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Anna Maria holiday lettings

We found 4,888 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Anna Maria by choosing from 508 houses, 30 flats and other holiday rentals. 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:24 Apr - 1 May

Image gallery for Newly Renovated Beach Retreat

Room
10 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)

Newly Renovated Beach Retreat

Bradenton

7% off
Price is £781
for 7 nights, 1 home
£112 per night
includes taxes & fees
Newly Renovated Beach Retreat

Find spaces that suit your style

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Why visit Anna Maria

  • Beautiful beaches: Enjoy the stunning sands and crystal-clear waters of Anna Maria Island, perfect for sunbathing and relaxation.
  • Outdoor adventures: Engage in various activities such as kayaking, paddleboarding, and fishing in the area's picturesque waters.
  • Rich cultural heritage: Discover local history museums and the vibrant culture of the island, showcasing its unique charm.
  • Family-friendly atmosphere: Experience a welcoming environment ideal for families, with activities for all ages.
  • Diverse accommodation options: Choose from charming condos, spacious villas, and inviting apartments for a comfortable stay.

Popular types of accommodation in Anna Maria

If you're contemplating a stay on Anna Maria Island, look no further for your ideal accommodation. Our selection includes charming condos, spacious houses, and inviting apartments, ensuring you'll find the perfect holiday rental. Whether you’re after holiday lettings or the best villas in the area, we provide a variety of accommodation options to suit your needs and preferences. Enjoy a delightful getaway with transparency and reassurance in every booking.

  • Condos: The top choice for visitors to Anna Maria, offering modern amenities and easy access to the beach.
  • Houses: A fantastic option for families or groups seeking spacious accommodations with a home-like feel.
  • Apartments: A convenient and comfortable choice, ideal for couples or solo travellers wanting to enjoy the local vibe.
  • Cottages: These quaint and charming retreats provide a delightful, cosy atmosphere for a relaxing getaway.
  • Villas: A luxurious option, perfect for those looking for an upscale experience with plenty of space.**

Top attractions in and around Anna Maria

Anna Maria is an idyllic destination for those seeking beach and outdoor experiences, offering stunning scenery and a rich cultural heritage. Visitors can explore beautiful beaches, marinas, and local history museums, making it an ideal spot for both relaxation and adventure. Whether you're interested in sunbathing or immersing yourself in the area's history, Anna Maria has something to cater to every traveller's taste.

  • Anna Maria Beach: This lovely beach, located 435m from Anna Maria, offers a quintessential beach atmosphere with soft sands and gentle waves, perfect for relaxation and sunbathing.
  • Bean Point Beach: Situated within Anna Maria, this scenic cape presents breathtaking views and a tranquil beach vibe, ideal for picturesque strolls and enjoying the sunset.
  • IMG Academy: Located 6.2km from Anna Maria, this renowned academy offers a unique glimpse into sports training and development, attracting aspiring athletes from around the world.

Things to do recommended for couples

Seeking a romantic getaway in Anna Maria? Consider paddleboarding at AMI Paddleboard Adventures for an exhilarating experience, indulge in relaxation at Aluna Wellness Center & Spa, or enjoy a playful round of mini-golf at Fish Hole Adventure Golf. Each offers a unique vibe perfect for couples.

Things to do recommended for families

During your family vacation in Anna Maria, visit LECOM Park for a lively sports experience, enjoy ice skating at Ellenton Ice and Sports Complex, and unwind at Maximo Park, perfect for relaxation amidst nature's beauty.

Things to do recommended for groups

Groups visiting Anna Maria can enjoy a captivating performance at the Island Players theatre, browse surf gear at the West Coast Surf Shop just 1.9km away, and indulge in retail therapy at the Ellenton Premium Outlets, located 8.7km from the island.

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

If you're travelling with a group, family, or pets, or if you're seeking extended stays, be sure to use the appropriate filters to align with your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Anna Maria with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas suitable for group gatherings. Thankfully, you can easily refine your search for all of these options, and many more, on Vrbo.
  • Traveling to Anna Maria with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, as well as seek out suitable amenities, such as a private swimming pool. Additionally, it's wise to think about your closeness to attractions that are suitable for families.
  • Taking your pets with you to Anna Maria: For many families, a holiday wouldn’t feel complete without their furry companions. 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 with 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 accommodations. Don't forget to include amenities 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, a charming city on Florida's picturesque coastline, offers a delightful blend of beautiful beaches and outdoor adventures. Explore the stunning Anna Maria Island, where you can bask in the sun or embark on exciting excursions. With its family-friendly atmosphere and welcoming locals, this beach destination is perfect for those seeking relaxation or a bit of adventure. Don't miss the chance to experience the serene beauty of the barrier islands and the vibrant local culture.

  • Anna Maria Island: Anna Maria Island is a picturesque barrier island renowned for its stunning beaches and relaxed atmosphere. Located a mere 1.2km from the main town of Anna Maria, it offers a delightful escape for families and outdoor enthusiasts. Visitors can indulge in a variety of activities, from sunbathing on powdery white sands to exploring the charming local shops and dining options. Notable attractions include the beautiful family-friendly beaches and nearby recreational areas, making it an ideal destination for those seeking a serene beach experience.
  • St. Pete Beach: Situated approximately 9.3km from Anna Maria, St. Pete Beach is a vibrant city that boasts a lively coastal scene. Known for its expansive sandy shores and family-friendly atmosphere, it’s perfect for a day of beach fun or leisurely strolls along the promenade. The area features an array of resorts and shopping venues, ensuring visitors have ample opportunities for relaxation and entertainment. Highlights include the stunning beach and the welcoming town neighbourhood, making it a fantastic spot for those looking to blend beach time with local culture.
  • Holmes Beach: Just 1.9km from Anna Maria, Holmes Beach is a charming coastal city that offers a perfect blend of beach life and family-oriented activities. Its scenic beaches and outdoor recreational opportunities attract visitors seeking both relaxation and adventure. With a variety of resorts and shopping centres, it caters to all your holiday needs. Attractions like the beautiful beaches and the tranquil cape are just a few of the highlights that make Holmes Beach a must-visit destination for families and outdoor lovers alike.

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

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits 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 Trip Board offers a helpful platform for planning your journeys. You can easily start new trips, continue from where you last stopped, or manage your existing plans all in one place. Your saved or booked properties will be conveniently sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply head over to: 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. Lido Beach and Tampa Bay are just a couple of the must-see attractions in the area. 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:

  • 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)
  • Splash Island Water Park (13.7 mi / 22.1 km)
  • Islandside 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:

  • Lido Beach (18.2 mi / 29.3 km)
  • Tampa Bay (19.8 mi / 31.9 km)
  • Anna Maria Beach (0.7 mi / 1.1 km)
  • Bean Point Beach (0.8 mi / 1.2 km)
  • Bradenton Beach (2 mi / 3.2 km)
  • Holmes Beach Beaches (2.4 mi / 3.8 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 booking a holiday rental in Anna Maria, Florida, one of the best areas to consider is the northern part of the island, particularly around Pine Avenue. This charming neighbourhood boasts a delightful mix of quaint shops, local eateries, and beautiful beaches, making it an ideal spot for visitors. The proximity to Anna Maria Island Historical Society Museum offers a glimpse into the local history, while the stunning beaches, such as Bean Point, provide a great backdrop for relaxation and outdoor activities.

Another wonderful area is the Holmes Beach region, which offers a range of rental properties, from cosy cottages to spacious family homes. This area is known for its friendly atmosphere and easy access to the stunning Gulf of Mexico. The nearby Manatee Public Beach is a popular attraction where visitors can enjoy sunbathing, swimming, and beachside dining. Holmes Beach also features various amenities, including shops and restaurants, ensuring that everything you need is within reach.
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, Florida, the island offers several picturesque areas great for a seaside getaway. The northern part of the island, particularly around Bean Point, is renowned for its idyllic, sandy beaches and serene atmosphere. Here, holiday rentals often come equipped with amenities such as private pools, outdoor grilling areas, and spacious decks for sunbathing, making them ideal for families or groups seeking relaxation by the water.

In the central region, near Pine Avenue, visitors can find charming cottages and bungalows within walking distance to both the beach and local shops, cafes, and restaurants. Many of these properties feature modern kitchens, outdoor seating areas, and some may even provide bicycles for exploring the island. The vibrant community atmosphere allows guests to immerse themselves in local culture while enjoying easy access to the stunning Gulf coastline. 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 rental, with approximately 683 available throughout the area. These houses are typically situated close to the beach and offer a charming, home-like atmosphere. Most properties feature multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or decks, great for enjoying the warm Florida weather after a day at the beach.
Are there any family house rentals in Anna Maria?
In Anna Maria, Florida, there are numerous family-friendly house rentals available—specifically, around 557 options throughout the area. This charming island destination is great for families seeking a fun-filled getaway. Many of these homes boast spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play or enjoy barbecues. Visitors can also expect amenities such as private pools, laundry facilities, and Wi-Fi to ensure a comfortable stay.
Can I rent a holiday home with a pool or hot tub in Anna Maria?
In Anna Maria, there are plenty of holiday homes available for rent that feature pools and hot tubs, with approximately 653 options to choose from. The island is renowned for its beautiful beaches and charming atmosphere, making it an ideal getaway. Many of these properties are located in neighbourhoods close to the shore, such as Anna Maria City and Holmes Beach, offering easy access to the sandy coastline. 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, there are numerous pet-friendly house rentals available, with a count of 254 properties to choose from. This charming island community, known for its stunning beaches and laid-back atmosphere, offers a variety of holiday homes that are welcoming to pets. Many of these rentals feature amenities such as spacious yards, outdoor seating areas, and fully equipped kitchens, making them ideal for families and groups travelling with their furry companions.
Are there any remote work holiday rentals in Anna Maria?
In Anna Maria, Florida, there are numerous remote work-friendly holiday rentals available, with around 775 options to choose from. The island is known for its stunning beaches, charming shops, and a relaxed atmosphere, making it a great backdrop for both work and leisure. Many of these properties come equipped with essential remote work amenities, including high-speed Wi-Fi, dedicated desk spaces, and comfortable chairs. Some even feature additional conveniences such as laptop workspaces and computer monitors, ensuring a productive environment. 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 heated pools, fully equipped kitchens, complimentary Wi-Fi, private pools, and patios for outdoor relaxation. Many of these holiday rentals are situated near the picturesque beaches and charming local shops, providing easy access to the area's natural beauty and vibrant community. The presence of these amenities ensures a comfortable and enjoyable stay for visitors, whether they are looking to unwind by the pool or prepare meals in a convenient kitchen after a day of exploring.
When is the best time to visit Anna Maria for a holiday rental?
The best time to book a holiday rental in Anna Maria is during the peak season from May to July, with June being particularly popular. This is when the warm sunshine and pleasant temperatures, typically in the mid to high 20s Celsius, create an ideal setting for beach lovers and outdoor enthusiasts alike. The inviting Gulf waters beckon visitors for swimming, kayaking, and paddle boarding, while the charming coastal scenery provides a superb backdrop for leisurely strolls along the shore.

As the summer progresses, you'll find plenty of vibrant activities and events, making it a lively period for family holidays and gatherings. The island's friendly atmosphere and beautiful sunsets offer an unforgettable experience for those seeking relaxation or adventure.

For those who prefer a quieter escape, visiting in November can be a wonderful option. Although it's considered low season, the weather remains mild, averaging around 24°C, and the beaches are less crowded, allowing you to soak in the serene beauty of Anna Maria at your own pace. This is a great time for peaceful walks, exploring local shops, and enjoying the natural surroundings without the hustle and bustle of peak summer travel.
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 range of attractions that highlight the area's natural beauty and charm. The picturesque Anna Maria Island is known for its stunning beaches, such as Manatee Beach and Coquina Beach, where holiday rentals are often just a short stroll from the shore. The island's relaxed atmosphere is complemented by the scenic views and opportunities for water sports, including kayaking and paddleboarding.

The Anna Maria City Pier is another must-see, offering a lovely spot for fishing and enjoying sunsets over the Gulf of Mexico. Nearby, the quaint shops and dining options along Pine Avenue provide a delightful experience for those looking to explore local cuisine and unique boutiques.
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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