Discover a selection of 4,000 vacation rentals in Anna Maria, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $146 per night, and houses and cottages are popular options for a stay in Anna Maria. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Anna Maria
Destination guide

With beaches and fun activities, you’ll love Anna Maria

Visitors to Anna Maria Island always find a fun vacation haven, perfect for kayaking and experiencing island life. Tucked away on Anna Maria’s north end is Bean Point Beach, ideal for those seeking an island paradise with an Old Florida vibe. Anna Maria Bayfront Park offers sweeping views of Tampa Bay, and in addition to its beaches is also home to numerous restaurants. Spend your afternoons with your toes in the sand or shopping till you drop—either way, your Anna Maria vacation rental gives you access to a getaway the whole family will enjoy.

Things to do

Immerse yourself in the Anna Maria experience

The beaches are just one reason to book an Anna Maria vacation rental. The island boasts museums as well as restaurants serving everything from fresh seafood to specialty cupcakes and donuts. Take a stroll on the pier—or down Pine Avenue with its colorful, eclectic shops. It’s not every day you get to soar hundreds of feet over the ocean, so if you’re feeling brave, try parasailing. If staying in the water is more your speed, check out Bean Point, and keep an eye open for manatees, which are known to mingle with human swimmers.


Pack the sunscreen—there’s lots to do in Anna Maria

Anna Maria vacation rentals are perfect if you love the beach. There are endless entertainment options for those who love the sun, sand, and water. Rent Segways for the family and tour the island in style. Go on a sightseeing dolphin cruise, or have some high-powered fun on a jet ski. Spend hours relaxing on the beach, or keep things active and sign up for a kayak lesson or tour. Paddleboard rentals, boat trips, fishing excursions and more are yours for the taking when you book a vacation rental in Anna Maria.


Expect pleasant weather any time of the year

Anna Maria has sun, sand, beautiful beaches, and exceptional weather. The climate is warm and temperate with plentiful rainfall, and when it does rain, it’s often short-lived before the clear blue skies return. Most of the year sees abundant sunshine, and in the heart of summer, the average high is a pleasant 88 degrees. Winter is mild with an average January low of 52. The best time to book a vacation rental in Anna Maria depends on what you’d like to do, but even winter is typically comfortable enough for outdoor activities.

Natural features

Exploring the natural features in Anna Maria

Travelers enjoy Anna Maria for its island views, beaches and sunrises. Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Anna Maria is a great spot to appreciate mother nature. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Lido Beach (18.2 mi / 29.3 km)
  • Bean Point Beach (0.6 mi / 1 km)
  • Anna Maria Beach (0.9 mi / 1.4 km)
  • Manatee Public Beach (2.7 mi / 4.3 km)
  • Brandenton Beach (4.2 mi / 6.8 km)
  • Cortez Beach (5.2 mi / 8.4 km)
How to get there

Transportation to and around Anna Maria

The nearest airport is in Tampa Intl. Airport (TPA), located 33.2 mi (53.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Sarasota-Bradenton Intl. Airport (SRQ), which is 14.8 mi (23.9 km) away.

What are the top vacation rentals in or near Anna Maria?

Whether you're searching for an intimate retreat for you and your sweetheart or someplace roomy to fit family and friends, you'll find some top vacation rentals in and around Anna Maria. Here are a couple to get you inspired:

  • "Best Little Beach House On Anna Maria Island. . . With A Pool" is popular with guests. Around 3 miles from Anna Maria, it has 1 bedroom and plenty of handy amenities, including a phone and a nearby hospital.
  • "New Completely Renovated Beach Front With Heated Pool Gulf View #102" also promises a memorable getaway, offering 2 bedrooms, a microwave oven, a garage and more. It's around 5 miles from Anna Maria.

For even more great options, use the search bar at the top of the page to find the perfect Anna Maria vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Anna Maria?

Clock off on Friday and then forget about your cares. If you're ready for some relaxation and fun, these retreats in and around Anna Maria promise the ideal weekend getaway:

  • "Seaside Sanctuary - 1 Minute Walk From Front Door To Toes In The Sand" is a popular option around 1 mile west of the center of Anna Maria. You won't have to venture far to find something cool to do around this property. Get outdoors and explore Spa Beach and Feather Sound Country Club. Activities like horse riding and parasailing will add the finishing touch to your quick break.
  • Alternatively, enjoy a more leisurely pace of life at "Ami North End Ground Level Close To Beach Heated Saltwater Pool". Approximately 0.1 miles east of Anna Maria, activities around here include fishing and basketball. Rather see the sights? Pencil in a visit to Coffee Pot Bayou & the Old Northeast and War Veteran Memorial Park.

Can I find studio apartments for rent in and around Anna Maria?

Studio apartments set the bar high when it comes to character, convenience and location. Stay in one of these studio apartments for rent in or near Anna Maria and get a taste of the local vibe and energy:

  • Make "Best Little Beach House On Anna Maria Island. . . With A Pool" your home for a week or more. This great vacation rental comes with amenities including a TV and an iron and ironing board.
  • "Snead Island Tree House' Waterfront Apartment On 2 Acre Lot" is another tempting option. Settle in and take advantage of a phone, internet services and more.

With the cash you save on your studio apartment, you'll be able to discover more of Anna Maria. Cultural attractions like Island Players and Madira Bickel Mound State Archaeological Site will help you get a feel for the personality of this destination.

Can I find short term rentals in or near Anna Maria?

Sure can. Vrbo's short-term rentals in Anna Maria provide a refreshing alternative to your typical cookie-cutter hotel room. Offering many creature comforts of home, you'll easily shift into vacation mode the moment you arrive. Try one of these fabulous rentals on for size:

  • Book a few days at "Snead Island Tree House' Waterfront Apartment On 2 Acre Lot" in central Anna Maria. Here, you'll enjoy easy access to attractions like Premier Sports Campus at Lakewood Ranch.
  • "Aqua Beach - Luxury Villa Very Close To Beach With Private Pool" is another fantastic property that accepts short-term guests. Make the most of your brief visit by stopping off at local hot spots, including TreeUmph! Adventure Course.

What are the best romantic weekend getaways in or near Anna Maria?

Whether spent in a rustic cabin or a luxury condo, a romantic weekend getaway is a wonderful way to add some zing to your relationship. Whisk your sweetheart off for a couple of relaxing days at one of these enticing escapes in or near Anna Maria:

  • Slip away on Friday for a couple of passion-filled evenings at "Best Little Beach House On Anna Maria Island. . . With A Pool". Approximately 3 miles from Anna Maria, it comes with plenty of nice touches, including beauty services and beach sun loungers.
  • Another place where you can enjoy a few relaxing days together is "New Completely Renovated Beach Front With Heated Pool Gulf View #102". Around 5 miles from Anna Maria, a nearby bay and beauty services add to the atmosphere here.

Are there mansions for rent in or near Anna Maria?

Nothing screams "best vacation evvv-er" like staying in a mansion. Spoil the family with a memorable getaway at one of these mansions for rent in or near Anna Maria:

  • Approximately 11 miles to the southeast of Anna Maria is "Cretan Mansion From The 1900 Century Lovingly Restored With Garden". Along with its grand design and posh interiors, you'll be impressed by its top-notch amenities, such as a garden and a restaurant dining guide.
  • Another popular option is "Garden Apartment With Its Own Terrace In A Historic Mansion". Around 13 miles to the east of Anna Maria, this fancy vacation rental is the crème-de-la-crème of style and character and comes with a swimming pool, a firepit and more.

What are the best large group vacation rentals in or near Anna Maria?

Vacation with others and have twice as much fun. Whether you're planning an action-packed escape with your best friends or a big family get-together, you'll have your pick of large group vacation rentals in and around Anna Maria:

  • A range of amenities including a swimming pool and a kitchen make "Blue Water Beach House: 5+ Bedroom" a top pick for groups. This expansive retreat has 6 bedrooms and sleeps up to 12 people. From central Anna Maria, it's around 4 miles away to the southeast.
  • Nothing is more important than hanging out with the people you love, and "Family Fun Close To Beach, Pool Slide Spa And Elevator" is the perfect place to do that. Located around 4 miles to the southeast of Anna Maria, as many as 12 people can stay in this vacation rental which has 4 bedrooms. A kitchen and a garden are among the many amenities at hand here.

Are there large vacation rentals that sleep 30 or more in or near Anna Maria?

If you're planning a fun event and your invite list fills a few pages, don't worry about finding a space big enough for all those people. We have large vacation rentals in and around Anna Maria perfect for family breaks, wedding receptions and more. These are a few ideas:

  • "Villa 70 Meters From The Sea, With Infinity Pool And Stunning Views": With 2 bedrooms accommodating as many as 99 people, space isn't a problem at this sprawling stunner. A swimming pool and a garden are just a taste of its numerous amenities.
  • "The Rod And Reel Resort: Private Beachfront Luxury Group Getaway": Get the whole family's nod of approval at this rental which features a beach view and a swimming pool. With 11 bedrooms, up to 30 loved ones can stay and play here.

What are the best houses for rent with a pool in or near Anna Maria?

Nothing spells fun like a pool does. Pull out your inflatable unicorn and check out these houses in or near Anna Maria that feature this added perk:

  • Treat the gang to a memorable break at "Best Little Beach House On Anna Maria Island. . . With A Pool". There's plenty to love about this retreat besides its pool, such as a kitchen and a separate dining area.
  • "Snead Island Tree House' Waterfront Apartment On 2 Acre Lot" is the type of place you go to get away from it all and enjoy your surroundings, starting with its inviting pool. Coffee and tea making facilities and a stereo are also on hand to make your stay a memorable one.

Not sure how to pack for your Anna Maria getaway? This popular destination has a humid subtropical climate. During the summer months, you can expect average temperatures of between 80 ºF and 90 ºF. Look up our selection of Anna Maria vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Anna Maria?

No matter if your ideal escape is out in the country or by the ocean, you'll have a lot more fun if you share the experience with loved ones. Book one of these large family vacation rentals in or near Anna Maria and bring the whole gang:

  • Invite your nearest and dearest to "Ami North End Ground Level Close To Beach Heated Saltwater Pool", which has 3 bedrooms sleeping up to 8 guests. This retreat is around 0.1 miles to the east of Anna Maria and features amenities such as free toiletries and coffee and tea making facilities.
  • "Blue Sky: Luxury 5 Bedroom/4 Bath With Heated Pool" is another top pick for families. It's about 1 mile to the southeast of Anna Maria, has 5 bedrooms and accommodates up to 10 guests. Useful amenities here include coffee and tea making facilities and a microwave oven.

If you're eager to visit some family-friendly attractions in the area, you're spoiled for choice. TreeUmph! Adventure Course, Main Street at Lakewood Ranch and Historic Bridge Street Pier offer fun for all ages.