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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.
Shell offers a charming selection of freshly baked goods and pastries, perfect for a cozy treat any day of the week, with expanded varieties on weekends to delight every visitor.
Walgreens offers a convenient shopping experience with a variety of grocery items, including specialty foods, snacks, and pantry staples. It also provides fresh and frozen options, making it a one-stop shop for everyday essentials.
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.
Publix Super Market at Holmes Beach offers a wide selection of fresh groceries, with a standout deli featuring freshly sliced meats, specialty cheeses, and ready-to-eat meals perfect for beachside dining. Conveniently stocked for quick and quality meal solutions.
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.
CVS offers a convenient selection of groceries, including plant-based and organic options, as well as frozen meals and snacks catering to various dietary preferences. It serves as a one-stop shop for health and wellness needs.
AMI Beach Hut offers the basics, along with wine, beer, and delicious ice cream, making it a convenient stop for last-minute grocery needs and sweet treats. It's a great place to pick up essentials and enjoy a refreshing dessert.
Island Fresh Market Ami specializes in local seafood, gourmet soups, and specialty items like Cuban sandwiches and Key Lime pies. They also offer party platters and sunset boat cruises for a unique island experience.
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.
Olive Oil Outpost offers a curated selection of gourmet items, including extra virgin olive oils, balsamic vinegars, artisanal cheeses, and small-production wines. This haven on Anna Maria Island elevates culinary experiences with its diverse and high-quality products.
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.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Oct 23, 2025 | $1100 | Not Available |
| Oct 24, 2025 | $1100 | Not Available |
| Oct 25, 2025 | $1100 | Not Available |
| Oct 26, 2025 | $800 | Not Available |
| Oct 27, 2025 | $800 | Not Available |
| Oct 28, 2025 | $800 | Not Available |
| Oct 29, 2025 | $800 | Not Available |
| Oct 30, 2025 | $800 | Not Available |
| Oct 31, 2025 | $900 | Not Available |
| Nov 1, 2025 | $900 | Not Available |
| Nov 2, 2025 | $700 | Available |
| Nov 3, 2025 | $700 | Available |
| Nov 4, 2025 | $700 | Available |
| Nov 5, 2025 | $700 | Available |
| Nov 6, 2025 | $700 | Available |
| Nov 7, 2025 | $900 | Not Available |
| Nov 8, 2025 | $1000 | Not Available |
| Nov 9, 2025 | $800 | Available |
| Nov 10, 2025 | $800 | Available |
| Nov 11, 2025 | $800 | Available |
| Nov 12, 2025 | $1300 | Not Available |
| Nov 13, 2025 | $1300 | Not Available |
| Nov 14, 2025 | $1300 | Not Available |
| Nov 15, 2025 | $900 | Not Available |
| Nov 16, 2025 | $900 | Not Available |
| Nov 17, 2025 | $900 | Not Available |
| Nov 18, 2025 | $900 | Not Available |
| Nov 19, 2025 | $900 | Not Available |
| Nov 20, 2025 | $900 | Not Available |
| Nov 21, 2025 | $1500 | Not Available |
| Nov 22, 2025 | $1500 | Not Available |
| Nov 23, 2025 | $1500 | Not Available |
| Nov 24, 2025 | $1500 | Not Available |
| Nov 25, 2025 | $1500 | Not Available |
| Nov 26, 2025 | $1500 | Not Available |
| Nov 27, 2025 | $1500 | Not Available |
| Nov 28, 2025 | $1500 | Not Available |
| Nov 29, 2025 | $1600 | Not Available |
| Nov 30, 2025 | $1300 | Not Available |
| Dec 1, 2025 | $1300 | Not Available |
| Dec 2, 2025 | $1300 | Not Available |
| Dec 3, 2025 | $1300 | Not Available |
| Dec 4, 2025 | $1300 | Not Available |
| Dec 5, 2025 | $1000 | Not Available |
| Dec 6, 2025 | $1000 | Not Available |
| Dec 7, 2025 | $1000 | 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 | $1000 | Available |
| Dec 14, 2025 | $1000 | Available |
| Dec 15, 2025 | $1000 | Available |
| Dec 16, 2025 | $1000 | Available |
| Dec 17, 2025 | $1000 | 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 | $1400 | Available |
| Dec 23, 2025 | $1400 | Available |
| Dec 24, 2025 | $1400 | Available |
| Dec 25, 2025 | $1400 | 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 | $1500 | Available |
| Jan 3, 2026 | $1500 | 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 | $1500 | Available |
| Jan 10, 2026 | $1500 | 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 | $1500 | Available |
| Jan 17, 2026 | $1500 | Available |
| Jan 18, 2026 | $1500 | Available |
| Jan 19, 2026 | $1500 | Available |
| Jan 20, 2026 | $1500 | Available |
| Jan 21, 2026 | $1500 | Available |