$296 Cheap flights to Province of Siena

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Top places to visit in Province of Siena

Siena

Montalcino

Pienza

Cheap flights to Province of Siena from $296 One Way, $176 Round Trip

$176 return flights and $296 one-way flights to Province of Siena were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Oct 15 - Thu, Oct 22

BOS

Boston

FLR

Florence

$558

Roundtrip

found 5 hours ago

Sat, Apr 10 - Sat, Apr 17

EWR

New York

FLR

Florence

$595

Roundtrip

found 1 day ago

Fri, Sep 11 - Fri, Sep 25

EWR

New York

PSA

Pisa

$605

Roundtrip

found 5 days ago

Wed, Oct 28 - Fri, Nov 6

JFK

New York

FLR

Florence

$607

Roundtrip

found 3 hours ago

Sat, Sep 12 - Sat, Sep 19

JFK

New York

PSA

Pisa

$616

Roundtrip

found 1 hour ago

Mon, Apr 12 - Mon, Apr 26

LAX

Los Angeles

FLR

Florence

$622

Roundtrip

found 1 hour ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
LGW	Pisa	June 26 to June 30	$176
CDG	Florence	June 26 to June 28	$182
ORY	Pisa	June 26 to June 29	$195
FCO	Florence	June 26 to June 29	$222
BCN	Florence	June 26 to June 28	$252
AMS	Florence	June 27 to June 29	$279
LGW	Florence	June 26 to June 29	$286
JFK	Florence	June 27 to July 9	$1,199
JFK	Pisa	June 26 to July 5	$1,662

*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Province of Siena Accommodation Deals

Il Chiostro del Carmine

Via Della Diana 4 Siena SI

$115 nightly

$131 total

Jun 27 - Jun 28

Total with taxes and fees

Stay at this B&B in Siena. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Piazza ...

8.6/10 Excellent! (914 reviews)

"Beautiful large room with incredible staff and great breakfast. Positively recommend the place."

Reviewed on Jun 20, 2026

La Perla

Via Delle Terme 25 Siena SI

$101 nightly

$117 total

Jun 24 - Jun 25

Total with taxes and fees

Stay at this hotel in Siena. Enjoy free WiFi, daily housekeeping, and pillowtop beds. Popular attractions Piazza del Campo and Teatro dei Rozzi are located ...

7.8/10 Good! (310 reviews)

"2 minutes walk to center of Siena"

Reviewed on Jun 10, 2026

Sangallo Park Hotel

Strada Di Vico Alto 2 Siena SI

$99 nightly

$115 total

Jul 19 - Jul 20

Total with taxes and fees

Book a stay at this business-friendly hotel in Siena. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Piazza del Campo and Palasport Mens ...

9/10 Wonderful! (614 reviews)

"Great hotel extremely helpful staff"

Reviewed on Jun 13, 2026

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Hotel Italia

Viale Camillo Benso Conte di Cavour, 67 Siena SI

Fully refundableReserve now, pay when you stay

$98 nightly

$113 total

Jul 13 - Jul 14

Total with taxes and fees

Stay at this hotel in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. ...

9.2/10 Wonderful! (1,000 reviews)

"Hotel Italia is welcoming and comfortable. It is conveniently located a short distance from the railway station (which is connected to street level by ten escalators and relatively easy to access with luggage if they're all working). The included breakfast buffet offered a great array of tempting ..."

Reviewed on Jun 17, 2026

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Our Top Province of Siena Apartment Hotels

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Montepulciano Siena

Stay at this vacation home in Montepulciano. Enjoy a garden, laundry facilities, and patios. Popular attractions Medici Fortress and Torre del Pulcinella are ...

9.6/10 Exceptional! (87 reviews)

"We had a wonderful stay at Erika’s apartment in Montepulciano. The location was ideal, just a short walk (less than 5 mins) from the town center, making it easy to enjoy the restaurants and shops. The apartment was comfortable, spotless, and well-equipped, providing the perfect place to relax after ..."

Reviewed on Jun 4, 2026

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VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

San Gimignano

Book a stay at this family-friendly villa in San Gimignano. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Tenuta Torciano Winery ...

10/10 Exceptional! (120 reviews)

"Beautiful property. Spacious. Well equipped kitchen. Very accommodating host. Great location. Clean rooms. Cleaning service included. Only negative was the heat was turned off for the season but we had a few cold days. The stone house retains the cold."

Reviewed on Jun 3, 2026

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Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi

CASTELNUOVO BERARDENGA Tuscany

Book a stay at this family-friendly villa in Castelnuovo Berardenga. Enjoy free WiFi, private pools, and a fitness center. Popular attractions San Felice Winery ...

10/10 Exceptional! (33 reviews)

"Wonderful experience for our family of four in this delightful, large, fully restored Tuscany villa. This is part of Arceno properties a highly professional company that manages several properties in the area and takes care of all the details. This seems to be their more luxurious villa. It is set ..."

Reviewed on Aug 15, 2025

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Farmhouse in the heart of the real chiantishire

Castellina in Chianti Tuscany

Stay at this vacation home in Castellina in Chianti. Enjoy a garden, laundry facilities, and patios. Popular attractions Montecalvario and Castellina Fortress ...

10/10 Exceptional! (154 reviews)

"This quiet farmhouse was a lovely experience and a gem in our Italy travels. The kitchen is stocked with all the comforts of home, including olive oil and balsamic vinegar. Our sweet Nonna host showed us around the farmhouse and told us where to find a nearby market. We had private outdoor seating ..."

Reviewed on Jun 12, 2026

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Score Epic Province of Siena Accommodation Deals

Precise Tale Poggio Alla Sala

Via Poggio alla Sala 10 Montepulciano SI

Fully refundableReserve now, pay when you stay

$545 nightly

$606 total

Jun 25 - Jun 26

Total with taxes and fees

Book a stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...

9.6/10 Exceptional! (146 reviews)

"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"

Reviewed on Jun 19, 2026

Hotel Athena

P Mascagni 55 Siena SI

Fully refundableReserve now, pay when you stay

$147 nightly

$167 total

Jul 19 - Jul 20

Total with taxes and fees

Book a stay at this business-friendly hotel in Siena. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...

9.2/10 Wonderful! (1,001 reviews)

"Excellent service from the staff on reception and the terrace restaurant. The room and balcony was clean and well maintained. Awesome breakfast."

Reviewed on Jun 14, 2026

Borgo Scopeto Wine & Country Relais

Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI

Fully refundableReserve now, pay when you stay

$403 nightly

$455 total

Jun 28 - Jun 29

Total with taxes and fees

Book a stay at this luxury hotel in Castelnuovo Berardenga. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

9.4/10 Exceptional! (205 reviews)

"Everything was amazing. The staff went above and beyond"

Reviewed on Jun 21, 2026

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Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI

$313 nightly

$356 total

Jul 4 - Jul 5

Total with taxes and fees

Book a stay at this luxury hotel in Siena. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...

9.2/10 Wonderful! (610 reviews)

"It is wonderful! Everything is nice!"

Reviewed on Jun 15, 2026

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Province of Siena

Piazza Paradiso Accomodation

Via di Stalloreggi, 38 Siena SI

$94 nightly

$108 total

Jul 16 - Jul 17

Total with taxes and fees

Book a stay at this luxury affittacamere in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Piazza del Campo and Pinacoteca ...

9.2/10 Wonderful! (157 reviews)

"Great room, amazing location. 5 minutes from the Duomo, a couple more from the piazza. Highly recommend."

Reviewed on Jun 19, 2026

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

San Gimignano

Book a stay at this family-friendly villa in San Gimignano. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Tenuta Torciano Winery ...

10/10 Exceptional! (120 reviews)

Families like: Private pool, kitchen, playground, game room

Travelers say...

Reviewed on Jun 3, 2026

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Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

Fully refundableReserve now, pay when you stay

$115 nightly

$131 total

Jun 23 - Jun 24

Total with taxes and fees

Stay at this hotel in Montepulciano. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Civic Museum and Palazzo Ricci are located ...

9.2/10 Wonderful! (207 reviews)

"Roberto and Victoria are lovely! So nice, very helpful and breakfast was so nice out in the garden! Roberto can’t do enough for you! Hotel is up around the middle of the town, well located to go up or down and near everything! The room we had was old, crowded and bathroom very tiny, even hard for ..."

Reviewed on May 29, 2026

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La Terrazza Sul Campo Rooming House

Via di Città 65 Siena SI

$122 nightly

$139 total

Jul 12 - Jul 13

Total with taxes and fees

Stay at this residence in Siena. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Piazza del Campo and Museum of Torture are located ...

9.8/10 Exceptional! (246 reviews)

"The location was amazing. I will never forget the view. Room was huge and access to restaurants and shopping. Also fantastic. We want to go back again already."

Reviewed on May 21, 2026

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a Car For After Your Flight?

Economy

Chevrolet Spark

4 people

Compact

Ford Focus

4 people

Midsize

Toyota Corolla

5 people

SUV

Jeep Compass

5 people

Province of Siena

Snag some “suite” deals when you add cheap hotel rooms to Province of Siena flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

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Fun for All

While shopping Orbitz sales on Province of Siena flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Province of Siena flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Province of Siena. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

Frequently asked questions

Which airlines fly to Province of Siena?

Book a fare with one of the 12 airlines that operate services to Fiumicino - Leonardo da Vinci Intl. Airport (FCO) and get set for awesome new adventures. This popular airport is the jumping-off point for exploring Province of Siena. When you're ready to cross off this region, these international airlines will take you there:

ITA Airways - 666 flights to Province of Siena per month
Ryanair - 423 flights to Province of Siena per month
Vueling - 286 flights to Province of Siena per month

How much is a flight to Province of Siena?

Prices for return flights to Province of Siena this past week ranged from $176 to $1,662. If you were flying one-way out of Boston (BOS), you could have landed fares from just $296.

How to book the cheapest flight to Province of Siena?

Picking up cheap flights to Province of Siena is as easy as booking with Orbitz. But if you're eager to make sure you're nabbing the best flight deals around, here are some tips to follow:

Depending on where you're coming from, select the 'Nearby airports' function (located under the departure and arrival form fields). On occasion, alternative departure points will have cheaper fares.
Similarly, click on the 'Show flexible dates' option to bring up the prices for days around your chosen departure. It's possible to find cheaper flight deals if your travel plans are flexible.
To refine your results, hit 'Show options.' You can search based on airlines, seating class, and nonstop and refundable flights. You can also choose your preferred departure and arrival times under 'Sort & Filter' to the left.
Once you've worked out your travel dates, don't delay booking. Airfares normally climb as the departure date gets closer.
Think about combining your hotels, flights and car rental into a package deal with Orbitz to make your budget go even further.
Don't travel during the busy season if possible. By avoiding school vacations and summer, you can make superb savings on your airfare.

What is the best time to book a flight to Province of Siena?

Book your tickets to Province of Siena in January. This is the best time of the year for bargain fares, closely followed by February and August. Catch cheap flights and let your dream vacation come true with Orbitz.

What day of the week is the cheapest to book a flight to Province of Siena?

If you're after inexpensive fares to Province of Siena, the best days of the week to make a booking are Tuesdays, Wednesdays and Saturdays. With Orbitz (and a bit of good timing!), an unbeatable flight deal will be all yours.

What is the cheapest day of the week to fly to Province of Siena?

Look into flying early in the week to nab cheap flights to Province of Siena. Orbitz data from 2020 indicates Monday is generally the cheapest day to head off, followed by Tuesday. Saturday was found to have the highest ticket fares. This is probably because most passengers choose to start their trip when the weekend rolls around.

What is the cheapest month to fly to Province of Siena?

If you have some flexibility with your travel plans, think about jetting off in August. Orbitz data has found that this is generally the best month to take off if you want cheap flights to Province of Siena. As you would imagine, airfares get pricier in the busy month of June and flights book out quickly.

Which airlines allow free cancellation?

Flexibility is important, that's why Orbitz lets you search for fares that won't slap on fees for amendments to your reservation. Fill out your departure and arrival points, then select "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 Province of Siena?

Any lengthy flight can be daunting, but it's nothing a little preparation can't solve. We've put together our top tips to make sure your trip flows without a hitch:

Nothing is more important than having your travel documents. Which to bring and how many depend on whether you're flying domestic or international. Be sure to check with your airline. In both cases, you'll need to show some sort of government-issued ID.
If you're flying direct to Province of Siena, chances are you're going to be in the sky for quite some time. Take lots of snacks and entertainment to keep you occupied. Now is a fantastic time to pick up that novel you haven't read yet!
Long-haul voyages can get very cold, especially if you're flying overnight. If you prefer not to stay awake shivering for the length of your journey, bring a sweater and some wool socks.

How do I get cheap first-class/business deals to Province of Siena?

There are ways of booking business or first-class tickets to Province of Siena that won't burn through your wallet. Snap up a seat at the front of the plane for less with these great tips:

Flexibility is key. By being open to different travel dates, you'll have better odds of landing a great deal on first or business-class airfares.
Low-cost airlines offer business-class seats at a fraction of the usual cost. Ditch the full-service carriers and go with one of these cheaper options.
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 may also be able to upgrade with points earned through a loyalty program.

What is the best time to go to Province of Siena?

Province of Siena is a fun getaway destination year-round, but the most popular months to visit are April, May and June. If you prefer warm weather, consider traveling in the summertime. Like most destinations in the Northern Hemisphere, the summer season starts June 20. During this time, temperatures generally hover between 60 ºF and 85 ºF during the daytime.

More to Explore

Siena Vacations

Things to do in Siena

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.