Welcome to Anna Maria, a peaceful barrier island on the Gulf of Mexico, where white sand beaches, laid-back charm, and coastal beauty create the ideal escape. Whether you are planning a relaxing family getaway, a romantic retreat, or a warm-weather work trip, Wander’s luxury vacation rentals in Anna Maria offer privacy, comfort, and style in one effortless stay.
Luxury Vacation Rentals in Anna Maria
Book a Wander with inspiring views, hotel-grade amenities, modern workstations, top-tier cleaning, and 24/7 concierge service. It’s a vacation home, but better.
Top-Rated Luxury Vacation Rentals in Anna Maria, Florida
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IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
A Guide to Luxury Travel in Anna Maria
Anna Maria is known for calm turquoise water, soft beaches, friendly local cafés, and a true small-island atmosphere. Life here moves at a softer pace, perfect for unwinding or working in the sunshine.
When you stay with Wander, you will enjoy:
- Spacious island homes with coastal design
- Private pools, outdoor showers, and breezy terraces
- High-speed Wi-Fi and dedicated workstations
- Concierge support for bike rentals, paddleboards, dining, and more
Every property blends Wander’s modern aesthetic with the warmth of island living. It creates a stay that feels both effortless and exceptional.
Where to Stay in Anna Maria
Anna Maria City
Located at the northern tip of the island, this area feels welcoming and walkable. Expect beach paths, boutique stores, and quiet streets lined with tropical greenery. Wander homes here are ideal if you want peaceful mornings, sunset walks, and a classic island atmosphere.
Holmes Beach
Holmes Beach offers a central location with casual restaurants, relaxed shopping, and easy beach access. It is perfect for families seeking plenty of space paired with convenience.
Bradenton Beach
At the southern end of the island, Bradenton Beach brings lively coastal energy, waterfront dining, and stunning gulf views. Great for travelers who enjoy a balance of quiet hours and nearby activity.
What Month is Best to Go to Anna Maria?
Anna Maria has warm, sunny weather throughout the year, accompanied by sea breezes and stunning sunsets. Here is a quick guide to help you plan:
December to April: Dry season with clear skies, gentle weather, and perfect beach days May to August: Long daylight hours and warm evenings ideal for swimming and outdoor dining
September to November: A quieter period with peaceful beaches and beautiful, calm water No matter the season, a Wander home provides space, comfort, and everything you need to relax.
Food and Drink in Anna Maria
Anna Maria’s food scene highlights fresh seafood, coastal flavors, and friendly island eateries. Expect fish tacos, grouper sandwiches, tropical cocktails, and seasonal produce.
In Anna Maria City, you will find intimate beachfront spots perfect for sunset dinners. Holmes Beach features relaxed cafés and artisan bakeries. Bradenton Beach brings waterfront grills, rooftop views, and lively evening dining. If you prefer cooking at home, stop by local markets for fresh ingredients or book a private chef to prepare a meal in your Wander kitchen.
Top Things to Do in Anna Maria
- Paddle through mangroves or explore the coastline by kayak
- Spend a day at Bean Point, one of Florida’s most peaceful beaches
- Visit Pine Avenue for charming shopping and tasty ice cream
- Try paddleboarding or fishing on calm Gulf waters
- Watch the sunset from your terrace or take a beach walk under pastel skies
Anna Maria offers a perfect blend of slow-paced relaxation and gentle adventure, and Wander homes place you right in the center of it.
Book Your Anna Maria Vacation Rental with Wander
With spacious layouts, comfortable amenities, and locations close to the water, Wander’s luxury vacation properties in Anna Maria deliver a refined island stay. Enjoy a full kitchen, private pool, reliable Wi-Fi, quiet work areas, and plenty of room to unwind.
Skip the hotel room and experience Anna Maria in comfort.
FAQs About Luxury Vacation Rentals in Anna Maria
Is Anna Maria Good for Families or Group Trips?
Yes. The area is known for calm beaches, walkable neighborhoods, and plenty of space to unwind. Many Wander homes also feature multiple bedrooms, large kitchens, and generous outdoor areas that make family holidays or group stays feel easy and relaxed.
Where Else Does Wander Have Luxury Vacation Rentals?
Beyond Anna Maria, Wander offers exclusive vacation homes across the U.S., Canada, and Mexico, including:
- Hudson Valley, New York
- Sedona, Arizona
- East Hampton, New York
- Lake Tahoe, California
- Telluride, Colorado
- Ponte Vedra Beach, Florida
- Bandon, Oregon
- Yucatán, Mexico
- Tulum, Mexico
Wherever you stay, Wander ensures elevated design, premium service, and spaces that feel like home, only better.
Do You Need a Car on Anna Maria Island?
A car can be helpful for exploring the wider area, but you do not need one to enjoy the island. Anna Maria offers a free trolley service, along with bike paths and walkable streets, making it easy to get around without driving. Many guests enjoy parking once and moving at an island pace.