Title: Siena Vacation Home Rentals from CA $162: Search Top Private Vacation Homes for Rent | Expedia.ca

[Siena Travel Guide](https://expedia.ca/Siena.dx9821)[Hotels in Siena](https://expedia.ca/Siena-Hotels.d9821.Travel-Guide-Hotels)[Vacation Rentals in Siena](https://expedia.ca/Siena-Vacation-Rentals.d9821.Travel-Guide-VacationRentals)[Flights to Siena](https://expedia.ca/Cheap-Flights-To-Siena.d9821.Travel-Guide-Flights)[Things to do in Siena](https://expedia.ca/Things-To-Do-In-Siena.d9821.Travel-Guide-Activities)[Siena Car Rentals](https://expedia.ca/Car-Rentals-In-Siena.d9821.Car-Rental-Guide)[Siena Vacation Packages](https://expedia.ca/Siena.d9821.Destination-Travel-Guides)

![](https://images.trvl-media.com/place/9821/7379d030-252a-4e26-a469-e10785470ebc.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Siena Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Siena vacation homes

![Property grounds](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/2419483e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/456c8609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/4e76a25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/d1a6db77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Toscana

[](https://www.expedia.ca/Siena-Hotels-Vrbo-Property.h114180505.Hotel-Information)

10/10

Exceptional

(1)

"Très bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable "

![France](https://a.travel-assets.com/egds/marks/flags/fr.svg)

YVES A.

CA $210

CA $263 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Siena-Hotels-Vrbo-Property.h114180505.Hotel-Information)

![Spa](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/d008e9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/6c75b5ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/e41ddf9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/5527a0da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Toscana

[](https://www.expedia.ca/Monteriggioni-Hotels-Vrbo-Property.h118760780.Hotel-Information)

CA $95

CA $219 total

includes taxes & fees

Dec 13 - Dec 14

[](https://www.expedia.ca/Monteriggioni-Hotels-Vrbo-Property.h118760780.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/5bec1a68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/9dbd798b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/8a1c07ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/42f20907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Siena City Centre

[](https://www.expedia.ca/Siena-Hotels-IL-TOLOMEI-Central-In-The-Middle-Of-Main-Street.h21793404.Hotel-Information)

8.0/10

Very good

(4)

"Excellent location, very nice apartment was just like the pictures. Painless check-in, we had a comfortable wonderful 3 days in Siena. The only negative was the drain in the master shower backs up, but there's a second bathroom so we just showered in there. Great place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Serena F.

CA $137

CA $238 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Siena-Hotels-IL-TOLOMEI-Central-In-The-Middle-Of-Main-Street.h21793404.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/df1d957c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/c2de7201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/80b09a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Duplex, 2 Bedrooms (Mimosa) | Living area](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/0b31f6fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Castellina in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information)

9.4/10

Exceptional

(9)

"Very nice agriturismo. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ruth

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/39997d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/a67674df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/4734ab61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/4e7093c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in San Gimignano

[](https://www.expedia.ca/San-Gimignano-Hotels-Casa-Vacanze-Le-Case.h28401463.Hotel-Information)

9.0/10

Wonderful

(8)

"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10\. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jackie

CA $147

CA $170 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/San-Gimignano-Hotels-Casa-Vacanze-Le-Case.h28401463.Hotel-Information)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/3b47f5e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/901e36a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/05c4a567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/dd2a0574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Poggibonsi

[](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.Hotel-Information)

10/10

Exceptional

(2)

"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"

![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg)

Anonymous traveller

CA $128

CA $183 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.Hotel-Information)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/32000000/31660000/31651200/31651151/6388e44c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/32000000/31660000/31651200/31651151/036b2519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31660000/31651200/31651151/290e7ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31660000/31651200/31651151/0ee3e5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Boccheggiano

[](https://www.expedia.ca/Montieri-Hotels-Private-House-With-Exclusive-Swimming-Pool-Heated-And-Amazing-View.h31651151.Hotel-Information)

9.6/10

Exceptional

(56)

"Everything was great. The pool was warm. Views are fantastic stretching out to the sea. The town has a good supermarket. Only went to one restaurant, Dell'Upo, but it was good so went back most nights. The hosts were helpful and informative. Planning a return."

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Patrick H.

CA $4,679

CA $5,550 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/Montieri-Hotels-Private-House-With-Exclusive-Swimming-Pool-Heated-And-Amazing-View.h31651151.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/65000000/64180000/64173800/64173725/2bbb35c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64180000/64173800/64173725/270-23129a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/65000000/64180000/64173800/64173725/d2694dc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/65000000/64180000/64173800/64173725/02cc50e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Monticiano

[](https://www.expedia.ca/Monticiano-Hotels-Comodita.h64173725.Hotel-Information)

10/10

Exceptional

(1)

"Appartamento perfetto non manca nulla e proprietari accoglienti, e gentilissimi. Da tornare"

![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg)

Sandra V.

CA $116

CA $165 total

includes taxes & fees

Dec 13 - Dec 14

[](https://www.expedia.ca/Monticiano-Hotels-Comodita.h64173725.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/77d8ad70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/f52ea845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/a27ccb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/15eff195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Barberino Tavarnelle

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.Hotel-Information)

9.8/10

Exceptional

(9)

"Great food in the area. Beautiful church tour and a fantastic host for our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Craig & Conny M.

CA $239

CA $339 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/b5d9a4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/4b443108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/6b68301b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/62b86b12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Trequanda, Siena

[](https://www.expedia.ca/Trequanda-Hotels-Romantic-Farm-In-The-Sienese-Hills.h39866124.Hotel-Information)

"Gemischt.Sehr gut: Zentrale Lage, viele Ausflugsmöglichkeiten (Siena, Cortona, Arezzo Pienza). Gepflegt, schöner Pool. Antonio ist die gute Seele des Hauses, freundlich, hilfsbereit und scheinbar immer fröhlich.Gut: Ausstattung des Hauses (wir haben im kleineren Poggiolino) gewohnt.Nicht gut: Zentrale Lage, direkt an einer wichtigen Regionalstraße. Also Ruhe in den Hügeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....

![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg)

Heike K.

CA $130

CA $282 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Trequanda-Hotels-Romantic-Farm-In-The-Sienese-Hills.h39866124.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/cb24f428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/e641bc55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/f35937ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/5047e046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Casciano

[](https://www.expedia.ca/Murlo-Hotels-Exclusive-Tower-In-Stone.h40221427.Hotel-Information)

9.8/10

Exceptional

(7)

"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael G.

CA $144

CA $240 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Murlo-Hotels-Exclusive-Tower-In-Stone.h40221427.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/0ff1b26b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/3dabcf3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/f9b59b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/fbd3a173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Montalcino

[](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno-Camera-Lavanda.h69548805.Hotel-Information)

10/10

Exceptional

(4)

"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"

![Austria](https://a.travel-assets.com/egds/marks/flags/at.svg)

Johannes S.

CA $193

CA $225 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno-Camera-Lavanda.h69548805.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/c8f6c584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/f8032427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/c5e43f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/812c14c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Volterra

[](https://www.expedia.ca/Volterra-Hotels-Holiday-Home-La-Casetta-With-Private-Terrace.h117985575.Hotel-Information)

CA $136

CA $162 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Volterra-Hotels-Holiday-Home-La-Casetta-With-Private-Terrace.h117985575.Hotel-Information)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/db850afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV, books](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/1a6006b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/w4029h2268x0y0-afe178cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/4bcceb91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Impruneta

[](https://www.expedia.ca/Impruneta-Hotels-La-Suite-Dei-Ricordi-Apartment-Between-Florence-And-Chianti.h33675891.Hotel-Information)

10/10

Exceptional

(1)

"Carina abitazione ristrutturata tipica del centro di un paesino toscano di campagna (Impruneta a pochi chilometri da Firenze). Ottimi impianti e sistemi che rendono l'abitazione molto comoda ed attrezzata (un televisore piatto per stanza, condizionatore presente, cucina attrezzata, ecc. Parcheggi a pochi passi e gratuiti dalla sera alla mattina con negozietti a pochi passi. Massima disponibilità dei proprietari e tipica gentilezza toscana."

![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg)

Anonymous traveller

CA $161

CA $240 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Impruneta-Hotels-La-Suite-Dei-Ricordi-Apartment-Between-Florence-And-Chianti.h33675891.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/36000000/35560000/35556300/35556207/d2d2359e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/36000000/35560000/35556300/35556207/4c866191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/36000000/35560000/35556300/35556207/691f3ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/36000000/35560000/35556300/35556207/332581bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Casole d'Elsa

[](https://www.expedia.ca/Casole-DElsa-Hotels-House-With-Pool-For-4-Pax.h35556207.Hotel-Information)

9.4/10

Exceptional

(3)

"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"

![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg)

Oliver E.

CA $226

CA $439 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Casole-DElsa-Hotels-House-With-Pool-For-4-Pax.h35556207.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/124000000/123090000/123081100/123081040/18a5af85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/124000000/123090000/123081100/123081040/8ed83f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123090000/123081100/123081040/b92cdaf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123090000/123081100/123081040/a8e5cb70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Località Gerfalco Montieri

[](https://www.expedia.ca/Montieri-Hotels-Casa-Di-Via-Del-Corallo-Gerfalco-Charming-Apartment-In-Medieval-Village.h123081040.Hotel-Information)

CA $258

CA $306 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Montieri-Hotels-Casa-Di-Via-Del-Corallo-Gerfalco-Charming-Apartment-In-Medieval-Village.h123081040.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/124000000/123080000/123075800/123075794/a59cfc66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123080000/123075800/123075794/39b0bbc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123080000/123075800/123075794/918abf7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123080000/123075800/123075794/edc6d031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Montieri

[](https://www.expedia.ca/Montieri-Hotels-Casale-Torricella-Relax-Among-Woods-With-Sea-View.h123075794.Hotel-Information)

CA $335

CA $335 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Montieri-Hotels-Casale-Torricella-Relax-Among-Woods-With-Sea-View.h123075794.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89670000/89668500/89668415/5a71f7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/90000000/89670000/89668500/89668415/0affff28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/90000000/89670000/89668500/89668415/7e5ff4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89670000/89668500/89668415/d50ab1a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Toscana

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Apartment-House-With-Garden-Tuscany-Chianti.h89668415.Hotel-Information)

9.8/10

Exceptional

(74)

"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"

![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg)

Robert M.

CA $194

CA $337 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Apartment-House-With-Garden-Tuscany-Chianti.h89668415.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/6e6f272f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/6671f978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/acc5b1eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/dc51c1fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in impruneta

[](https://www.expedia.ca/Impruneta-Hotels-Beautiful-Tuscan-Farmhouse-With-Large-Spaces-And-Panoramic-Views.h39983368.Hotel-Information)

9.6/10

Exceptional

(25)

"Loved the property and views,the owner was very helpful and informative would definitely come back"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andy P.

CA $134

CA $407 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Impruneta-Hotels-Beautiful-Tuscan-Farmhouse-With-Large-Spaces-And-Panoramic-Views.h39983368.Hotel-Information)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/2a16bc08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/9d75a9e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/aaa36b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/54f20ef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Certaldo

[](https://www.expedia.ca/Certaldo-Hotels-Holiday-Home-Sandra-House-With-Private-Garden-And-Wi-Fi.h106003929.Hotel-Information)

10/10

Exceptional

(1)

"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."

![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg)

Anonymous traveller

CA $137

CA $221 total

includes taxes & fees

Jan 10 - Jan 11, 2026

[](https://www.expedia.ca/Certaldo-Hotels-Holiday-Home-Sandra-House-With-Private-Garden-And-Wi-Fi.h106003929.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-25&endDate=2025-12-26&regionId=9821&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

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Aparthotels

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy&regionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=VILLA)

Private vacation homes

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Residences

[](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy&regionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=RESIDENCE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy&regionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy&regionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=COTTAGE)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy&regionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=CHALET)

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## Top Siena Hotel Reviews

![Villa del Sole Siena](https://images.trvl-media.com/lodging/9000000/8680000/8674600/8674503/a259e0b9_y.jpg)

### Villa del Sole Siena

10/10 Excellent

"Amazing rooms and service!!"

[](https://expedia.ca/Siena-Hotels-Villa-Del-Sole-Siena.h8674503.Hotel-Information)

![Hotel Minerva](https://images.trvl-media.com/lodging/1000000/800000/800000/799995/bc9bd928_y.jpg)

### Hotel Minerva

10/10 Excellent

"Helpful staff and overall vibe. "

[](https://expedia.ca/Siena-Hotels-Hotel-Minerva.h799995.Hotel-Information)

![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg)

### Hotel Athena

10/10 Excellent

"Excellent hotel, very helpful staff, highly recommended "

[](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information)

![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/7edddb53_y.jpg)

### Hotel Italia

10/10 Excellent

"This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended"

[](https://expedia.ca/Siena-Hotels-Hotel-Italia.h996973.Hotel-Information)

![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/9acb6317_y.jpg)

###  Palazzo Ravizza

10/10 Excellent

"Ideal in every way."

[](https://expedia.ca/Siena-Hotels-Pensione-Palazzo-Ravizza.h1760168.Hotel-Information)

![Hotel Certosa Di Maggiano](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/edea64a5_y.jpg)

### Hotel Certosa Di Maggiano

10/10 Excellent

"La habitación muy amplia, teníamos armario vestidor, sala, habitación amplia y un gran baño. Excelente la atención del personal. El lugar mágico maravilloso de epoca"

[](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information)

![Hotel Palazzetto Rosso](https://images.trvl-media.com/lodging/17000000/16290000/16288700/16288621/59460b3a_y.jpg)

### Hotel Palazzetto Rosso

10/10 Excellent

"Amazing"

[](https://expedia.ca/Siena-Hotels-Hotel-Palazzetto-Rosso.h16288621.Hotel-Information)

![Hotel Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/a501ded1_y.jpg)

### Hotel Chiusarelli

10/10 Excellent

"The room was very clean and the bathroom was nice. The staff was very helpful especially because we had personal issues to deal with and places we had to get to for resolution. They helped us navigate several things that we could not have done on our own. We are grateful! "

[](https://expedia.ca/Siena-Hotels-Hotel-Chiusarelli.h1110843.Hotel-Information)

![Villa Scacciapensieri Boutique Hotel](https://images.trvl-media.com/lodging/3000000/2700000/2693500/2693499/b46a6593_y.jpg)

### Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The villa was wonderful and absolutely beautiful. My friends and I absolutely loved our stay here. "

[](https://expedia.ca/Siena-Hotels-Villa-Scacciapensieri-Boutique-Hotel.h2693499.Hotel-Information)

## Find out more about Siena

## Siena Vacation Homes information

| Number of reviews | 143                |
| ----------------- | ------------------ |
| Accommodation     | 121 Vacation Homes |
| Lowest Price      | CA $162            |
| Highest Price     | CA $5,550          |

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- [Lgbt Friendly Hotels in Siena City Centre ](https://www.expedia.ca/Siena-City-Centre-Siena-Hotels-LGBT-Friendly-Hotel.0-n553248633938945205-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
- [Siena City Centre Hotels ](https://www.expedia.ca/Siena-City-Centre-Siena-Hotels.0-n553248633938945205-0.Travel-Guide-Filter-Hotels)
- [Siena Historical Center Hotels ](https://www.expedia.ca/Siena-Historical-Center-Siena-Hotels.0-n6285925-0.Travel-Guide-Filter-Hotels)
- [Lgbt Friendly Hotels in Sovicille ](https://www.expedia.ca/Sovicille-Hotels-LGBT-Friendly-Hotel.0-0-d602594-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
- [Sovicille Hotels ](https://www.expedia.ca/Sovicille-Hotels.d602594.Travel-Guide-Hotels)
- [Taverne d'Arbia Hotels ](https://www.expedia.ca/Taverne-DArbia-Hotels.d3000388927.Travel-Guide-Hotels)
- [Vagliagli Hotels ](https://www.expedia.ca/Vagliagli-Hotels.d6047102.Travel-Guide-Hotels)
- [Aparthotels in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Apart-Hotels.d6047917-aaApartHotels.Travel-Guide-Accommodation)
- [B&B in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Bed-And-Breakfast.d6047917-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Chalets.d6047917-aaChalets.Travel-Guide-Accommodation)
- [Guest Houses in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Guest-Houses.d6047917-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Hostels.d6047917-aaHostels.Travel-Guide-Accommodation)
- [Inns in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Inns.d6047917-aaInns.Travel-Guide-Accommodation)
- [Resorts in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Resort-Hotels.d6047917-aaResortHotels.Travel-Guide-Accommodation)
- [Villa Parigini Hotels ](https://www.expedia.ca/Villa-Parigini-Hotels.d553248622847106390.Travel-Guide-Hotels)
- [Resorts in Villa ](https://www.expedia.ca/Villa-Resort-Hotels.d553248635118822693-aaResortHotels.Travel-Guide-Accommodation)
- [Ville di Corsano Hotels ](https://www.expedia.ca/Ville-Di-Corsano-Hotels.d6361513.Travel-Guide-Hotels)
- [Volte Basse Hotels ](https://www.expedia.ca/Volte-Basse-Hotels.d3000416925.Travel-Guide-Hotels)

- [Flights to Province of Siena ](https://www.expedia.ca/Destinations-In-Province-Of-Siena.d6047850.Flight-Destinations)
- [Flights from Taverne d'Arbia ](https://www.expedia.ca/lp/flights/3000388927/flights-from-taverne-darbia)
- [Flights from Val di Pugna ](https://www.expedia.ca/lp/flights/553248635149838501/flights-from-val-di-pugna)
- [Flights from London (LHR) to Siena (SAY) ](https://www.expedia.ca/lp/flights/lhr/say/london-to-siena)
- [Flights from Ottawa (YOW) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yow/say/ottawa-to-siena)
- [Flights from Québec (YQB) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yqb/say/quebec-to-siena)
- [Flights from Montreal (YUL) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yul/say/montreal-to-siena)
- [Flights from Vancouver (YVR) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yvr/say/vancouver-to-siena)
- [Flights from Calgary (YYC) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yyc/say/calgary-to-siena)
- [Flights from Toronto (YYZ) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yyz/say/toronto-to-siena)

- [Visit Badesse ](https://www.expedia.ca/Badesse.dx553248635118858455)
- [Fortezza Medicea ](https://www.expedia.ca/Fortezza-Medicea-Siena-Historical-Center.d6287282.Vacation-Attraction)
- [Visit Le Tolfe ](https://www.expedia.ca/Le-Tolfe.dx553248622897701422)
- [Monteriggioni Castle ](https://www.expedia.ca/Monteriggioni-Castle-Monteriggioni.d6258231.Vacation-Attraction)
- [Visit Monteriggioni ](https://www.expedia.ca/Monteriggioni.dx5722)
- [Visit Monteroni d'Arbia ](https://www.expedia.ca/Monteroni-DArbia.dx6053877)
- [Province of Siena Vacations ](https://www.expedia.ca/Province-Of-Siena.d6047850.Destination-Travel-Guides)
- [Visit Province of Siena ](https://www.expedia.ca/Province-Of-Siena.dx6047850)
- [Visit San Giovanni A Cerreto ](https://www.expedia.ca/San-Giovanni-A-Cerreto.dx553248622859516344)
- [Visit San Rocco a Pilli ](https://www.expedia.ca/San-Rocco-A-Pilli.dx6285685)
- [Visit Siena City Centre ](https://www.expedia.ca/Siena-Siena-City-Centre.dx553248633938945205)
- [Visit Siena Historical Center ](https://www.expedia.ca/Siena-Siena-Historical-Center.dx6285925)
- [Visit Ville di Corsano ](https://www.expedia.ca/Ville-Di-Corsano.dx6361513)

- [Car rental Monteriggioni ](https://www.expedia.ca/Car-Rentals-In-Monteriggioni.d5722.Car-Rental-Guide)

- [Province of Siena Vacation Rentals ](https://www.expedia.ca/Destinations-In-Province-Of-Siena.d6047850.Vacation-Rental-Destinations)

- [Things to do in Monteriggioni ](https://www.expedia.ca/Things-To-Do-In-Monteriggioni.d5722.Travel-Guide-Activities)
- [Things to do in Province of Siena ](https://www.expedia.ca/Things-To-Do-In-Province-Of-Siena.d6047850.Travel-Guide-Activities)
- [Things to do in Quercegrossa ](https://www.expedia.ca/Things-To-Do-In-Quercegrossa.d6047905.Travel-Guide-Activities)
- [Things to do in Sovicille ](https://www.expedia.ca/Things-To-Do-In-Sovicille.d602594.Travel-Guide-Activities)

- [Book Vacation Homes in Siena on Expedia.it ](https://www.expedia.it/Siena-Case-Vacanze-Private.d9821-aaCaseVacanzePrivate.Guida-Viaggi-Alloggi)