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The Ugly Grouper offers a lively dining experience with American and seafood cuisine, featuring dishes like coconut fried shrimp and grouper tacos. Its outdoor seating area features live music and a fun atmosphere, perfect for a relaxed meal on Anna Maria Island.
Sandbar Seafood + Spirits offers a laid-back beachfront dining experience with fresh Gulf seafood, local organic vegetables, and a stunning sunset view, perfect for toes-in-the-sand relaxation and great drinks on Anna Maria Island.
Anna Maria Island Beach Cafe offers casual gulf-front dining with a laid-back vibe, famous for all-you-can-eat pancakes and sausage, fresh seafood platters, and island-sized drinks enjoyed alongside stunning sunsets and nightly live music. Perfect for families and beach lovers alike.
Rod and Reel Pier offers a relaxed dining experience with fresh seafood and stunning views of Tampa Bay. Its quaint, waterside setting provides an authentic Florida charm.
At Compass Hotel Anna Maria Sound, enjoy a blend of tropical fun and fine dining, with options like Floridays Woodfire Grill & Bar offering fresh seafood and Compass Bar & Chill serving signature Margaritaville drinks. The hotel's waterfront setting adds to its lively, beachy ambiance.
The Waterfront Restaurant in Anna Maria offers casual dining with fresh, locally sourced seafood and classic American flavors, all enjoyed in a relaxed old Florida waterfront setting with stunning views of Tampa Bay.
Skinny's Place is a classic beachside eatery offering giant burgers and homemade onion rings in a rustic, no-frills setting. It's a great spot for casual dining with a nostalgic Old Florida charm.
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 beer and wine make it a standout on Anna Maria Island.
Ginny's & Jane E's Cafe offers a cozy blend of delicious breakfast and lunch options, complemented by a unique gift store featuring local art and quirky souvenirs. The cafe embodies "Old Florida" hospitality in a charming setting.
Hurricane Hanks offers a casual, island-inspired dining experience with fresh seafood, steaks, and plant-based options. Its warm atmosphere reflects the laid-back vibe of Anna Maria Island, making it a must-visit for locals and visitors alike.
Ana Maria Island offers serene beaches and calm waters perfect for swimming and water activities. It's ideal for families and those seeking a peaceful beach getaway.
Manatee Public Beach offers a serene escape with pristine white sand and crystal-clear waters, perfect for those seeking relaxation and water activities like swimming and paddleboarding. It's ideal for families and beach lovers alike.
Anna Maria Island Beach offers serene, untouched shores perfect for relaxation and nature lovers. Its tranquil atmosphere and stunning views make it ideal for those seeking a peaceful beach experience.
Experience the charm of Holmes Beach with its picturesque beaches, volleyball courts, and playgrounds. This destination is perfect for families and sun-seekers looking for a relaxing getaway with plenty of outdoor activities.
Robinson Preserve offers a unique blend of natural beauty and outdoor adventure, perfect for nature lovers and families. Explore its scenic trails, kayak through mangrove forests, and enjoy panoramic views from observation towers.
Fort De Soto Dog Park / Beach offers a spacious, off-leash beach and fenced playground where dogs can swim, run, and socialize freely—perfect for active dog owners who want a fun, safe place for their pets to play and cool off.
Palma Sola Botanical Park offers a tranquil escape with its diverse tropical plants and scenic trails, perfect for nature lovers and families. The park's unique fruit trails and gardens make it a must-visit for anyone interested in botany and natural beauty.
De Soto National Memorial offers a blend of history and nature, perfect for those who enjoy outdoor activities like hiking and kayaking amidst scenic landscapes and historical reenactments. It's ideal for nature lovers and history enthusiasts alike.
Enjoy the serene tranquility of Bean Point Beach, a hidden gem offering stunning sunsets and peaceful surroundings perfect for nature lovers. Its secluded location makes it ideal for those seeking a quiet beach experience.
Explore Fort De Soto Park's historic batteries and military post, featuring the last surviving carriage-mounted 12-inch seacoast mortars. This site is perfect for history buffs and those interested in military heritage.
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 the private heated pool, hot tub and beach toys like kayaks and paddleboards, the unbeatable beachfront ocean views and walkable location, the spotless well maintained rooms, and the hosts' fast responsiveness plus thoughtful family friendly touches.
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.
Pool Service
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 5, 2025 | $1000 | Not Available |
| Dec 6, 2025 | $1000 | Not Available |
| Dec 7, 2025 | $1000 | Not Available |
| Dec 8, 2025 | $1400 | Not Available |
| Dec 9, 2025 | $1400 | Not Available |
| Dec 10, 2025 | $1400 | Not Available |
| Dec 11, 2025 | $1400 | Not Available |
| Dec 12, 2025 | $950 | Not Available |
| Dec 13, 2025 | $950 | Not Available |
| Dec 14, 2025 | $950 | Not Available |
| Dec 15, 2025 | $950 | Not Available |
| Dec 16, 2025 | $900 | Not Available |
| Dec 17, 2025 | $900 | Not Available |
| Dec 18, 2025 | $900 | Not Available |
| Dec 19, 2025 | $1400 | Not Available |
| Dec 20, 2025 | $1400 | Not Available |
| Dec 21, 2025 | $1200 | Not Available |
| Dec 22, 2025 | $1200 | Not Available |
| Dec 23, 2025 | $1200 | Not Available |
| Dec 24, 2025 | $2000 | Not Available |
| Dec 25, 2025 | $2000 | Not 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 | $1600 | Not Available |
| Jan 2, 2026 | $1600 | Not Available |
| Jan 3, 2026 | $1600 | Available |
| Jan 4, 2026 | $1500 | Available |
| Jan 5, 2026 | $1500 | Available |
| Jan 6, 2026 | $1500 | Available |
| Jan 7, 2026 | $1500 | Available |
| Jan 8, 2026 | $1500 | Available |
| Jan 9, 2026 | $1600 | Available |
| Jan 10, 2026 | $1600 | Available |
| Jan 11, 2026 | $1500 | Available |
| Jan 12, 2026 | $1500 | Available |
| Jan 13, 2026 | $1500 | Available |
| Jan 14, 2026 | $1500 | Available |
| Jan 15, 2026 | $1500 | Available |
| Jan 16, 2026 | $1600 | Available |
| Jan 17, 2026 | $1600 | Available |
| Jan 18, 2026 | $1500 | Available |
| Jan 19, 2026 | $1500 | Available |
| Jan 20, 2026 | $1500 | Available |
| Jan 21, 2026 | $1500 | Available |
| Jan 22, 2026 | $1500 | Available |
| Jan 23, 2026 | $1600 | Available |
| Jan 24, 2026 | $1600 | Available |
| Jan 25, 2026 | $1500 | Available |
| Jan 26, 2026 | $1500 | Available |
| Jan 27, 2026 | $1500 | Available |
| Jan 28, 2026 | $1500 | Available |
| Jan 29, 2026 | $1500 | Not Available |
| Jan 30, 2026 | $1600 | Not Available |
| Jan 31, 2026 | $1600 | Not Available |
| Feb 1, 2026 | $1500 | Not Available |
| Feb 2, 2026 | $1500 | Available |
| Feb 3, 2026 | $1500 | Available |
| Feb 4, 2026 | $1500 | Available |
| Feb 5, 2026 | $1500 | Available |
| Feb 6, 2026 | $1800 | Not Available |
| Feb 7, 2026 | $1800 | Not Available |
| Feb 8, 2026 | $1800 | Not Available |
| Feb 9, 2026 | $1800 | Not Available |
| Feb 10, 2026 | $1500 | Available |
| Feb 11, 2026 | $1500 | Available |
| Feb 12, 2026 | $1500 | Available |
| Feb 13, 2026 | $1500 | Available |
| Feb 14, 2026 | $1800 | Not Available |
| Feb 15, 2026 | $1800 | Not Available |
| Feb 16, 2026 | $1800 | Not Available |
| Feb 17, 2026 | $1800 | Not Available |
| Feb 18, 2026 | $1800 | Not Available |
| Feb 19, 2026 | $1800 | Not Available |
| Feb 20, 2026 | $1800 | Not Available |
| Feb 21, 2026 | $1800 | 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 | $1800 | Not Available |
| Feb 28, 2026 | $2200 | Not Available |
| Mar 1, 2026 | $2000 | Not Available |
| Mar 2, 2026 | $1800 | Available |
| Mar 3, 2026 | $1800 | Available |
| Mar 4, 2026 | $1800 | Available |
| Mar 5, 2026 | $1800 | Available |