Cheap flights To Anna Maria Island (PIE) from $73

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Anna Maria Island from $73 One Way, $142 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Aug 26 - Sat, Sep 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$142 Roundtrip, found 23 hours ago
$142
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 12, priced at $142 found 23 hours ago
Wed, Sep 23 - Sat, Oct 3
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$152 Roundtrip, found 16 hours ago
$152
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Wed, Sep 23 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Oct 3, priced at $152 found 16 hours ago
Wed, Aug 26 - Sat, Sep 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$154 Roundtrip, found 23 hours ago
$154
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 12, priced at $154 found 23 hours ago
Wed, Aug 5 - Wed, Aug 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 5 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 12, priced at $162 found 2 days ago
Sat, Aug 29 - Sat, Sep 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$164 Roundtrip, found 17 hours ago
$164
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Sat, Aug 29 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 12, priced at $164 found 17 hours ago
Wed, Aug 5 - Wed, Aug 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$173 Roundtrip, found 5 days ago
$173
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Aug 5 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 12, priced at $173 found 5 days ago
Wed, Sep 16 - Sat, Sep 26
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$174 Roundtrip, found 5 days ago
$174
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Sep 16 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 26, priced at $174 found 5 days ago
Sat, Aug 29 - Sat, Sep 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$174 Roundtrip, found 7 hours ago
$174
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sat, Aug 29 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 12, priced at $174 found 7 hours ago
Wed, Aug 5 - Wed, Aug 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$178 Roundtrip, found 5 days ago
$178
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Aug 5 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 12, priced at $178 found 5 days ago
Wed, Sep 23 - Sat, Sep 26
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Sep 23 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 26, priced at $178 found 2 days ago

Anna Maria Island Flight Information

Traveling To
Anna Maria Island
Destination Airport IATA Code
PIE
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$142
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Anna Maria Island economy flight packages

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

ChartHouse Clearwater Beach Marina Hotel

Jul 19 - Jul 23

4 night stay

Boston (BOS) to Tampa (TPA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $850, price is now $582 per person
$582
per person
found 1 day ago
The Avalon Club
4.0-star property

The Avalon Club

Jul 19 - Jul 23

4 night stay

Boston (BOS) to Tampa (TPA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,906, price is now $1,299 per person
$1,299
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Boston to Anna Maria Island
View all trips

Anna Maria Island premium economy flight packages

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

ChartHouse Clearwater Beach Marina Hotel

9.6/10 Exceptional! (1,034 reviews)

Jul 13 - Jul 18

5 night stay

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,237, price is now $886 per person
$886
per person
found 23 hours ago
Clean , nice location near beach

Reviewed on May 14, 2026

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (543 reviews)

Jul 13 - Jul 18

5 night stay

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,667, price is now $1,890 per person
$1,890
per person
found 23 hours ago
A lot of attention to detail, high quality space with quality things like bedsheets, mattress and pillows. Above all.. incredible staff! Very friendly and thoughtful.

Reviewed on Mar 28, 2026

Wyndham Grand Clearwater Beach
4.0-star property

Wyndham Grand Clearwater Beach

9.4/10 Exceptional! (3,252 reviews)

Jul 13 - Jul 18

5 night stay

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,719, price is now $1,231 per person
$1,231
per person
found 23 hours ago
Could not be happier. Staff were attentive, welcoming and super knowledgeable. Property was pristine, amazing amazing location and tons of onsite activities and luxuries. If we could have given ten stars we would have.

Reviewed on Apr 10, 2026

Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Anna Maria Island
View all trips

Anna Maria Island

Are you in the mood for a cruise? Shop Orbitz today for cheap cruises and flights to Anna Maria Island. Our award-winning cruise site features exclusive offers, information for first-timers and top destinations and activities. Make discount domestic and international travel plans in an instant with cutting-edge mobile tools from Orbitz.

Top Pick

Orbitz holds a “Best of the Web” Cruise Site Award from Forbes Magazine. You won’t find better deals anywhere on low cost cruises and low fare Anna Maria Island flights. Our Customer Care and guaranteed low prices make Orbitz the team to beat in budget cruises and air ticket sales.

Exclusive Offers

Register for Orbitz email updates and our cruise experts will notify you of bargain tickets on cruises as they’re posted. Install our free mobile apps on your iPad, iPhone or Android for easy booking and mobile-only savings on flights to Anna Maria Island. Visit www.Orbitz.com to learn more about these amazing benefits and our 110% Best Price Guarantee.

First-Timers

Are you and your family cruise newbies? Orbitz offers Cruising 101 and Cruise FAQ to answer any questions you may have. Book your cruise and air travel with Orbitz On the Go for greater savings on Anna Maria Island flights.

Ports and Play

Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Anna Maria Island and Anna Maria Island flights. Get more bang for your travel buck at Orbitz.

Frequently asked questions

How much is a flight to Anna Maria Island?
This week, prices fluctuated between $142 and $178 for a return flight to Anna Maria Island. One-way tickets originating from Hartford (BDL) dropped down to $73 during the same period.
How to book the cheapest flight to Anna Maria Island?
With some of the most competitive flight deals around, you're guaranteed value for money with Orbitz. The following suggestions will help you land cheap flights to Anna Maria Island — and leave you with more cash to splash:

  • Depending on your place of departure, choose the 'Nearby airports' function (located under the departure and arrival form fields). At times, alternative departure points offer better priced fares.
  • If you're flexible with your travel itinerary, click on the 'Show flexible dates' option. You'll see the flight deals for the days around your chosen departure. Ticket prices often vary depending on what day it is.
  • To refine your results, hit 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • Once you've sorted out your travel dates, don't delay booking. Prices generally get more expensive as the departure date nears.
  • Consider bundling your hotels, flights and car rentals into a package with Orbitz to get more for your money.
  • Don't fly during the busy season if you can. By steering clear of summer, school vacations and other popular dates, you can save plenty on your airfare.

What is the best time to book a flight to Anna Maria Island?
Catch a bargain and secure your seats to Anna Maria Island in January. If you've missed this month, fear not. February and August often have affordable airfares as well. Just be careful you don't snooze on a sale — cheap flights appear and vanish in an instant!
What day of the week is the cheapest to book a flight to Anna Maria Island?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days to book flights to Anna Maria Island. If you're looking for the most competitive airfares, search across those days and you're likely to pick up a fantastic flight deal.
What is the cheapest day of the week to fly to Anna Maria Island?
Everybody enjoys saving money, so we recommend flying out early in the week for cheap flights to Anna Maria Island. Orbitz data from 2020 shows you can pick up the best prices on flights taking off on Mondays. Tuesdays are the next most affordable day, while Saturdays are likely to cost an arm and a leg. Many passengers like to start their vacation when the working week is over, so leave those Saturdays for catching up with friends.
What is the cheapest month to fly to Anna Maria Island?
You can jet for less in August. This is generally an excellent month to get on a plane if you're looking for cheap flights to Anna Maria Island, according to Orbitz data. The most expensive time to fly is June, so avoid this month if you're watching your pennies.
Which airlines allow free cancellation?
Flexibility is more important than ever, that's why Orbitz lets you search for carriers that won't slap you with a fee for any amendments. Add your departure and arrival destinations, then choose "Filter by flexible change policies." We'll show you options that include free cancellation within 24 hours of booking and no change fees.
What do I need for the flight to Anna Maria Island?
From onboard entertainment to travel necessities like noise-canceling headphones, there are a number of things a frequent flyer won't leave home without. To make sure you're organized for your flight, have a look at this helpful list:

  • Make sure you've packed your travel documents and some identification. For international journeys, you'll need your passport. When reserving your seats, always use the exact details written on your current ID.
  • A well-stocked carry-on bag is important for any medium-haul journey. With a few hours or more to kill, you'll need something to keep you busy on your trip. We suggest a good book (or trashy magazine), and something to nibble on.
  • Together, air conditioning and high altitudes make for a chilly environment. No matter what the season is in Anna Maria Island, carry an extra layer with you to keep nice and warm during the journey.

How many direct flights are there to Anna Maria Island?
Every month, there are 80 direct flights to Anna Maria Island. Take your pick of an impressive range of airline companies, including Southwest Airlines, Delta Air Lines and American Airlines. Other carriers that fly nonstop are Allegiant Air, United Airlines and JetBlue Airways.
How do I get cheap first-class/business deals to Anna Maria Island?
If you think a business or first-class ticket is beyond your reach, you may want to think again. Here are some top tips to help you pick up a premium flight to Anna Maria Island for a whole lot less:

  • Flexibility is key. By being open to a range of travel dates, you'll have a better chance of picking up a deal on business or first-class airfares.
  • Plenty of budget airlines nowadays have outstanding business-class seating that doesn't cost a bundle.
  • Make a bid for an upgrade. Some carriers hold online auctions that let you offer a price for a seat at the front of the plane. You can also try upgrading with points earned through a loyalty scheme.

What is the best time to go to Anna Maria Island?
There's loads of fun to be had no matter what time of year you visit Anna Maria Island, but January, February and March are the busiest months. Like to fill your itinerary with plenty of warm-weather experiences? Plan your getaway around June 20. This is when summer starts in the Northern Hemisphere. Expect the mercury to span between 80 ºF and 90 ºF at this time of year.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.