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Rod and Reel Pier offers a relaxed dining experience with fresh seafood and stunning views of Tampa Bay. Its quaint, waterfront setting makes it a local favorite for casual meals amidst the charm of Anna Maria Island.
Skinny's Place is a classic beach bar serving juicy burgers and crispy fries in a casual, Old Florida setting. It's a laid-back spot perfect for a cold beer and a relaxed meal.
The Ugly Grouper offers a laid-back dining experience with fresh seafood and American cuisine, set amidst a lively atmosphere featuring live music and outdoor games. Its extensive beverage menu complements the delicious food options, making it a perfect spot for a fun-filled evening.
Sandbar Seafood + Spirits offers fresh, gulf-to-table seafood and vibrant local flavors in a relaxed beachfront setting where you can dine with your toes in the sand while enjoying stunning Gulf of Mexico sunsets. Perfect for casual meals or romantic evenings by the water.
Anna Maria Island Beach Cafe offers casual dining with stunning Gulf views, serving up favorites like all-you-can-eat pancakes and seafood. Enjoy live music and beach activities in a lively, beachfront setting.
Compass Hotel Anna Maria Sound offers a blend of dining experiences, including Floridays Woodfire Grill & Bar, which serves fresh seafood with waterfront views, and Compass Bar & Chill, featuring signature Margaritaville drinks in a relaxed setting. The hotel's atmosphere combines coastal charm with modern comforts.
The Waterfront Restaurant offers fresh, locally inspired seafood and classic American dishes in a relaxed, old Florida-style setting with stunning views of Tampa Bay and the Sunshine Skyway Bridge. It's perfect for casual waterfront dining with a welcoming atmosphere.
The Porch Restaurant offers a sophisticated dining experience with signature dishes, top-quality steak, and fresh fish in a historic setting. Its intimate ambiance and extensive selection of drinks make it a standout on Anna Maria Island.
Ginny's & Jane E's Cafe offers a blend of classic and seasonal dishes in a vibrant, retro-inspired setting, complemented by a unique gift store featuring local art and quirky souvenirs. Its warm ambiance and "Old Florida" hospitality make it a charming local favorite.
Hurricane Hanks offers a casual, come-as-you-are island dining experience featuring fresh Gulf seafood, flavorful Caribbean dishes, and something for every palate in a warm, welcoming atmosphere. It's a local favorite for memorable meals and relaxed vibes on Anna Maria Island.
Explore Anna Maria Island's serene waters by paddleboarding or kayaking, perfect for beginners and nature lovers alike. Enjoy the peaceful scenery and local wildlife in a tranquil setting.
Palma Sola Botanical Park offers a serene escape with its diverse tropical and native plant collections, perfect for nature lovers and families. The park's unique gardens and scenic trails make it an ideal spot for relaxation and exploration.
Explore Fort De Soto Park's historic batteries and military post, featuring the last four surviving 12-inch seacoast mortars, perfect for history buffs and those interested in military heritage. This unique site offers a glimpse into the past amidst stunning Gulf views.
Anna Maria Island Beach offers serene white sands, clear waters, and picturesque sunsets, perfect for beachcombers and those seeking a tranquil coastal escape. It's ideal for families and couples looking for a relaxing getaway.
Manatee Public Beach offers a serene escape with its white sands and tranquil waters, perfect for families and sun-seekers. Enjoy activities like swimming, volleyball, and paddleboarding in a picturesque setting.
Explore De Soto National Memorial for a blend of history and nature, with activities like kayaking, bird watching, and picnicking amidst scenic landscapes. This site is ideal for history buffs and outdoor enthusiasts alike.
Fort De Soto Dog Park and Beach offers a unique experience where dogs can play off-leash and swim, making it a haven for dog owners seeking fun and socialization for their pets. It's perfect for families and dog lovers alike.
Explore Robinson Preserve's diverse ecosystem through hiking, biking, and kayaking, with stunning views from observation towers and a canopy walkway. Nature lovers and families will enjoy the preserve's unique blend of natural beauty and recreational activities.
Holmes Beach offers a serene escape with its beautiful beaches, paddleboard tours, and dolphin sightings. It's perfect for those seeking relaxation and outdoor adventures in a picturesque setting.
Bean Point Beach is a secluded gem offering serene views and stunning sunsets, ideal for those seeking a peaceful beach experience. It's perfect for locals and visitors looking for a tranquil escape from more crowded beaches.
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.
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.

Guests love this home for its private pool, included electric golf cart and plentiful beach gear and kayaks, its prime beachfront location and easy walkability to shops, pristine cleanliness and the hosts' highly responsive concierge service, plus a spacious family friendly layout.
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 will not need access to the house.
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 the pool is 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 contains features that may be difficult for elderly and guests with mobility-challenges - including climbing a set of stairs to enter the property and access additional levels.
Please be advised that the home next door is currently under construction, as such, it is possible that you will hear construction noise during the daytime hours. We appreciate your understanding and apologize for any inconvenience.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Dec 5, 2025 | $550 | Not Available |
| Dec 6, 2025 | $550 | Not Available |
| Dec 7, 2025 | $500 | Available |
| Dec 8, 2025 | $500 | Available |
| Dec 9, 2025 | $500 | Available |
| Dec 10, 2025 | $500 | Available |
| Dec 11, 2025 | $500 | Available |
| Dec 12, 2025 | $550 | Available |
| Dec 13, 2025 | $550 | Available |
| Dec 14, 2025 | $500 | Not Available |
| Dec 15, 2025 | $500 | Not Available |
| Dec 16, 2025 | $500 | Not Available |
| Dec 17, 2025 | $500 | Not Available |
| Dec 18, 2025 | $500 | Not Available |
| Dec 19, 2025 | $1000 | Available |
| Dec 20, 2025 | $1000 | Available |
| Dec 21, 2025 | $900 | Available |
| Dec 22, 2025 | $900 | Available |
| Dec 23, 2025 | $900 | Available |
| Dec 24, 2025 | $1100 | Available |
| Dec 25, 2025 | $1100 | Available |
| Dec 26, 2025 | $1200 | Not Available |
| Dec 27, 2025 | $1200 | Not Available |
| Dec 28, 2025 | $1200 | Not Available |
| Dec 29, 2025 | $1200 | Not Available |
| Dec 30, 2025 | $1200 | Not Available |
| Dec 31, 2025 | $1200 | Not Available |
| Jan 1, 2026 | $1200 | Not Available |
| Jan 2, 2026 | $900 | Not Available |
| Jan 3, 2026 | $900 | Not Available |
| Jan 4, 2026 | $900 | Not Available |
| Jan 5, 2026 | $700 | Available |
| Jan 6, 2026 | $700 | Available |
| Jan 7, 2026 | $700 | Available |
| Jan 8, 2026 | $700 | Available |
| Jan 9, 2026 | $800 | Available |
| Jan 10, 2026 | $800 | Available |
| Jan 11, 2026 | $700 | Available |
| Jan 12, 2026 | $700 | Available |
| Jan 13, 2026 | $700 | Available |
| Jan 14, 2026 | $700 | Available |
| Jan 15, 2026 | $700 | Available |
| Jan 16, 2026 | $1000 | Not Available |
| Jan 17, 2026 | $1000 | Not Available |
| Jan 18, 2026 | $1000 | Not Available |
| Jan 19, 2026 | $1000 | Not Available |
| Jan 20, 2026 | $1000 | Not Available |
| Jan 21, 2026 | $1000 | Not Available |
| Jan 22, 2026 | $1000 | Not Available |
| Jan 23, 2026 | $1000 | Not Available |
| Jan 24, 2026 | $1000 | Not Available |
| Jan 25, 2026 | $1000 | Not Available |
| Jan 26, 2026 | $1000 | Not Available |
| Jan 27, 2026 | $1000 | Not Available |
| Jan 28, 2026 | $1000 | Not Available |
| Jan 29, 2026 | $1000 | Not Available |
| Jan 30, 2026 | $1000 | Not Available |
| Jan 31, 2026 | $1000 | Not Available |
| Feb 1, 2026 | $1000 | Not Available |
| Feb 2, 2026 | $1000 | Not Available |
| Feb 3, 2026 | $1000 | Not Available |
| Feb 4, 2026 | $1000 | Not Available |
| Feb 5, 2026 | $1000 | Not Available |
| Feb 6, 2026 | $1000 | Not Available |
| Feb 7, 2026 | $1000 | Not Available |
| Feb 8, 2026 | $1000 | Not Available |
| Feb 9, 2026 | $1000 | Not Available |
| Feb 10, 2026 | $1000 | Not Available |
| Feb 11, 2026 | $1000 | Not Available |
| Feb 12, 2026 | $1000 | Not Available |
| Feb 13, 2026 | $1000 | Not Available |
| Feb 14, 2026 | $1000 | Not Available |
| Feb 15, 2026 | $1000 | Not Available |
| Feb 16, 2026 | $1000 | Not Available |
| Feb 17, 2026 | $1000 | Not Available |
| Feb 18, 2026 | $1000 | Not Available |
| Feb 19, 2026 | $1000 | Not Available |
| Feb 20, 2026 | $1000 | Not Available |
| Feb 21, 2026 | $1200 | Available |
| Feb 22, 2026 | $1000 | Available |
| Feb 23, 2026 | $1000 | Available |
| Feb 24, 2026 | $1000 | Available |
| Feb 25, 2026 | $1000 | Available |
| Feb 26, 2026 | $1200 | Not Available |
| Feb 27, 2026 | $1200 | Not Available |
| Feb 28, 2026 | $1200 | Not Available |
| Mar 1, 2026 | $1250 | Available |
| Mar 2, 2026 | $1250 | Available |
| Mar 3, 2026 | $1250 | Available |
| Mar 4, 2026 | $1250 | Available |
| Mar 5, 2026 | $1250 | Available |