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 13 private pool vacation rentals – enter your dates for availability.
Anna Maria, Florida
Wander Serendipity Beach
Next avail.
Dec 2 - Dec 4
48
5
Anna Maria, Florida
Wander Serendipity Sol
Next avail.
Dec 2 - Dec 4
48
Anna Maria, Florida
Wander Anna Maria Salty
Next avail.
Dec 6 - Dec 8
48
Anna Maria, Florida
Wander Serendipity Drift
Next avail.
Dec 16 - Dec 18
48
5
Anna Maria, Florida
Wander Anna Maria Tides
Next avail.
Dec 6 - Dec 8
58
Anna Maria, Florida
Wander Anna Maria Gulf
Next avail.
Dec 9 - Dec 11
38
Anna Maria, Florida
Wander Serendipity Haven
Next avail.
Dec 2 - Dec 4
48
Anna Maria, Florida
Wander Serendipity Waves
Next avail.
Dec 2 - Dec 4
48
4.5
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.
Anna Maria, Florida
Wander Serendipity Drift
Next avail.
Dec 16 - Dec 18
48
5
Anna Maria, Florida
Wander Serendipity Beach
Next avail.
Dec 2 - Dec 4
48
5
Anna Maria, Florida
Wander Serendipity Haven
Next avail.
Dec 2 - Dec 4
48
Anna Maria, Florida
Wander Serendipity Waves
Next avail.
Dec 2 - Dec 4
48
4.5
Anna Maria, Florida
Wander Serendipity Sea
Next avail.
Dec 2 - Dec 4
48
5
Anna Maria, Florida
Wander Serendipity Cloud
Next avail.
Dec 15 - Dec 17
58
5
Holmes Beach, Florida
Wander Holmes Beach
Next avail.
Dec 9 - Dec 15
38
Anna Maria, Florida
Wander Anna Maria Shores
Next avail.
Dec 20 - Dec 22
48
Anna Maria, Florida
Wander Serendipity Sol
Next avail.
Dec 5 - Dec 8
48
Anna Maria, Florida
Wander Anna Maria Salty
Next avail.
Dec 6 - Dec 8
48
Anna Maria, Florida
Wander Anna Maria Tides
Next avail.
Dec 6 - Dec 8
58
Anna Maria, Florida
Wander Anna Maria Gulf
Next avail.
Dec 12 - Dec 14
38
Anna Maria, Florida
Wander Anna Maria Palms
Next avail.
Dec 5 - Dec 7
68
Anna Maria, Florida
Wander Anna Maria Shores
Next avail.
Dec 20 - Dec 22
48
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.
All homes in Anna Maria
Anna Maria, Florida
Wander Serendipity Beach
Next avail.
Dec 2 - Dec 4
48
5
Anna Maria, Florida
Wander Serendipity Sol
Next avail.
Dec 2 - Dec 4
48
Anna Maria, Florida
Wander Anna Maria Salty
Next avail.
Dec 6 - Dec 8
48
Anna Maria, Florida
Wander Serendipity Drift
Next avail.
Dec 16 - Dec 18
48
5
Anna Maria, Florida
Wander Anna Maria Tides
Next avail.
Dec 6 - Dec 8
58
Anna Maria, Florida
Wander Anna Maria Gulf
Next avail.
Dec 9 - Dec 11
38
Anna Maria, Florida
Wander Serendipity Haven
Next avail.
Dec 2 - Dec 4
48
Anna Maria, Florida
Wander Serendipity Waves
Next avail.
Dec 2 - Dec 4
48
4.5
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.