maria Beach and Bean Point Beach. Anna Maria City Pier and Bayfront Park are also within 10 minutes.

9.8

Exceptional

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

10/10 Excellent

Sylvia H.

21 Mar, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

jackeline r.

18 May, 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

is beautifull and George house

amazing house I love the house

Stayed 3 nights in May 2023

10/10 Excellent

Anthony C.

11 Aug, 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Anna Maria

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

Stayed 6 nights in Jul 2023

10/10 Excellent

Marissa C.

25 Jun, 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Sheri M.

17 Apr, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.

29 Mar, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Chris M.

23 Dec, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

8/10 Good

Sandi S.

16 Aug, 2025

Stayed 9 nights in Jul 2025

About the host

Hosted by Rick or Lyn Puskas

Serendipity Circle:
Philosophy:
Our dedicated team aligns with our simple core values “CARE”: Customers First, Friendly and Helpful Attitude, Treat all of our clients with Respect, Enjoying life in the process

Who we Are:
Rick and Lyn Puskas have diverse, complimentary backgrounds. Rick’s “Rock and Roll” background and natural love of people accentuates his passion for customer satisfaction. Anyone who has met Rick has heard his motto, “We want you to become our distant cousins”. Lyn’s legal background, passion for details and love of architecture inspire each new creation. She is a problem solver and welcomes unique challenges.

Maria and her Family are lifelong friends and partners with Lyn and Rick. Maria is a vibrant, enthusiastic “doer”! Give her a challenge and it will get done quickly! Her two adult sons are often on the island helping with the business.

Courtney is our ray of sunshine, talented photographer and filled with local insight.

Diego is our miracle worker with a never-ending smile on his face!

Our simple motto is to create a unique experience for guests through thoughtful design and a caring attitude with the backdrop of mother nature at her best.