Anna Maria vacation rentals

We found 4,928 vacation rentals — enter your dates for availability

Welcome to the enchanting Anna Maria Island, where soft sands meet crystal-clear waters, inviting you to unwind in a tropical paradise. This idyllic destination boasts a perfect blend of outdoor adventures, such as kayaking and fishing, alongside charming local culture and family-friendly excursions. With a variety of cozy vacation rentals, from comfy condos to spacious private homes, you can enjoy the comfort and convenience of a home-like experience while creating unforgettable memories with loved ones.

Holiday rentals with weekly discounts - Anna Maria

Showing deals for:Dec 11 - Dec 18

Interior
Four barstools and large area for eating
dining room with seating for 8
Interior
Exceptional
(87 reviews)

Large pool/spa home minutes from beach with arcade games and canal for fishing.

Bradenton

8% off
$366
$2,561 for 7 nights
All fees included
Large pool/spa home minutes from beach with arcade games and canal for fishing.
Rainbow at The Cut House
Kitchen
Landscaping behind the Cut House
Manatee River with 120 ft dock
Exceptional
(64 reviews)

Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly

Palmetto

8% off
$350
$2,449 for 7 nights
All fees included
Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly
Pool
Anna Maria, Florida's ocean is your ultimate fun zone!
Shopping on Anna Maria Island is like discovering hidden gems!
Living, lounging, cooking—our space does it all.
Exceptional
(56 reviews)

Luxury 4BR, Private Screened Pool, Near AMI

Bradenton

8% off
$442
$3,091 for 7 nights
All fees included
Luxury 4BR, Private Screened Pool, Near AMI
Exterior
Private kitchen
Pool
Interior
Excellent
(18 reviews)

Pool | Hot Tub | Waterfront Views | Sunsets

Bradenton

11% off
$529
$3,705 for 7 nights
All fees included
Pool | Hot Tub | Waterfront Views | Sunsets
Beachfront Local Restaurant. Perfect For Sunset on The Beach.
Longboat Pass
Front Wrought Iron Private Gates Entering- “Sea La Vie” Pond, Meditation Garden.
Private Swimming Pool & Relaxing Area.
Exceptional
(83 reviews)

Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches

Bradenton

8% off
$637
$4,458 for 7 nights
All fees included
Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches
Terrace/patio
Sport court
Private kitchen
Interior
Exceptional
(45 reviews)

Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches

Bradenton

6% off
$214
$1,500 for 7 nights
All fees included
Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches
Property grounds
Pool
Private kitchen
Dining
Exceptional
(39 reviews)

6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach

Holmes Beach

28% off
$1,025
$7,172 for 7 nights
All fees included
6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach
Dining
Outdoor dining
Pool
Private kitchen
Exceptional
(158 reviews)

OCTOBER, Nov & Dec DISCOUNTS! Cortez Boat Resort/AMIsland White Sand Beaches BOAT DOCK & LAUNCH on site

Cortez

7% off
$353
$2,474 for 7 nights
All fees included
OCTOBER, Nov & Dec DISCOUNTS! Cortez Boat Resort/AMIsland White Sand Beaches BOAT DOCK & LAUNCH on site
Living area
Private kitchen
Terrace/patio
Marina
Exceptional
(111 reviews)

75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated

Anna Maria

8% off
$436
$3,049 for 7 nights
All fees included
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Interior
Private kitchen
Pool
Living area
Exceptional
(61 reviews)

Newly Renovated Family Vacation Rental with Pool & Spa

Bradenton

9% off
$247
$1,730 for 7 nights
All fees included
Newly Renovated Family Vacation Rental with Pool & Spa
Exterior
private rooftop deck
living room
Private dock for residents and guests
Exceptional
(82 reviews)

Anna Maria Sunrise on the Bay, Sunsets on the beach.Luxury 3BR with Rooftop Deck

Bradenton Beach

8% off
$365
$2,557 for 7 nights
All fees included
Anna Maria Sunrise on the Bay, Sunsets on the beach.Luxury 3BR with Rooftop Deck
Private kitchen
Exterior
Beach
65" Smart LED TV with NetFlix included.
Exceptional
(58 reviews)

Happy Turtle A: Cute Beach Cottage, 60 Steps to Sand, Sun Room

Bradenton Beach

8% off
$329
$2,304 for 7 nights
All fees included
Happy Turtle A: Cute Beach Cottage, 60 Steps to Sand, Sun Room
Interior
Interior
Private kitchen
Living area
Exceptional
(44 reviews)

3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!

Holmes Beach

8% off
$193
$1,354 for 7 nights
All fees included
3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!
One of the Living Rooms
Pool
Private kitchen
Dining
Exceptional
(44 reviews)

2 Homes, 1 Private Pool Near IMG & AMI

Bradenton

11% off
$318
$2,228 for 7 nights
All fees included
2 Homes, 1 Private Pool Near IMG & AMI
Private kitchen
Beach
Room
Outdoor dining
Exceptional
(103 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
$458
$3,208 for 7 nights
All fees included
Low Rider - Bottom Unit -
Terrace/patio
Living area
Room
Pool
Exceptional
(13 reviews)

Hometown Paradise- Canalfront home with dock and heated pool

Bradenton

8% off
$412
$2,881 for 7 nights
All fees included
Hometown Paradise- Canalfront home with dock and heated pool
Living area
Bookcases open to let in more sunlight from the bedroom.
A great place to watch beach goers on their way to Bean Point.
Open kitchen with eat-at-island and drop-leaf table for additional dining.
Exceptional
(206 reviews)

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

Anna Maria

8% off
$474
$3,317 for 7 nights
All fees included
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Condo pool with tables and chairs and large shaded seating area!
Living area / king size bed with balcony, overlooking the beach.
spare bedding & pillows for the futon is in the closet.
Dining table looking into kitchenette, fridge, microwave, two burner stove.
Exceptional
(5 reviews)

The Pelican's Perch, a Beachfront studio condo w/ balcony

Bradenton Beach

13% off
$252
$1,767 for 7 nights
All fees included
The Pelican's Perch, a Beachfront studio condo w/ balcony
Interior
Terrace/patio
Dining
Interior
Exceptional
(13 reviews)

Gracie's Cottage 15 min to Beach

Bradenton

9% off
$316
$2,213 for 7 nights
All fees included
Gracie's Cottage 15 min to Beach
Come play golf on several luxurious courses in the Sarasota/Bradenton area.
Watch the sunrise at the Bradenton Beach. Great place for a morning run or walk.
Amped Fitness is within walking distance from the condo.
Inside photo of the Shorewalk clubhouse.
Exceptional
(161 reviews)

Charming 2BR Condo By IMG Academy & Anna Maria Island w/ Heated Pools & Hot Tubs

Bradenton

8% off
$182
$1,272 for 7 nights
All fees included
Charming 2BR Condo By IMG Academy & Anna Maria Island w/ Heated Pools & Hot Tubs
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    Enjoy full kitchens, laundry, pools, yards and more
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    We stand for diversity, inclusion and families everywhere.
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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.

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.

With beaches and fun activities, you’ll love Anna Maria

Visitors to Anna Maria Island always find a fun vacation haven, perfect for kayaking and experiencing island life. Tucked away on Anna Maria’s north end is Bean Point Beach, ideal for those seeking an island paradise with an Old Florida vibe. Anna Maria Bayfront Park offers sweeping views of Tampa Bay, and in addition to its beaches is also home to numerous restaurants. Spend your afternoons with your toes in the sand or shopping till you drop—either way, your Anna Maria vacation rental gives you access to a getaway the whole family will enjoy.

Immerse yourself in the Anna Maria experience

The beaches are just one reason to book an Anna Maria vacation rental. The island boasts museums as well as restaurants serving everything from fresh seafood to specialty cupcakes and donuts. Take a stroll on the pier—or down Pine Avenue with its colorful, eclectic shops. It’s not every day you get to soar hundreds of feet over the ocean, so if you’re feeling brave, try parasailing. If staying in the water is more your speed, check out Bean Point, and keep an eye open for manatees, which are known to mingle with human swimmers.

Pack the sunscreen—there’s lots to do in Anna Maria

Anna Maria vacation rentals are perfect if you love the beach. There are endless entertainment options for those who love the sun, sand, and water. Rent Segways for the family and tour the island in style. Go on a sightseeing dolphin cruise, or have some high-powered fun on a jet ski. Spend hours relaxing on the beach, or keep things active and sign up for a kayak lesson or tour. Paddleboard rentals, boat trips, fishing excursions and more are yours for the taking when you book a vacation rental in Anna Maria.

Expect pleasant weather any time of the year

Anna Maria has sun, sand, beautiful beaches, and exceptional weather. The climate is warm and temperate with plentiful rainfall, and when it does rain, it’s often short-lived before the clear blue skies return. Most of the year sees abundant sunshine, and in the heart of summer, the average high is a pleasant 88 degrees. Winter is mild with an average January low of 52. The best time to book a vacation rental in Anna Maria depends on what you’d like to do, but even winter is typically comfortable enough for outdoor activities.

Exploring the natural features in Anna Maria

Travelers enjoy Anna Maria for its island views, beaches and sunrises. Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Anna Maria is a great spot to appreciate mother nature. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Lido Beach (18.2 mi / 29.3 km)
  • Bean Point Beach (0.6 mi / 1 km)
  • Anna Maria Beach (0.9 mi / 1.4 km)
  • Manatee Public Beach (2.6 mi / 4.2 km)
  • Brandenton Beach (4.2 mi / 6.8 km)
  • Cortez Beach (5.2 mi / 8.4 km)

Transportation to and around Anna Maria

The nearest airport is in Tampa Intl. Airport (TPA), located 33.2 mi (53.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Sarasota-Bradenton Intl. Airport (SRQ), which is 14.8 mi (23.9 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Anna Maria?
Based on our research, condos are the most sought-after vacation property type in Anna Maria. But as you might expect, everyone's idea of an epic stay isn't the same. Vrbo has vacation rentals of all sizes and shapes, and we'll help you to find your ideal fit.
How much does it cost to rent a vacation rental in Anna Maria?
Property type, season and length of stay are some of the conditions that can affect the price of a vacation home. Simply click on your travel dates to find your perfect match. From comfy cottages to expansive luxury villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Anna Maria?
Prices for beach houses in Anna Maria may differ depending on the size and type of the property and when you plan to travel. Just enter your travel dates into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filters to refine your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Anna Maria?
Yes. You'll have a choice of 760 vacation homes that welcome pets in Anna Maria on Vrbo. Our furry friends need a getaway too, so simply use our search function for pet-friendly vacation rentals to book a place where your puppy dog can get in on the fun.
Can I rent a house with a pool in Anna Maria?
Dig out your swimwear and swim ring, because there are 633 houses with a private pool in Anna Maria. Unwind at one of these superb vacation rentals and make every day a pool day. Simply enter your 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 prefer in Anna Maria include a chef, a garden and a sauna. Whether you're on a trip with family, friends or even pets, Vrbo vacation homes include the best amenities for fun and relaxation with the people who matter most.
Are there large group vacation rentals in Anna Maria?
With 82 properties that can sleep 10 or more guests in Anna Maria, there's no need to limit the invite list. From fun family get-togethers to special events like Christmas or New Year's Eve parties, Vrbo will help you find a large group rental that fits the occasion.
Are there vacation rentals in Anna Maria that welcome kids?
Anna Maria has 759 family-friendly vacation rentals to pick from. And securing a stay that welcomes kiddos is a cinch with our "Properties good for families" filter. Besides having the whole place to yourselves, you'll also enjoy access to conveniences and perks like multiple bedrooms, pools and kitchens.
What are the top attractions for families in Anna Maria?
Keep the kids entertained at these top family-friendly attractions in Anna Maria:
  • Anna Maria Island Museum and Historical Park
  • Bean Point Beach
  • Palmetto Avenue Beach
Are there one-bedroom vacation rentals in Anna Maria?
Yes, you'll find 47 one-bedroom properties in Anna Maria to select from. A one-bedroom vacation rental is a great choice if it's just two of you or if you're vacationing solo. Add in more privacy, space and convenience compared to a regular hotel, and you've got the makings of a memorable trip.
Can I find two-bedroom vacation rentals in Anna Maria?
Gather your besties and enjoy peace, privacy and comfort in one of the 157 two-bedroom vacation homes Anna Maria has to offer.
Are there vacation rentals with WiFi in Anna Maria?
Whether you'd like to keep up with the latest headlines, look over emails or surf your social networks, there are 211 vacation homes with WiFi in Anna Maria. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Anna Maria?
Select your dates and then make use of the filters to view vacation rentals with air conditioning in Anna Maria on Vrbo. With 747 air-conditioned properties available, you can enjoy a cool and comfortable break.
How old do you have to be to rent a vacation rental in Anna Maria?
You'll need to check with the Anna Maria vacation rental you're considering on Vrbo as the age limit differs. However, typically it's 16, 18 or 21.
How long can I rent a vacation rental in Anna Maria for?
The amount of time you can stay in an Anna Maria vacation home for is down to each property. Simply tap in your preferred travel dates to view available options offering longer term stays. They come with the things you need to make your extended break more comfortable such as laundries and air conditioning. Some properties might also offer weekly or monthly discounts, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Anna Maria?
On Vrbo, you'll find fabulous discounts and deals for Anna Maria. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're looking for a weekend retreat or an extended stay, Vrbo has a variety of options for every budget and style.

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