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The Ugly Grouper offers a lively dining experience with fresh seafood, American favorites, and a vibrant atmosphere featuring live music and outdoor seating. Enjoy a relaxed meal amidst a fun, laid-back setting on Anna Maria Island.
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 beach activities alongside delicious meals.
Sandbar Seafood + Spirits offers fresh Gulf-to-table seafood and local organic dishes in a relaxed beachfront setting where you can dine with your toes in the sand while enjoying breathtaking sunsets over the Gulf of Mexico. Perfect for casual meals, sunset cocktails, and soaking up Old Florida charm.
The Waterfront Restaurant offers a blend of fresh seafood and upscale dining with stunning views. Its welcoming atmosphere and diverse menu make it a perfect spot for both casual and special occasions.
Compass Hotel Anna Maria Sound offers a vibrant dining experience with Floridays Woodfire Grill & Bar, serving fresh seafood in a casual waterfront setting, and Compass Bar & Chill, featuring signature Margaritaville drinks. The hotel's tropical ambiance complements its delicious cuisine.
Rod and Reel Pier offers a charming, laid-back dining experience perched over Tampa Bay, serving fresh seafood and casual fare with stunning water views and a glimpse of local fishing life. Its cozy atmosphere and historic pier setting make it a beloved spot on Anna Maria Island.
Ginny's & Jane E's Cafe offers a blend of delicious breakfast and lunch options, complemented by a unique gift store filled with local art and quirky souvenirs. This charming spot embodies the warm hospitality of "Old Florida" in a historic setting.
Skinny's Place is a classic beachside eatery offering juicy burgers and crispy fries in a casual, Old Florida setting. It's a rustic spot perfect for a laid-back meal near the beach.
The Porch Restaurant offers a sophisticated dining experience with top-quality steak, fresh fish, and seasonal entrées, set within a historic home on Anna Maria Island. Its intimate ambiance and extensive wine selection make it a sought-after destination for special occasions.
Hurricane Hanks offers a casual, island-style dining experience with a focus on fresh seafood and classic American fare. The restaurant provides a laid-back atmosphere perfect for enjoying great food and drinks in the heart of Holmes Beach.
Explore Anna Maria Island's serene beaches and tranquil waters, perfect for swimming and water activities. Nature lovers and families will enjoy the island's peaceful atmosphere and diverse wildlife.
Manatee Public Beach offers a serene escape with pristine white sand, calm Gulf waters, and activities like swimming and paddleboarding. It's perfect for families and those seeking relaxation and recreation in a beautiful coastal setting.
Experience the serene beauty of Holmes Beach, where you can relax on sandy shores, enjoy water sports, and soak up the Florida sun. It's perfect for families and beach lovers seeking a tranquil getaway.
Anna Maria Island Beach offers serene white sands and clear, warm Gulf waters perfect for swimming, shelling, and dolphin watching, making it ideal for families, nature lovers, and anyone seeking a peaceful beach escape. Its tranquil vibe and stunning sunsets create unforgettable moments.
Explore Robinson Preserve, a 600-acre haven offering hiking, kayaking, and bird-watching amidst mangroves and scenic waterways. Nature lovers and outdoor enthusiasts will delight in its diverse ecosystems and panoramic views.
Fort De Soto Dog Park and Beach offers a unique experience for pet owners, allowing dogs to play and swim freely in a designated beach area. It's perfect for those seeking a fun, social outing with their furry friends.
De Soto National Memorial offers a blend of history and nature, perfect for those who enjoy hiking, kayaking, and exploring historical sites. It's ideal for families and nature enthusiasts seeking a mix of adventure and educational experiences.
Bean Point Beach is a secluded gem on Anna Maria Island, offering serene views and tranquil waters perfect for those seeking a peaceful escape. Locals and nature lovers alike enjoy its stunning sunsets and pristine sand.
Palma Sola Botanical Park offers a peaceful stroll through lush gardens featuring rare tropical fruits, vibrant butterfly habitats, and themed plant collections—perfect for nature lovers, families, and anyone seeking a serene outdoor escape.
Explore historic Fort De Soto Park, featuring the last four surviving 12-inch seacoast mortars in the continental U.S. and offering a glimpse into military history and stunning Gulf views. This site is perfect for history buffs and nature lovers 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.

Guests love the home's premium amenities like the hot tub, kayaks, paddle boards and golf cart, its direct beachfront location with unbeatable ocean views and sunsets, the spotless well maintained rooms, and the hosts' responsive helpful service and abundance of beach gear.
Sea turtle nesting season runs from May 1 through October 31. Please observe the following guidelines at the beach from sunrise to sunset: keep outdoor lights off, dispose trash properly, fill in holes, take down erected temporary structures and sandcastles, avoid using flashlights and lanterns, do not use motorized vehicles, do not light bonfires, and avoid touching the turtles and their nests under any circumstances.
If you find a dead or injured sea turtle, call FWC at 888-404-3922.
Noise regulations are strictly enforced, particularly during nighttime hours. Quiet hours for pools, spas, and hot tubs are from 10 PM - 8 AM. Disturbances such as loud music, shouting, or other disruptive sounds may be considered a violation if they are excessively loud, last for a prolonged period, happen late at night, or are close to neighboring homes.
Guests may be fined for violations (with fines starting at $500), so we kindly ask that noise be kept to a reasonable level.
This home follows a strict maximum occupancy rule. Please make sure that the total number of guests accompanying you (including both children and adults) doesn’t exceed the indicated maximum occupancy above to avoid cancellation of your stay and additional fees.
The pool is available year-round, with heating available outside of the summer months at no additional cost. Please contact the Concierge team at least 72 hours before your arrival if you would like the pool heated during your stay.
The pool is serviced twice weekly, on Mondays and Thursdays in the morning. The pool technician does not need access to the house.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Dec 5, 2025 | $700 | Not Available |
| Dec 6, 2025 | $700 | Not Available |
| Dec 7, 2025 | $700 | Not Available |
| Dec 8, 2025 | $700 | Not Available |
| Dec 9, 2025 | $700 | Not Available |
| Dec 10, 2025 | $700 | Not Available |
| Dec 11, 2025 | $700 | Not Available |
| Dec 12, 2025 | $700 | Not Available |
| Dec 13, 2025 | $700 | Not Available |
| Dec 14, 2025 | $700 | Not Available |
| Dec 15, 2025 | $700 | Not Available |
| Dec 16, 2025 | $700 | Not Available |
| Dec 17, 2025 | $700 | Not Available |
| Dec 18, 2025 | $700 | Not Available |
| Dec 19, 2025 | $1400 | Not Available |
| Dec 20, 2025 | $1400 | Not Available |
| Dec 21, 2025 | $1400 | Not Available |
| Dec 22, 2025 | $1400 | Not Available |
| Dec 23, 2025 | $1400 | Not Available |
| Dec 24, 2025 | $1400 | Not Available |
| Dec 25, 2025 | $1400 | Not Available |
| Dec 26, 2025 | $1400 | Not Available |
| Dec 27, 2025 | $1800 | Not Available |
| Dec 28, 2025 | $1800 | Not Available |
| Dec 29, 2025 | $1800 | Not Available |
| Dec 30, 2025 | $1800 | Not Available |
| Dec 31, 2025 | $1800 | Not Available |
| Jan 1, 2026 | $1500 | Available |
| Jan 2, 2026 | $1500 | Available |
| Jan 3, 2026 | $1800 | Not Available |
| Jan 4, 2026 | $1500 | Not Available |
| Jan 5, 2026 | $1500 | Not Available |
| Jan 6, 2026 | $1500 | Not Available |
| Jan 7, 2026 | $1500 | Not Available |
| Jan 8, 2026 | $1500 | Not Available |
| Jan 9, 2026 | $1500 | Not Available |
| Jan 10, 2026 | $1500 | Not Available |
| Jan 11, 2026 | $1500 | Not Available |
| Jan 12, 2026 | $1500 | Not Available |
| Jan 13, 2026 | $1500 | Not Available |
| Jan 14, 2026 | $1500 | Not Available |
| Jan 15, 2026 | $1500 | Not Available |
| Jan 16, 2026 | $1500 | Not Available |
| Jan 17, 2026 | $1500 | Not Available |
| Jan 18, 2026 | $1500 | Not Available |
| Jan 19, 2026 | $1500 | Not Available |
| Jan 20, 2026 | $1500 | Not Available |
| Jan 21, 2026 | $1500 | Not Available |
| Jan 22, 2026 | $1500 | Not Available |
| Jan 23, 2026 | $1500 | Not Available |
| Jan 24, 2026 | $1500 | Not Available |
| Jan 25, 2026 | $1500 | Not Available |
| Jan 26, 2026 | $1500 | Not Available |
| Jan 27, 2026 | $1500 | Not Available |
| Jan 28, 2026 | $1500 | Not Available |
| Jan 29, 2026 | $1500 | Not Available |
| Jan 30, 2026 | $1500 | Not Available |
| Jan 31, 2026 | $1500 | Not Available |
| Feb 1, 2026 | $1500 | Not Available |
| Feb 2, 2026 | $1500 | Not Available |
| Feb 3, 2026 | $1500 | Not Available |
| Feb 4, 2026 | $1500 | Not Available |
| Feb 5, 2026 | $1500 | Not Available |
| Feb 6, 2026 | $1500 | Not Available |
| Feb 7, 2026 | $1500 | Not Available |
| Feb 8, 2026 | $1500 | Not Available |
| Feb 9, 2026 | $1500 | Not Available |
| Feb 10, 2026 | $1500 | Not Available |
| Feb 11, 2026 | $1500 | Not Available |
| Feb 12, 2026 | $1500 | Not Available |
| Feb 13, 2026 | $1500 | Not Available |
| Feb 14, 2026 | $1500 | Not Available |
| Feb 15, 2026 | $1500 | Not Available |
| Feb 16, 2026 | $1500 | Not Available |
| Feb 17, 2026 | $1500 | Not Available |
| Feb 18, 2026 | $1500 | Not Available |
| Feb 19, 2026 | $1500 | Not Available |
| Feb 20, 2026 | $1500 | Not Available |
| Feb 21, 2026 | $1500 | Not Available |
| Feb 22, 2026 | $1500 | Not Available |
| Feb 23, 2026 | $1500 | Not Available |
| Feb 24, 2026 | $1500 | Not Available |
| Feb 25, 2026 | $1500 | Not Available |
| Feb 26, 2026 | $1500 | Not Available |
| Feb 27, 2026 | $1500 | Not Available |
| Feb 28, 2026 | $1500 | Not Available |
| Mar 1, 2026 | $1500 | Not Available |
| Mar 2, 2026 | $1500 | Not Available |
| Mar 3, 2026 | $1500 | Not Available |
| Mar 4, 2026 | $1500 | Not Available |
| Mar 5, 2026 | $1500 | Not Available |