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5 reviews
Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
Experience the ultimate Anna Maria Island getaway at Tripletail! This stunning 4-bedroom, 4-bath bayfront home offers breathtaking waterfront views and is perfectly located near Pine Avenue and the City Pier. Enjoy mornings watching dolphins, afternoons by the private pool, and evenings relaxing in the hot tub. With beach access and a host of amenities, Tripletail promises an unforgettable vacation.
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
Getting around is easy! Tripletail is conveniently located near Pine Avenue, just a short walk from the beach, shops, and restaurants. The free island trolley has a stop on Pine Avenue, offering easy access to explore the island. You'll find free parking both on the property and on the street. For those arriving by air, the closest major airport is about an hour's drive away.
Heated Pool, hot tub and fenced yard with turf.
Four adult bikes, paddle boards, kayak, beach chairs all included.
Please review and agree to the Reservation Agreement. Rates and Availability are subject to change until reservation is completed. A deposit must be received in order to reserve the dates you desire.
Pets- Non-Aggressive breeds, vaccinated & current on a flea prevention program allowed only with prior approval. Pet Fee and Pet Waiver Required. $300 per pet
Any unauthorized pets= 25% surcharge
Traveler must provide photo ID and guest list
If for some reason the property you booked is unavailable, we may offer to rebook the Traveler at another property, if a substantially similar property is available for the same period and under a new reservation. Owner is not responsible for events beyond our control, ie: inclement weather, storms, evacuations, etc. Travel Insurance is recommended and may be purchased independently from several sites (Red Sky Travel Insurance, Square Mouth, etc.)
Due to the extensive equipment provided at the home, there are additional documents required. The use of the bikes, SUP and Kayak require a signed Equipment Waiver for anyone 18+
All Drivers of the property's Golf Cart must be 25, and provide a copy of a valid U.S. Driver's License and Insurance.
We give our guests space to relax but are always available if needed! You’ll receive a personal smart lock code before check-in, and we’re just a message, call, or email away if you have any questions or need anything during your stay.
For direct support, contact our office phone.
Anonymous
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3 weeks ago
Anonymous
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July 2026
Anonymous
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May 2026
Bradenton Beach, Florida 34217, United States of America
Bradenton Beach, Florida, United States of AmericaThe Ugly Grouper is a laid-back Anna Maria Island favorite known for fresh seafood, especially grouper, served in a fun outdoor setting with live music and a lively beach-town vibe. It’s a casual, family-friendly spot with great drinks and a relaxed atmosphere.
Sandbar Seafood + Spirits serves fresh seafood and coastal-inspired dishes in a relaxed, beachy setting. With a lively atmosphere and a menu built for casual nights out, it’s a great spot for great food and good company.
Wicked Cantina Bradenton Beach serves up fresh Austin-style Tex Mex and American favorites in a lively, family-friendly setting with Gulf views. Stop in for margaritas, happy hour deals, live music, and a relaxed island vibe.
Anna Maria Island Beach Cafe serves casual American fare with beachside favorites like all-you-can-eat pancakes, burgers, and seafood. With Gulf-front views, outdoor seating, and live music, it’s a laid-back spot for breakfast, lunch, or dinner right on Holmes Beach.
The Porch Restaurant serves fresh, made-from-scratch American cuisine with standout steaks, seafood, and seasonal dishes. Set in a beautifully restored historic cottage on Anna Maria Island, it offers a warm, charming atmosphere with a relaxed coastal feel.
The Kokonut Hut is a laid-back Anna Maria Island beach bar serving fresh seafood, casual grill favorites, and tropical cocktails right on the Gulf. With live music, dog-friendly vibes, and sunset views over the sand, it’s a lively spot to relax and unwind.
Beach House Waterfront Restaurant serves fresh coastal-inspired cuisine in a relaxed setting with beautiful waterfront views. It’s the perfect spot to enjoy great food, sunset drinks, and a breezy, laid-back atmosphere.
Ginny’s & Jane E’s is a charming Anna Maria Island cafe known for hearty breakfast and lunch favorites, fresh-baked cinnamon rolls, and great coffee. Its quirky coastal boutique atmosphere makes it part cozy diner, part treasure-filled gift shop.
A breezy spot where dogs can splash, run, and play off-leash along the sand and water. Perfect for pet owners who love a relaxed beach day with plenty of room for their dogs to explore.
Explore a scenic waterfront memorial where history comes alive through trails, exhibits, and living history at Camp Uzita. It’s a great stop for history buffs, families, and anyone who enjoys peaceful nature walks with a story.
Bean Point Beach offers a secluded escape at Anna Maria Island's northern tip, perfect for those seeking a quieter, more pristine shoreline away from crowded beaches. Shell collectors and sunset enthusiasts will love this hidden gem with its wide sandy shores and stunning Gulf views.
A peaceful botanical park with winding paths, lush gardens, and plenty of native plants to explore. Great for nature lovers, photographers, and anyone looking for a calm outdoor escape.
Holmes Beach is a laid-back Anna Maria Island escape known for its soft white sand, gentle Gulf waters, and easy access to great beachside dining and local shops. It’s perfect for families, couples, and anyone looking to relax, swim, or soak up the Florida sun.
Enjoy a relaxing day at Coquina Beach, where soft sand, gentle waves, and beautiful Gulf views make the perfect backdrop for swimming, strolling, and soaking up the sun. It’s a great spot for families, couples, and anyone looking for a peaceful beach escape.
Anna Maria Island is a laid-back Gulf Coast escape with soft white beaches, calm turquoise water, and charming small-town vibes. It’s perfect for travelers who love relaxing beach days, stunning sunsets, and a slower pace.
Robinson Preserve is a scenic coastal escape with mangrove trails, boardwalks, kayaking, birdwatching, and a towering observation deck with sweeping views. It’s ideal for nature lovers, families, and anyone looking for an easy outdoor adventure near Anna Maria Island.
# Anna Maria Island Beach Activity Description Discover pristine white-sand beaches and crystal-clear waters perfect for swimming, shelling, and sunset watching. Ideal for families, couples, and nature lovers seeking a peaceful Florida coastal escape with excellent opportunities for beach walks and water activities.
Free cancellation up to 30 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 |
|---|---|---|
| Aug 24, 2026 | $960 | Not Available |
| Aug 25, 2026 | $960 | Not Available |
| Aug 26, 2026 | $960 | Not Available |
| Aug 27, 2026 | $960 | Not Available |
| Aug 28, 2026 | $960 | Not Available |
| Aug 29, 2026 | $900 | Available |
| Aug 30, 2026 | $900 | Available |
| Aug 31, 2026 | $900 | Available |
| Sep 1, 2026 | $900 | Available |
| Sep 2, 2026 | $900 | Available |
| Sep 3, 2026 | $960 | Not Available |
| Sep 4, 2026 | $1248 | Not Available |
| Sep 5, 2026 | $1329 | Not Available |
| Sep 6, 2026 | $1279 | Not Available |
| Sep 7, 2026 | $900 | Available |
| Sep 8, 2026 | $900 | Available |
| Sep 9, 2026 | $900 | Available |
| Sep 10, 2026 | $1061 | Not Available |
| Sep 11, 2026 | $1160 | Not Available |
| Sep 12, 2026 | $1111 | Not Available |
| Sep 13, 2026 | $1038 | Not Available |
| Sep 14, 2026 | $971 | Not Available |
| Sep 15, 2026 | $1082 | Not Available |
| Sep 16, 2026 | $1105 | Not Available |
| Sep 17, 2026 | $1122 | Not Available |
| Sep 18, 2026 | $1206 | Not Available |
| Sep 19, 2026 | $1177 | Not Available |
| Sep 20, 2026 | $960 | Available |
| Sep 21, 2026 | $960 | Available |
| Sep 22, 2026 | $960 | Available |
| Sep 23, 2026 | $960 | Available |
| Sep 24, 2026 | $960 | Available |
| Sep 25, 2026 | $1153 | Not Available |
| Sep 26, 2026 | $1134 | Not Available |
| Sep 27, 2026 | $1023 | Not Available |
| Sep 28, 2026 | $962 | Not Available |
| Sep 29, 2026 | $960 | Not Available |
| Sep 30, 2026 | $990 | Available |
| Oct 1, 2026 | $1058 | Not Available |
| Oct 2, 2026 | $1116 | Not Available |
| Oct 3, 2026 | $1158 | Not Available |
| Oct 4, 2026 | $1062 | Not Available |
| Oct 5, 2026 | $1166 | Available |
| Oct 6, 2026 | $1187 | Available |
| Oct 7, 2026 | $1124 | Available |
| Oct 8, 2026 | $1226 | Available |
| Oct 9, 2026 | $1409 | Available |
| Oct 10, 2026 | $1447 | Available |
| Oct 11, 2026 | $1423 | Available |
| Oct 12, 2026 | $1384 | Available |
| Oct 13, 2026 | $1320 | Available |
| Oct 14, 2026 | $1362 | Available |
| Oct 15, 2026 | $1276 | Available |
| Oct 16, 2026 | $1344 | Not Available |
| Oct 17, 2026 | $1230 | Not Available |
| Oct 18, 2026 | $1338 | Not Available |
| Oct 19, 2026 | $1314 | Not Available |
| Oct 20, 2026 | $1380 | Not Available |
| Oct 21, 2026 | $1251 | Not Available |
| Oct 22, 2026 | $1198 | Not Available |
| Oct 23, 2026 | $1328 | Available |
| Oct 24, 2026 | $1192 | Available |
| Oct 25, 2026 | $1130 | Not Available |
| Oct 26, 2026 | $1067 | Not Available |
| Oct 27, 2026 | $1059 | Not Available |
| Oct 28, 2026 | $1076 | Not Available |
| Oct 29, 2026 | $1125 | Not Available |
| Oct 30, 2026 | $1141 | Available |
| Oct 31, 2026 | $1103 | Available |
| Nov 1, 2026 | $960 | Available |
| Nov 2, 2026 | $960 | Available |
| Nov 3, 2026 | $1125 | Available |
| Nov 4, 2026 | $1198 | Available |
| Nov 5, 2026 | $1213 | Available |
| Nov 6, 2026 | $1352 | Available |
| Nov 7, 2026 | $1351 | Available |
| Nov 8, 2026 | $1210 | Not Available |
| Nov 9, 2026 | $1086 | Not Available |
| Nov 10, 2026 | $1192 | Not Available |
| Nov 11, 2026 | $1226 | Not Available |
| Nov 12, 2026 | $1315 | Not Available |
| Nov 13, 2026 | $1366 | Not Available |
| Nov 14, 2026 | $1416 | Not Available |
| Nov 15, 2026 | $1074 | Available |
| Nov 16, 2026 | $1051 | Available |
| Nov 17, 2026 | $1075 | Available |
| Nov 18, 2026 | $970 | Available |
| Nov 19, 2026 | $1054 | Available |
| Nov 20, 2026 | $1286 | Available |
| Nov 21, 2026 | $2001 | Not Available |
| Nov 22, 2026 | $2057 | Not Available |