Anna Maria Holidays

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Anna Maria Beach Holiday

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 holiday. If you want to save on your trip to Anna Maria, here's a tip — book one of our Anna Maria holiday deals. Lock in one near Palmetto Avenue Beach, only 0.97 kilometres from the centre 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.

Top hotels in Anna Maria

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is S$257 per night from 22 Jul to 23 Jul
S$257
22 Jul - 23 Jul
includes taxes & fees
9.4/10 Exceptional! (3,392 reviews)
"Great place to stay if flying out early in the morning. Everyone was nice and hotel had a great pool deck area to watch the planes land and take off."

Reviewed on 20 Jul, 2025

Hyatt Regency Orlando International Airport
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
4441 Collins Avenue, Miami Beach, FL
8/10 Very Good! (6,582 reviews)
"That property was great I do not have any issues with the property. It was clean the pools are nice, and the hotel itself is very nice."

Reviewed on 19 Jul, 2025

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Fontainebleau Miami Beach
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is S$122 per night from 10 Aug to 11 Aug
S$122
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (6,421 reviews)
"H"

Reviewed on 18 Jul, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
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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.

What to do in Anna Maria

Our Cruise gives you the best seat there is to the Skyway Bridge Light Show! Different display every night of the week!

Island Sunset and Skyway Light Show - 3hr Boat Cruise in St. Pete

S$108
per adult
88% of travellers recommend
Island Sunset and Skyway Light Show - 3hr Boat Cruise in St. Pete
Clear Kayak LED Night Glass Bottom Tour - Anna Maria Island

Anna Maria Island - Clear Kayak LED Night Glass Bottom Tour

S$83
per adult
90% of travellers recommend
Anna Maria Island - Clear Kayak LED Night Glass Bottom Tour
Shared 2 Hours Dolphin Watch Cruise with Snorkeling to Shell Key

Small Group 2 Hour Dolphin Cruise with Snorkeling to Shell Key

S$96
per adult
88% of travellers recommend
Small Group 2 Hour Dolphin Cruise with Snorkeling to Shell Key
See all activities in Anna Maria

Frequently asked questions

How much does an Anna Maria holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday 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 holiday 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 neighbourhoods like Ilexhurst and Sunny Shores during your Anna Maria holiday. 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 holiday 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 holiday.
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 holiday package well in advance.
Is it cheaper to book an Anna Maria holiday as a package?
Expedia holiday 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 holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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, favourite 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 accommodation, 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 accommodation: Once you've nailed down your trip dates and duration, lock in the right Anna Maria holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.