Luxury Vacation Rentals with a Private Pool 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 1 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Anna Maria

Home in Holmes Beach

3 bedrooms•2 baths

New

Welcome to private poolside luxury in Anna Maria

Claim your own slice of island luxury with Wander’s private-pool homes in Anna Maria, Florida. Our collection delivers resort polish with residential comfort, placing shimmering pools at the heart of every stay.

From heated pools, sun shelves, and spillover spas to alfresco lounges, each space invites all-day relaxation. Inside, expect designer furnishings, chef-ready kitchens, ultra fast WiFi, and quiet bedrooms dressed in hotel-grade linens.

Every home is meticulously maintained, true to the photos, and supported by pristine cleaning and 24/7 concierge. Features like outdoor kitchens, shaded cabanas, and screened lanais make poolside hours effortless, and our luxury private-pool vacation rentals in Anna Maria turn easy island days into something unforgettable.

All homes in Anna Maria

Home in Holmes Beach

3 bedrooms•2 baths

New

View all homes

Highlights in Anna Maria

Discover a slice of 'Old Florida' with pristine beaches, stunning sunsets, and a relaxed island pace perfect for unwinding.

Bean Point Beach

Anna Maria City Pier

Rod and Reel Pier

Pine Avenue

Manatee Public Beach

Coquina Beach

Historic Bridge Street Pier

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.

Most popular amenities for private pool vacation rentals in Anna Maria

Outdoor Dining Area (1)

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Discover more beyond the pool in Anna Maria

Where Tampa Bay meets the Gulf, Anna Maria blends sugar-soft beaches with a laid-back coastal rhythm. Bean Point’s dune-fringed shoreline, calm emerald water, and wide skies set the stage for slow mornings and spectacular sunsets.

Stroll the historic Anna Maria City Pier, watch dolphins cruise the channel, and bike quiet lanes shaded by sea grapes. With gentle surf, powdery sand, and warm breezes, the island suits families, couples, and friends seeking unhurried days outdoors.

If you want a serene base with privacy and easy access to the best of the island, this is why Wander’s luxury private-pool 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 private pool vacation rentals?

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

Some of our most popular private pool vacation rentals in Anna Maria include Wander Holmes Beach and Wander Holmes 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 private pool vacation rentals does Wander have available in Anna Maria?

Wander offers 1 private pool 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 private pool vacation rentals in Anna Maria?

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

Do Wander’s private pool 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.