Anna Maria Island Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Anna Maria Island

Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
6306 Gulf Dr, Holmes Beach, FL
9.2/10 Wonderful! (220 reviews)
"Beautiful relaxing resort! Staff very friendly and helpful."

Reviewed on 9 Jul, 2025

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Anna Maria Beach Resort
Silver Surf Gulf Beach Resort

Silver Surf Gulf Beach Resort

3 out of 5
1301 Gulf Dr N, Bradenton Beach, FL
The price is S$321 per night from 29 Jul to 30 Jul
S$321
29 Jul - 30 Jul
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"2nd year we have stayed here and we love it! Perfect location! Walking distance to beach, restaurants, bars, and shops! Always clean, spacious, and well taken care of. Our favorite part about staying here is the beach access with chairs and umbrellas provided by the hotel. Definitely recommend."

Reviewed on 2 Jul, 2025

Silver Surf Gulf Beach Resort
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
6900 Gulf Dr, Holmes Beach, FL
8.4/10 Very Good! (564 reviews)
"Staff members were very efficient and helpful.The pool and beach were very nice. The suite on the pool side was comfortly furnished. For a resort , the entrance lobby coul be upgraded."

Reviewed on 1 Jul, 2025

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Bali Hai Beachfront Resort and Spa
See all 3,583 properties in Anna Maria Island
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 Island

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
Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour

Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour

S$77
per adult
100% of travellers recommend
Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

S$127
per adult
Anna Maria Island & Bradenton Beach Parasailing Tour
See all activities in Anna Maria Island

Frequently asked questions

How much does an Anna Maria Island holiday package cost?
Get ready to book, because a trip to Anna Maria Island starts from just . When you combine your hotels, flights and car rentals into a travel package, you'll score the best prices.
How do I get a cheap travel package to Anna Maria Island?
It's easy. Just bundle everything together. Flights, hotels and rental cars --- combine whatever you need into an Anna Maria Island holiday package to save loads of cash. Score even more bargains when you add extras such as experiences or tours to your booking. But that's not the only impressive part. You have the flexibility to customize your trip your own way. We offer more than 550 airlines and 1,000,000 hotel options globally, so that everyone has a chance to travel and live out those holiday dreams.
How far in advance should I book my Anna Maria Island holiday?
It's always wise to book early. Air carriers usually release flight tickets up to 12 months prior to departure, and this is an excellent opportunity to pick up some of the cheapest prices. Just been told you need to take your holiday time in a few weeks? That's fine too --- Expedia are never short on fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Anna Maria Island travel package include?
From flights and hotels to rental cars, Expedia can help you craft an Anna Maria Island package that suits you. Holidaying for a few weeks? Check out a rental car, hotel and flight bundle. If you're taking a short break, an airfare and hotel deal could suit you better. Experiences can also be added once you've made your booking. Our packages make it a cinch to plan and save.
What should I know before booking an Anna Maria Island travel package?
Whether it's adventure or relaxation you're chasing, an Anna Maria Island holiday package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with an Anna Maria Island Expedia holiday package?
Yes, and with more than 550 airlines to select from globally, you're not short on choice. Have a look through the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Anna Maria Island holiday package?
We totally get it --- life sometimes gets in the way of your plans. If you've locked in an Anna Maria Island holiday package and need to cancel or amend it, we're here to help. It's always worth visiting our Customer Service Portal first for information. But generally speaking, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

* 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.