Luxury Vacation Rentals for Families 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 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals 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

Welcome to family adventures in Anna Maria

Bring the whole crew to Anna Maria with confidence. Our luxury family vacation rentals in Anna Maria deliver the polish of a top hotel with the privacy and ease of a beach home.

Expect soothing coastal design, generous living spaces, and flexible bedroom layouts that make bedtime simple. Every stay includes hotel-grade linens, pristine cleaning, ultra fast WiFi, and 24/7 concierge support so parents can actually relax. Thoughtfully designed outdoor areas and light-filled common spaces keep everyone connected without crowding.

Settle into a beautiful coastal home that feels made for families, with room to spread out and the consistency Wander is known for.

Popular family 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

Next avail.

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

Next avail.

Dec 20 - Dec 22

Highlights in Anna Maria

Discover a slice of old Florida charm with pristine beaches, gentle Gulf waters, and endless family-friendly fun on this idyllic island.

Manatee Public Beach

Bean Point Beach

Anna Maria City Pier

Coquina Beach

Bridge Street Pier

Robinson 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

View all homes

Most popular amenities for family vacation rentals in Anna Maria

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Discover more family fun in Anna Maria

Sun-splashed shores, sugar-soft sand, and a no-rush rhythm define Anna Maria. Calm Gulf waters and wide, gently sloped beaches make it easy for little ones to play while parents enjoy dazzling sunsets. Bike-friendly streets and a charming trolley keep everything close without the stress.

Nature takes center stage, from dolphins cresting offshore to seabirds tracing the tide line, and the absence of high-rises keeps the horizon open. Between the Gulf and the bay, you are never far from a quiet morning, a shell-strewn walk, or a brilliant evening sky. This is why Wander's luxury family vacation rentals in Anna Maria are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Anna Maria

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

Wander offers a level of consistency and quality you won’t find with most family 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 family vacation rentals in Anna Maria?

Some of our most popular family 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 family vacation rentals does Wander have available in Anna Maria?

Wander offers 15 family 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 family vacation rentals in Anna Maria?

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

Do Wander’s family 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.