Title: Villa Vacation Rentals from CA $101: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Villa](https://expedia.ca/Villa-Hotels.d553248635118822693.Travel-Guide-Hotels)[Villa Car Rentals](https://expedia.ca/Car-Rentals-In-Villa.d553248635118822693.Car-Rental-Guide)[Villa Vacation Packages](https://expedia.ca/Villa.d553248635118822693.Destination-Travel-Guides)

![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium)

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635118822693&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248635118822693&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=553248635118822693&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=553248635118822693&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Villa vacation rentals

![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)

![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.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)

### Townhouse in Loro Ciuffenna

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

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

CA $220

CA $242 total

includes taxes & fees

Mar 24 - Mar 25

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

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/12ea27d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/96a7251a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/c5858744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room, City View](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/f7c15fe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in San Gimignano City Centre

[](https://www.expedia.ca/San-Gimignano-Hotels-La-Casa-Di-Ines.h117149866.Hotel-Information)

9.0/10

Wonderful

(9 reviews)

"Love this town. Location is great "

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

William

CA $111

CA $131 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/San-Gimignano-Hotels-La-Casa-Di-Ines.h117149866.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/190e02d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Single Room](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/914c3e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/64c8d4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/a47cb16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Siena

[](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

9.8/10

Exceptional

(16 reviews)

"Great host, lovely place near Siena"

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

Prem

CA $133

CA $153 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

![Studio, Patio, Ground Floor | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/291b1398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, Patio, Ground Floor | Private kitchen](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/04effc95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom, Patio (3 people)](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/dd9dbe0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/d64344d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Siena

[](https://www.expedia.ca/Siena-Hotels-Fullino-Nero.h2524503.Hotel-Information)

9.6/10

Exceptional

(50 reviews)

"Great stay! Clean rooms with air conditioning. Beautiful grounds "

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

Christian

CA $143

CA $164 total

includes taxes & fees

Apr 11 - Apr 12

[](https://www.expedia.ca/Siena-Hotels-Fullino-Nero.h2524503.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/994aad7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, soundproofing, free WiFi](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/2b26409c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/aba3f4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/735b790e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Gaiole in Chianti

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-L-Eroico.h22746331.Hotel-Information)

10/10

Exceptional

(13 reviews)

"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."

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

Perry

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-L-Eroico.h22746331.Hotel-Information)

![Food court](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/cb376ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Apartment, 1 Bedroom, Terrace | Terrace/patio](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/ccba610a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (for 2 - 4 People)](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/53451d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (for 4 - 6 People) | Terrace/patio](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/4cdc2384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Monteriggioni

[](https://www.expedia.ca/Monteriggioni-Hotels-Antico-Borgo-Poggiarello.h3620800.Hotel-Information)

9.0/10

Wonderful

(20 reviews)

"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "

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

James Bakley

CA $351

CA $391 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/Monteriggioni-Hotels-Antico-Borgo-Poggiarello.h3620800.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)

![Exterior detail](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/521d6cbe.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)

### Residence in Monte San Savino

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

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

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

![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/eab05df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Concierge desk](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/bdf789e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/4366b9ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Double Room, 1 Double Bed](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/c7b333e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Sovicille

[](https://www.expedia.ca/Sovicille-Hotels-Casa-Di-Campagna-In-Toscana.h12642590.Hotel-Information)

9.4/10

Exceptional

(21 reviews)

"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"

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

Alasdair

CA $133

CA $151 total

includes taxes & fees

Mar 26 - Mar 27

[](https://www.expedia.ca/Sovicille-Hotels-Casa-Di-Campagna-In-Toscana.h12642590.Hotel-Information)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/7fe98579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/a763977c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/65f6d95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/971773cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Sovicille

[](https://www.expedia.ca/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information)

9.0/10

Wonderful

(26 reviews)

"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "

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

Sergey

CA $95

CA $125 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information)

![Interior detail](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/cdb3c15d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | In-room dining](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/424f0a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Garden View](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/3a6f7416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family dining](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/56594a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Siena

[](https://www.expedia.ca/Siena-Hotels-La-Coroncina-Lodging.h15906915.Hotel-Information)

10/10

Exceptional

(42 reviews)

"Fantastic place, and I highly recommend it."

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

Hassan

CA $145

CA $166 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Siena-Hotels-La-Coroncina-Lodging.h15906915.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)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/de85b0c3.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

(10 reviews)

"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 $207

CA $301 total

includes taxes & fees

Mar 24 - Mar 25

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

![Villa, Air conditioning, Courtyard View | Exterior](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/6b3321e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/fee64891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/6427b5b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa, Air conditioning, Courtyard View | Property grounds](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/1f2094c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Monteriggioni

[](https://www.expedia.ca/Monteriggioni-Hotels-Villa-Montecastello.h126444856.Hotel-Information)

CA $234

CA $262 total

includes taxes & fees

Apr 3 - Apr 4

[](https://www.expedia.ca/Monteriggioni-Hotels-Villa-Montecastello.h126444856.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/4c3be6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/c9ef69ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/36dbdc56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast served, Italian cuisine, alfresco dining ](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/bfbda0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in San Casciano in Val di Pesa

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information)

9.6/10

Exceptional

(100 reviews)

"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "

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

rose

CA $209

CA $237 total

includes taxes & fees

Mar 24 - Mar 25

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33150000/33140400/33140330/1e065a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room | View from room](https://images.trvl-media.com/lodging/34000000/33150000/33140400/33140330/358911f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/34000000/33150000/33140400/33140330/d353f2da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33150000/33140400/33140330/54bc2210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Siena

[](https://www.expedia.ca/Siena-Hotels-Ca-Bianca.h33140330.Hotel-Information)

10/10

Exceptional

(43 reviews)

"Great time, perfect property and location."

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

Christopher

CA $297

CA $334 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Siena-Hotels-Ca-Bianca.h33140330.Hotel-Information)

![Tasting room](https://images.trvl-media.com/lodging/11000000/10540000/10536200/10536156/bc901666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Double or Twin Room, Air conditioning](https://images.trvl-media.com/lodging/11000000/10540000/10536200/10536156/74f0dd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, 1 Double Bed](https://images.trvl-media.com/lodging/11000000/10540000/10536200/10536156/23aa0514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Concierge desk](https://images.trvl-media.com/lodging/11000000/10540000/10536200/10536156/163ec176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Siena City Centre

[](https://www.expedia.ca/Siena-Hotels-Il-Battistero-Siena-Residenza-DEpoca.h10536156.Hotel-Information)

9.6/10

Exceptional

(200 reviews)

"Room was excellent, location was perfect for seeing Siena and restaurant was also excellent"

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

John

[](https://www.expedia.ca/Siena-Hotels-Il-Battistero-Siena-Residenza-DEpoca.h10536156.Hotel-Information)

![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/a247f3f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/e87f673d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/c8ba4843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/05e1fe83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Castellina in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Residenzia-Del-Sogno.h25163522.Hotel-Information)

9.6/10

Exceptional

(15 reviews)

"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "

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

Katherine

CA $178

CA $202 total

includes taxes & fees

Mar 24 - Mar 25

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Residenzia-Del-Sogno.h25163522.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/a64418f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/de3fa368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, body treatments, body wraps, body scrubs](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/a7311095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/d186b654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in San Casciano in Val di Pesa

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-BB-Le-Dimore-Mezza-Costa.h27397624.Hotel-Information)

9.4/10

Exceptional

(25 reviews)

"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"

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

Raymundo

CA $121

CA $139 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-BB-Le-Dimore-Mezza-Costa.h27397624.Hotel-Information)

![Breakfast area](https://images.trvl-media.com/lodging/5000000/4670000/4668200/4668168/cad07d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment, Kitchenette | Balcony](https://images.trvl-media.com/lodging/5000000/4670000/4668200/4668168/aac0ce8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/5000000/4670000/4668200/4668168/24756513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4670000/4668200/4668168/120b913f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Civitella in Val di Chiana

[](https://www.expedia.ca/Civitella-In-Val-Di-Chiana-Hotels-Locanda-Antico-Borgo.h4668168.Hotel-Information)

9.2/10

Wonderful

(20 reviews)

"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "

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

Mr Andy

CA $163

CA $179 total

includes taxes & fees

Mar 24 - Mar 25

[](https://www.expedia.ca/Civitella-In-Val-Di-Chiana-Hotels-Locanda-Antico-Borgo.h4668168.Hotel-Information)

![Panoramic Apartment](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/de61baae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/f41ed065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![32-inch TV with cable channels](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/4f6d217b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/b87dac4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Impruneta

[](https://www.expedia.ca/Impruneta-Hotels-Residence-Il-Connubio.h3620731.Hotel-Information)

8.8/10

Excellent

(32 reviews)

"Such a cute little place! Very clean and easy to get around! Would highly recommend!"

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

Desiree

[](https://www.expedia.ca/Impruneta-Hotels-Residence-Il-Connubio.h3620731.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/1f917275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/848fae17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Studio, Valley View | Living area](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/59370526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/ac32e408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Certaldo Alto

[](https://www.expedia.ca/Certaldo-Hotels-Borgo-Antico-Residence.h110872226.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Great place to relax take in the local culture and enjoy Tuscany."

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

jane

CA $102

CA $157 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Certaldo-Hotels-Borgo-Antico-Residence.h110872226.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=2026-04-06&endDate=2026-04-07&regionId=553248635118822693&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Villa%2C+Radda+in+Chianti%2C+Tuscany%2C+Italy&regionId=553248635118822693&latLong=43.49123%2C11.390555&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VILLA)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Villa%2C+Radda+in+Chianti%2C+Tuscany%2C+Italy&regionId=553248635118822693&latLong=43.49123%2C11.390555&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Villa%2C+Radda+in+Chianti%2C+Tuscany%2C+Italy&regionId=553248635118822693&latLong=43.49123%2C11.390555&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Villa%2C+Radda+in+Chianti%2C+Tuscany%2C+Italy&regionId=553248635118822693&latLong=43.49123%2C11.390555&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=APART_HOTEL)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Villa%2C+Radda+in+Chianti%2C+Tuscany%2C+Italy&regionId=553248635118822693&latLong=43.49123%2C11.390555&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Villa%2C+Radda+in+Chianti%2C+Tuscany%2C+Italy&regionId=553248635118822693&latLong=43.49123%2C11.390555&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CONDO)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Villa%2C+Radda+in+Chianti%2C+Tuscany%2C+Italy&regionId=553248635118822693&latLong=43.49123%2C11.390555&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=RESIDENCE)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Villa%2C+Radda+in+Chianti%2C+Tuscany%2C+Italy&regionId=553248635118822693&latLong=43.49123%2C11.390555&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CHALET)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

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

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FVilla-Vacation-Rentals.d553248635118822693.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FVilla-Vacation-Rentals.d553248635118822693.Travel-Guide-VacationRentals)

## Top Villa Hotel Reviews

![Hotel Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/f43eb5fd_y.jpg)

### Hotel Chiusarelli

8/10 Good

"The hotel was just outside of the town, so the location was good. It was a beautiful property. The breakfast was good. Just be prepared to walk stairs. No lifts. But overall, good. "

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

![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/5eddd92b_y.jpg)

###  Palazzo Ravizza

10/10 Excellent

"This is a gem and well worth the stay!!! So so amazing"

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

![Villa Scacciapensieri Boutique Hotel](https://images.trvl-media.com/lodging/3000000/2700000/2693500/2693499/7ece5a56_y.jpg)

### Villa Scacciapensieri Boutique Hotel

8/10 Good

"Stayed in this villa for a couple of nights. It’s a great option if you’re looking to escape the hustle and bustle of the city center. The location is lovely, with birds chirping in the background. The rooms were small, but they had all the necessary amenities for travelers. I had dinner and breakfast once each day. While the food was sufficient, I think it would be better to have more options given the 4-star rating of the property. The staff members were helpful and friendly."

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

![Hotel Leon Bianco](https://images.trvl-media.com/lodging/2000000/1320000/1315000/1314959/6c69e565_y.jpg)

### Hotel Leon Bianco

10/10 Excellent

"The best hotel we stayed during this trip. I recommend it to anyone."

[](https://expedia.ca/San-Gimignano-Hotels-Hotel-Leon-Bianco.h1314959.Hotel-Information)

![NH Siena](https://images.trvl-media.com/lodging/1000000/20000/15800/15716/w3840h2562x0y0-25695984_y.jpg)

### NH Siena

10/10 Excellent

"I didn't use it. I only stayed one night."

[](https://expedia.ca/Siena-Hotels-NH-Siena.h15716.Hotel-Information)

![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/e3da527a_y.jpg)

### Hotel Italia

10/10 Excellent

"Very close to the bus and train station, lovely staff, clean room but a bit too warm even in February and no water kettle in the room, which was a bit surprising. "

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

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

### Hotel Minerva

8/10 Good

"Property was clean a tidy, was a little dated but still nice, view over Siena from the terrace was stunning. Staff were helpful and friendly giving us a map and guide of places of interest in the town. Included breakfast had great options and car park was convenient and safe."

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

![Radisson Blu Hotel, Florence](https://images.trvl-media.com/lodging/1000000/20000/14500/14476/efa5cbd4_y.jpg)

### Radisson Blu Hotel, Florence

10/10 Excellent

"The hotel was great, just the location was a little difficult to get in."

[](https://expedia.ca/Florence-Hotels-Conference-Florentia-Hotel.h14476.Hotel-Information)

![La Certosa di Pontignano](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/8b3eb5da_y.jpg)

### La Certosa di Pontignano

6/10 Okay

"Here is a polished version of your review with improved grammar and structure, keeping your message clear and balanced: --- Great and beautiful place. The food is also very good, and the overall atmosphere is charming. However, the bed was terrible. The mattress was old, and the springs made it very uncomfortable, so I couldn’t sleep well. I’ve stayed in many different hotels and have never experienced such a bad bed. I understand that the concept and vibe of the place are meant to feel historic or classic, but for a property of this level, the bed should match the quality of the rest of the experience. Upgrading the mattresses would make a big difference."

[](https://expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information)

## Find out more about Villa

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Villa. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
- All accommodation types in Villa

### Trending destinations on Expedia.ca

- [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
- [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals)
- [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals)
- [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals)
- [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals)
- [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations)
- [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals)
- [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals)
- [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals)
- [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals)
- [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
- [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals)
- [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals)
- [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Resorts in Villa ](https://expedia.ca/Villa-Resort-Hotels.d553248635118822693-aaResortHotels.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Villa?

### What's the top vacation rental in Villa?

### What’s there to see and do in Villa?

### What’s a vacation rental in Villa like?

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app