$339 Cheap flights to Province of Siena

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

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 $339 One Way, $226 Round Trip

$226 return flights and $339 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.

Sun, Nov 15 - Mon, Nov 23

BOS

Boston

FLR

Florence

$593

Roundtrip

just found

Wed, Oct 21 - Fri, Nov 20

JFK

New York

FLR

Florence

$607

Roundtrip

found 2 hours ago

Wed, Oct 21 - Fri, Nov 20

EWR

New York

FLR

Florence

$607

Roundtrip

found 2 hours ago

Tue, Aug 25 - Mon, Aug 31

IAD

Washington

FLR

Florence

$662

Roundtrip

found 5 hours ago

Fri, Apr 9 - Sun, Apr 18

EWR

New York

PSA

Pisa

$669

Roundtrip

found 1 day ago

Wed, Oct 7 - Sun, Oct 18

JFK

New York

PSA

Pisa

$681

Roundtrip

found 1 day ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
BCN	Florence	August 21 to August 22	$226
ORY	Florence	August 22 to August 26	$242
LGW	Pisa	August 22 to August 24	$247
ORY	Pisa	August 21 to August 24	$293
LGW	Florence	August 22 to August 26	$293
FCO	Florence	August 23 to August 24	$318
AMS	Pisa	August 22 to September 1	$353
JFK	Florence	August 21 to August 30	$1,012
JFK	Pisa	August 23 to August 27	$1,085

*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

Fully refundableReserve now, pay when you stay

$91 nightly

$105 total

Aug 24 - Aug 25

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 ...

La Perla

Via Delle Terme 25 Siena SI

Fully refundableReserve now, pay when you stay

$82 nightly

$96 total

Aug 19 - Aug 20

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

Fully refundableReserve now, pay when you stay

$108 nightly

$125 total

Aug 29 - Aug 30

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! (618 reviews)

"Great hotel extremely helpful staff"

Reviewed on Jun 13, 2026

Save an average of 15% on thousands of hotels when you're signed in

Hotel Italia

Viale Camillo Benso Conte di Cavour, 67 Siena SI

Fully refundableReserve now, pay when you stay

$96 nightly

$111 total

Aug 26 - Aug 27

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! (1,007 reviews)

"Clean, nice small room. Nothing fancy. Basic, but very clean."

Reviewed on Aug 8, 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

Get rates

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

Get rates

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

Get rates

Save an average of 15% on thousands of hotels when you're signed in

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! (157 reviews)

"Amazing views across the valley. At night we watched the fireflies and sun set. Close to Castilla in Chianti, lovely places to eat and a Co-op for all your needs. Lots of Vineyards and hilltop villages to explore."

Reviewed on Jul 25, 2026

Get rates

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

Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI

Fully refundableReserve now, pay when you stay

$368 nightly

$417 total

Aug 26 - Aug 27

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 ...

Hotel Athena

P Mascagni 55 Siena SI

Fully refundableReserve now, pay when you stay

$174 nightly

$197 total

Aug 27 - Aug 28

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! (1,008 reviews)

"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will ..."

Reviewed on Aug 17, 2026

Precise Tale Poggio Alla Sala

Via Poggio alla Sala 10 Montepulciano SI

Fully refundableReserve now, pay when you stay

$524 nightly

$583 total

Aug 20 - Aug 21

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! (161 reviews)

"Horrible service at best. Not a 5 star hotel. Save your money."

Reviewed on Aug 17, 2026

Save an average of 15% on thousands of hotels when you're signed in

La Certosa di Pontignano

loc. Pontignano, 5 Castelnuovo Berardenga SI

$67 nightly

$83 total

Sep 8 - Sep 9

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! (554 reviews)

"Great property with unique setting being an old monastery. We thought we had booked a room with A/C but there wasn’t. They moved us to a room with A/C at no additional cost."

Reviewed on Aug 4, 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

Fully refundableReserve now, pay when you stay

$82 nightly

$95 total

Aug 27 - Aug 28

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

Get rates

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

$116 nightly

$132 total

Aug 20 - Aug 21

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! (210 reviews)

"A wonderful experience in the heart of Montepulciano. Roberto was really helpful and accommodating, as we were traveling with my 99 year old mother. The property is super clean, and the terrace where we had breakfast really charming. Everything was excellent. Highly recommend this charming ..."

Reviewed on Jul 14, 2026

Save an average of 15% on thousands of hotels when you're signed in

La Terrazza Sul Campo Rooming House

Via di Città 65 Siena SI

$121 nightly

$138 total

Aug 26 - Aug 27

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! (248 reviews)

"Perfect location, our room had the best Hotel room view ever overlooking the Campo. The room itself was huge with 15 foot ceilings and nicely decorated. The house was an oasis in a busy tourist area and quiet with double panes windows. Not a full service hotel with only limited front desk hours if ..."

Reviewed on Jun 28, 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

Save more on flights to Province of Siena while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Province of Siena

Now it is easier than ever to find a discount Province of Siena flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To Province of Siena

We now offer free apps for the most commonly used mobile devices. You can use your mobile phone to share relevant information pertaining to your trips, view images of local lodgings and take advantage of hotel and car rental discounts that may be available only to mobile device users.

Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Province of Siena flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Province of Siena a breeze.

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 $226 to $1,085. If you were flying one-way out of Washington (IAD), you could have landed fares from just $339.

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.