Tripletail
🌅 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.
Amenities
- Cable TV
- Internet
- Wireless
- Air conditioning
- Swimming pool
- Kitchen
- Gym
- Hot tub
- Washing Machine
- Dryer
- 24-hour checkin
- Hair Dryer
- Heating
- Smoke detector
- Carbon Monoxide Detector
- First aid kit
- Fire Extinguisher
- Essentials
- Shampoo
- Hangers
- Iron
- Laptop Friendly workspace
- TV
- Pets allowed
- Free parking
- Suitable for events
- Balcony
- Electronic key card access
- Private living room
- Suitable for children
- Suitable for infants
- Heated swimming pool
- Iron board
- Linens
- Outdoor grill
- Toaster
- Dishwasher
- Microwave
- Oven
- Electric kettle
- Coffee/tea maker
- Shower
- Tub
- Baby crib
- Deck patio uncovered
- Stove
- Refrigerator
- Towels
- Dining room
- Garden or backyard
- High chair
- Kitchen utensils
- Hot water
- Private entrance
- Extra pillows and blankets
- Cooking basics
- Beach essentials
- Laundromat
- Bay
- Coin laundry
- Health beauty spa
- Marina
- Museums
- Theme parks
- Water parks
- Winery tours
- Zoo
- Toilet
- Car not necessary
- Babysitter recommendations
- Childrens dinnerware
- Pack n play travel crib
- Dining area
- Antiquing
- Bird watching
- Boating
- Eco tourism
- Horseback riding
- Outlet shopping
- Paddle boating
- Shopping
- Water sports
- Wildlife viewing
- Beach
- Beach front
- Beach view
- Near ocean
- Ocean front
- Ocean view
- Village
- Water view
- Waterfront
- Bicycle
- Boat
- Golf
- Kayak canoe
- Tennis
- Water sports gear
- Luggage dropoff allowed
- Long term stays allowed
- Cleaning before checkout
- Private pool
- Stair gates
- Deadbolt lock
- Fire emergency contact
- Hospital nearby
- Medical emergency contact
- Outdoor lighting
- Police emergency contact
- Breakfast possible
- Cleaning optional
- Chauffeur
- Private chef
- Basketball court
- Cycling
- Deepsea fishing
- Fishing
- Fishing bay
- Fishing fly
- Fishing freshwater
- Fishing surf
- Golf
- Hiking
- Hunting
- Jet skiing
- Kayaking
- Mountain biking
- Pier fishing
- Sailing
- Scuba or snorkeling
- Water Skiing
- Snorkeling
- Snorkeling diving
- Surfing
- Swimming
- Tubing water
- Wind surfing
- Family
- Historic
- Romantic
- Enhanced Cleaning Practices
- Contactless Check-In/Out
- Fenced yard
- Dishes & utensils for children
- Meal delivery
- Free WiFi
- WiFi speed (500+ Mbps)
- Smart TV
- Dining table
- Outdoor furniture
- Cleaning products
- Body soap
- Shower gel
- Clothing storage
- Baby safety gates
- Board games
- Ceiling fan
- Baking sheet
- Barbeque utensils
- Blender
- Coffee
- Freezer
- Wine glasses
Other Details
- Check-In: 04:00 PM
- Check-Out: 10:00 AM
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Additional Rules:
House Rules (Summary)Show more
• Reservation is not confirmed until payment and agreement are completed.
• Cancellations: 91+ days prior to arrival are refundable (minus $300). Within 90 days are non-refundable.
• Pets: Allowed with prior approval only. $500 per pet + signed pet waiver. Unauthorized pets incur a 25% surcharge.
• Guest Verification: Photo ID and guest list required for all reservations.
Amenities & Equipment Use
• All guests 18+ must sign an Equipment & Amenity Waiver
• A valid email address is required to complete all documents via electronic signature
• Pool, hot tub, bikes, paddleboards, kayaks, and all on-property equipment require a signed waiver
• Golf cart use is limited to guests age 25+ with a valid driver’s license, proof of auto insurance, and signed agreement
Important Notes
• Documents are completed electronically prior to arrival
• We are not responsible for weather, evacuations, or events beyond our control
• Travel insurance is strongly recommended
We look forward to hosting you and helping you enjoy a relaxing stay on Anna Maria Island
Book This Home
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Reviews
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Our stay was a 10/10! The location is fantastic, within walking distance to restaurants and shops, or just a short golf cart ride away. Having the gol ... See moreSeptember 15, 2025
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The Serendipity staff went out of their way to help us with everything we needed. I would use Serendipity again. ... See moreApril 6, 2026
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Our favorite family vacation! The perfect house for everything! ... See moreApril 5, 2026