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Siesta Key

$69+ Cheap flights from Boston (BOS) to Siesta Key, FL

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — TPA
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Siesta Key are usually found in January or September, booked 77 days in advance, depart on a Monday or Friday and return on a Friday

Cheap flight deals from Boston to Siesta Key

Keep the following information in mind while searching for Boston to Siesta Key flight deals. Data was last updated September 17, 2025.

Round-trip from

$112
(Cheapflightsfares)

One-way from

$69
(JetBlue)

Popular in

April

Cheapest in

January

Average price

$158
From Boston Logan Intl to Siesta Key
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One-way flight from Boston Logan Intl to Siesta Key
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Highest demand for flights based on searches. 9% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Boston to Siesta Key

Cheapest flights from Boston to Siesta Key
Explore the most affordable flight options available from Boston to Siesta Key. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:26 amBOS - SRQ
Nonstop3h 18mAllegiant Air
Fri 11/77:31 amSRQ - BOS
Nonstop3h 02mAllegiant Air
Deal found 9/16$112
This JetBlue deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/57:15 amBOS - SRQ
Nonstop3h 30mJetBlue
Wed 10/811:45 amSRQ - BOS
Nonstop3h 21mJetBlue
Deal found 9/15$117
This Trip.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/313:30 pmBOS - SRQ
Nonstop3h 21mJetBlue
Tue 11/41:15 pmSRQ - BOS
Nonstop3h 11mJetBlue
Deal found 9/17$121
This JetBlue deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/188:40 amBOS - SRQ
Nonstop3h 25mJetBlue
Wed 12/36:34 pmSRQ - BOS
Nonstop3h 08mJetBlue
Deal found 9/17$127
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:26 amBOS - SRQ
Nonstop3h 18mAllegiant Air
Mon 10/277:31 amSRQ - BOS
Nonstop3h 05mAllegiant Air
Deal found 9/17$132
This JetBlue deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/42:10 pmBOS - SRQ
Nonstop3h 21mJetBlue
Mon 12/86:34 pmSRQ - BOS
Nonstop3h 08mJetBlue
Deal found 9/16$137
This JetBlue deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/198:40 amBOS - SRQ
Nonstop3h 25mJetBlue
Wed 12/36:34 pmSRQ - BOS
Nonstop3h 08mJetBlue
Deal found 9/17$147
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/19:25 amBOS - SRQ
1 stop7h 40mSouthwest
Fri 10/33:35 pmSRQ - BOS
1 stop9h 05mSouthwest
Deal found 9/15$151
This JetBlue deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/298:40 amBOS - SRQ
Nonstop3h 25mJetBlue
Tue 11/41:15 pmSRQ - BOS
Nonstop3h 11mJetBlue
Deal found 9/16$154
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/215:00 amBOS - SRQ
1 stop6h 20mSouthwest
Fri 10/317:05 amSRQ - BOS
2 stops8h 40mSouthwest
Deal found 9/15$156

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Siesta Key that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Boston to Siesta Key that are best for you.

Fly from

Boston

Fly to

Siesta Key

Route

Depart

Return

Price

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Wed 11/5

7:20 am-1:35 pm

1 stop6h 15m

Sarasota Bradenton Intl

Wed 11/5

5:25 pm-10:15 pm

1 stop4h 50m

$151

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Tue 10/21

5:00 am-11:20 am

1 stop6h 20m

Sarasota Bradenton Intl

Fri 10/31

2:45 pm-8:40 pm

1 stop5h 55m

$151

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Wed 10/29

5:00 am-11:20 am

1 stop6h 20m

Sarasota Bradenton Intl

Sat 11/8

5:30 am-1:10 pm

1 stop7h 40m

$151

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Sat 11/8

3:20 pm-10:53 pm

1 stop7h 33m

Sarasota Bradenton Intl

Tue 11/11

6:39 pm-1:22 am

1 stop6h 43m

$157

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Thu 10/2

7:15 am-6:30 pm

2 stops11h 15m

Sarasota Bradenton Intl

Mon 10/6

3:35 pm-12:40 am

1 stop9h 05m

$162

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Fri 11/7

1:30 pm-11:30 pm

1 stop10h 00m

Sarasota Bradenton Intl

Sun 11/9

6:35 am-6:10 pm

1 stop11h 35m

$162

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Mon 11/10

3:30 pm-6:51 pm

Nonstop3h 21m

Sarasota Bradenton Intl

Thu 11/20

7:50 pm-10:56 pm

Nonstop3h 06m

$177

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Tue 11/18

8:40 am-12:05 pm

Nonstop3h 25m

Sarasota Bradenton Intl

Thu 11/27

12:10 pm-3:20 pm

Nonstop3h 10m

$177

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Mon 10/27

8:40 am-12:05 pm

Nonstop3h 25m

Sarasota Bradenton Intl

Sat 11/8

2:34 pm-8:12 pm

1 stop5h 38m

$195

BostonSarasota

BOS - SRQ

BOSSRQ

Boston Logan Intl

Tue 10/7

5:45 am-2:13 pm

1 stop8h 28m

Sarasota Bradenton Intl

Wed 10/15

5:15 pm-1:13 am

1 stop7h 58m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 21 results
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2
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Best time to book a flight from Boston to Siesta Key

Have a flexible travel schedule? Discover the best time to fly to Siesta Key from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Boston to Siesta Key

How far ahead should I book a flight from Boston to Siesta Key?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Siesta Key. Price data was last updated on September 12, 2025.

Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Boston to Siesta Key. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Boston to Siesta Key?

Currently, January is the cheapest month in which you can book a flight from Boston to Siesta Key (average of $208). Flying from Boston to Siesta Key in March is currently the most expensive (average of $268). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from BOS to S1E?

Find hourly flight availability from Boston to Siesta Key. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

When flying from Boston to Siesta Key, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Boston to Siesta Key?

Use this chart to determine the cheapest time to fly round-trip from Boston to Siesta Key. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Boston to Siesta Key flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Boston to Siesta Key

Explore weekly flight availability from Boston to Siesta Key. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 17, 2025.

The most flights from BOS to S1E are scheduled on a Wednesday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

Reviews of airlines servicing Siesta Key

Get insights into the airlines that provide service to Siesta Key. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Siesta Key. Reviews last updated September 17, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and American Airlines from Boston to Siesta Key by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,914 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Allegiant Air
7.2
Good
699 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Boston to Siesta Key. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Boston to Siesta Key?

    Most people fly from Boston Logan Intl (BOS) if they book a flight from Boston to Siesta Key. On average, Logan Intl has 0 outbound flights to Siesta Key per day from 10 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • How popular is this Boston to Siesta Key flight route?

    Within the past month, 81 users have taken a look at flights from Boston Logan Intl to Siesta Key.

  • How long is the flight from Boston to Siesta Key?

    There are many flights that can get you from Boston to Siesta Key in 6h 15m. Fly via Southwest or Delta to get the fastest option. The distance from Boston to Siesta Key is about 1220 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most reliable airlines from Boston to Siesta Key?

    No one likes to see their flight delayed. When booking a flight from Boston to Siesta Key consider choosing Frontier (82%), JetBlue (81%) or Hawaiian Airlines (80%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Siesta Key?

    Looking at all options, your cheapest flight can be booked for $57. While the most popular route (Boston Logan Intl - Sarasota Bradenton Intl) can be booked for $112 on average, our data indicates $416 when flying from Boston to Siesta Key.

  • Can I find deals for flights from Boston to Siesta Key that include hotel bookings?

    Yes. In addition to deals on Boston to Siesta Key flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Siesta Key?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Siesta Key.

  • Can I find deals for business class flights from Boston to Siesta Key?

    Yes. Cheapflights offers flight deals from Boston to Siesta Key by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Boston to Siesta Key?

    Currently, January is the cheapest month in which you can book a flight from Boston to Siesta Key (average of $208). Flying from Boston to Siesta Key in March is currently the most expensive (average of $268). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 10 airlines flying from Boston to Siesta Key

Discover the top 10 airlines that operate flights from Boston to Siesta Key. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$147FlexibilityNo cancel feeOn-time65%
FrontierCheapest$44Average$128FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$61Average$205FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$62Average$264FlexibilityNo cancel feeOn-time88%
DeltaCheapest$100Average$255FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$105Average$255FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$146Average$403FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$158Average$302FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$166Average$261FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$186Average$309FlexibilityNo cancel feeOn-time69%

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