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Home in Anna Maria, Florida

Tripletail

4 bedrooms

4 beds

4 bathrooms

8 guests

2303 sq. ft.

About the property

🌅 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.

Where you’ll sleep

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

Amenities

Common Amenities

  • Free parking
  • BBQ Area
  • Luggage drop off allowed
  • Long term stays allowed
  • Beachfront
  • Beach access
  • Kayaks
  • Wifi
  • Paddle board
  • Patio
  • Hot water
  • Carbon monoxide detector
  • Ocean view
  • Hangers
  • Dedicated workspace
  • Pet relief area
  • Balcony
  • Bedroom door lock
  • Heated pool
  • BBQ Utensils
  • Kettle
  • Crib
  • Garden
  • Extra pillows
  • Laundromat nearby
  • Bay views
  • Massage table
  • Boat
  • Water slide
  • Wine Cellar
  • Children dinnerware
  • Pack n play
  • Waterfront
  • Golf Course
  • Tennis court
  • Stair gate
  • Private Chef
  • Basketball Court
  • Fishing Area
  • Hike trail nearby
  • Board games
  • Baking sheet
  • Safe
  • Air conditioning
  • Smoke detector
  • Fire extinguisher
  • First aid kit
  • Kitchen
  • Gym
  • Heating

Pool

  • Outdoor pool

Patio

  • Outdoor seating
  • Outdoor dining area
  • TV

Back Deck

  • Hot tub
  • Outdoor seating

Balcony

  • Outdoor seating

Living Room

  • TV
  • Ceiling fan

Dining Room

  • Dining table

Kitchen

  • Coffee
  • Coffee maker
  • Dishwasher
  • Freezer
  • Fridge
  • Oven
  • Pots and pans
  • Spices
  • Tea
  • Toaster
  • Ice maker
  • Garbage disposal
  • Microwave
  • Blender
  • Cooking basics
  • Stove
  • Dishes
  • Silverware
  • Wine glasses

Bedroom 1

  • Bed linens
  • Ceiling fan
  • TV

Ensuite Bathroom 1

  • Bath linens
  • Ensuite bathroom
  • Body soap
  • Shampoo
  • Conditioner
  • Shower
  • Shower gel
  • Toilet
  • Hair dryer

Bedroom 2

  • Bed linens
  • TV
  • Ceiling fan

Ensuite Bathroom 2

  • Bath linens
  • Body soap
  • Shampoo
  • Conditioner
  • Shower
  • Shower gel
  • Toilet
  • Ensuite bathroom

Bedroom 3

  • Bed linens
  • TV
  • Ceiling fan

Ensuite Bathroom 3

  • Ensuite bathroom
  • Bath linens
  • Toilet
  • Shower
  • Shower gel
  • Shampoo
  • Conditioner
  • Body soap

Bedroom 4

  • Ceiling fan
  • TV
  • Bed linens

Office

  • Desk
  • Ceiling fan

Bathroom 1

  • Bath linens
  • Body soap
  • Shampoo
  • Conditioner
  • Shower
  • Shower gel
  • Toilet
  • Bathtub

Garage

  • Bicycle
  • Beach essentials
  • Pool toys

Laundry Room

  • Washer
  • Dryer
  • Iron
  • Ironing board
  • Cleaning supplies

Entry

  • High chair

4.9 · 202 reviews

Where you’ll be

Anna Maria, Florida 34216, United States

Anna Maria, Florida, United States
27.5318108-82.7300851
Timezone: Pacific/Easter

Restaurants

The Ugly Grouper

The 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

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

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

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

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.

Compass Hotel Anna Maria Sound by Margaritaville

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

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

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 Bradenton Beach

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

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.

Attractions

Manatee Public Beach

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.

Ana Maria island

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

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

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 / Beach

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

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

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 Access

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

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

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.

Beach N Rides

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.

Coconut Rentals

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.

Things to know

Cancellation policy

Cancel within 24 hours for a full refund.

Property rules

Pets allowed with fee

No smoking - fees will apply

Events require approval

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

8 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
May 5, 2026$1500Not Available
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