Cheap flights To Anna Maria Island (PIE) from $62

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Cheap Flights to Anna Maria Island from $62 One Way, $142 Round Trip

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

Sat, May 9 - Wed, May 13
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, May 9 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, May 13, priced at $142 found 1 day ago
Wed, May 20 - Wed, May 27
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$142 Roundtrip, found 14 hours ago
$142
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Wed, May 20 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, May 27, priced at $142 found 14 hours ago
Wed, Aug 26 - Wed, Sep 2
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 2, priced at $147 found 2 days ago
Wed, Aug 12 - Sat, Aug 22
PVD
T.F. Green
SRQ
Sarasota-Bradenton Intl.
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Aug 12 from T.F. Green to Sarasota-Bradenton Intl., returning Sat, Aug 22, priced at $147 found 6 days ago
Mon, Feb 2 - Wed, Feb 11
CAK
Akron-Canton
SRQ
Sarasota-Bradenton Intl.
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Feb 2 from Akron-Canton to Sarasota-Bradenton Intl., returning Wed, Feb 11, priced at $149 found 1 day ago
Mon, Jan 26 - Wed, Feb 4
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$151 Roundtrip, found 4 hours ago
$151
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Mon, Jan 26 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Feb 4, priced at $151 found 4 hours ago
Mon, Feb 2 - Fri, Feb 6
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$151 Roundtrip, found 4 days ago
$151
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Feb 2 from Bradley Intl. to Sarasota-Bradenton Intl., returning Fri, Feb 6, priced at $151 found 4 days ago
Wed, Jun 10 - Sat, Jun 13
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Jun 10 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Jun 13, priced at $152 found 2 days ago
Mon, Feb 2 - Sat, Feb 7
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Feb 2 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Feb 7, priced at $155 found 1 day ago
Mon, Feb 2 - Wed, Feb 4
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$156 Roundtrip, found 16 hours ago
$156
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Feb 2 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Feb 4, priced at $156 found 16 hours ago

Anna Maria Island Flight Information

Traveling To
Anna Maria Island
Destination Airport IATA Code
PIE
Number of Airlines Serving
Airlines
Breeze Airways, JetBlue 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.
voco Sarasota by IHG
3.5-star property

voco Sarasota by IHG

Mar 12 - Mar 17

5 night stay

Boston (BOS) to Tampa (TPA)

Southwest Airlines • Non-stop • Coach

Tampa (TPA) to Boston (BOS)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,457, price is now $876 per person
$876
per person
found 1 day ago
The Westin Sarasota
4.0-star property

The Westin Sarasota

Feb 27 - Mar 5

6 night stay

Boston (BOS) to Tampa (TPA)

Delta • Non-stop • Coach

Tampa (TPA) to Boston (BOS)

American Airlines • Non-stop • Coach
Price was $1,873, price is now $1,144 per person
$1,144
per person
found 1 day ago
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5-star property

The Residences at Siesta Key Beach by Hyatt Vacation Club

Mar 6 - Mar 8

2 night stay

Boston (BOS) to Sarasota (SRQ)

Spirit Airlines • Non-stop • Coach

Sarasota (SRQ) to Boston (BOS)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,752, price is now $1,085 per person
$1,085
per person
found 1 day ago
Don't see what you're looking for?
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 11 - Mar 19

8 night stay

Boston (BOS) to Tampa (TPA)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,501, price is now $945 per person
$945
per person
found 13 hours ago
The Barrymore Hotel Tampa Riverwalk
3.0-star property

The Barrymore Hotel Tampa Riverwalk

8.4/10 Very Good! (2,509 reviews)

Mar 10 - Mar 18

8 night stay

Boston (BOS) to Tampa (TPA)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,845, price is now $1,151 per person
$1,151
per person
found 14 hours ago
We left to have breakfast somewhere else

Reviewed on Jan 4, 2026

Kompose Boutique Hotel
3.0-star property

Kompose Boutique Hotel

9.2/10 Wonderful! (4,624 reviews)

Mar 10 - Mar 18

8 night stay

Boston (BOS) to Tampa (TPA)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,720, price is now $1,093 per person
$1,093
per person
found 14 hours ago
Housekeeping everyday should be included The QR check in is annoying A/C makes noice and seems it was working but the room did not change temperature Room smelled muggy

Reviewed on Dec 15, 2025

Don't see what you're looking for?
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.
Wyndham Grand Clearwater Beach
4.0-star property

Wyndham Grand Clearwater Beach

9.4/10 Exceptional! (2,803 reviews)

Mar 7 - Mar 11

4 night stay

Minneapolis (MSP) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Price was $2,769, price is now $2,405 per person
$2,405
per person
found 17 hours ago
Incredible staff, incredible location and amenities.

Reviewed on Nov 6, 2025

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (481 reviews)

Mar 7 - Mar 11

4 night stay

Minneapolis (MSP) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Price was $3,692, price is now $2,944 per person
$2,944
per person
found 17 hours 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

Two Amazing Homes at The Gemma
2.0-star property

Two Amazing Homes at The Gemma

No reviews

Mar 7 - Mar 11

4 night stay

Minneapolis (MSP) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $16,305, price is now $13,945 per person
$13,945
per person
found 17 hours ago
Don't see what you're looking for?
See all available trips from Minneapolis to Anna Maria Island
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Anna Maria Island

Orbitz makes it easy for you to find cheap prices for flights to Anna Maria Island. When you search for your tickets on Orbitz, you don’t have to look any further for the best Anna Maria Island flights available ever again.

Orbitz Offers Exceptional Customer Service

Orbitz understands that your travel plans may change. That’s why we make it simple to cancel your ticket for Anna Maria Island flights if necessary. All you have to do is contact the Orbitz Customer Service department to adjust your travel plans after booking. When you’re ready book your trip, just do a fresh search for the perfect flights to Anna Maria Island again.

Earn with Your Frequent Flyer Program and Orbitz

If you’re a member of a frequent flyer or airline loyalty program, you can keep earning points or miles while making your travel reservations for flights to Anna Maria Island with Orbitz! Just enter your account number during the ticket booking process and your points will be added to your account every time you book with Orbitz.

Low Prices for Anna Maria Island Flights

Orbitz has the scoop on cheap tickets and bargain airfare for flights to Anna Maria Island. You can research the best flights for your trip and make your reservations all on our website with the confidence that you’re getting a great price.

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Frequently asked questions

How much is a flight to Anna Maria Island?
This week, prices fluctuated between $142 and $156 for a return flight to Anna Maria Island. One-way tickets originating from Providence (PVD) dropped down to $62 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.