Anna Maria vacation rentals

We found 4,654 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Anna Maria by choosing from 785 houses, 51 condos, and other vacation rentals. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll have the amenities you expect and more, including WiFi and parking. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Anna Maria

Showing deals for:Dec 5 - Dec 12

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Anna Maria Vacation Rental | 2BR | 1BA | 750 Sq Ft | 1 Step Required
10 out of 10 rating
Exceptional
(5 reviews)

Fish, Swim & Unwind: Anna Maria Apt

Anna Maria, FL

7% off
Price is $337
$2,361 for 7 nights
All fees included
Fish, Swim & Unwind: Anna Maria Apt

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Find out more about Anna Maria

Find out more about Anna Maria

Why visit Anna Maria

  • Beautiful beaches: Enjoy the pristine sandy shores and stunning sunsets at Anna Maria's picturesque beaches.
  • Rich cultural experiences: Discover local history at charming museums and engage with the vibrant arts scene.
  • Outdoor activities: Participate in various outdoor adventures, including kayaking, fishing, and biking along scenic trails.
  • Family-friendly atmosphere: Experience a welcoming environment perfect for families, with activities for all ages.
  • Luxurious accommodations: Stay in cozy vacation rentals, from beachfront condos to spacious private homes.

Popular types of accommodation in Anna Maria

Discover the perfect getaway with our Anna Maria vacation rentals. Whether you're seeking a cozy condo, a spacious private vacation home, or a charming apartment, we have options to suit every traveler's needs. With a variety of Anna Maria Island rentals available, you can enjoy the beautiful beaches and vibrant local culture in comfort. Explore our selection of Anna Maria Island vacation homes and find your ideal retreat today.

  • Condos: Renowned for their modern amenities, condos are the top choice for vacationers seeking comfort and a stunning view of Anna Maria.
  • Houses: Ideal for families and groups, these spacious homes offer a home-like atmosphere and privacy during your stay.
  • Apartments: Perfect for couples or solo travelers, apartments provide a cozy and convenient base for exploring the island.
  • Cottages: Charming and quaint, cottages deliver a unique, rustic experience, often just steps from the beach.
  • Villas: Luxurious and spacious, villas offer upscale accommodations with exquisite designs and amenities.**

Top attractions in and around Anna Maria

Anna Maria, Florida, is perfect for beach lovers and outdoor enthusiasts seeking scenic beauty and cultural experiences. With attractions like stunning beaches, fascinating history museums, and vibrant marinas, visitors can enjoy a variety of activities. This charming destination offers a delightful blend of relaxation and exploration, making it an ideal spot for a memorable vacation.

  • Anna Maria Beach: A stunning beach located 0.7 miles from Anna Maria, this spot offers a tranquil atmosphere with soft sands and beautiful sunsets. Perfect for relaxing, sunbathing, and enjoying the gentle waves.
  • Bean Point Beach: Situated within Anna Maria, this picturesque cape features stunning scenery and a serene beach vibe. It's an ideal location for peaceful walks and breathtaking views of the Gulf.
  • IMG Academy: Located 10 miles away, IMG Academy is renowned for its sports training programs and athletic facilities, making it a unique destination for sports enthusiasts and aspiring athletes.

Things to do recommended for couples

For a romantic getaway in Anna Maria, indulge in a soothing treatment at Aluna Wellness Center & Spa, just 4 miles away. For an adventure, try paddleboarding with AMI Paddleboard Adventures, 3 miles away. End your day with some fun at Fish Hole Adventure Golf, located 5 miles from the island.

Things to do recommended for families

Families can enjoy a game at LECOM Park, explore ice skating at Ellenton Ice and Sports Complex, or unwind at Maximo Park for a relaxing day outdoors. Each location offers unique experiences perfect for creating lasting memories together.

Things to do recommended for groups

Enjoy a night out at the Island Players theater for a cultural experience, shop for unique items at the West Coast Surf Shop just 3 miles away, and explore Bridge Street's family-friendly atmosphere 5 miles from Anna Maria for a perfect blend of entertainment and shopping.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Anna Maria

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize the right features. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Anna Maria with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Anna Maria with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions to make the trip more enjoyable.
  • Taking your pets with you to Anna Maria: For many families, a vacation isn't truly fulfilling without their furry companion joining in. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Anna Maria: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search to enhance your experience.

Where to stay near Anna Maria

Anna Maria, Florida, is a charming beach destination perfect for outdoor enthusiasts and families alike. Explore stunning beaches, indulge in luxury vacation properties, and immerse yourself in the friendly atmosphere of this quaint city. Nearby, you can discover vibrant neighborhoods offering excursions and budget-friendly options, making it an ideal getaway for all types of travelers. Experience the best of island life and create lasting memories in this picturesque coastal paradise.

  • Anna Maria Island: Nestled just 2 miles from the vibrant town of Anna Maria, this picturesque island boasts stunning beaches and a relaxed atmosphere perfect for families and outdoor enthusiasts. Visitors will find an array of resorts and recreational areas, making it an ideal spot for beach activities and relaxation. The local attractions include beautiful family beaches and a nearby theme park, offering fun for all ages. Explore charming shops and indulge in delicious dining options while soaking in the breathtaking coastal views.
  • St. Pete Beach: Located 15 miles away, St. Pete Beach is a lively city known for its beautiful sandy shores and family-friendly atmosphere. This destination is perfect for those seeking outdoor adventures and relaxation by the sea. St. Pete Beach offers a variety of resorts and shopping areas, ensuring a delightful experience for visitors. Enjoy the stunning local beaches and discover the unique charm of the town’s neighborhoods, where you can find dining, shopping, and entertainment options that cater to all tastes.
  • Holmes Beach: Just 3 miles from Anna Maria, Holmes Beach is a charming city that embodies the quintessential beach getaway. With its family-friendly vibe and outdoor activities, it’s an excellent choice for travelers seeking sun and fun. Highlights include a selection of resorts and shopping mall centers, as well as access to beautiful beaches and scenic recreational areas. Visitors can also explore the nearby cape, making it a perfect location for those who want to enjoy the natural beauty and laid-back lifestyle of Florida’s Gulf Coast.

Best time to go to Anna Maria

If you're planning a trip to Anna Maria, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from May to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.4°F (16.9°C)Light RainMostly SunnyAverageSlightly Low
February64.8°F (18.2°C)No Rain (Dry)Mostly SunnyAverageAverage
March67.8°F (19.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High
April73.0°F (22.8°C)Light RainSunnyAverageSlightly High
May77.5°F (25.3°C)Light RainMostly SunnyHighAverage
June81.7°F (27.6°C)Light RainMostly SunnyHighAverage
July83.1°F (28.4°C)Light RainMostly SunnyHighSlightly High
August83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
September81.7°F (27.6°C)Light RainMostly SunnyAverageSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyLowSlightly Low
November70.5°F (21.4°C)Light RainMostly SunnyLowAverage
December66.4°F (19.1°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travel plans? Being open to adjusting your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash on the full booking amount. It's certainly rewarding to be the planner. Become a part of our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash on eligible stays. Sign up today and start reaping the benefits.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and organize your travel plans. You can find properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Key information on Anna Maria Island

Anna Maria Island vacation rentals 

Take your pick from a plethora of inviting places to rent on Anna Maria Island and let the countdown begin to your Florida escape. Here, the soft white sands set the scene for long, sunny days by the Gulf. Be sure to catch the sunset at Bean Point. After a day on the beach, there's nothing better than washing the sand away with a dip in your private pool. Don't feel like cooking? The bustling Pine Avenue comes to life at night with welcoming restaurants serving up freshly caught seafood for dinner. Anna Maria Island vacation rentals promise all this and more.  

Is Anna Maria Island good for vacation rentals? 

You'll encounter a vast array of Anna Maria Island rentals with pools, ocean views, air conditioning, and countless more amenities. The variety is as impressive as the destination itself. There are cozy apartments along Pine Avenue, trendy condos near the beach, and quaint cottages tucked away overlooking the sea. Anna Maria Island's beachfront rentals are especially popular.  

When is the most popular time of year to visit? 

Anna Maria Island vacation rentals are typically booked the most between January and May. While winter bites in the rest of the country, here you'll enjoy comfortable temperatures averaging in the low-to-mid 70s. 

When is the cheapest time of year to visit? 

Some of the cheapest times to stay in Anna Maria Island rentals in Florida are October and November. The summer crowds have left, and the winter ones are yet to arrive. Cheaper rental rates mean you can often save money by visiting at this time of year. 

Find vacation homes in Anna Maria offering discounts

In Anna Maria you can often discover great deals and discounts on Vrbo, especially for newly listed homes as well as weekly or monthly vacation rentals. Whether you’re planning a short getaway or an extended stay, Vrbo offers a variety of options to suit your needs and budget.

Frequently asked questions

What is the best area to stay in Anna Maria when booking a vacation rental?
When planning a vacation in Anna Maria, Florida, one of the best areas to consider for your stay is the charming Holmes Beach. This neighborhood is known for its beautiful, powdery beaches and relaxed atmosphere, making it an ideal spot for families and couples alike. Holmes Beach features a variety of vacation rental properties, from cozy cottages to spacious beachfront homes, allowing you to choose the superb setting for your getaway.

This area also boasts easy access to some of the island's top attractions. For example, the nearby Manatee Public Beach offers a fantastic place to soak up the sun and enjoy various water activities, while the Anna Maria Island Historical Society Museum provides insight into the rich history of the area. Moreover, you'll find several delightful local restaurants and shops that add to the charm of Holmes Beach, making it a convenient and enjoyable base for your vacation.

Another excellent option is the northern part of Anna Maria Island, particularly the picturesque Anna Maria City. This area captures the essence of a quaint beach town, with its small-town vibe and beautiful scenery. Staying here gives you proximity to the serene Bean Point Beach, famous for its stunning sunsets and tranquil atmosphere.
How much does it cost to rent a vacation home in Anna Maria?
Prices for vacation rentals in Anna Maria vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Anna Maria to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Anna Maria vacation house rentals?
You can find great discounts on house rentals in Anna Maria on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Anna Maria?
For renting a beach house in Anna Maria, Florida, the areas along the Gulf of Mexico are particularly appealing. The northern end of the island, around Bean Point, offers stunning views and a tranquil atmosphere, making it a favorite for families and couples. Here, you can find beach houses with amenities such as private pools, spacious decks for outdoor dining, and direct access to quiet, sandy beaches. Many properties in this area also feature modern kitchens and open living spaces, great for entertaining after a day of sun and surf.

Moving south towards Holmes Beach, travelers will find a vibrant community with a mix of vacation rentals that cater to a variety of preferences. This area often has properties equipped with amenities like beach gear, outdoor showers, and barbecues, ideal for enjoying the beautiful Florida weather. The proximity to shops, restaurants, and local attractions enhances the experience, allowing easy access to dining and entertainment options.

In the southern part of the island, near Anna Maria City, beach houses often showcase charming island decor and lush landscaping. Many of these rentals come with family-friendly amenities, such as game rooms or play areas, and some may even offer bicycles for exploring the scenic pathways that connect the island. Find your rental near the beach in Anna Maria.
What is the most popular type of vacation rental accomodation in Anna Maria?
In Anna Maria, vacation houses are the predominant type of accommodation, with around 690 available across the island. These homes are often located in charming neighborhoods, just a short stroll from beautiful beaches and local attractions like the Anna Maria Island Pier and the Sandbar Restaurant. Most vacation houses come equipped with spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor patios or decks, making them ideal for families and groups.

Condos are also a popular option, with about 44 rooms offering amenities such as pools, fitness centers, and easy beach access. Cottages and villas provide a cozier atmosphere, often featuring unique decor and proximity to local shops and dining.
Are there any family house rentals in Anna Maria?
In Anna Maria, Florida, there is a substantial selection of family-friendly vacation rentals, with around 569 options available throughout the area. This charming locale is known for its beautiful beaches and laid-back atmosphere, making it ideal for family getaways. Rentals are common in neighborhoods close to the Gulf of Mexico, such as Anna Maria City and Holmes Beach, where families can enjoy easy access to white sandy shores and family-friendly attractions.

Many properties feature spacious living areas, full kitchens for preparing meals, and outdoor patios or decks great for barbecues and relaxation. Additionally, some homes may offer amenities like private pools, game rooms, and beach gear, ensuring that families have everything they need for a fun and comfortable stay.

Nearby, visitors can explore attractions like the Anna Maria Island Historical Museum, which provides insight into the area's rich history, or take a leisurely stroll on the scenic Anna Maria Island Pier. See all family-friendly rentals in Anna Maria.
Can I rent a vacation home with a pool or hot tub in Anna Maria?
In Anna Maria, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 648 options to choose from. This picturesque island offers a charming atmosphere with its stunning beaches and tropical surroundings. Travelers can find rentals in various neighborhoods, including the quiet and residential North End, known for its serene beaches and family-friendly vibe, as well as the more lively areas closer to the city center, where shops and restaurants are within easy reach.

Many of these vacation homes come equipped with private pools and hot tubs, superb for relaxing after a day at the beach. Additional amenities often include fully equipped kitchens, spacious living areas, and outdoor patios, making them ideal for both families and groups looking to enjoy a comfortable stay. Find your rental in Anna Maria with a pool or a hot tub.
Can I find long-stay vacation rentals in Anna Maria?
A long-stay vacation rental in Anna Maria is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Anna Maria?
In Anna Maria, travelers can find a variety of pet-friendly house rentals, with around 248 options available. This charming island destination offers vacation homes that often come equipped with amenities such as private pools, outdoor grills, and fully equipped kitchens, making them superb for families or groups looking to enjoy a beach getaway with their furry friends. Many properties are just a short walk from the beach, allowing easy access to the sandy shores and stunning Gulf views.

The island's quaint neighborhoods, such as Anna Maria City and Holmes Beach, provide a laid-back atmosphere with pet-friendly parks and walking trails. In particular, the Anna Maria Island Beach offers ample space for pets to enjoy a day by the water. Additionally, nearby spots like the Bayfront Park feature picnic areas and scenic views, making it a great place to relax with pets. See all pet-friendly rentals in Anna Maria.
Are there any remote work vacation rentals in Anna Maria?
In Anna Maria, Florida, there is a wide selection of remote work vacation rentals available, with approximately 760 options to choose from. This charming island destination offers a unique blend of relaxation and productivity, making it an ideal spot for those looking to combine work and leisure. Many properties come equipped with essential remote work amenities, including high-speed Wi-Fi, dedicated office spaces, and ergonomic desk setups, such as desk chairs and laptop workspaces.

The vacation rentals are often located within close proximity to beautiful beaches, local shops, and dining establishments, allowing for convenient breaks and leisure activities after work hours. Travelers can expect spacious living areas, fully equipped kitchens, and outdoor spaces for enjoying the pleasant Florida weather. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Anna Maria vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Anna Maria with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Anna Maria?
In Anna Maria, popular vacation rental amenities include WiFi, kitchens, and private pools, with many properties also featuring heated pools for year-round enjoyment. Travelers can expect outdoor spaces like patios, superb for relaxing or dining al fresco after a day at the beach.
When is the best time to visit Anna Maria for a vacation rental?
The best time to visit Anna Maria for a vacation rental is during the peak season from May to July, with June being the most popular month. This vibrant time of year beckons beachgoers and families eager to enjoy the sun-kissed shores, warm temperatures, and a plethora of outdoor activities such as kayaking, paddleboarding, and beachcombing along the stunning Gulf Coast.

During this peak season, you can expect pleasant temperatures ranging from the mid-70s to low 90s Fahrenheit, great for sunbathing on the beach or exploring the local shops and dining options that line the island. The lively atmosphere is complemented by various community events and festivals, making it an ideal choice for those seeking a spirited vacation experience.

For travelers looking for a more budget-friendly option, November offers a wonderful opportunity to enjoy the beauty of Anna Maria without the crowds. The weather remains mild, typically in the low to mid-70s Fahrenheit, and you can experience the tranquil charm of the island as the busy summer season winds down.
How early should I book a Anna Maria vacation rental?
Book your Anna Maria vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Anna Maria?
In Anna Maria, visitors can enjoy a charming beach town atmosphere with several attractions scattered throughout the island. The Anna Maria City Pier offers stunning views of the Gulf of Mexico and is a popular spot for fishing and enjoying sunset strolls. Nearby, the Historic Green Village features quaint shops and local eateries, providing a taste of the island's laid-back vibe.

The northern tip of the island boasts Bean Point Beach, known for its serene surroundings and beautiful white sands, superb for a relaxed day by the water. For those interested in local culture, the Anna Maria Island Historical Society Museum provides insights into the area's history and heritage.

For outdoor enthusiasts, the surrounding areas offer opportunities for kayaking and paddleboarding, particularly in the calm waters of the bay. The nearby Coquina Beach is also a favorite for both locals and visitors, with its beautiful coastline and picnic facilities.
Can I change or cancel my Anna Maria home rental booking on Vrbo?
To find Anna Maria vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Anna Maria vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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