Anna Maria holiday lettings

We found 4,964 holiday rentals — enter your dates for availability
Select from 583 houses, 23 flats and other holiday rentals to find the perfect place for your stay in Anna Maria. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include parking and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Anna Maria

Showing deals for:9 Oct - 16 Oct

Image gallery for Waterfront pool and dock, family stay

Exterior
9.8 out of 10, Exceptional, (133 reviews)
Exceptional
(133 reviews)

Waterfront pool and dock, family stay

Bradenton

8% off
Price is £6,424
for 7 nights, 1 home
£918 per night
includes taxes & fees
Waterfront pool and dock, family stay

Find spaces that suit your style

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Why visit Anna Maria

  • Stunning Beaches: Anna Maria boasts beautiful sandy shores perfect for sunbathing and swimming.
  • Charming Boutiques: Explore quaint streets filled with local shops offering unique finds and souvenirs.
  • Vibrant Local Art: Discover the artistic flair of the area through galleries and public art displays.
  • Delicious Seafood: Indulge in fresh seafood at waterfront eateries with picturesque views.
  • Outdoor Activities: Enjoy various excursions, from kayaking to nature walks, showcasing the island's natural beauty.

Popular types of accommodation in Anna Maria

Discover the charm of Anna Maria, Florida, a delightful city renowned for its stunning beaches and quaint atmosphere. Here, you can explore picturesque parks, enjoy vibrant local art, and indulge in fresh seafood at waterfront eateries. With a variety of vacation rental options including condos, private homes, and apartments, Anna Maria Island offers a perfect getaway tailored to your needs. Whether you're seeking relaxation or adventure, the island promises unforgettable experiences for every traveller.

  • Condos: These modern, self-contained units offer a fantastic blend of comfort and convenience, making them the top choice for visitors in Anna Maria.
  • Houses: Ideal for families or groups, these spacious homes provide a cozy atmosphere and the privacy you desire during your stay.
  • Apartments: A practical option, these fully-equipped living spaces are perfect for those looking for a home-like environment while exploring the area.
  • Cottages: Charming and quaint, these delightful retreats offer a unique and picturesque experience on the island.
  • Villas: Luxurious and often set in beautiful locations, villas provide an upscale option for discerning travellers seeking a memorable holiday.**

Top attractions in and around Anna Maria

Anna Maria, Florida, offers a delightful blend of stunning beaches, scenic views, and outdoor activities perfect for a relaxing holiday. Visitors can explore historic sites, enjoy the local marina, and immerse themselves in the area's rich culture. Whether you're seeking sun-soaked days by the shore or peaceful strolls through nature, Anna Maria presents a charming destination for every traveller looking to experience the beauty and history of this coastal gem.

  • Bean Point Beach: A serene cape within Anna Maria, Bean Point Beach boasts stunning scenery and tranquil vibes. It's an ideal spot for sunbathing, picnicking, and enjoying breathtaking sunsets over the Gulf of Mexico.
  • Anna Maria Beach: Located a short distance from the city centre, Anna Maria Beach offers a classic beach experience with soft sands and gentle waves, perfect for relaxing or beachcombing.
  • Anna Maria City Pier: This charming pier provides opportunities for fishing and scenic excursions, featuring beautiful views of the bay and local wildlife, making it a lovely spot for leisurely strolls.

Things to do recommended for couples

For a romantic getaway in Anna Maria, explore the stunning beaches hand-in-hand, enjoy a sunset cruise on the bay, or dine at a charming seaside restaurant. Don’t miss the local art galleries for a touch of culture, perfect for couples seeking unique experiences together.

Things to do recommended for families

Families visiting Anna Maria can explore the beautiful beaches, enjoy a delightful day at the Anna Maria Island Historical Society Museum, and take a fun-filled trip on a dolphin-watching cruise, creating unforgettable memories together in this charming coastal paradise.

Things to do recommended for groups

Groups visiting Anna Maria can enjoy a relaxing day on its beautiful beaches, explore the charming local shops, and indulge in fresh seafood at waterfront restaurants. Don't miss a group bike ride along the scenic paths or a sunset cruise for a memorable evening on the water.

*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

If you're travelling with a group, family, pets, or planning for an extended stay, it's essential to prioritise your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Anna Maria with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options, and much more, on Vrbo.
  • Traveling to Anna Maria with young kids: Travelling with young children can be quite challenging. It’s important to prioritise their comfort and safety, along with ensuring access to 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 holiday wouldn't be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Anna Maria: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Anna Maria

Anna Maria, Florida, offers a delightful escape for beach lovers and outdoor enthusiasts alike. With its stunning sandy shores, charming boutiques, and friendly atmosphere, visitors can indulge in the perfect beach vacation. Explore the quaint streets lined with local shops, enjoy picturesque sunsets, and partake in various excursions that showcase the island's natural beauty. Anna Maria is truly a hidden gem, promising a memorable getaway for families and couples seeking relaxation and adventure.

  • Anna Maria Island: Nestled off the coast of Florida, Anna Maria Island is a picturesque barrier island renowned for its stunning beaches and vibrant community. Located approximately 3km from the main town, this idyllic getaway is perfect for families seeking outdoor adventures and relaxation. Visitors can enjoy a variety of activities, including lounging on soft sandy beaches, exploring the local shopping mall, or indulging in delicious meals at nearby resorts. Key attractions include the pristine family beaches and scenic Cape, making it a delightful destination for all ages.
  • Bradenton Beach: Situated around 8km from Anna Maria, Bradenton Beach offers a lively atmosphere with a focus on family-friendly activities. This charming city boasts beautiful beaches that invite sunbathers and water sports enthusiasts alike. Visitors can explore the local shopping centres and recreational areas, which are perfect for unwinding after a day of adventure. The city's quaint neighbourhoods complement its laid-back vibe, while its proximity to the beach ensures a relaxing experience. From beachside dining to outdoor fun, Bradenton Beach is a must-visit for any traveller.
  • Holmes Beach: Located just 5km from Anna Maria, Holmes Beach is a welcoming city that embodies the true spirit of coastal living. Known for its family-friendly beaches, this area offers ample recreational opportunities, including water sports and nature walks. Visitors can explore local resorts and shopping centres that cater to all needs, making it an excellent base for your vacation. Holmes Beach features scenic landscapes and charming beachfront spots, with attractions such as the family beach and nearby Cape, ensuring a memorable stay for all.

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 simple

Looking to make your next holiday more affordable? Consider being flexible with your travel dates, as this can lead to significant price differences. Moreover, extending your stay often results in substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated area to plan new journeys, pick up from where you last paused, or review and sort your travel arrangements. You can easily access properties you’ve saved or booked previously, now categorised under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips

**Based on Vrbo properties bookings.

The waterfront setting of Anna Maria is ready to explore

The island views and surrounding scenery provide a peaceful ambience to your holiday home in Anna Maria. Renowned for its bird watching, fishing and surfing, this city welcomes all visitors. Take in top local attractions such as Anna Maria Beach and Bean Point Beach. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Anna Maria

Do you want to discover attractions to visit in the city? Venture out of your holiday home and experience everything that makes Anna Maria a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Splash Island Water Park (13.7 mi / 22.1 km)
  • Sarasota Jungle Gardens (15.8 mi / 25.4 km)
  • Mote Marine Laboratory & Aquarium (16.7 mi / 26.9 km)
  • Aluna Wellness Center & Spa (4 mi / 6.5 km)
  • Harborside Golf Course at Longboat Key Club (16.3 mi / 26.2 km)
  • H2O Watersportz (4.9 mi / 7.9 km)

Exploring the natural features in Anna Maria

Travellers enjoy Anna Maria for its island views, beaches and sunrises. Whether you're looking for adventure or just want to appreciate the scenery, Anna Maria is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Anna Maria Beach (0.7 mi / 1.1 km)
  • Bean Point Beach (0.8 mi / 1.2 km)
  • Lido Beach (18.2 mi / 29.3 km)
  • Tampa Bay (19.8 mi / 31.9 km)
  • St. Petersburg - Clearwater Beaches (21.7 mi / 34.9 km)
  • Bradenton Beach (2 mi / 3.2 km)

Seasonal weather in Anna Maria

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 28°C.

Transport to and around Anna Maria

The nearest airport is in Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), located 14.8 mi (23.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to St. Petersburg, FL (SPG-Albert Whitted), which is 17.3 mi (27.8 km) away.

Frequently asked questions

What is the best area to stay in Anna Maria when booking a holiday rental?
When considering a holiday rental in Anna Maria, Florida, a popular area to stay is the charming city of Anna Maria itself. This quaint coastal community is known for its stunning beaches, particularly the serene Anna Maria Beach, which offers soft sands and crystal-clear waters, great for sunbathing or leisurely strolls. The area features a delightful mix of local shops, cafes, and restaurants, providing a pleasant atmosphere for visitors.

Another excellent option is Holmes Beach, which is situated nearby. This area boasts several properties that cater to various preferences, ranging from cosy beachfront cottages to spacious family homes. In addition to its beautiful beach, Holmes Beach is home to the popular Manatee Public Beach, where you can enjoy amenities such as picnic areas, volleyball courts, and a café.

For those interested in local attractions, the Anna Maria Island Historical Museum offers fascinating insights into the island's rich heritage, making it a worthwhile visit. The charming city pier in Anna Maria is also a lovely spot for fishing or simply enjoying picturesque sunset views over the water.
How much does it cost to rent a holiday home in Anna Maria?
Prices for holiday 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 holiday 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, the island offers some delightful options along its picturesque coastline. The area around Anna Maria City boasts beautiful sandy beaches and charming local shops, making it an ideal spot for holiday rentals. Visitors can expect properties with amenities such as private pools, outdoor dining areas, and quick access to the beach, great for families or groups looking to enjoy a relaxed seaside holiday.

Particularly, the beaches near Bean Point offer a more tranquil atmosphere, with rental homes often featuring stunning views of the Gulf of Mexico. Many of these properties come equipped with modern kitchens, spacious living areas, and outdoor showers, which are great after a day spent on the beach. The nearby Rod and Reel Pier not only provides a great spot for fishing but also features a restaurant with local seafood, enhancing the beach experience.

For those seeking a bit more activity, the northern part of the island near Coquina Beach offers a lively scene, complete with picnic areas and playgrounds. Rentals here may include amenities such as bicycles for exploring the island and beach gear for a day by the water. Find your rental near the beach in Anna Maria.
What is the most popular type of holiday rental accomodation in Anna Maria?
In Anna Maria, holiday houses are the most popular type of holiday rental, with approximately 2,908 available throughout the area. These spacious homes are often situated in charming neighbourhoods close to the beach, providing easy access to the stunning coastline and local attractions. Most holiday houses feature multiple bedrooms, fully equipped kitchens, and outdoor spaces, such as patios or decks, superb for enjoying the warm Florida weather.

In addition to holiday houses, there are about 160 condos, which offer a more compact option with amenities like pools and fitness centres, often located near shopping and dining. Cottages, apartments, and villas are also available, though in smaller numbers, suiting various preferences.
Are there any family house rentals in Anna Maria?
In Anna Maria, Florida, there are numerous family-friendly house rentals available, with around 638 options to choose from. This charming island community offers a variety of properties suitable for families, particularly in neighbourhoods like Holmes Beach and Anna Maria City. Many of these homes feature spacious living areas, fully equipped kitchens for family meals, and outdoor patios great for barbecues and relaxation.

Visitors can enjoy easy access to beautiful beaches, such as the powdery sands of Anna Maria Beach and the tranquil waters of Bean Point. Additionally, families will appreciate amenities like private pools, game rooms, and proximity to local parks with playgrounds. The area is also known for its relaxed atmosphere, bike paths, and nearby dining options, making it an ideal location for a memorable family getaway.
Can I rent a holiday home with a pool or hot tub in Anna Maria?
In Anna Maria, there are many holiday homes available for rent that feature pools and hot tubs, with around 683 options to choose from. This picturesque island destination is known for its stunning beaches and charming coastal atmosphere. Visitors can find properties in various neighbourhoods, including the serene Anna Maria City and the lively Holmes Beach.

Travellers can expect a range of amenities in these rentals, such as private swimming pools, hot tubs, outdoor dining areas, and fully equipped kitchens, superb for enjoying a relaxing holiday. Find your rental in Anna Maria with a pool or a hot tub.
Can I find long-stay holiday rentals in Anna Maria?
A long-stay holiday rental in Anna Maria is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Anna Maria?
In Anna Maria, Florida, there are numerous pet-friendly house rentals available, offering a delightful getaway for both you and your furry companions. Many of these properties are situated within close proximity to the stunning beaches and local parks, providing ample opportunities for walks and outdoor activities with pets. The island's relaxed atmosphere is complemented by charming neighbourhoods, where you can find homes featuring amenities such as spacious backyards, outdoor seating areas, and sometimes even private pools, making them ideal for enjoying the sunny Florida weather.

The area around Bean Point is particularly appealing, known for its picturesque views and tranquil beaches, where pets are welcome. Additionally, the nearby Anna Maria Island Historical Society provides a glimpse into the local culture, and the various parks scattered throughout the island are superb for leisurely strolls with your pets.
Are there any remote work holiday rentals in Anna Maria?
In Anna Maria, Florida, there are a wealth of options for remote work holiday rentals, with around 3,232 available. This charming island destination offers a delightful combination of relaxation and productivity, making it ideal for those looking to balance work with leisure. Many properties are equipped with dedicated office spaces, desks, and comfortable chairs, ensuring a conducive work environment.

Additionally, high-speed internet and free Wi-Fi are commonly included, allowing for seamless connectivity. The amenities often extend beyond just work, with many rentals featuring fully equipped kitchens, spacious living areas, and outdoor patios or balconies where you can unwind after a day's work.

The picturesque beaches and local attractions, such as the Anna Maria Island Historical Museum and the scenic views from the Anna Maria City Pier, provide ample opportunities for relaxation and exploration during your downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Anna Maria holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Anna Maria with parking available—perfect for families or travellers 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 rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy home-cooked dining. Onsite parking is a convenient feature for those travelling by car. Many rentals also boast decks or patios, great for relaxing outdoors and soaking up the sun. Coffee and tea makers are commonly found in these properties, ensuring that guests can enjoy a warm beverage at their leisure. Additionally, the proximity to the beach is a significant draw, with many rentals located just a short walk away from the sandy shores, making it easy to enjoy the coastal lifestyle.
When is the best time to visit Anna Maria for a holiday rental?
The peak travel season for a holiday rental in Anna Maria stretches from May to July, with June being the most popular month for visitors. During this vibrant period, the island buzzes with activity, offering plenty of opportunities for beachgoers and families to enjoy the sun, sand, and surf. The warm temperatures, typically ranging from 24 to 32 degrees Celsius, create the superb environment for outdoor activities, such as kayaking, paddleboarding, and exploring the picturesque beaches.

While the summer months are bustling with tourists, those looking for a more tranquil experience might consider visiting in November. This time of year offers a peaceful retreat, with pleasant weather and fewer crowds, allowing you to fully appreciate the beauty of Anna Maria's natural surroundings at a more relaxed pace.

Whether you're drawn to the lively summer atmosphere filled with outdoor concerts and beach activities, or the serene charm of the off-peak season, Anna Maria has something special for every type of traveller.
How early should I book a Anna Maria holiday rental?
Book your Anna Maria holiday 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 holiday 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, Florida, visitors can enjoy a variety of attractions that showcase the area's natural beauty and laid-back charm. The pristine beaches along the Gulf of Mexico, such as Bean Point and Manatee Beach, are superb for sunbathing, swimming, and water sports. The Anna Maria Island Historical Museum offers insights into the island's rich history and culture, providing a quaint local experience.

For those who appreciate nature, the Anna Maria Island Nature Preserve features scenic trails and wildlife viewing opportunities, making it an excellent spot for birdwatching and exploring the coastal ecosystem. The charming Pine Avenue is lined with local shops, cafes, and restaurants where visitors can savour fresh seafood and enjoy a relaxing meal with a view.

Additionally, outdoor enthusiasts can take advantage of the numerous kayaking and paddleboarding opportunities available in the surrounding waters, allowing for an immersive experience in the area's beautiful marine environment.
Can I change or cancel my Anna Maria home rental booking on Vrbo?
To find Anna Maria holiday 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 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 travellers 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 cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Anna Maria holiday 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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