Anna Maria Vacation Rentals
Discover Anna Maria vacation rentals with stunning Gulf beaches, perfect for families, couples, and groups. Enjoy comfort, privacy, and a true island escape just steps from the shoreline.
About our Anna Maria vacation rentals
Our handpicked vacation rentals in Anna Maria offer the perfect base for experiencing the charm and beauty of one of Florida’s most beloved barrier islands.
Set along powdery white beaches, sparkling turquoise waters, and peaceful waterfronts, each home combines comfort, style, and a relaxed island vibe. Whether you’re seeking a beachfront escape steps from the sand, a serene retreat near local shops and restaurants, or a family-friendly home close to outdoor activities, our rentals are designed to help you unwind and fully enjoy island living.
Perfect for families, couples, or groups, these properties provide everything you need for an unforgettable stay, spacious interiors, fully equipped kitchens, outdoor dining and lounging areas, private pools, and stunning views of the Gulf or surrounding waterways. Spend your days exploring charming boutiques, enjoying fresh seafood, cycling along scenic trails, or kayaking in calm waters, then return to your rental for a peaceful evening watching the sunset over the Anna Maria sky.
Popular Anna Maria vacation rentals
Yes! Many of our handpicked rentals are just steps from the sand, with direct access to the Gulf of Mexico. Others are slightly inland but still within walking or short driving distance to beaches, restaurants, and shops.
The island is a year-round destination, but the most popular months are winter and spring (December–April) for pleasant weather and lower humidity. Summer offers warm weather and fewer crowds but can be hotter and more humid.
Yes, Anna Maria vacation rentals range from small 1–2 bedroom cottages to expansive 8–10 bedroom homes, ideal for family reunions, group getaways, or multi-generational trips.
The closest major airport is Sarasota-Bradenton International Airport (SRQ), just a short drive from the island. Tampa International Airport (TPA) and St. Pete-Clearwater International Airport (PIE) are also within driving distance.
Vacation rentals in Anna Maria are conveniently located near restaurants, boutiques, fishing piers, golf courses, and water sports activities. Many are also within a short drive of Sarasota and Bradenton attractions.
Relax on the BeachesAnna Maria’s soft, white-sand beaches and calm waters are perfect for sunbathing, swimming, or enjoying a peaceful sunset picnic. Coquina Beach and Manatee Public Beach are ideal for a serene day by the Gulf.
Explore Bridge Street in Bradenton BeachStroll along Bridge Street, filled with charming shops, galleries, and waterfront dining. Scenic marina views and opportunities for kayaking or paddleboarding make it a must-visit spot on the island.
Take a Boat or Dolphin TourSee the island from the water with a dolphin-watching tour, fishing trip, or sunset cruise. Small-group tours offer close-up views of marine life and scenic Florida waterways.
Visit the Historic Town of Holmes BeachStep back in time in Holmes Beach, where local landmarks, boutique shops, and cozy cafés give a glimpse into Anna Maria’s island lifestyle. It’s a relaxing spot to stroll, shop, and enjoy authentic local culture.
Visit SarasotaJust a short drive from Anna Maria, Sarasota is perfect for a day trip. Explore its art galleries, museums, parks, and historic landmarks while enjoying local dining and boutique shopping for a full cultural experience
Concierge services
Our dedicated concierge services are designed to make your stay effortless and unforgettable. From arranging private transportation, restaurant reservations, and guided tours to booking spa treatments or family-friendly activities, our team ensures every detail is taken care of. Whether you’re planning a romantic getaway, a family vacation, or a large group retreat, we cater to your unique needs to make your time with us seamless and stress-free.
We go beyond standard service to create personalized experiences that match your interests and schedule. Want a private chef to prepare a special dinner, tickets to a popular show, or an exclusive excursion? Our team can handle it all. By anticipating your needs and providing insider tips, we help you explore the destination with ease and enjoy every moment to the fullest.
Beachfront Anna Maria vacation rentals
Our beachfront Anna Maria vacation rentals put you just steps away from the island’s pristine white sand beaches and sparkling turquoise waters. Imagine waking up to gentle waves, enjoying morning coffee on a private terrace, and spending your days swimming, sunbathing, or strolling along the shoreline. Each rental is thoughtfully designed to combine comfort, style, and modern amenities, providing the perfect base for families, couples, or groups seeking an unforgettable Florida beach escape.
Staying in one of our beachfront Anna Maria rentals also gives you easy access to local attractions, restaurants, and water-based activities. Whether you want to try kayaking through mangroves, paddleboarding at sunrise, or exploring nearby parks and historic sites, our properties make it simple to experience the best of Anna Maria Island. With direct beach access, scenic views, and luxurious interiors, our rentals offer the ultimate combination of convenience, relaxation, and coastal charm for your Florida vacation.
Popular beachfront Anna Maria vacation rentals
Anna Maria vacation rentals with private pool
Enjoy the perfect blend of relaxation, luxury, and privacy with our Anna Maria vacation rentals with private pools. Whether you’re visiting with family, friends, or a partner, having your own pool means you can unwind, sunbathe, and take refreshing swims whenever you like. Each home is designed for comfort, featuring spacious interiors, modern amenities, and beautiful outdoor areas ideal for lounging, dining, or gathering by the pool in the evenings.
Staying in an Anna Maria rental with a private pool also places you close to the island’s best attractions, beaches, and restaurants. Spend your days exploring Coquina Beach, paddling in the calm Gulf waters, or visiting nearby Bradenton and Sarasota for shopping and cultural experiences.
With your private pool as your personal retreat, these rentals offer the perfect mix of convenience, fun, and luxury, creating an unforgettable Florida getaway.
Popular Anna Maria vacation rentals with private pool
Anna Maria vacation rentals with games room
Our Anna Maria vacation rentals with games rooms are ideal for families, friends, and groups who want to blend relaxation with fun. Each home features spacious interiors, modern amenities, and a dedicated games area complete with pool tables, foosball, board games, and more.
Whether you’re enjoying a friendly competition after a beach day or spending a rainy afternoon indoors, these rentals offer the perfect space to stay entertained and create lasting memories.
You’ll also be close to Anna Maria Island’s best attractions, beaches, and local restaurants. After sunbathing at Coquina Beach, exploring Bradenton Beach, or taking a trip to nearby Sarasota, you can return to your rental for an evening of games and relaxation.
With a private games room at the heart of your stay, these vacation homes offer the perfect mix of comfort, convenience, and entertainment for an unforgettable getaway.
Anna Maria vacation rentals with games room
