Title: Castiglion Fiorentino Vacation Rentals from $88: Search Short-Term Rentals | Expedia.com

[Castiglion Fiorentino Travel Guide](https://expedia.com/Castiglion-Fiorentino.dx6047858)[Hotels in Castiglion Fiorentino](https://expedia.com/Castiglion-Fiorentino-Hotels.d6047858.Travel-Guide-Hotels)[Flights to Castiglion Fiorentino](https://expedia.com/Cheap-Flights-To-Castiglion-Fiorentino.d6047858.Travel-Guide-Flights)[Things to do in Castiglion Fiorentino](https://expedia.com/Things-To-Do-In-Castiglion-Fiorentino.d6047858.Travel-Guide-Activities)[Car Rentals in Castiglion Fiorentino](https://expedia.com/Car-Rentals-In-Castiglion-Fiorentino.d6047858.Car-Rental-Guide)[Castiglion Fiorentino Vacation Packages](https://expedia.com/Castiglion-Fiorentino.d6047858.Destination-Travel-Guides)

![Castiglion Fiorentino e i girasoli della Val di Chio](https://images.trvl-media.com/place/6047858/283772a8-9464-465e-a2df-85ffd89fc89a.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Pigellino

![](https://images.trvl-media.com/place/6047858/283772a8-9464-465e-a2df-85ffd89fc89a.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## Check prices for these dates

In two weeks

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6047858&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)

In two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=6047858&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=6047858&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=6047858&startDate=2026-07-10&endDate=2026-07-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Castiglion Fiorentino vacation rentals

![Exterior](https://images.trvl-media.com/lodging/49000000/48620000/48613700/48613662/ab9da5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily cooked-to-order breakfast](https://images.trvl-media.com/lodging/49000000/48620000/48613700/48613662/dac9c270.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double or Twin Room | Minibar, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48620000/48613700/48613662/6530f866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/49000000/48620000/48613700/48613662/148c0133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### San Michele al Borgo

[](https://www.expedia.com/Castiglion-Fiorentino-Hotels-Suite-San-Michele.h48613662.Hotel-Information)

Castiglion Fiorentino

9.8/10

Exceptional

(9 reviews)

"Excellent staff and tasty breakfast!"

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

Vern

$101 nightly

$116 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Castiglion-Fiorentino-Hotels-Suite-San-Michele.h48613662.Hotel-Information)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/2f7e4438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/58ae2bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/29e7195d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/093f1a7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relais La Saracina

[](https://www.expedia.com/Pienza-Hotels-Relais-La-Saracina.h8195080.Hotel-Information)

Pienza

[](https://www.expedia.com/Pienza-Hotels-Relais-La-Saracina.h8195080.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/b50d05a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Steam room, Turkish bath, body scrubs, massages](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/e763d814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/7a95d976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Cassia di Baccano

[](https://www.expedia.com/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information)

Loro Ciuffenna

9.4/10

Exceptional

(23 reviews)

"The staff were great and the villa was amazing"

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

Ralphvincent

$158 nightly

$174 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information)

![Panoramic Cottage, 1 Bedroom | Exterior](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/020483c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Cottage, 1 Bedroom | Premium bedding, desk, laptop workspace, soundproofing](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/83ad69a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/a39f2057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/6e2ad2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Affitacamere Maria Gabriella

[](https://www.expedia.com/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information)

Pienza

9.8/10

Exceptional

(51 reviews)

"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "

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

Lenise

[](https://www.expedia.com/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/f0bca152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/5c9c109c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/65f08668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/08c45c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury resort in the Tuscan countryside

[](https://www.expedia.com/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.Hotel-Information)

Trequanda

[](https://www.expedia.com/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.Hotel-Information)

![Suite, 2 Bedrooms | Courtyard view](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/b9cf6769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/972c2d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/36131190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/17f0963e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### L'Olmo

[](https://www.expedia.com/Pienza-Hotels-LOlmo.h12569107.Hotel-Information)

Pienza

10/10

Exceptional

(22 reviews)

"Absolutely first class and friendly Perfect location "

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

Jennifer

$458 nightly

$509 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Pienza-Hotels-LOlmo.h12569107.Hotel-Information)

![1 treatment room, massages](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/9867dcf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, Terrace, Valley View | Minibar, in-room safe, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/2f810565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/ba51ed0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/ce312570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casanova - Panoramic Rooms and Suites

[](https://www.expedia.com/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information)

San Quirico d'Orcia

9.2/10

Wonderful

(79 reviews)

"Fantastic place"

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

Clifford

$160 nightly

$181 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information)

![Lunch and dinner served, local cuisine](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/98406b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch and dinner served, local cuisine](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/13e470bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/277a67f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/521d6cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castello di Gargonza

[](https://www.expedia.com/Monte-San-Savino-Hotels-Castello-Di-Gargonza.h21339462.Hotel-Information)

Monte San Savino

9.2/10

Wonderful

(40 reviews)

"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."

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

David

$282 nightly

$315 total

Apr 17 - Apr 18

Total with taxes and fees

[](https://www.expedia.com/Monte-San-Savino-Hotels-Castello-Di-Gargonza.h21339462.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/d732a716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room | Bathroom | Free toiletries, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/8842009b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/a8e96dc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, Terrace | Desk, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/93858826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Piccola Locanda

[](https://www.expedia.com/Chiusi-Hotels-La-Piccola-Locanda.h42001140.Hotel-Information)

Chiusi

8.6/10

Excellent

(9 reviews)

"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "

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

Jeffery

$118 nightly

$133 total

Mar 28 - Mar 29

Total with taxes and fees

[](https://www.expedia.com/Chiusi-Hotels-La-Piccola-Locanda.h42001140.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/39e29e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Suite, Hot Tub (SPA) | Private spa tub](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/8f72c3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/9c2d8838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 1 Double Bed | Living room | Flat-screen TV](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/274ea02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Abbadia Sicille Relais

[](https://www.expedia.com/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information)

Trequanda

8.8/10

Excellent

(168 reviews)

"Room was beyond expectations. Helpful staff and overall great experience. "

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

Robert

$111 nightly

$126 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information)

![Food and drink](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/4a89a1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double or Twin Room, 1 Bedroom | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/47a2d1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast buffet](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/cd7670ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel San Gregorio

[](https://www.expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information)

Pienza

9.4/10

Exceptional

(137 reviews)

"This hotel was the highlight of our Tuscany trip. It is very well decorated, stunning italian furniture and arts on the wall. There is a restaurant for dining. About 2 minutes walking from Pienza old town entrance. Staff was super nice, even their mascot, an yellow cat, came to greet us. It is a must come back for us."

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

Edison

$149 nightly

$171 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information)

![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/258f72ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/c755ff2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/920701e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room (Camera 2) | Premium bedding, down comforters, individually furnished, desk](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/38f4bf63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa di Sotto

[](https://www.expedia.com/Castelnuovo-Berardenga-Hotels-Villa-Di-Sotto.h2432264.Hotel-Information)

Castelnuovo Berardenga

9.4/10

Exceptional

(28 reviews)

"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."

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

Amelia

$159 nightly

$174 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Castelnuovo-Berardenga-Hotels-Villa-Di-Sotto.h2432264.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/8dbfb990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/236bbc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Elite Apartment | Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/fbb1db35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Elite Apartment | Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/c7f9cf0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Albergo Diffuso Borgo Santo

[](https://www.expedia.com/Asciano-Hotels-Albergo-Diffuso-Borgo-Santo.h96934275.Hotel-Information)

Asciano

$222 nightly

$251 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Asciano-Hotels-Albergo-Diffuso-Borgo-Santo.h96934275.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/0aaa13a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (EUR 10 per person)](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/8011dd87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/cabc4072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, Balcony | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/2ef8f95c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Meublé Il Riccio

[](https://www.expedia.com/Montepulciano-Hotels-Meuble-Il-Riccio.h46279780.Hotel-Information)

Montepulciano

9.6/10

Exceptional

(90 reviews)

"Amazing room staff atmoshpehere, there is no other hotel my wife will stay at in the heart of the town."

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

Michael.

$157 nightly

$178 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Montepulciano-Hotels-Meuble-Il-Riccio.h46279780.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/782fdb3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/8b91ef4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/cdd9a264.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/dc2ef8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Borgo Lucignanello Bandini

[](https://www.expedia.com/Montalcino-Hotels-Borgo-Lucignanello-Bandini.h11031336.Hotel-Information)

Montalcino

9.4/10

Exceptional

(12 reviews)

"Beautiful stay "

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

Marc

$303 nightly

$343 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Montalcino-Hotels-Borgo-Lucignanello-Bandini.h11031336.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/16000000/15440000/15434500/15434499/7fc2c578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/16000000/15440000/15434500/15434499/e040eb5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/16000000/15440000/15434500/15434499/c32d3de0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15440000/15434500/15434499/593e3ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa La Ginestra

[](https://www.expedia.com/Subbiano-Hotels-Villa-La-Ginestra.h15434499.Hotel-Information)

Subbiano

9.6/10

Exceptional

(5 reviews)

"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."

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

Philippe

[](https://www.expedia.com/Subbiano-Hotels-Villa-La-Ginestra.h15434499.Hotel-Information)

![Food court](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/0263d307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/26e5f82d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch, dinner served; local cuisine, alfresco dining ](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/0ce3602b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/bfee31ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Locanda di San Francesco

[](https://www.expedia.com/Montepulciano-Hotels-La-Locanda-Di-San-Francesco.h7272465.Hotel-Information)

Montepulciano

9.8/10

Exceptional

(133 reviews)

"Spotless, clean. Staff were friendly. Location and view was spectacular"

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

Kim

$148 nightly

$168 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Montepulciano-Hotels-La-Locanda-Di-San-Francesco.h7272465.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/17ae36fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/12afb28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/a1afa9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residenza Fabroni

[](https://www.expedia.com/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information)

Montepulciano

8.8/10

Excellent

(96 reviews)

"gorgeous historical property, very attentive host, great location"

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

Sarah

$76 nightly

$88 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information)

![Suite Aria | Terrace/patio](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/17c800cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/7ee71db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/6f74c993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily cooked-to-order breakfast](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/4522b02a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Delcorto Suites

[](https://www.expedia.com/Montepulciano-Hotels-Delcorto-Suites.h95240092.Hotel-Information)

Montepulciano

10/10

Exceptional

(35 reviews)

"Wonderful "

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

Rocio Q

$177 nightly

$199 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Montepulciano-Hotels-Delcorto-Suites.h95240092.Hotel-Information)

![Courtyard](https://images.trvl-media.com/lodging/1000000/580000/573300/573299/45afcf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/580000/573300/573299/f10ff9a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden views ](https://images.trvl-media.com/lodging/1000000/580000/573300/573299/49f6e464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/1000000/580000/573300/573299/5d45374a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fontelunga Hotel & Villas

[](https://www.expedia.com/Arezzo-Hotels-Fontelunga-Hotel-Villas.h573299.Hotel-Information)

Foiano della Chiana

10/10

Exceptional

(5 reviews)

"Amazing stay at this hotel I would recommend it. Great hospitality, clean and picture postcard views. "

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

Liam

[](https://www.expedia.com/Arezzo-Hotels-Fontelunga-Hotel-Villas.h573299.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.com/Hotel-Search?startDate=2026-04-03&endDate=2026-04-04&regionId=6047858&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Castiglion+Fiorentino%2C+Tuscany%2C+Italy&regionId=6047858&latLong=43.341667%2C11.923695&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Castiglion+Fiorentino%2C+Tuscany%2C+Italy&regionId=6047858&latLong=43.341667%2C11.923695&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=VILLA)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Castiglion+Fiorentino%2C+Tuscany%2C+Italy&regionId=6047858&latLong=43.341667%2C11.923695&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=VACATION_HOME)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Castiglion+Fiorentino%2C+Tuscany%2C+Italy&regionId=6047858&latLong=43.341667%2C11.923695&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=CABIN)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Castiglion+Fiorentino%2C+Tuscany%2C+Italy&regionId=6047858&latLong=43.341667%2C11.923695&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=APART_HOTEL)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Castiglion+Fiorentino%2C+Tuscany%2C+Italy&regionId=6047858&latLong=43.341667%2C11.923695&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Castiglion+Fiorentino%2C+Tuscany%2C+Italy&regionId=6047858&latLong=43.341667%2C11.923695&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=COTTAGE)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Castiglion+Fiorentino%2C+Tuscany%2C+Italy&regionId=6047858&latLong=43.341667%2C11.923695&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=RESIDENCE)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Castiglion+Fiorentino%2C+Tuscany%2C+Italy&regionId=6047858&latLong=43.341667%2C11.923695&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=CHALET)

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## Top Castiglion Fiorentino Hotel Reviews

![Hotel San Gregorio](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd_y.jpg)

### Hotel San Gregorio

10/10 Excellent

"This hotel was the highlight of our Tuscany trip. It is very well decorated, stunning italian furniture and arts on the wall. There is a restaurant for dining. About 2 minutes walking from Pienza old town entrance. Staff was super nice, even their mascot, an yellow cat, came to greet us. It is a must come back for us."

[](https://expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information)

![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/ba2de8ee_y.jpg)

### Hotel Corsignano

10/10 Excellent

"Excelente opção na região da Toscana ótimo hotel, excelente café da manhã e estacionamento disponível na rua proximo"

[](https://expedia.com/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information)

![Albergo San Biagio](https://images.trvl-media.com/lodging/4000000/3230000/3224200/3224141/cd88e58c_y.jpg)

### Albergo San Biagio

10/10 Excellent

"Room was a good size and had a lovely view of Montepulciano old town from the balcony. Staff were friendly. Evening meal in restaurant was good and therecwas a good choice for breakfast. Excellent location and vety good value for money. "

[](https://expedia.com/Montepulciano-Hotels-Albergo-San-Biagio.h3224141.Hotel-Information)

![Il Gentiluomo Hotel & SPA](https://images.trvl-media.com/lodging/9000000/8200000/8198300/8198248/0ffc98e7_y.jpg)

### Il Gentiluomo Hotel & SPA

6/10 Okay

"3 star hotel only"

[](https://expedia.com/Arezzo-Hotels-Hotel-Il-Gentiluomo.h8198248.Hotel-Information)

![Hotel Relais II Chiostro di Pienza](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/45dfbbfc_y.jpg)

### Hotel Relais II Chiostro di Pienza

10/10 Excellent

"A little tired, extremely clean, with an amazing staff"

[](https://expedia.com/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information)

![ Hotel Garden Experience](https://images.trvl-media.com/lodging/2000000/1650000/1640200/1640183/8eb899be_y.jpg)

###  Hotel Garden Experience

4/10 Poor

"The room was very cold, and despite raising this with staff, I was initially told that the heating was functioning correctly. After complaining again, the heating was eventually turned on, which was appreciated; however, the unit was extremely loud and could not be used throughout the evening. The walls are also very thin, and noise from neighbouring rooms is easily heard. The room did not include any tea or coffee facilities, which I would consider a basic expectation for a four-star hotel. I also requested an iron but was informed that one was not available and that I would need to pay €5 for a shirt to be ironed instead. On a positive note, the breakfast was of good quality and the staff were very friendly. However, I would choose to stay at a different hotel on my next visit."

[](https://expedia.com/Citta-Di-Castello-Hotels-Hotel-Garden.h1640183.Hotel-Information)

![Borgo Sant'Ambrogio Resort](https://images.trvl-media.com/lodging/25000000/24050000/24047000/24046952/ec2d862b_y.jpg)

### Borgo Sant'Ambrogio Resort

10/10 Excellent

"It was very clean, excellent service and communication with every staff member was great, location was incredible, and overall a very pleasant stay. If you have the opportunity, the stay is great!"

[](https://expedia.com/Trequanda-Hotels-Borgo-SantAmbrogio-Resort.h24046952.Hotel-Information)

![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/c358cc6c_y.jpg)

### Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly "

[](https://expedia.com/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information)

![Precise Tale Poggio Alla Sala](https://images.trvl-media.com/lodging/91000000/90890000/90888700/90888666/33c1dfc6_y.jpg)

### Precise Tale Poggio Alla Sala

10/10 Excellent

"Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany"

[](https://expedia.com/Montepulciano-Hotels-Precise-Tale-Poggio-Alla-Sala.h90888666.Hotel-Information)

## Find out more about Castiglion Fiorentino

**Everything you need to know about Castiglion Fiorentino vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castiglion Fiorentino vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castiglion Fiorentino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Castiglion Fiorentino vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Castiglion Fiorentino. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castiglion Fiorentino in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $88 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Castiglion Fiorentino rentals**

At Expedia, we put the best Castiglion Fiorentino vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castiglion Fiorentino rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castiglion Fiorentino vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castiglion Fiorentino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Villas in Castiglion Fiorentino ](https://expedia.com/Castiglion-Fiorentino-Villas.d6047858-aaVillas.Travel-Guide-Accommodation)
- [Apartments in Castiglion Fiorentino ](https://expedia.com/Castiglion-Fiorentino-Apartments.d6047858-aaApartments.Travel-Guide-Accommodation)
- [B&B in Castiglion Fiorentino ](https://expedia.com/Castiglion-Fiorentino-Bed-And-Breakfast.d6047858-aaBedAndBreakfast.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Castiglion Fiorentino?

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### How many vacation rentals are there in Castiglion Fiorentino?

### What can I see and do in Castiglion Fiorentino?

### What are vacation rentals like in Castiglion Fiorentino?

### Expedia's Latest Trends

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Flights

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Cars

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- [Florence Vacation](https://expedia.com/Florence.d1222.Destination-Travel-Guides)

Vacation Rentals

- [Florence Rentals](https://expedia.com/Florence-Vacation-Rentals.d1222.Travel-Guide-VacationRentals)

General

- [Visit Follonica](https://expedia.com/Follonica.dx6123914)
- [Visit San Gimignano](https://expedia.com/San-Gimignano.dx11091)
- [Visit Florence](https://expedia.com/Florence.dx1222)
- [Visit Viareggio](https://expedia.com/Viareggio.dx4894)
- [Visit Portoferraio](https://expedia.com/Portoferraio.dx4876)
- [Visit Monte Argentario](https://expedia.com/Monte-Argentario.dx602888)
- [Visit Siena](https://expedia.com/Siena.dx9821)