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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 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.

Guests love the oceanfront amenities like the private beach, pool and hot tub, plus kayaks, paddle boards and a golf cart. They praise the unbeatable walkable location, immaculate cleanliness, and attentive responsive hosts, making it perfect for families.
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 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 on Mondays and Thursdays in the morning, the pool technician will not need access to the house.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Dec 7, 2025 | $800 | Not Available |
| Dec 8, 2025 | $1100 | Not Available |
| Dec 9, 2025 | $1100 | Not Available |
| Dec 10, 2025 | $1100 | Not Available |
| Dec 11, 2025 | $1100 | Not Available |
| Dec 12, 2025 | $1100 | Not Available |
| Dec 13, 2025 | $900 | Available |
| Dec 14, 2025 | $800 | Available |
| Dec 15, 2025 | $800 | Not Available |
| Dec 16, 2025 | $800 | Available |
| Dec 17, 2025 | $800 | Available |
| Dec 18, 2025 | $1300 | Not Available |
| Dec 19, 2025 | $1600 | Not Available |
| Dec 20, 2025 | $1600 | Not Available |
| Dec 21, 2025 | $1600 | Not Available |
| Dec 22, 2025 | $1200 | Available |
| Dec 23, 2025 | $1200 | Available |
| Dec 24, 2025 | $1200 | Available |
| Dec 25, 2025 | $1200 | Available |
| Dec 26, 2025 | $2000 | Not Available |
| Dec 27, 2025 | $2000 | Not Available |
| Dec 28, 2025 | $2000 | Not Available |
| Dec 29, 2025 | $2000 | Not Available |
| Dec 30, 2025 | $2000 | Not Available |
| Dec 31, 2025 | $2000 | Not Available |
| Jan 1, 2026 | $2000 | Not Available |
| Jan 2, 2026 | $1300 | Not Available |
| Jan 3, 2026 | $1300 | Not Available |
| Jan 4, 2026 | $1200 | Not Available |
| Jan 5, 2026 | $1200 | Not Available |
| Jan 6, 2026 | $1200 | Not Available |
| Jan 7, 2026 | $1200 | Not Available |
| Jan 8, 2026 | $1200 | Not Available |
| Jan 9, 2026 | $1300 | Available |
| Jan 10, 2026 | $1300 | Available |
| Jan 11, 2026 | $1200 | Available |
| Jan 12, 2026 | $1200 | Available |
| Jan 13, 2026 | $1200 | Available |
| Jan 14, 2026 | $1200 | Available |
| Jan 15, 2026 | $1200 | Available |
| Jan 16, 2026 | $1300 | Available |
| Jan 17, 2026 | $1300 | Available |
| Jan 18, 2026 | $1200 | Available |
| Jan 19, 2026 | $1200 | Available |
| Jan 20, 2026 | $1200 | Available |
| Jan 21, 2026 | $1200 | Available |
| Jan 22, 2026 | $1200 | Available |
| Jan 23, 2026 | $1300 | Available |
| Jan 24, 2026 | $1300 | Available |
| Jan 25, 2026 | $1200 | Available |
| Jan 26, 2026 | $1200 | Available |
| Jan 27, 2026 | $1200 | Available |
| Jan 28, 2026 | $1200 | Available |
| Jan 29, 2026 | $1200 | Available |
| Jan 30, 2026 | $1300 | Available |
| Jan 31, 2026 | $1300 | Available |
| Feb 1, 2026 | $1300 | Available |
| Feb 2, 2026 | $1300 | Available |
| Feb 3, 2026 | $1300 | Available |
| Feb 4, 2026 | $1300 | Not Available |
| Feb 5, 2026 | $1300 | Not Available |
| Feb 6, 2026 | $1500 | Not Available |
| Feb 7, 2026 | $1500 | Not Available |
| Feb 8, 2026 | $1300 | Available |
| Feb 9, 2026 | $1300 | Available |
| Feb 10, 2026 | $1300 | Available |
| Feb 11, 2026 | $1300 | Available |
| Feb 12, 2026 | $1300 | Available |
| Feb 13, 2026 | $1500 | Available |
| Feb 14, 2026 | $1500 | Available |
| Feb 15, 2026 | $2000 | Not Available |
| Feb 16, 2026 | $2000 | Not Available |
| Feb 17, 2026 | $2000 | Not Available |
| Feb 18, 2026 | $2000 | Not Available |
| Feb 19, 2026 | $2000 | Not Available |
| Feb 20, 2026 | $2000 | Not Available |
| Feb 21, 2026 | $2000 | Not Available |
| Feb 22, 2026 | $2000 | Not Available |
| Feb 23, 2026 | $2000 | Not Available |
| Feb 24, 2026 | $2000 | Not Available |
| Feb 25, 2026 | $2000 | Not Available |
| Feb 26, 2026 | $2000 | Not Available |
| Feb 27, 2026 | $2000 | Not Available |
| Feb 28, 2026 | $2000 | Not Available |
| Mar 1, 2026 | $1500 | Available |
| Mar 2, 2026 | $1500 | Available |
| Mar 3, 2026 | $1500 | Available |
| Mar 4, 2026 | $1500 | Available |
| Mar 5, 2026 | $1500 | Not Available |
| Mar 6, 2026 | $1600 | Not Available |
| Mar 7, 2026 | $1600 | Not Available |