Cheap flights To Anna Maria Island (PIE) from $49

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 $49 One Way, $97 Round Trip

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

Thu, Dec 4 - Wed, Dec 10
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$97 Roundtrip, found 5 hours ago
$97
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Thu, Dec 4 from Logan Intl. to Sarasota-Bradenton Intl., returning Wed, Dec 10, priced at $97 found 5 hours ago
Sat, Oct 25 - Mon, Nov 3
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$99 Roundtrip, just found
$99
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Oct 25 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Nov 3, priced at $99 just found
Mon, Jan 12 - Fri, Jan 16
PVD
T.F. Green
SRQ
Sarasota-Bradenton Intl.
$102 Roundtrip, found 23 hours ago
$102
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Mon, Jan 12 from T.F. Green to Sarasota-Bradenton Intl., returning Fri, Jan 16, priced at $102 found 23 hours ago
Thu, Sep 11 - Mon, Sep 15
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$107 Roundtrip, found 9 hours ago
$107
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Thu, Sep 11 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Mon, Sep 15, priced at $107 found 9 hours ago
Mon, Sep 8 - Wed, Sep 10
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$109 Roundtrip, found 5 hours ago
$109
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Mon, Sep 8 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 10, priced at $109 found 5 hours ago
Tue, Sep 9 - Sat, Sep 20
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$109 Roundtrip, found 6 days ago
$109
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Sep 9 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $109 found 6 days ago
Fri, Jan 23 - Fri, Jan 30
PVD
T.F. Green
SRQ
Sarasota-Bradenton Intl.
$112 Roundtrip, found 23 hours ago
$112
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Fri, Jan 23 from T.F. Green to Sarasota-Bradenton Intl., returning Fri, Jan 30, priced at $112 found 23 hours ago
Sat, Sep 20 - Sat, Sep 27
PVD
T.F. Green
SRQ
Sarasota-Bradenton Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Sep 20 from T.F. Green to Sarasota-Bradenton Intl., returning Sat, Sep 27, priced at $112 found 5 days ago
Sat, Oct 25 - Sun, Oct 26
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$114 Roundtrip, found 3 days ago
$114
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Oct 25 from Logan Intl. to Sarasota-Bradenton Intl., returning Sun, Oct 26, priced at $114 found 3 days ago
Fri, Jan 23 - Fri, Jan 30
PVD
T.F. Green
SRQ
Sarasota-Bradenton Intl.
$117 Roundtrip, found 23 hours ago
$117
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Fri, Jan 23 from T.F. Green to Sarasota-Bradenton Intl., returning Fri, Jan 30, priced at $117 found 23 hours ago

Anna Maria Island Flight Information

Traveling To
Anna Maria Island
Destination Airport IATA Code
PIE
Number of Airlines Serving
Airlines
JetBlue Airways, Breeze Airways
Flight Price
$97
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.
Clearwater Suites
2.5-star property

Clearwater Suites

Oct 2 - Oct 6

4 night stay

Boston (BOS) to Tampa (TPA)

Frontier Airlines • Coach

Tampa (TPA) to Boston (BOS)

JetBlue Airways • Coach
Save 100% on your flight
Price was $650, price is now $378 per person
$378
per person
found 1 day ago
Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

Oct 2 - Oct 5

3 night stay

Boston (BOS) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $777, price is now $451 per person
$451
per person
found 1 day ago
voco Sarasota by IHG
3.5-star property

voco Sarasota by IHG

Oct 14 - Oct 18

4 night stay

Boston (BOS) to Tampa (TPA)

American Airlines • Non-stop • Coach

Tampa (TPA) to Boston (BOS)

JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $847, price is now $506 per person
$506
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.
Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

9.6/10 Exceptional! (609 reviews)

Oct 10 - Oct 13

3 night stay

Boston (BOS) to Tampa (TPA)

Delta • Roundtrip • PremiumEconomy
Price was $1,401, price is now $1,062 per person
$1,062
per person
found 1 day ago
This was our second time staying at this property. We stayed for eight nights this time. The rooms are lovely but our stay was not nearly as enjoyable as the first time a year ago. There were a lot of children there during our stay. It was practically impossible to use the pool because the kids took over with their inflatables and games. We will likely look elsewhere next time due to the volume of children.

Reviewed on Apr 29, 2025

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (445 reviews)

Oct 10 - Oct 13

3 night stay

Boston (BOS) to Tampa (TPA)

Delta • Roundtrip • PremiumEconomy
Price was $1,722, price is now $1,267 per person
$1,267
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

Inn on the Beach
2.5-star property

Inn on the Beach

9.8/10 Exceptional! (330 reviews)

Oct 10 - Oct 13

3 night stay

Boston (BOS) to Tampa (TPA)

Delta • Roundtrip • PremiumEconomy
Price was $1,472, price is now $1,232 per person
$1,232
per person
found 1 day ago
Best Bouquet Hotel I have ever stayed at and I build hotels for a living.

Reviewed on Jan 3, 2023

Don't see what you're looking for?
See all available trips from Boston to Anna Maria Island
View all trips

Anna Maria Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Hotel Zamora
4.0-star property

The Hotel Zamora

8.4/10 Very Good! (158 reviews)

Oct 22 - Oct 26

4 night stay

Detroit (DTW) to Tampa (TPA)

Delta • Non-stop roundtrip • FirstClass
Price was $1,318, price is now $1,135 per person
$1,135
per person
found 1 day ago
Will definetely come back.

Reviewed on May 18, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5-star property

The Residences at Siesta Key Beach by Hyatt Vacation Club

9.8/10 Exceptional! (284 reviews)

Oct 22 - Oct 26

4 night stay

Detroit (DTW) to Sarasota (SRQ)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,494, price is now $1,957 per person
$1,957
per person
found 1 day ago
We had a fantastic vacation at the Hyatt. The rooms are immaculate and have everything you need for your vacation. Beach staff was wonderful with daily umbrella service and the continental breakfast was very convenient. We look forward to returning!

Reviewed on May 10, 2025

Captiva Beach Resort
2.0-star property

Captiva Beach Resort

9/10 Wonderful! (1,124 reviews)

Oct 22 - Oct 26

4 night stay

Detroit (DTW) to Sarasota (SRQ)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,359, price is now $1,159 per person
$1,159
per person
found 1 day ago
Loved the location and the quietness.

Reviewed on Feb 9, 2023

Don't see what you're looking for?
See all available trips from Detroit to Anna Maria Island
View all trips

Anna Maria Island

When you plan to buy tickets for flights to Anna Maria Island, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

Reliable Customer Service

Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best Anna Maria Island flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

Bargain Tickets for Anna Maria Island Flights

Orbitz offers deeply discounted flights to Anna Maria Island, and we provide the resources to research your travel destination and plan your complete itinerary.

Use Orbitz to Earn Points with Your Frequent Flyer Program

Saving your frequent flyer miles for your flights to Anna Maria Island? You can use Orbitz to make your budget ticket reservation for all your flights and still earn points or miles on your frequent flyer program! Just enter your program account number while you’re booking your ticket to have your points added automatically, every time you book with Orbitz.

Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Anna Maria Island flights.

Frequently asked questions

How much is a flight to Anna Maria Island?
This week, prices fluctuated between $97 and $117 for a return flight to Anna Maria Island. One-way tickets originating from Boston (BOS) dropped down to $49 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.

Nearby

Flights To

Book on Expedia

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.