Planning a vacation to Anna Maria Island? If you’re searching for the best Anna Maria Island vacation rentals, you’re in the right place. At Duncan Real Estate, we offer trusted, locally managed homes that let you experience the island like a true insider — without the hassle of third-party platforms.
Whether you’re looking for a beachfront cottage, a luxury pool home, or a cozy North End escape, we’ll help you find the perfect rental for your group, budget, and vacation style.
Why Book an Anna Maria Island Vacation Rental?
There’s a reason more travelers are choosing vacation rentals over hotels — especially on Anna Maria Island. Rentals offer more privacy, more space, and a more authentic way to experience the island. You can cook, unwind, and settle in with the comfort of home while enjoying the beach just steps away.
At Duncan Real Estate, our Anna Maria Island vacation rentals are locally managed. That means faster service, personalized recommendations, and high-quality homes that meet our standards — not just anyone’s listing on a national site.
Where to Stay on Anna Maria Island: Neighborhood Rental Guide
Anna Maria Island is about seven miles long, but each area has its own feel. Here’s how to choose the right part of the island for your stay.
Anna Maria (North End)
- Peaceful, residential, and historic
- Walkable to Pine Avenue shops, City Pier, and Bayfront Park
- Best for: couples, families, those seeking quiet luxury
Holmes Beach
- The central hub of the island
- Close to grocery stores, cafes, and family-friendly beaches
- Best for: first-time visitors, families, easy access
Bradenton Beach
- Colorful, lively, and close to nightlife
- Bridge Street, beach bars, and waterfront restaurants
- Best for: groups, nightlife, walkable dining
We offer Anna Maria Island vacation rentals in all three areas, and we’re happy to help you find the one that suits your group and travel style.
Benefits of Booking Duncan Real Estate Vacation Rentals
When you book with Duncan Real Estate, you’re booking with a team that lives and works on Anna Maria Island. We’re not a call center or a mega-corporation — we’re your neighbors and your local hosts. Here’s what sets us apart:
- A hand-selected portfolio of top-tier Anna Maria Island vacation rentals
- Responsive, personalized service before and during your stay
- 24/7 support from a local team that truly knows the island
- In-house maintenance, cleaning, and guest care
- No hidden booking fees or third-party platform charges
Your vacation deserves more than an anonymous booking. It deserves the care and attention of a local team invested in your experience. Whether you’re booking a beachfront cottage, a private pool home, or a cozy coastal bungalow, we’ll make your stay unforgettable — and hassle-free.
Popular Rental Categories
No two vacations are alike, which is why we offer a diverse selection of properties to fit your group’s size, needs, and preferences. Browse our:
- Beachfront Vacation Rentals
- Pet-Friendly Homes
- Homes with Private Pools
- Family-Sized Properties
- Luxury Vacation Rental Homes
Whether you’re planning a couples’ escape or a multi-family gathering, we’ll match you with one of our trusted Anna Maria Island vacation rentals that suits your trip perfectly.
Anna Maria Island Vacation Rental FAQs
Is it better to stay in a vacation rental or hotel?
Vacation rentals offer more space, privacy, and amenities — plus kitchens and living areas for groups and families. Most AMI visitors prefer the comfort of a home-like space.
When should I book my rental?
For high season (January–April, summer, and holidays), book at least 6 months in advance. For last-minute openings, contact us directly.
What’s the best area of the island to stay?
The North End of Anna Maria is often the top pick for returning guests — it’s peaceful, walkable, and full of charm.
Start Planning Your Stay
Browse our full selection of vacation rentals on Anna Maria Island or give us a call for personalized recommendations. We’re proud to offer some of the most trusted and thoughtfully maintained Anna Maria Island vacation rentals on the island. With Duncan Real Estate, you’re not just booking a home — you’re choosing a better vacation experience from the moment you start planning.
📞 Call us at (941) 779-0304
💻 Or contact us online
