Anna Maria holiday lettings

We found 4,620 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts - Anna Maria

Showing deals for:17 Oct - 24 Oct

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.

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

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.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Anna Maria?
Houses are the most popular kind of holiday rental in Anna Maria, according to our data. Even if you have a different idea about what you'd like, Vrbo has properties in many shapes and sizes. Filter our options to find your perfect Anna Maria pad.
How much does it cost to rent a holiday rental in Anna Maria?
The average price for a holiday rental in Anna Maria is based on a number of factors, such as length of stay, property type and season. Whether you're dreaming about a villa with space for extended family or an apartment for just you and the kids, just enter your dates of travel to view stays with great value.
How much does it cost to rent a beach house in Anna Maria?
The average price for a holiday rental by the beach in Anna Maria depends on when you're going and the type and size of property you're looking for. Find prices easily and quickly on Vrbo by entering your travel dates. Then use the handy filter tool to pick the number of bedrooms and amenities that you prefer, such as air conditioning, a pool and WiFi.
Are there pet-friendly holiday rentals in Anna Maria?
Yes. You can choose from 729 holiday rentals that allow pets in Anna Maria. Several of our pet-friendly holiday rentals come with a garden for your fur child to play around in, special dog beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect digs on Vrbo.
Can I rent a house with a pool in Anna Maria?
Pack your swimsuit and pool noodle, because there are 607 houses with a private pool in Anna Maria. Base yourself at one of these sought-after holiday rentals and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Anna Maria?
The most popular rental amenities people are searching for in Anna Maria include a fireplace, a beach view and an ocean view. Whether you're taking a trip with your besties, family or even pets, Vrbo holiday properties come with the best amenities for fun and relaxation with your loved ones.
Are there large group holiday rentals in Anna Maria?
With 73 properties that can host 10 or more people in Anna Maria, there's no need to limit the invite list. From fun family get-togethers to special events like birthday and Christmas parties, Vrbo will help you find a large group rental to suit the occasion.
Are there holiday rentals in Anna Maria that welcome kids?
Bring the whole group together for fun-filled adventures in Anna Maria at one of our 729 family-friendly holiday rentals. Many of these stays offer conveniences that are great for getaways with the little ones, including dining rooms, bunk beds and entertainment areas. Just check the "Properties good for families" filter box and book your favourite.
What are the top attractions for families in Anna Maria?
There are plenty of awesome things to see and do with the family in Anna Maria, including:

  • Coquina Beach
  • Anna Maria Beach
  • Bradenton Beach

Are there one-bedroom holiday rentals in Anna Maria?
Yes, you can take your pick from 41 one-bedroom rentals in Anna Maria. Whether you want a cosy cottage or a cabin, Vrbo's one-bedroom properties are just right if you don't require huge amounts of space. One of the best parts about having your own place? You'll never need to share your getaway with strangers.
Can I find two-bedroom holiday rentals in Anna Maria?
Anna Maria has 159 two-bedroom properties that you can choose from. Enjoy a holiday home with all the comfort and privacy you want at a price that's hard to resist on Vrbo.
Are there holiday rentals with WiFi in Anna Maria?
Pick from 191 holiday rentals with WiFi in Anna Maria. If you'd like to disconnect from the world during your break, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Anna Maria?
Choose from 723 holiday rentals with air conditioning in Anna Maria offering that cooling breeze and extra comfort level. Simply enter your preferred travel dates and then make use of our filter tool to help you locate properties with air conditioning.
How old do you have to be to rent a holiday rental in Anna Maria?
The minimum required age is typically 16, 18 or 21. It can differ from property to property on Vrbo, so look at the rules of your preferred Anna Maria holiday home before booking your trip.
How long can I rent a holiday rental in Anna Maria for?
It's down to the Anna Maria property. To browse available options offering extended stays, just enter your travel dates and number of people into Vrbo's search page. You can enjoy having the property to yourself, along with the comforts of home like a fully-equipped kitchen, air conditioning and a backyard where the little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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