Anna Maria Vacations from ￥67,739

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The Latest Anna Maria Vacation Packages

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was ￥83,016, price is now ￥67,739 per person
￥67,739
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
9.6/10 Exceptional! (1,206 reviews)
It was new and updated! I loved my stay there!

Reviewed on Jul 10, 2026

CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was ￥125,072, price is now ￥86,348 per person
￥86,348
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
No reviews
We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!

Reviewed on Jul 8, 2026

The Marker

The Marker

2 out of 5
Price was ￥131,370, price is now ￥99,209 per person
￥99,209
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
6/10 (3 reviews)

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was ￥119,571, price is now ￥90,567 per person
￥90,567
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
9.4/10 Exceptional! (3,447 reviews)
Everything was great. Beach was beautiful and just steps away from the beach. The water for the outdoor pool could have been colder. It was warm but service around the pool was great. Definitely would go back

Reviewed on Jul 11, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was ￥129,000, price is now ￥98,936 per person
￥98,936
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
9.4/10 Exceptional! (564 reviews)
The property was not what I was expecting. It was breathtaking. Stellar views of the water. The balcony was huge and my entire party was able to sit out and have morning coffee/tea. Our family will be back for future visits.

Reviewed on Jul 10, 2026

Find the Best Anna Maria Vacation Packages

Anna Maria Beach Vacation

The smell of fresh sea air and beautiful coastal views are just the start of things you can look forward to on your Anna Maria vacation. If you want to save on your trip to Anna Maria, here's a tip — book one of our Anna Maria vacation deals. Lock in one near Palmetto Avenue Beach, only 0.97 kilometers from the center of town and a must-do while here. Alternatively, pick a package that puts you close to Bay Boulevard Beach, another stunning coastline. Either way, you'll be left with extra money in your budget to have fun with.

Anna Maria Hotel Deals

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Anna Maria FL
10/10 Exceptional! (199 reviews)
"The way the property is presented on-line you believe is a shared unit and it includes access to the pool and wash and dyer. You do not have access to the pool. It also miss leads you about parking and does not tell you that you must walk down a narrow path, that your suitcase will not easily fit ..."

Reviewed on Jun 22, 2026

Get rates
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
JUNE, JULY SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

JUNE, JULY SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

Anna Maria FL
The price is ￥76,644 per night from Jul 13 to Jul 14
￥76,644
￥159,411 total
Jul 13 - Jul 14
includes taxes & fees
9.6/10 Exceptional! (203 reviews)
"Great location walking distance to AMI pier. Excellent restaurants and ice cream shop also within walking distance. Home was clean and excellent for large families. Generous on site parking.Private beach right behind the house. Host was very friendly and helpful."

Reviewed on Jun 22, 2026

JUNE, JULY SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
Sun and Seader North |Charming Cottage | Steps from the Beach in Anna Maria | 2 bedrooms | 1 king bed + 2 twin beds |

Sun and Seader North |Charming Cottage | Steps from the Beach in Anna Maria | 2 bedrooms | 1 king bed + 2 twin beds |

Anna Maria FL
9.2/10 Wonderful! (33 reviews)
"Loved this sweet l little cottage. Perfect for our l purposes. Had to use outlet behind mattress for my CPAP, but it was fine! The twin beds were suoer comfy!! We are 66, so the master want them enough, but I'm sure fine for most!! Had a little living room with tv, clean kitchen with all sorts of ..."

Reviewed on May 20, 2026

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Sun and Seader North |Charming Cottage | Steps from the Beach in Anna Maria | 2 bedrooms | 1 king bed + 2 twin beds |
See all 1,000 properties in Anna Maria
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Anna Maria attractions

A sandy beach with seagulls and a clear blue sky.

Bean Point Beach

10.0/10 (1 review)
Nothing says vacation like spending a lazy day at Bean Point Beach, a popular beach in Anna Maria. Take in the museums and sunsets in the area.
See properties

What to do in Anna Maria

Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

￥17,717
per adult
100% of travellers recommend
Anna Maria Island & Bradenton Beach Parasailing Tour
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

￥8,940
per adult
100% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
Anna Maria Island - Clear Kayak LED Night Glass Bottom Tour

Anna Maria Island - Clear Kayak LED Night Glass Bottom Tour

￥10,565
per adult
96% of travellers recommend
Anna Maria Island - Clear Kayak LED Night Glass Bottom Tour
See all activities in Anna Maria

Frequently asked questions

How much does an Anna Maria vacation package cost?
Offering excellent value package deals from ￥67,739 on Expedia, you'll be surprised at how little a vacation to Anna Maria costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Anna Maria?
January, September and October are great times to search for cheap Anna Maria vacation packages. Choosing to travel in less busy periods means you'll typically find reduced prices on hotels and flights.
How many days is enough for Anna Maria?
With about 5 days, you'll have enough time to visit popular neighborhoods like Ilexhurst and Sunny Shores during your Anna Maria vacation. Be sure to also add Island Players and Bayfront Park to your must-see list. In the mood for more adventures? Consider venturing outside of Anna Maria on tours and day trips.
Is it worth booking a vacation package to Anna Maria?
Anna Maria has all the ingredients you need for a fantastic trip — nature, bars and pubs and coastal beaches are just the start. Whether you want to check out attractions such as Bean Point Beach and Palmetto Avenue Beach, or take the path less traveled, you'll find plenty to see and do on your Anna Maria vacation.
How to find the best Anna Maria package deals?
Use Expedia's handy filters to help you find some tempting Anna Maria package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Anna Maria package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book an Anna Maria vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Anna Maria vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Anna Maria?
Enjoy amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Anna Maria getaway.
How to plan a trip to Anna Maria?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to go to Anna Maria.
  2. Plan your budget wisely: As well as the price of your accommodations, you'll need to consider other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Anna Maria.
  3. Decide how long to go away for: Now that you know more about Anna Maria, you can work out the ideal length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the right Anna Maria vacation package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.