Luxury Vacation Rentals in Anna Maria Island

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 115 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Anna Maria Island

Home in Bradenton Beach

7 bedrooms•7.5 baths

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New

Luxury

Home in Bradenton Beach

5 bedrooms•5.5 baths

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New

Property in Anna Maria

3 bedrooms•3 baths

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New

Luxury

Home in Anna Maria

4 bedrooms•4 baths

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New

Home in Anna Maria

5 bedrooms•3.5 baths

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New

Property in Anna Maria

3 bedrooms•2 baths

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Home in Anna Maria

4 bedrooms•4.5 baths

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New

Home in Bradenton Beach

7 bedrooms•6 baths

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Welcome to Anna Maria Island

Welcome to Wander on Anna Maria Island, where coastal elegance meets five-star consistency. Our collection of luxury vacation rentals in Anna Maria Island blends magazine-worthy design with effortless operations, so every arrival feels like a reset.

Expect sunlit living spaces, chef-ready kitchens, plush linens, and thoughtful tech that supports both work and downtime. Many homes showcase gulf or bay views, generous outdoor lounges, and refreshing pools, all maintained to exacting hotel standards. With ultra fast WiFi, pristine cleaning, and 24/7 concierge, you get the polish of a luxury hotel with the privacy of a standalone retreat.

Settle in, spread out, and let the island set the rhythm while we handle every detail.

Destinations near Anna Maria Island

Available soon in Anna Maria Island

Home in Bradenton Beach

7 bedrooms•7.5 baths

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New

Property in Anna Maria

3 bedrooms•3 baths

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New

Home in Anna Maria

5 bedrooms•3.5 baths

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New

Property in Anna Maria

3 bedrooms•2 baths

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Home in Anna Maria

4 bedrooms•4.5 baths

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New

Home in Bradenton Beach

7 bedrooms•6 baths

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Home in Bradenton Beach

7 bedrooms•7 baths

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New

Luxury

Home in Bradenton Beach

7 bedrooms•7.5 baths

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New

Featured vacation rentals in Anna Maria Island

Luxury

Home in Anna Maria

6 bedrooms•6.5 baths

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New

Luxury

Home in Anna Maria

4 bedrooms•4.5 baths

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New

Home in Bradenton Beach

9 bedrooms•6.5 baths

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New

Luxury

Home in Bradenton Beach

8 bedrooms•8.5 baths

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New

Home in Bradenton Beach

8 bedrooms•7.5 baths

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New

Luxury

Home in Bradenton Beach

8 bedrooms•6.5 baths

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New

Home in Anna Maria

4 bedrooms•4 baths

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New

Luxury

Home in Anna Maria

5 bedrooms•5.5 baths

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New

Highlights in Anna Maria Island

Discover a laid-back Old Florida paradise featuring pristine white-sand beaches, historic piers, and charming, golf-cart-friendly coastal streets.

Bean Point Beach

Anna Maria Island Pier

Pine Avenue

Manatee Public Beach

Historic Bridge Street

Coquina Beach

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Anna Maria Island

Home in Bradenton Beach

7 bedrooms•7.5 baths

•

New

Luxury

Home in Bradenton Beach

5 bedrooms•5.5 baths

•

New

Property in Anna Maria

3 bedrooms•3 baths

•

New

Luxury

Home in Anna Maria

4 bedrooms•4 baths

•

New

Home in Anna Maria

5 bedrooms•3.5 baths

•

New

Property in Anna Maria

3 bedrooms•2 baths

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Home in Anna Maria

4 bedrooms•4.5 baths

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New

Home in Bradenton Beach

7 bedrooms•6 baths

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View all homes

Most popular amenities for vacation rentals in Anna Maria Island

Beach essentials (21)

Bicycle (15)

Other popular amenities & vacation types in Anna Maria Island

Family vacation rentals in Anna Maria Island

Discover more of Anna Maria Island

Set on Florida’s Gulf Coast, Anna Maria Island stretches seven miles of powder-soft sand and turquoise water. With no high-rises and an easygoing pace, it preserves a rare Old Florida charm while sitting within a simple hop of Sarasota and Tampa Bay.

Calm Gulf beaches invite long swims and sunrise strolls, while mangrove pathways at Leffis Key and Coquina Baywalk reveal shorebirds, manatees, and endless blue horizons. Evenings belong to golden-hour shows at Bean Point and along Bradenton Beach, where pastel cottages and sea oats frame unforgettable sunsets.

Warm breezes, year-round sunshine, and water at every turn make it an effortless escape. That is why Wander’s luxury vacation rentals in Anna Maria Island are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Anna Maria Island

Why should I book a Wander in Anna Maria Island over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Anna Maria Island delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Anna Maria Island?

Some of our most popular vacation rentals in Anna Maria Island include Luna Sea, Salt Life, and High Tide (AMIL). Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Anna Maria Island?

Wander offers 115 vacation rentals in Anna Maria Island, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Anna Maria Island?

You can check-in to Wander vacation rentals in Anna Maria Island after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Anna Maria Island have WiFi access?

Yes. Every Wander home in Anna Maria Island has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.