Cheap Anna Maria Island Vacation Packages

You’re on the hunt for a steal of a deal on your Anna Maria Island vacation package. You’ve got your list of things you want, and you’re checking it twice: a ballin’ (on a budget) Anna Maria Island hotel, a champagne poppin’ flight (for a knock-off beer price), and maybe even a super-nice car rental (for a borrowed bike fee).

Think it’s all just a dream? Not when you book your Anna Maria Island vacation deal with Hotwire.

Are you for real with these vacation package deals

Daydreaming is even better when wildly good deals become your reality. Scoring hotel and flight deals to Anna Maria Island for a price that works with your budget is realer than real when you book your package with Hotwire. Ready to get all of your wildest dreams fulfilled (for way less than you expected)? Don’t sleep on these Hotwire deals.

Frequently Asked Questions About Vacation Packages

How much is a vacation to Anna Maria Island?

When you want to book the very best Anna Maria Island getaway, but you aren’t looking to empty your bank account on planning your trip, cheap vacation packages are the way to go. You can jump into an incredible vacay to Anna Maria Island for as low as $408 and keep your cash for the necessities—like the dreamiest fun times in town.

When is the best time to book a vacation package to Anna Maria Island?

Looking to save some extra cash on your Anna Maria Island vacation? Try going on your getaway in , which is the off-season, and avoid the most popular time to vacation in the month of . Want to get away now-ish and still save? Book a last-minute vacation package with a Hot Rate hotel deal. You could save up to 60% off on your hotel versus booking a listed rate two weeks earlier.

How to get the best vacation package deals to Anna Maria Island?

If scoring the very best deal on your Anna Maria Island vacation is at the top of your to-do list, book your package with Hotwire and prepare to get way more bang for your buck.

What is the cheapest day to book a vacation package?

Reserving a Anna Maria Island vacation package on a Tuesday is the cheapest day to book, or you can save more any day on Hotwire, with packages as low as $408.

Can I vacation in Anna Maria Island right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Anna Maria Island right now?” When it’s time to book your vacation package, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

What does Hotwire Anna Maria Island travel package include?

When you book a package deal on Hotwire, you can expect a Anna Maria Island vacation package with airfare and hotel. Want a rental car too? No biggie‚ you can add it to your package. Everything you need for an amazing trip? Check.

Anna Maria Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Thunderbird Beach Resort

Save 100% on your flight

per person

Jul 3 - Jul 6

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

Stay at this 3-star beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the bar in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby. Discover genuine guest reviews for Thunderbird Beach Resort along with the latest prices and availability – book now.

The Avalon Club

Save 100% on your flight

per person

Jun 20 - Jun 25

Roundtrip non-stop flight included

Hartford (BDL) to Tampa (TPA)

Stay at this 4-star beach aparthotel in Clearwater Beach. Enjoy a beach locale, WiFi, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby. Discover genuine guest reviews for The Avalon Club along with the latest prices and availability – book now.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

per person

Jun 20 - Jun 25

Roundtrip non-stop flight included

Hartford (BDL) to Tampa (TPA)

Stay at this 3-star beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and room service. Our guests praise the pool and the bar in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby. Discover genuine guest reviews for Plaza Beach Hotel Beachfront Resort along with the latest prices and availability – book now.

Hyatt Regency Clearwater Beach Resort & Spa

Save 100% on your flight

per person

Jul 4 - Jul 11

Roundtrip non-stop flight included

Hartford (BDL) to Tampa (TPA)

Stay at this 4-star beach resort in Clearwater Beach. Enjoy free WiFi, 2 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Beach Walk and Pier 60 Park are located nearby. Discover genuine guest reviews for Hyatt Regency Clearwater Beach Resort & Spa along with the latest prices and availability – book now.

Bayview Plaza Waterfront Resort

Save 100% on your flight

per person

Jun 24 - Jun 27

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

Stay at this 3-star family-friendly hotel in St. Pete Beach. Enjoy free WiFi, a marina, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby. Discover genuine guest reviews for Bayview Plaza Waterfront Resort, in Belle Vista neighborhood, along with the latest prices and availability – book now.

TradeWinds Island Grand

Save 100% on your flight

per person

Jun 20 - Jun 25

Roundtrip non-stop flight included

Hartford (BDL) to Tampa (TPA)

Stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Tropicana Field are located nearby. Discover genuine guest reviews for TradeWinds Island Grand along with the latest prices and availability – book now.

RumFish Beach Resort by TradeWinds

Save 100% on your flight

per person

Jun 20 - Jun 25

Roundtrip non-stop flight included

Hartford (BDL) to Tampa (TPA)

Stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Tropicana Field are located nearby. Discover genuine guest reviews for RumFish Beach Resort by TradeWinds along with the latest prices and availability – book now.

Bellwether Beach Resort

Save 100% on your flight

per person

Jul 3 - Jul 6

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

Stay at this beach hotel in St. Pete Beach. Enjoy 3 restaurants, a private beach, and breakfast. Our guests praise the bar and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Tropicana Field are located nearby. Discover genuine guest reviews for Bellwether Beach Resort along with the latest prices and availability – book now.