Cheap flights To Anna Maria Island (PIE) from $71

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Cheap Flights to Anna Maria Island from $71 One Way, $137 Round Trip

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

Tue, Mar 3 - Thu, Mar 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Mar 3 from Logan Intl. to Sarasota-Bradenton Intl., returning Thu, Mar 5, priced at $137 found 3 days ago
Mon, Mar 9 - Wed, Mar 11
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$140 Roundtrip, found 3 days ago
$140
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Mar 9 from Logan Intl. to Sarasota-Bradenton Intl., returning Wed, Mar 11, priced at $140 found 3 days ago
Wed, May 13 - Wed, May 20
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$142 Roundtrip, found 7 hours ago
$142
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Wed, May 13 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, May 20, priced at $142 found 7 hours ago
Sat, May 2 - Wed, May 13
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, May 2 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, May 13, priced at $142 found 2 days ago
Wed, Jun 10 - Sat, Jun 13
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$147 Roundtrip, found 2 hours ago
$147
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Jun 10 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Jun 13, priced at $147 found 2 hours ago
Sat, Feb 28 - Wed, Mar 4
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Feb 28 from Logan Intl. to Sarasota-Bradenton Intl., returning Wed, Mar 4, priced at $147 found 4 days ago
Sat, Feb 7 - Sun, Feb 15
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Feb 7 from Logan Intl. to Sarasota-Bradenton Intl., returning Sun, Feb 15, priced at $147 found 4 days ago
Fri, Feb 20 - Thu, Feb 26
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Feb 20 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Thu, Feb 26, priced at $147 found 4 days ago
Sat, Feb 28 - Wed, Mar 4
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$148 Roundtrip, found 4 days ago
$148
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Feb 28 from Logan Intl. to Sarasota-Bradenton Intl., returning Wed, Mar 4, priced at $148 found 4 days ago
Tue, Feb 10 - Fri, Feb 13
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$150 Roundtrip, found 3 days ago
$150
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Feb 10 from Logan Intl. to Sarasota-Bradenton Intl., returning Fri, Feb 13, priced at $150 found 3 days ago

Anna Maria Island Flight Information

Traveling To
Anna Maria Island
Destination Airport IATA Code
PIE
Number of Airlines Serving
Airlines
Breeze Airways, Delta, JetBlue Airways, American Airlines
Flight Price
$137
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.
Mar Bay Motel &Suites
2.0-star property

Mar Bay Motel &Suites

Feb 26 - Mar 2

4 night stay

Boston (BOS) to Tampa (TPA)

Delta • Coach

Tampa (TPA) to Boston (BOS)

Frontier Airlines • Coach
Save 100% on your flight
Price was $753, price is now $507 per person
$507
per person
found 1 day ago
Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

Mar 14 - Mar 21

7 night stay

Boston (BOS) to Sarasota (SRQ)

Delta • Coach

Sarasota (SRQ) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $4,456, price is now $2,765 per person
$2,765
per person
found 1 day ago
voco Sarasota by IHG
3.5-star property

voco Sarasota by IHG

Mar 14 - Mar 21

7 night stay

Boston (BOS) to Tampa (TPA)

Delta • Coach

Tampa (TPA) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $2,322, price is now $1,521 per person
$1,521
per person
found 1 day ago
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See all available trips from Boston to Anna Maria Island
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Anna Maria Island premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort
4.0-star property

Saddlebrook Resort

No reviews

Mar 19 - Mar 24

5 night stay

Boston (BOS) to Tampa (TPA)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,195, price is now $945 per person
$945
per person
found 8 hours ago
Hotel Tampa Riverwalk
4.0-star property

Hotel Tampa Riverwalk

7/10 Good! (1,744 reviews)

Mar 19 - Mar 24

5 night stay

Boston (BOS) to Tampa (TPA)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,341, price is now $1,631 per person
$1,631
per person
found 8 hours ago
Very old room, bad air conditioning

Reviewed on Dec 16, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4.0-star property

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

8.6/10 Excellent! (1,751 reviews)

Mar 19 - Mar 24

5 night stay

Boston (BOS) to Tampa (TPA)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,492, price is now $1,815 per person
$1,815
per person
found 8 hours ago
Fantastic only the beds feel more like full size beds than queen beds that could be better and better size pillows

Reviewed on Nov 16, 2025

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See all available trips from Boston to Anna Maria Island
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Anna Maria Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4.0-star property

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

8.6/10 Excellent! (1,751 reviews)

Mar 5 - Mar 10

5 night stay

Detroit (DTW) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Price was $1,937, price is now $1,479 per person
$1,479
per person
found 1 day ago
Fantastic only the beds feel more like full size beds than queen beds that could be better and better size pillows

Reviewed on Nov 16, 2025

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (481 reviews)

Mar 8 - Mar 14

6 night stay

Minneapolis (MSP) to Tampa (TPA)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,940, price is now $3,688 per person
$3,688
per person
found 1 day ago
You can walk to different restaurants. The only bad thing is that the bed in the master bedroom was not in good condition and the metal base was broken. I had to move to another room within the same unit.

Reviewed on Aug 17, 2025

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Anna Maria Island

End your search for discount fares on flights to Anna Maria Island. Orbitz has all the best prices on Anna Maria Island flights. With Orbitz, you can expect:

Cheap Deals on Flights to Anna Maria Island

We offer big discounts and last-minute savings on Anna Maria Island flights. We make it easy for you to research, plan, and book your flight to Anna Maria Island — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

Travel Convenience on the Go

Get alerts, updates, or book your Anna Maria Island flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Anna Maria Island flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Anna Maria Island flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Anna Maria Island flights to the actual booking. If you want to cancel your flight to Anna Maria Island, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Anna Maria Island with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

Frequently asked questions

How much is a flight to Anna Maria Island?
This week, prices fluctuated between $137 and $150 for a return flight to Anna Maria Island. One-way tickets originating from Hartford (BDL) dropped down to $71 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.