Luxury Vacation Rentals with a Private Pool in Anna Maria Island

Luxury Vacation Rentals with a Private Pool 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 90 private pool vacation rentals – enter your dates for availability.
Welcome to private poolside luxury in Anna Maria Island

Welcome to private poolside luxury in Anna Maria Island

Find your own Gulf-side indulgence with Wander’s collection of luxury private-pool vacation rentals in Anna Maria Island. We pair the polish of a luxury hotel with the privacy of a standalone home, so every arrival feels effortless and exactly like the photos.
Settle into coastal-modern spaces where indoor living flows to the water. Many homes feature heated pools framed by tropical landscaping, screened lanais for breezy afternoons, and chic loungers for sun-soaked downtime. Every Wander includes hotel-grade amenities, ultra fast WiFi, inspiring views, pristine cleaning, and 24/7 concierge service.
From first swim to last light, your private pool becomes the center of gravity, making it simple to blend deep relaxation with productive workdays.

Highlights in Anna Maria Island

Experience old Florida charm on Anna Maria Island, where pristine white-sand beaches, historic piers, and laid-back coastal vibes await.
Bean Point Beach
Anna Maria City Pier
Coquina Beach
Historic Bridge Street
Manatee Public Beach
Rod and Reel 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.

All homes in Anna Maria Island

Set in Sand property photo 1

Set in Sand

7 bedrooms6 baths
3,068 US dollars for 3 nights

~$270 less than other sites

Luna Sea property photo 1

Luna Sea

7 bedrooms7.5 baths
2,983 US dollars for 3 nights
New

~$260 less than other sites

Bleuphoria property photo 1
Luxury

Bleuphoria

4 bedrooms4 baths
3,925 US dollars for 4 nights
New

~$350 less than other sites

Crystal Waves Oasis property photo 1

Crystal Waves Oasis

7 bedrooms7 baths
3,490 US dollars for 4 nights

~$305 less than other sites

Florida Fling property photo 1
Luxury

Florida Fling

7 bedrooms7.5 baths
New
Palmetto Pointe property photo 1

Palmetto Pointe

5 bedrooms5.5 baths
2,440 US dollars for 3 nights
New

~$215 less than other sites

Bayfront Retreat property photo 1

Bayfront Retreat

5 bedrooms5.5 baths
2,899 US dollars for 3 nights
New

~$255 less than other sites

A Pirate's Dream property photo 1
Luxury

A Pirate's Dream

4 bedrooms3.5 baths
5,284 US dollars for 7 nights
New

~$470 less than other sites

View all homes

Other popular amenities & vacation types in Anna Maria Island

Discover more beyond the pool in Anna Maria Island

Discover more beyond the pool in Anna Maria Island

Seven miles of white-sand shoreline and calm Gulf waters set the pace on Anna Maria Island. Low-rise horizons, pastel cottages, and pine-shaded lanes keep the setting intimate, while sunsets paint the sky in vivid color night after night.
Mornings invite quiet beach strolls and dolphin watching. Afternoons bring gentle surf, glassy shallows, and a salt-tinged breeze that resets your senses. Come evening, the island slows even further, perfect for unwinding under starlit skies.
With its relaxed rhythm and natural beauty, Anna Maria Island makes every trip feel restorative. This is why Wander’s luxury private-pool vacation rentals in Anna Maria Island are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Anna Maria Island

Why should I book a Wander in Anna Maria Island 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 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 private pool vacation rentals in Anna Maria Island?

Some of our most popular private pool vacation rentals in Anna Maria Island include Set in Sand, Luna Sea, and Bleuphoria. 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 Island?

Wander offers 90 private pool 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 private pool vacation rentals in Anna Maria Island?

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

Do Wander’s private pool 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.