Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
🌅 Bayfront Pool Retreat + Walk to Pine Ave + Golf Cart | Tripletail
Welcome to Tripletail, your bayfront escape on the coveted north end of Anna Maria Island — where peaceful waterfront views, walkability to Pine Avenue, and resort-style outdoor living come together for an unforgettable stay.
Perfectly located just one block from Pine Avenue and the City Pier, this beautifully appointed 4-bedroom, 4-bath home offers the best of island living. Spend your mornings watching dolphins glide across the bay, your afternoons poolside, and your evenings soaking in the hot tub as the sky turns shades of pink and gold.
🏡 Comfortable Coastal Layout
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
With four king bedrooms and four bathrooms, every guest enjoys space, comfort, and convenience.
☀️ Waterfront Outdoor Living
The magic of Tripletail truly unfolds outdoors:
Private heated front-yard pool — perfect for relaxing on breezy or windy beach days
Waterfront hot tub for sunset relaxation
Spacious back deck with dolphin and boat-watching views
Beach access just steps from the home
Whether you’re sipping coffee at sunrise or unwinding with a cocktail at dusk, the bayfront setting provides a peaceful and picturesque backdrop.
🚲 Adventure & Island Exploring
Your stay includes amenities designed for both land and sea adventures:
Adult bikes for cruising charming island streets
Paddle boards and kayak for exploring calm bay waters
And with Pine Avenue just around the corner, you’re moments from boutique shopping, cafés, dining, and the historic City Pier.
🚗 Complimentary Golf Cart Included
For effortless island transportation, Tripletail includes a complimentary 6-passenger street-legal golf cart with your reservation.
Golf Cart Qualifications:
Drivers must:
Be age 25+
Sign a golf cart waiver
Provide a valid North American driver’s license
Provide proof of auto insurance
International Guests: While we cannot provide a golf cart directly, we’re happy to connect you with our preferred partners offering exclusive guest discounts:
Beach N Rides and Rentals
The Coconut Rentals (premium gas golf carts)
💫 Why Guests Love Tripletail
✔ Bayfront hot tub + heated front-yard pool for flexible outdoor living
✔ Walkable to Pine Avenue, City Pier, shops & dining
✔ Four king bedrooms with private bathrooms
✔ Dolphin sightings right from your deck
✔ Included golf cart and adventure gear for easy island living
Tripletail blends tranquility, walkability, and waterfront beauty — creating a stay guests return to year after year.
📌 Good to Know
Amenity & Equipment Waiver required for all guests 18+
Pets welcome with pre-approval, fee, signed waiver & vaccination proof
24/7 guest support available for a seamless stay
✨ Hosted by Serendipity Vacation Rentals
We look forward to welcoming you to your waterfront retreat at Tripletail.
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Anna Maria, Florida 34216, United States
Anna Maria, Florida, United StatesThe Ugly Grouper offers a laid-back dining experience with fresh seafood and American cuisine, complemented by live music and outdoor seating. Its fun atmosphere includes games and a full bar, making it a perfect spot for a casual, enjoyable meal.
Sandbar Seafood + Spirits offers a unique toes-in-the-sand dining experience with fresh seafood and local flavors, set against breathtaking Gulf of Mexico sunsets. Enjoy casual, waterfront dining with a relaxed atmosphere perfect for families and romantic evenings.
Beach House Waterfront Restaurant offers a blend of American and seafood cuisine with stunning Gulf views and toes-in-the-sand dining. Enjoy beautiful sunsets from the climate-friendly outdoor deck in a relaxed, environmentally conscious setting.
The Waterfront Restaurant offers breathtaking views and exceptional dining, often featuring fresh seafood and a cozy, inviting atmosphere. Its unique location makes it perfect for both casual meals and special occasions.
Anna Maria Island Beach Cafe offers casual dining with stunning Gulf views, featuring all-you-can-eat pancakes and Friday fish fries. Enjoy live music and "Island Size" drinks at the Bamboo Beach Bar.
Experience the laid-back charm of Compass Hotel Anna Maria Sound by Margaritaville, where you can enjoy fresh seafood and signature Margaritaville drinks in a breezy, coastal setting. The hotel features on-site dining options like Floridays Woodfire Grill & Bar and Compass Bar & Chill.
Rod and Reel Pier offers a relaxed dining experience with fresh seafood and stunning views of Tampa Bay. Its quaint, old Florida charm is enhanced by its unique pier setting.
The Kokonut Hut offers a beachside dining experience with American, seafood, and bar cuisine, complemented by live music and stunning island views. Enjoy cocktails and relaxed beach vibes in this dog-friendly tiki bar setting.
Wicked Cantina offers Austin-style Tex-Mex and American classics with a modern vibe, featuring a full liquor bar and stunning Gulf views. Enjoy live music and delicious meals in a family-friendly setting.
Ginny's & Jane E's Cafe and Gift Store is a charming Anna Maria Island favorite, blending a cozy bakery and café with hearty breakfast classics like waffles and creme brûlée French toast, alongside a quirky gift shop filled with local art and unique souvenirs. It’s known for friendly service in an eclectic atmosphere that feels like Old Florida.
Manatee Public Beach offers a serene escape with pristine white sands and crystal-clear waters perfect for swimming, paddleboarding, and spotting dolphins. It's ideal for families and those seeking relaxation and recreation in a beautiful coastal setting.
Explore the serene waters of Anna Maria Island by paddleboarding or kayaking, perfect for nature lovers and beginners alike. Enjoy the peaceful scenery and discover local wildlife in this tranquil setting.
Anna Maria Island Beach offers serene shores with warm waters, perfect for snorkeling and sunset walks. It's ideal for those seeking a tranquil beach experience with opportunities for bird watching and dolphin spotting.
Holmes Beach offers a serene escape with its beautiful beaches and vibrant activities like paddleboarding and boat tours. It's perfect for those seeking relaxation and adventure in a picturesque Florida setting.
Fort De Soto Dog Park and Beach offers a unique experience where dogs can play off-leash on the beach, making it perfect for dog owners and families. The park also features fenced areas and amenities for a fun day out.
De Soto National Memorial offers a blend of history and nature, perfect for those who enjoy outdoor activities like kayaking, bird watching, and hiking, while also exploring the rich historical significance of the area. Nature lovers and history enthusiasts alike will find something special here.
Robinson Preserve offers a perfect blend of outdoor adventure with scenic hiking trails, kayaking through mangrove forests, and peaceful picnic spots—ideal for nature lovers and families seeking active fun in a stunning natural setting.
Bean Point Beach offers a secluded getaway with stunning sunsets and tranquil waters, ideal for those seeking a peaceful retreat. Locals and nature lovers alike enjoy its serene atmosphere and picturesque views.
Palma Sola Botanical Park offers a serene escape with exotic plants, rare fruit trails, and beautiful gardens, perfect for nature lovers and families. It's a free, accessible haven for those seeking tranquility and botanical discovery.
Coquina Beach offers a spacious, family-friendly escape with white sands perfect for sunbathing, shell hunting, and dolphin spotting, plus safe swimming and scenic nature trails for outdoor lovers. Ideal for beachgoers seeking relaxation and adventure alike.
A trusted local provider to ensure you have easy access to high-quality golf cart rentals during your stay. You may contact Beach N Rides at 941-251-7916. Use the discount code: Serendipity at checkout to receive your special rate.
A trusted local provider to ensure you have easy access to high-quality golf cart rentals during your stay. You may contact Coconut Rentals at 941-269-1080. Use the discount code: Serendipity at checkout to receive your special rate.
Free cancellation up to 14 days before check-in. 50% refund up to 7 days before. No refund after that.
Pets allowed with fee
No smoking - fees will apply
Events allowed
Check-in after 4:00 pm
Check-out before 10:00 am
8 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jun 19, 2026 | $1600 | Available |
| Jun 20, 2026 | $1600 | Not Available |
| Jun 21, 2026 | $1600 | Not Available |
| Jun 22, 2026 | $1600 | Not Available |
| Jun 23, 2026 | $1600 | Not Available |
| Jun 24, 2026 | $1600 | Not Available |
| Jun 25, 2026 | $1600 | Not Available |
| Jun 26, 2026 | $1600 | Not Available |
| Jun 27, 2026 | $1600 | Not Available |
| Jun 28, 2026 | $1600 | Not Available |
| Jun 29, 2026 | $1600 | Not Available |
| Jun 30, 2026 | $1600 | Not Available |
| Jul 1, 2026 | $1600 | Not Available |
| Jul 2, 2026 | $2012 | Available |
| Jul 3, 2026 | $2012 | Not Available |
| Jul 4, 2026 | $2012 | Not Available |
| Jul 5, 2026 | $2025 | Not Available |
| Jul 6, 2026 | $1600 | Not Available |
| Jul 7, 2026 | $1600 | Not Available |
| Jul 8, 2026 | $1600 | Not Available |
| Jul 9, 2026 | $1600 | Not Available |
| Jul 10, 2026 | $1600 | Not Available |
| Jul 11, 2026 | $1600 | Not Available |
| Jul 12, 2026 | $1600 | Not Available |
| Jul 13, 2026 | $1600 | Available |
| Jul 14, 2026 | $1600 | Available |
| Jul 15, 2026 | $1600 | Available |
| Jul 16, 2026 | $1600 | Available |
| Jul 17, 2026 | $1600 | Not Available |
| Jul 18, 2026 | $1600 | Not Available |
| Jul 19, 2026 | $1600 | Not Available |
| Jul 20, 2026 | $1600 | Not Available |
| Jul 21, 2026 | $1600 | Available |
| Jul 22, 2026 | $1600 | Available |
| Jul 23, 2026 | $1600 | Not Available |
| Jul 24, 2026 | $1620 | Not Available |
| Jul 25, 2026 | $1634 | Not Available |
| Jul 26, 2026 | $1600 | Available |
| Jul 27, 2026 | $1600 | Not Available |
| Jul 28, 2026 | $1600 | Not Available |
| Jul 29, 2026 | $1600 | Not Available |
| Jul 30, 2026 | $1600 | Available |
| Jul 31, 2026 | $1701 | Not Available |
| Aug 1, 2026 | $1256 | Not Available |
| Aug 2, 2026 | $1134 | Not Available |
| Aug 3, 2026 | $1202 | Not Available |
| Aug 4, 2026 | $1202 | Not Available |
| Aug 5, 2026 | $1202 | Not Available |
| Aug 6, 2026 | $1202 | Not Available |
| Aug 7, 2026 | $1337 | Not Available |
| Aug 8, 2026 | $1337 | Not Available |
| Aug 9, 2026 | $1202 | Not Available |
| Aug 10, 2026 | $1202 | Available |
| Aug 11, 2026 | $1202 | Available |
| Aug 12, 2026 | $1202 | Available |
| Aug 13, 2026 | $1202 | Available |
| Aug 14, 2026 | $1337 | Available |
| Aug 15, 2026 | $1337 | Available |
| Aug 16, 2026 | $1202 | Available |
| Aug 17, 2026 | $1202 | Available |
| Aug 18, 2026 | $1202 | Available |
| Aug 19, 2026 | $1202 | Available |
| Aug 20, 2026 | $1202 | Available |
| Aug 21, 2026 | $1337 | Available |
| Aug 22, 2026 | $1337 | Available |
| Aug 23, 2026 | $1202 | Available |
| Aug 24, 2026 | $1202 | Available |
| Aug 25, 2026 | $1202 | Available |
| Aug 26, 2026 | $1202 | Available |
| Aug 27, 2026 | $1202 | Available |
| Aug 28, 2026 | $1337 | Available |
| Aug 29, 2026 | $1337 | Available |
| Aug 30, 2026 | $1202 | Available |
| Aug 31, 2026 | $1202 | Available |
| Sep 1, 2026 | $1000 | Available |
| Sep 2, 2026 | $1000 | Available |
| Sep 3, 2026 | $1000 | Not Available |
| Sep 4, 2026 | $1526 | Not Available |
| Sep 5, 2026 | $1526 | Not Available |
| Sep 6, 2026 | $1526 | Not Available |
| Sep 7, 2026 | $1526 | Available |
| Sep 8, 2026 | $1000 | Available |
| Sep 9, 2026 | $1000 | Available |
| Sep 10, 2026 | $1000 | Available |
| Sep 11, 2026 | $1121 | Available |
| Sep 12, 2026 | $1121 | Available |
| Sep 13, 2026 | $1000 | Available |
| Sep 14, 2026 | $1000 | Available |
| Sep 15, 2026 | $1000 | Available |
| Sep 16, 2026 | $1000 | Available |
| Sep 17, 2026 | $1000 | Available |