$325 Cheap flights to Province of Siena

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Top places to visit in Province of Siena

A historic town with tightly packed buildings, a prominent tower, and a church.

Siena

A historic tower with arches and a bell, surrounded by traditional buildings with tiled roofs and satellite dishes.

Montalcino

A historic square with a prominent tower and statues.

Pienza

Cheap flights to Province of Siena from $325 One Way, $165 Round Trip

$165 return flights and $325 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.

Wed, Feb 17 - Mon, Mar 15

BOS

Boston

FLR

Florence

$495

Roundtrip

found 3 days ago

Fri, Jan 22 - Mon, Jan 25

JFK

New York

FLR

Florence

$500

Roundtrip

found 4 hours ago

Wed, Dec 2 - Wed, Dec 9

JFK

New York

FLR

Florence

$501

Roundtrip

found 1 hour ago

Sun, Oct 25 - Wed, Nov 25

EWR

New York

FLR

Florence

$515

Roundtrip

found 4 days ago

Wed, Dec 9 - Mon, Dec 14

IAD

Washington

FLR

Florence

$534

Roundtrip

found 3 days ago

Tue, Oct 13 - Tue, Oct 20

EWR

New York

PSA

Pisa

$665

Roundtrip

found 7 hours ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
SEN	Pisa	September 25 to September 28	$165
FCO	Florence	September 26 to September 27	$172
ORY	Pisa	September 25 to September 28	$195
BCN	Florence	September 25 to October 1	$204
CDG	Florence	September 25 to September 28	$228
LHR	Florence	September 25 to September 27	$358
QDU	Florence	September 25 to September 27	$366
JFK	Florence	September 27 to December 12	$660
BCN	Perugia	September 25 to September 27	$700
JFK	Pisa	September 27 to October 6	$853
PVG	Florence	September 26 to October 3	$2,071

*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

$132 nightly

$150 total

Oct 5 - Oct 6

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! (941 reviews)

"Hotel reception was outstanding. Floors and bathroom were dirty. Shower was very uncomfortable. Water Temperature control was terrible. It constantly shifted from extremely hot to cold. Air conditioning was a farse. The coolest the room temperature ever reached was 27.3 centigrades. Never reported ..."

Reviewed on Sep 7, 2026

La Perla

Via Delle Terme 25 Siena SI

Fully refundableReserve now, pay when you stay

$101 nightly

$117 total

Oct 5 - Oct 6

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 ...

Sangallo Park Hotel

Strada Di Vico Alto 2 Siena SI

$110 nightly

$127 total

Oct 18 - Oct 19

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 Casalvento's ...

9/10 Wonderful! (620 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

$112 nightly

$129 total

Oct 22 - Oct 23

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)

"Clean, well maintained property that you’ll feel safe spending the night."

Reviewed on Sep 12, 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! (89 reviews)

"Great location and beautiful views. We stayed during a heat wave and it got hot in the house , but other than that very happy with everything. Great setup for a family with 2 levels. 5 min walk to restaurants and shops, 2 min drive to supermarket or 15 min walk."

Reviewed on Jun 22, 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 Fonti Medievali and Archaeological ...

10/10 Exceptional! (122 reviews)

"My family of 10, 2 grandparents, two adult children and their spouses plus 4 teenagers spent a wonderful week at that the Villa Iris. The house is lovely and has air conditioning. The 6 bedrooms with 6 bathrooms were great to have. Every day we went went to a different hill town, explored them and ..."

Reviewed on Jul 25, 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! (35 reviews)

"Such a beautiful home in a perfect setting, we immediately felt at home. The daily cleaning service was wonderful and friendly. We loved arriving to a fully stocked kitchen, with enough to make a great meal and several snacks throughout our time. I would highly recommend this home!"

Reviewed on Jul 8, 2026

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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 Castellina Fortress and Archaeological ...

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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

La Certosa di Pontignano

loc. Pontignano, 5 Castelnuovo Berardenga SI

Fully refundableReserve now, pay when you stay

$101 nightly

$120 total

Oct 6 - Oct 7

Total with taxes and fees

Book a stay at this business-friendly B&B in Castelnuovo Berardenga. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and ...

9.4/10 Exceptional! (564 reviews)

"Magical place! We loved jazz night and the amazing wine paired dinner. Fantastic place!"

Reviewed on Sep 16, 2026

Hotel Executive

Via Nazareno Orlandi 32 Siena SI

Fully refundableReserve now, pay when you stay

$81 nightly

$95 total

Oct 12 - Oct 13

Total with taxes and fees

Book a stay at this family-friendly hotel in Siena. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...

NH Siena

Piazza La Lizza 1 Siena SI

Fully refundableReserve now, pay when you stay

$155 nightly

$176 total

Oct 13 - Oct 14

Total with taxes and fees

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

8.2/10 Very Good! (1,001 reviews)

"El hotel está fuera de las murallas de la ciudad, fuera de la zona restringida para autos, pero cerca de las atracciones de la parte histórica de la ciudad."

Reviewed on Sep 19, 2026

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Hotel Athena

P Mascagni 55 Siena SI

Fully refundableReserve now, pay when you stay

$237 nightly

$266 total

Oct 20 - Oct 21

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 ...

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

Fully refundableReserve now, pay when you stay

$95 nightly

$110 total

Oct 19 - Oct 20

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! (160 reviews)

"Great location and lovely staff!"

Reviewed on Aug 3, 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 Fonti Medievali and Archaeological ...

10/10 Exceptional! (122 reviews)

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

Travelers say...

Reviewed on Jul 25, 2026

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Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

$115 nightly

$131 total

Sep 29 - Sep 30

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 ...

9.4/10 Exceptional! (211 reviews)

"One of the best stays we had on our Italy honeymoon trip! Wish we stayed longer. The staff and the owner were very friendly and made us feel like family. The breakfast was delicious and had a great outdoor patio to start the day. The room was very sanitary, and the hotel is located very close to ..."

Reviewed on Aug 22, 2026

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La Terrazza Sul Campo Rooming House

Via di Città 65 Siena SI

$182 nightly

$205 total

Oct 22 - Oct 23

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! (249 reviews)

"Great stay. Thanks for the hospitality and kindness."

Reviewed on Sep 19, 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

Orbitz is your one stop for guaranteed low prices on Province of Siena flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to Province of Siena and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Province of Siena Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to Province of Siena from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

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 $165 to $2,071. If you were flying one-way out of New York (JFK), you could have landed fares from just $325.

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.