Luxury Vacation Rentals in Anna Maria

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 15 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Anna Maria

Anna Maria, Florida

Wander Serendipity Beach

Next avail.

Dec 2 - Dec 4

Anna Maria, Florida

Wander Serendipity Breeze

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Dec 2 - Dec 4

Anna Maria, Florida

Wander Serendipity Sol

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Dec 2 - Dec 4

Anna Maria, Florida

Wander Anna Maria Salty

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Dec 6 - Dec 8

Anna Maria, Florida

Wander Serendipity Drift

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Dec 16 - Dec 18

Anna Maria, Florida

Wander Anna Maria Tides

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Dec 6 - Dec 8

Anna Maria, Florida

Wander Anna Maria Gulf

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Dec 9 - Dec 11

Anna Maria, Florida

Wander Serendipity Haven

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Dec 2 - Dec 4

Welcome to Anna Maria

Settle into coastal elegance with Wander’s luxury vacation rentals in Anna Maria. Our portfolio features beachfront and bayfront homes designed for open-air living, with bright interiors, expansive terraces, and panoramic Gulf or bay views. Think private pools that mirror the horizon, generous sun decks for sunset silhouettes, and easy access to the water right outside.

Every stay pairs residential comfort with hotel-grade amenities and thoughtful service. Expect ultra fast WiFi, plush bedding, chef-ready kitchens, pristine cleaning, and 24/7 concierge. Smart home tech, outdoor showers, and serene work nooks make it effortless to balance downtime and productivity. Book with confidence knowing each home is beautiful, consistent, and operated to exacting standards.

Destinations near Anna Maria

Popular vacation rentals in Anna Maria

Anna Maria, Florida

Wander Serendipity Breeze

Next avail.

Dec 2 - Dec 4

Anna Maria, Florida

Wander Serendipity Drift

Next avail.

Dec 16 - Dec 18

Anna Maria, Florida

Wander Serendipity Beach

Next avail.

Dec 2 - Dec 4

Anna Maria, Florida

Wander Serendipity Haven

Next avail.

Dec 2 - Dec 4

Anna Maria, Florida

Wander Serendipity Waves

Wander Serendipity Sea

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Dec 2 - Dec 4

Anna Maria, Florida

Wander Serendipity Cloud

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Dec 15 - Dec 17

Holmes Beach, Florida

Wander Holmes Beach

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Dec 9 - Dec 15

Available soon in Anna Maria

Anna Maria, Florida

Wander Serendipity Sol

Next avail.

Dec 5 - Dec 8

Anna Maria, Florida

Wander Anna Maria Salty

Next avail.

Dec 6 - Dec 8

Anna Maria, Florida

Wander Anna Maria Tides

Next avail.

Dec 6 - Dec 8

Anna Maria, Florida

Wander Anna Maria Gulf

Next avail.

Dec 12 - Dec 14

Anna Maria, Florida

Wander Anna Maria Palms

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Dec 5 - Dec 7

Anna Maria, Florida

Wander Anna Maria Shores

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Dec 20 - Dec 22

Highlights in Anna Maria

Experience old Florida charm on this barrier island, where pristine beaches, historic piers, and unique local shops await discovery.

Bean Point Beach

Anna Maria City Pier

Pine Avenue

Manatee Public Beach

Bridge Street Pier

Coquina Beach

Leffis Key Preserve

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

Anna Maria, Florida

Wander Serendipity Beach

Next avail.

Dec 2 - Dec 4

Anna Maria, Florida

Wander Serendipity Breeze

Next avail.

Dec 2 - Dec 4

Anna Maria, Florida

Wander Serendipity Sol

Next avail.

Dec 2 - Dec 4

Anna Maria, Florida

Wander Anna Maria Salty

Next avail.

Dec 6 - Dec 8

Anna Maria, Florida

Wander Serendipity Drift

Next avail.

Dec 16 - Dec 18

Anna Maria, Florida

Wander Anna Maria Tides

Next avail.

Dec 6 - Dec 8

Anna Maria, Florida

Wander Anna Maria Gulf

Next avail.

Dec 9 - Dec 11

Anna Maria, Florida

Wander Serendipity Haven

Next avail.

Dec 2 - Dec 4

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Most popular amenities for vacation rentals in Anna Maria

Other popular amenities & vacation types in Anna Maria

Family vacation rentals in Anna Maria

Pet-friendly vacation rentals in Anna Maria

Beachfront vacation rentals in Anna Maria

Hot tub vacation rentals in Anna Maria

Private pool vacation rentals in Anna Maria

Discover more of Anna Maria

Framed by the Gulf of Mexico and Tampa Bay, Anna Maria is a serene barrier-island enclave where gentle surf, sugar-white sand, and breezy palms set a calming rhythm. Low-rise architecture preserves wide-open horizons, and the water stays a translucent aquamarine that invites long swims and unhurried beach days.

Find quiet coves near Bean Point, watch dolphins crest offshore, and wander historic piers that glow at golden hour. Mangrove edges shelter shorebirds, and sandbars appear like secret pathways at low tide. Sunsets here are an event, washing the sky in watercolor hues night after night.

For a stay that matches the setting, Wander's luxury vacation rentals in Anna Maria are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Anna Maria

Why should I book a Wander in Anna Maria 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 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?

Some of our most popular vacation rentals in Anna Maria include Wander Serendipity Breeze, Wander Serendipity Drift, and Wander Serendipity Beach. 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?

Wander offers 15 vacation rentals in Anna Maria, 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?

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

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

Yes. Every Wander home in Anna Maria 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.