$49 Cheap flight deals from Boston (BOS) to Anna Maria (TPA)

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This Weekend's Flight Deals from Boston to Anna Maria

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Feb 15 - Thu, Feb 19
ORH
Worcester Regional
SRQ
Sarasota-Bradenton Intl.
$344 Roundtrip, found 3 days ago
$344
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Feb 15 from Worcester Regional to Sarasota-Bradenton Intl., returning Thu, Feb 19, priced at $344 found 3 days ago
Sat, Feb 14 - Sun, Feb 15
MHT
Manchester-Boston Regional
TPA
Tampa Intl.
$349 Roundtrip, found 4 days ago
$349
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Feb 14 from Manchester-Boston Regional to Tampa Intl., returning Sun, Feb 15, priced at $349 found 4 days ago
Sun, Feb 15 - Thu, Feb 19
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$376 Roundtrip, found 15 hours ago
$376
Roundtrip
found 15 hours ago
Select United flight, departing Sun, Feb 15 from Logan Intl. to Sarasota-Bradenton Intl., returning Thu, Feb 19, priced at $376 found 15 hours ago
Sun, Feb 15 - Thu, Feb 26
PVD
T.F. Green
SRQ
Sarasota-Bradenton Intl.
$405 Roundtrip, found 1 day ago
$405
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Feb 15 from T.F. Green to Sarasota-Bradenton Intl., returning Thu, Feb 26, priced at $405 found 1 day ago

Airfares from $49 One Way, $107 Round Trip from Boston to Anna Maria

Prices starting at $107 for return flights and $49 for one-way flights to Anna Maria were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Aug 31 - Wed, Sep 9
PVD
Providence
TPA
Tampa
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Aug 31 from Providence to Tampa, returning Wed, Sep 9, priced at $107 found 3 days ago
Thu, Feb 19 - Tue, Mar 10
BOS
Boston
TPA
Tampa
$111 Roundtrip, found 6 days ago
$111
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Feb 19 from Boston to Tampa, returning Tue, Mar 10, priced at $111 found 6 days ago
Mon, Aug 31 - Fri, Sep 11
MHT
Manchester
TPA
Tampa
$153 Roundtrip, found 14 hours ago
$153
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Mon, Aug 31 from Manchester to Tampa, returning Fri, Sep 11, priced at $153 found 14 hours ago
Mon, Feb 23 - Tue, Mar 3
BOS
Boston
TPA
Tampa
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Boston to Tampa, returning Tue, Mar 3, priced at $156 found 1 day ago
Sat, Jun 6 - Sat, Jun 13
PVD
Providence
SRQ
Sarasota
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Jun 6 from Providence to Sarasota, returning Sat, Jun 13, priced at $173 found 1 day ago

Anna Maria 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

9.2/10 Wonderful! (1,001 reviews)

Mar 24 - Mar 31

7 night stay

Boston (BOS) to Tampa (TPA)

JetBlue Airways • Coach

Tampa (TPA) to Boston (BOS)

Delta • Coach
Price was $2,229, price is now $1,133 per person
$1,133
per person
found 1 day ago
Hotel was great. They are close to restaurants and have a shuttle that will take you places like St Armand’s Circle. They also have beach towels, chairs and umbrellas that you can use at the beach. We would stay at hotel again for sure.

Reviewed on Jun 30, 2024

Seaside at Anna Maria Island Inn
2.5-star property

Seaside at Anna Maria Island Inn

9.6/10 Exceptional! (45 reviews)

Mar 24 - Mar 31

7 night stay

Boston (BOS) to Sarasota (SRQ)

JetBlue Airways • Coach

Sarasota (SRQ) to Boston (BOS)

Delta • Coach
Price was $6,330, price is now $3,526 per person
$3,526
per person
found 1 day ago
Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (480 reviews)

Mar 24 - Mar 31

7 night stay

Boston (BOS) to Sarasota (SRQ)

JetBlue Airways • Coach

Sarasota (SRQ) to Boston (BOS)

Delta • Coach
Save 100% on your flight
Price was $3,771, price is now $2,131 per person
$2,131
per person
found 1 day ago
Extremely clean. Friendly, helpful staff that went above and beyond. I traveled with my teenage daughter and her friend and we never once felt unsafe. I was fine using the free trolley transportation up and down the island, but the girls talked me into renting a golf cart. That did provide more freedom for our short time there. The resort has golf carts for rent. We will definitely be back!

Reviewed on Aug 10, 2025

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Anna Maria first class 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! (531 reviews)

Apr 1 - Apr 5

4 night stay

Boston (BOS) to Tampa (TPA)

Delta • Non-stop • FirstClass

Tampa (TPA) to Boston (BOS)

American Airlines • Non-stop • FirstClass
Price was $1,507, price is now $1,180 per person
$1,180
per person
found 1 day ago
Todo perfecto y el trato increible

Reviewed on Oct 24, 2025

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (481 reviews)

Apr 1 - Apr 5

4 night stay

Boston (BOS) to Tampa (TPA)

Delta • Non-stop • FirstClass

Tampa (TPA) to Boston (BOS)

American Airlines • Non-stop • FirstClass
Price was $3,622, price is now $2,674 per person
$2,674
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

Island Grand at TradeWinds
4.0-star property

Island Grand at TradeWinds

7.4/10 Good! (1,005 reviews)

Apr 1 - Apr 5

4 night stay

Boston (BOS) to Tampa (TPA)

Delta • Non-stop • FirstClass

Tampa (TPA) to Boston (BOS)

American Airlines • Non-stop • FirstClass
Price was $1,860, price is now $1,456 per person
$1,456
per person
found 1 day ago
The staff and visitors were some of the best people I have ever met. Jonel, Margot, Roman,

Reviewed on Jan 25, 2026

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More About Flying To Anna Maria from Boston

Route Information for Flights from Boston to Anna Maria

Origin Airport IATA Code
BOS
Destination Airport IATA Code
TPA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Boston to Anna Maria

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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.