Anna Maria vacation rentals

We found 4,599 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Anna Maria by choosing from 781 houses, 52 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:Nov 7 - Nov 14

Image gallery for ༄ Sunset Shore on Anna Maria Island ༄

Pool
10 out of 10 rating
Exceptional
(7 reviews)

༄ Sunset Shore on Anna Maria Island ༄

Anna Maria, FL

6% off
Price is $834
$5,837 for 7 nights
All fees included
༄ Sunset Shore on Anna Maria Island ༄

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Anna Maria

Find out more about Anna Maria

Why visit Anna Maria

  1. Stunning Beaches: Enjoy the pristine shores of Anna Maria Island, perfect for sunbathing and water activities.
  2. Outdoor Adventures: Engage in various outdoor activities such as kayaking, fishing, and biking along scenic trails.
  3. Local Cuisine: Savor delicious local dishes at charming waterfront restaurants and cafes.
  4. Rich History: Explore historical museums and learn about the island's vibrant past.
  5. Charming Accommodations: Find cozy condos and vacation homes that enhance your relaxing getaway experience.

Popular types of accommodation in Anna Maria

If you're considering a getaway to Anna Maria, you're in for a treat! Our most popular types of accommodations include condos, houses, and apartments. Each option offers unique charm and comfort, perfect for your Anna Maria vacations. Whether you're seeking a cozy retreat or a spacious home, our vacation rentals provide the ideal base for exploring the beauty of Anna Maria Island. Discover your perfect stay with us today!

  • Condos: Condos are the top choice for vacation rentals in Anna Maria, offering a blend of comfort and convenience for travelers.
  • Houses: Second in popularity, these homes provide spacious living and a homey atmosphere for families or groups.
  • Apartments: A practical option, apartments are perfect for those seeking a central location with essential amenities.
  • Cottages: Cottages offer a quaint and cozy retreat, ideal for a romantic getaway or peaceful escape.
  • Villas: Villas are a luxurious choice, featuring upscale amenities and beautiful surroundings for an unforgettable stay.**

Top attractions in and around Anna Maria

Anna Maria, Florida, is perfect for beach and outdoor vacations, offering beautiful scenery and a vibrant local culture. You'll find a range of attractions, including stunning beaches, marinas, and historical museums, catering to travelers seeking relaxation and cultural experiences. For a memorable getaway, consider exploring vacation properties on Anna Maria Island to fully enjoy the serene coastal charm and engaging activities the area has to offer.

  1. Anna Maria Beach: A stunning beach with soft sands and gentle waves, perfect for sunbathing and swimming. Enjoy the laid-back beach vibes while taking in beautiful sunsets and the sound of the surf.
  2. Bean Point Beach: A hidden gem at the northern tip of Anna Maria, Bean Point offers breathtaking scenery and a serene atmosphere. It's ideal for peaceful strolls along the shore and enjoying the natural beauty.
  3. IMG Academy: Renowned for its sports training facilities, IMG Academy is a premier institution located about 10 miles away. Visitors can watch elite athletes in action and enjoy various sports events.

Things to do recommended for couples

Experience romance in Anna Maria! Enjoy a paddleboard adventure with AMI Paddleboard Adventures, indulge in relaxation at Aluna Wellness Center & Spa, or have fun at Fish Hole Adventure Golf. Each activity is perfect for couples seeking adventure and tranquility, all within a short drive from the island.

Things to do recommended for families

Families visiting Anna Maria can experience the excitement of LECOM Park, just 10 miles away, catch some ice skating fun at the Ellenton Ice and Sports Complex, 14 miles away, or relax in the beautiful surroundings of Maximo Park, located 13 miles from Anna Maria.

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

When planning your trip—whether you're traveling with friends, family, pets, or seeking extended stays—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Anna Maria with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily narrow down your options for all of these amenities and more on Vrbo.
  • Traveling to Anna Maria with young kids: Traveling with young kids can be difficult. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Anna Maria: For many, a family vacation isn't truly fulfilled without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Anna Maria: If you're searching for vacation rentals that offer discounts 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 rental options. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Anna Maria

Explore the charming beauty of Anna Maria, Florida, where stunning beaches and vibrant outdoor activities await. This idyllic island getaway offers a perfect blend of relaxation and adventure, making it an ideal destination for families and couples alike. Discover the scenic shores of Anna Maria Island, indulge in local cuisine, and soak in the laid-back atmosphere. Whether you're seeking a romantic escape or a fun-filled beach vacation, Anna Maria promises unforgettable memories.

  • Anna Maria Island: Anna Maria Island is a picturesque barrier island located just 2 miles from the mainland, known for its stunning beaches and laid-back atmosphere. Visitors flock here for family-friendly activities and outdoor adventures, making it a perfect destination for vacationers seeking relaxation and recreation. Along the island, you'll find charming resorts, beautiful recreational areas, and inviting shopping centers. The local attractions include pristine beaches, a delightful family beach, and nearby theme parks that cater to all ages, offering a unique blend of fun and leisure.
  • St. Pete Beach: Situated 14 miles from Anna Maria, St. Pete Beach is a vibrant city renowned for its beautiful sandy shores and lively atmosphere. This destination is ideal for families and outdoor enthusiasts looking for beach fun and numerous recreational activities. St. Pete Beach features a variety of resorts and shopping areas, providing ample opportunities for relaxation and exploration. Highlights include stunning beaches, family-friendly coastal spots, and a charming town neighborhood, all contributing to a delightful vacation experience along the Gulf Coast.
  • Holmes Beach: Located just 3 miles from Anna Maria, Holmes Beach is a welcoming city that boasts excellent beach access and a friendly community vibe. It’s an ideal spot for families and outdoor lovers seeking sun and sand. Holmes Beach offers a range of resorts, shopping centers, and recreational areas, making it easy to unwind and enjoy your stay. Local attractions include gorgeous beaches, a family beach perfect for children, and the scenic cape, ensuring visitors have plenty of options for fun and relaxation during their vacation.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Planning truly has its rewards! When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash™ on eligible bookings. Sign up today and start enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, continue from where you last stopped, or review and arrange your itineraries. All the properties you’ve saved or booked are neatly organized under categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/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.

More Vacation Rentals ideas

Daytona Beach Vacation Rentals
Standard Link for Daytona Beach
Bradenton Vacation Rentals
Standard Link for Bradenton
Sarasota Vacation Rentals
Standard Link for Sarasota
New Smyrna Beach Vacation Rentals
Standard Link for New Smyrna Beach
Miramar Beach Vacation Rentals
Standard Link for Miramar Beach
St. George Island Vacation Rentals
Standard Link for St. George Island
Marathon Vacation Rentals
Standard Link for Marathon
Fort Myers Beach Vacation Rentals
Standard Link for Fort Myers Beach
Destin Vacation Rentals
Standard Link for Destin
Fort Walton Beach Vacation Rentals
Standard Link for Fort Walton Beach
Fort Myers Vacation Rentals
Standard Link for Fort Myers
Marco Island Vacation Rentals
Standard Link for Marco Island
Cape Coral Vacation Rentals
Standard Link for Cape Coral
Panama City Beach Vacation Rentals
Standard Link for Panama City Beach
Key West Vacation Rentals
Standard Link for Key West
Santa Rosa Beach Vacation Rentals
Standard Link for Santa Rosa Beach
Naples Vacation Rentals
Standard Link for Naples
Pensacola Beach Vacation Rentals
Standard Link for Pensacola Beach
Key Largo Vacation Rentals
Standard Link for Key Largo
St. Augustine Vacation Rentals
Standard Link for St. Augustine
Cocoa Beach Vacation Rentals
Standard Link for Cocoa Beach
The Villages Vacation Rentals
Standard Link for The Villages
Siesta Key Vacation Rentals
Standard Link for Siesta Key

People also search for

Oceanfront vacation rentals in Santa Rosa Beach
Standard Link for Santa Rosa Beach
Destin Apartments
Standard Link for Destin
Oceanfront vacation rentals in Destin
Standard Link for Destin
Beach vacation rentals in Destin
Standard Link for Destin
Pensacola Beach Apartments
Standard Link for Pensacola Beach
Beach vacation rentals in Miramar Beach
Standard Link for Miramar Beach
Panama City Beach Apartments
Standard Link for Panama City Beach