Title: San Gimignano Villas from CA $204 | Expedia.ca

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![F02522 San Gimignano, a UNESCO World Heritage Site, Tuscany, Province of Siena, Italy](https://images.trvl-media.com/place/11091/b9b485b8-13ff-42c2-b9b1-de2d359fa8c1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Search San Gimignano Villa Rentals from CA $204

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## Check prices for these dates

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=11091&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=11091&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=11091&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=11091&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for San Gimignano villas

![Exterior](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/87710dcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/80e6ed4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/de29df70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/3a8f67a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa "Arnilù" with Private Pool & Wi-Fi

[](https://www.expedia.ca/San-Gimignano-Hotels-Villa-Arnilu-With-Private-Pool-Wi-Fi.h96139408.Hotel-Information)

San Gimignano

CA $7,512

CA $8,112 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/San-Gimignano-Hotels-Villa-Arnilu-With-Private-Pool-Wi-Fi.h96139408.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/dcfa042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/afb73a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/52aa6660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/25aedd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information)

Gaiole in Chianti

CA $9,616

CA $10,424 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/1e6c21a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/fb904e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/2fd0fef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/c326d5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Milani with Shared Pool, Private Terrace & Wi-Fi

[](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information)

Montespertoli

10/10

Exceptional

(1)

"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"

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

Scott M.

CA $2,618

CA $2,621 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/d88438f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/w745h499x12y7-5d6f59fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/b9fc2e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/96286a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### panoramica casa con piscina privata

[](https://www.expedia.ca/Chiusdino-Hotels-Panoramica-Casa-Con-Piscina-Privata.h27125149.Hotel-Information)

siena

7.0/10

Good

(10)

"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....

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

Olivier B.

[](https://www.expedia.ca/Chiusdino-Hotels-Panoramica-Casa-Con-Piscina-Privata.h27125149.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/c92c20b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/aa63342e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/b48487ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/76c1c946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information)

Colle Val D'Elsa

CA $19,071

CA $19,071 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/b8286297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/4a362287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/b2bb8dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/513cbcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

[](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information)

Radda in Chianti

10/10

Exceptional

(1)

"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."

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

Anonymous traveller

CA $2,602

CA $3,634 total

includes taxes & fees

Dec 25 - Dec 26

[](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/w1920h1279x0y1-a132bf6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/bc5dd1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![9 bedrooms, free WiFi](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/0a5c24e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/09d64836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information)

Castellina in Chianti

CA $7,597

CA $8,405 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108050000/108044000/108043978/b8f65e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108050000/108044000/108043978/e16e4ba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108050000/108044000/108043978/ce82673e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/109000000/108050000/108044000/108043978/9f085457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Cattleya

[](https://www.expedia.ca/Casciana-Terme-Lari-Hotels-Vrbo-Property.h108043978.Hotel-Information)

Casciana Terme

10/10

Exceptional

(1)

"Tout était impeccable. "

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

Stéphane S.

CA $145

CA $204 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Casciana-Terme-Lari-Hotels-Vrbo-Property.h108043978.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/116000000/115910000/115909300/115909202/129066f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Villa, Hill View | Terrace/patio](https://images.trvl-media.com/lodging/116000000/115910000/115909300/115909202/657dbb27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115910000/115909300/115909202/a408caff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/116000000/115910000/115909300/115909202/1168f9c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wine Apartments Florence Lawrence

[](https://www.expedia.ca/Scandicci-Hotels-Wine-Apartments-Florence-Lawrence.h115909202.Hotel-Information)

Scandicci

CA $114

CA $495 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Scandicci-Hotels-Wine-Apartments-Florence-Lawrence.h115909202.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106400000/106395500/106395493/094b0927.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/107000000/106400000/106395500/106395493/be9cfc06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106400000/106395500/106395493/1689c219.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106400000/106395500/106395493/6ff3df28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa dei Renai by Rentbeat

[](https://www.expedia.ca/Signa-Hotels-Casa-Dei-Renai-By-Rentbeat.h106395493.Hotel-Information)

Signa

CA $75

CA $394 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Signa-Hotels-Casa-Dei-Renai-By-Rentbeat.h106395493.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/7f0bb06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/57059e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/7c521815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/633059fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Dei Pavoni - Luxury Villa on top of hills in Florence

[](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Dei-Pavoni-Luxury-Villa-On-Top-Of-Hills-In-Florence.h110132299.Hotel-Information)

Toscana

10/10

Exceptional

(1)

"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "

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

Leopard I.

CA $2,880

CA $3,291 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Dei-Pavoni-Luxury-Villa-On-Top-Of-Hills-In-Florence.h110132299.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/106000000/105350000/105347600/105347550/7e102377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105350000/105347600/105347550/3b8ff1ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105350000/105347600/105347550/20d8811a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105350000/105347600/105347550/fda24de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "A Casa di Franca Villa con piscina"

[](https://www.expedia.ca/Gambassi-Terme-Hotels-A-Casa-Di-Franca-Villa-Nel-Chianti-With-Private-Pool.h105347550.Hotel-Information)

Gambassi Terme

10/10

Exceptional

(1)

"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...

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

Anonymous traveller

CA $1,202

CA $1,798 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Gambassi-Terme-Hotels-A-Casa-Di-Franca-Villa-Nel-Chianti-With-Private-Pool.h105347550.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/bd7589fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/57f40b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![7 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/8f497170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/87d9fa0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Tuscan home between Florence & Siena

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Beautiful-Tuscan-Home-Between-Florence-Siena.h86496746.Hotel-Information)

Florence

10/10

Exceptional

(6)

"Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation"

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

Frank V.

CA $1,164

CA $2,069 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Beautiful-Tuscan-Home-Between-Florence-Siena.h86496746.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/81953563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/ae2c6602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/0e2eec35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/a822b4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information)

Gaiole in Chianti

10/10

Exceptional

(8)

"Country location but easy access to a great local winery/restaurant and the town of Gaiole."

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

russ h.

CA $1,867

CA $1,905 total

includes taxes & fees

Jan 8 - Jan 9, 2026

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/96000000/95200000/95197600/95197595/c0f07cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95200000/95197600/95197595/c7e7eb65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/96000000/95200000/95197600/95197595/w1920h1218x0y4-5123788a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95200000/95197600/95197595/w1920h1218x0y4-15652bd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Altea - Homelike Villas

[](https://www.expedia.ca/Lajatico-Hotels-Villa-Altea-Homelike-Villas.h95197595.Hotel-Information)

Lajatico

10/10

Exceptional

(1)

"Wir hatten eine wunderschöne Woche in einem tollen Haus und mit einem sehr aufmerksamen Gastgeber, danke Riccardo! Die Kommunikation mit der Agentur (Home Villas) war unterirdisch!!! Auf keine Email kam eine Reaktion, außer dass man sich melden würde. Wir wollten vorab einige Dinge abklären (Anzahl der Personen hatte sich reduziert, wäre früherer Check In möglich, etc.), selbst das vorzeitige Anmelden aller Personen mit Ausweisen wurde nicht an den Vermieter weitergeleitet!! Vor Ort gab es...

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

Stephan H.

[](https://www.expedia.ca/Lajatico-Hotels-Villa-Altea-Homelike-Villas.h95197595.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/06053989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/682c69f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/08415ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/89d7e684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information)

Montespertoli

10/10

Exceptional

(38)

"Excellent in every way. Highly recommend"

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

Ed M.

CA $2,101

CA $2,406 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/38e5a789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h863x2y0-ddee714e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/b0a52e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h854x2y0-790f85bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Firenze‼️\~Integer VILLA in hillside 7 places & 4 bathrooms\~

[](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information)

Impruneta

10/10

Exceptional

(3)

"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."

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

Lidija M.

CA $555

CA $726 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/w2189h1640x4y5-0fbf58c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/09a8ec09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/51bd2610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/87c073f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information)

Montespertoli

10/10

Exceptional

(12)

"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"

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

Elise D.

CA $2,069

CA $2,369 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/a34e800d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/a26a2615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/52fb9f8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool, sun loungers](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/65e72921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whole Estate w concierge service & heated pool at 20 minute from Florence center

[](https://www.expedia.ca/Impruneta-Hotels-Tailored-To-YouVilla-Wheated-Pool-And-Concierge-Only-8-Mile-To-Florence-Center.h33956712.Hotel-Information)

impruneta

10/10

Exceptional

(105)

"The Villa and grounds are absolutely beautiful! Caterina and her family members were the most gracious hosts. They could not do enough to make sure we had a "once in a lifetime" multi-generational family trip and truly made us feel like part of their family during our stay. We loved every second of our time in Tuscany and would highly recommend this amazing property."

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

Charles S.

CA $1,306

CA $1,499 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Impruneta-Hotels-Tailored-To-YouVilla-Wheated-Pool-And-Concierge-Only-8-Mile-To-Florence-Center.h33956712.Hotel-Information)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/101000000/100220000/100214800/100214713/bb1e9ba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room | Terrace/patio](https://images.trvl-media.com/lodging/101000000/100220000/100214800/100214713/dd7a1490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/101000000/100220000/100214800/100214713/7495c52c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room | Living area](https://images.trvl-media.com/lodging/101000000/100220000/100214800/100214713/10cf5a53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Tosca

[](https://www.expedia.ca/Peccioli-Hotels-Villa-Tosca.h100214713.Hotel-Information)

Peccioli

CA $2,134

CA $2,347 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Peccioli-Hotels-Villa-Tosca.h100214713.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.

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## Find vacation rentals that suit your style

Apartments

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Villas

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Aparthotels

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Residences

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Cottages

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Condos

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Chalets

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## Top San Gimignano Hotel Reviews

![Hotel Leon Bianco](https://images.trvl-media.com/lodging/2000000/1320000/1315000/1314959/f531fd35_y.jpg)

### Hotel Leon Bianco

10/10 Excellent

"Clean and surprisingly large room, with a spacious closet and bathroom. My room happened to have a window to the inside courtyard. Front desk staff/owner is exceptionally friendly, helpful, and generous. Property located right at the central plaza - cannot be more convenient!"

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

![Residenza d'Epoca Palazzo Buonaccorsi](https://images.trvl-media.com/lodging/6000000/5940000/5933000/5932999/71d708e5_y.jpg)

### Residenza d'Epoca Palazzo Buonaccorsi

10/10 Excellent

"Lovely room, great hosts, convenient location!"

[](https://expedia.ca/San-Gimignano-Hotels-Residenza-DEpoca-Palazzo-Buonaccorsi.h5932999.Hotel-Information)

![San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view](https://images.trvl-media.com/lodging/34000000/33600000/33595600/33595546/52700ac2_y.jpg)

### San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

10/10 Excellent

"This is a beautiful property in a lovely part of the world. Our family enjoyed the property’s spaciousness, beautiful grounds, and location. The kitchen and bathrooms are well-appointed and the dining room/indoor patio had a comforting wood pellet stove that made the room cozy as our family hangout. And we watched Christmas decorations installed in the charming town of San Gimignano."

[](https://expedia.ca/San-Gimignano-Hotels-San-Gimignano-Villa-With-Pool.h33595546.Hotel-Information)

![Hotel Sovestro](https://images.trvl-media.com/lodging/2000000/1530000/1521600/1521591/3fc35bbb_y.jpg)

### Hotel Sovestro

10/10 Excellent

"Great Hotel"

[](https://expedia.ca/San-Gimignano-Hotels-Hotel-Sovestro.h1521591.Hotel-Information)

![Mormoraia](https://images.trvl-media.com/lodging/6000000/5130000/5126300/5126300/1db616da_y.jpg)

### Mormoraia

10/10 Excellent

"This resort is gorgeous and every single staff member was so gracious and friendly! It was a short drive away from San Gimignano which was nice to explore. The restaurant was delicious and their spa was very nice! "

[](https://expedia.ca/San-Gimignano-Hotels-La-Mormoraia.h5126300.Hotel-Information)

![Hotel Bel Soggiorno](https://images.trvl-media.com/lodging/3000000/2550000/2541800/2541764/caa423d4_y.jpg)

### Hotel Bel Soggiorno

10/10 Excellent

"Just a delightful stay at a beautiful hotel with great location. Could not be happier with our stay in all respects!"

[](https://expedia.ca/San-Gimignano-Hotels-Hotel-Bel-Soggiorno.h2541764.Hotel-Information)

![La Cisterna](https://images.trvl-media.com/lodging/3000000/2530000/2520300/2520221/0063883f_y.jpg)

### La Cisterna

10/10 Excellent

"The room was spacious and the hotel is in a great location right in the middle of town. The balcony looked out over the town and landscape. It could not have been prettier. Also the staff was very friendly."

[](https://expedia.ca/San-Gimignano-Hotels-La-Cisterna.h2520221.Hotel-Information)

![Villasanpaolo](https://images.trvl-media.com/lodging/1000000/920000/916100/916031/2ff21fdc_y.jpg)

### Villasanpaolo

10/10 Excellent

"Spa and massage is heavenly, breakfast is amazing!! The property it self is very beautiful and relaxing. The views you get from the property are spectacular, and very close 10 min drive to San Gimignano. "

[](https://expedia.ca/San-Gimignano-Hotels-Villasanpaolo.h916031.Hotel-Information)

![Hotel Pescille - Tuscany Charme](https://images.trvl-media.com/lodging/3000000/2530000/2525300/2525287/e08a63e0_y.jpg)

### Hotel Pescille - Tuscany Charme

10/10 Excellent

"The hotel is beautiful great view of San Gimignano on one side, and the tuscan countryside all around."

[](https://expedia.ca/San-Gimignano-Hotels-Hotel-Pescille.h2525287.Hotel-Information)

## Find out more about San Gimignano

## San Gimignano Villas information

| Number of reviews | 150        |
| ----------------- | ---------- |
| Accommodation     | 85 Villas  |
| Lowest Price      | CA $204    |
| Highest Price     | CA $10,424 |

## Frequently asked questions

### How much do villas in San Gimignano cost?

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- [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)
- [Hotels & Resorts for Couples in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Hotels-Couples-Resorts-Hotels.0-0-d6047917-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Hotels with Waterslides in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Hotels-Hotels-With-Waterslides.0-0-d6047917-tHotelswithWaterslides.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Hotels-Luxury-Hotel.0-0-d6047917-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Hotels-Pet-Friendly-Hotel.0-0-d6047917-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Val d'Elsa Hotels ](https://www.expedia.ca/Val-DElsa-Hotels.d6047917.Travel-Guide-Hotels)
- [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)
- [Varna Hotels ](https://www.expedia.ca/Varna-Hotels.d553248635975876031.Travel-Guide-Hotels)
- [Villa del Monte Hotels ](https://www.expedia.ca/Villa-Del-Monte-Hotels.d6285676.Travel-Guide-Hotels)
- [Farmstay in Volterra ](https://www.expedia.ca/Volterra-Agritourism.d603154-aaAgritourism.Travel-Guide-Accommodation)
- [Aparthotels in Volterra ](https://www.expedia.ca/Volterra-Apart-Hotels.d603154-aaApartHotels.Travel-Guide-Accommodation)
- [Apartments in Volterra ](https://www.expedia.ca/Volterra-Apartments.d603154-aaApartments.Travel-Guide-Accommodation)
- [B&B in Volterra ](https://www.expedia.ca/Volterra-Bed-And-Breakfast.d603154-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Volterra ](https://www.expedia.ca/Volterra-Chalets.d603154-aaChalets.Travel-Guide-Accommodation)
- [Condo Rentals in Volterra ](https://www.expedia.ca/Volterra-Condos.d603154-aaCondos.Travel-Guide-Accommodation)
- [Guest Houses in Volterra ](https://www.expedia.ca/Volterra-Guest-Houses.d603154-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Volterra ](https://www.expedia.ca/Volterra-Hostels.d603154-aaHostels.Travel-Guide-Accommodation)
- [Palaces in Volterra ](https://www.expedia.ca/Volterra-Palaces.d603154-aaPalaces.Travel-Guide-Accommodation)
- [Vacation Homes in Volterra ](https://www.expedia.ca/Volterra-Private-Vacation-Homes.d603154-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Resorts in Volterra ](https://www.expedia.ca/Volterra-Resort-Hotels.d603154-aaResortHotels.Travel-Guide-Accommodation)
- [Villas in Volterra ](https://www.expedia.ca/Volterra-Villas.d603154-aaVillas.Travel-Guide-Accommodation)

- [Flights to Certaldo ](https://www.expedia.ca/Cheap-Flights-To-Certaldo.d603153.Travel-Guide-Flights)
- [Flights from Chicago to Val d'Elsa ](https://www.expedia.ca/lp/flights/178248/6047917/chicago-to-val-delsa)
- [Flights from Colle di Val d'Elsa ](https://www.expedia.ca/lp/flights/4935/flights-from-colle-di-val-delsa)
- [Flights from Poggibonsi ](https://www.expedia.ca/lp/flights/4964/flights-from-poggibonsi)

- [Visit Casole d'Elsa ](https://www.expedia.ca/Casole-DElsa.dx603292)
- [Visit Castel San Gimignano ](https://www.expedia.ca/Castel-San-Gimignano.dx6285675)
- [Visit Colle di Val d'Elsa ](https://www.expedia.ca/Colle-Di-Val-DElsa.dx4935)
- [Collegiate Church of Santa Maria Assunta ](https://www.expedia.ca/Collegiate-Church-Of-Santa-Maria-Assunta-San-Gimignano-City-Centre.d6105346.Vacation-Attraction)
- [Visit Gambassi Terme ](https://www.expedia.ca/Gambassi-Terme.dx602568)
- [Medieval Criminal and Torture Museum ](https://www.expedia.ca/Medieval-Criminal-And-Torture-Museum-San-Gimignano-City-Centre.d6287299.Vacation-Attraction)
- [Monsanto Vacations ](https://www.expedia.ca/Monsanto.d553248622859260555.Destination-Travel-Guides)
- [Visit Pancole ](https://www.expedia.ca/Pancole.dx6361505)
- [Piazza della Cisterna ](https://www.expedia.ca/Piazza-Della-Cisterna-San-Gimignano-City-Centre.d6105348.Vacation-Attraction)
- [Piazza Luigi Pecori ](https://www.expedia.ca/Piazza-Luigi-Pecori-San-Gimignano-City-Centre.d553248635976772612.Vacation-Attraction)
- [Visit Poggibonsi ](https://www.expedia.ca/Poggibonsi.dx4964)
- [Visit San Donnino ](https://www.expedia.ca/San-Donnino.dx6359579)
- [Tenuta Torciano Winery ](https://www.expedia.ca/Tenuta-Torciano-Winery-San-Gimignano.d6252546.Vacation-Attraction)
- [Val d'Elsa Vacations ](https://www.expedia.ca/Val-DElsa.d6047917.Destination-Travel-Guides)
- [Visit Vico d'Elsa ](https://www.expedia.ca/Vico-DElsa.dx3000025842)

- [Car rental Barberino Val d'Elsa ](https://www.expedia.ca/Car-Rentals-In-Barberino-Val-DElsa.d6046188.Car-Rental-Guide)
- [Car rentals near Certaldo Alto ](https://www.expedia.ca/Car-Rentals-In-Certaldo-Alto.d6223743.Car-Rental-Guide)
- [Car rental Certaldo ](https://www.expedia.ca/Car-Rentals-In-Certaldo.d603153.Car-Rental-Guide)
- [Car rental Colle di Val d'Elsa ](https://www.expedia.ca/Car-Rentals-In-Colle-Di-Val-DElsa.d4935.Car-Rental-Guide)
- [Car rental Poggibonsi ](https://www.expedia.ca/Car-Rentals-In-Poggibonsi.d4964.Car-Rental-Guide)
- [Car rentals near San Gimignano City Centre ](https://www.expedia.ca/Car-Rentals-In-San-Gimignano-City-Centre.d553248635810302977.Car-Rental-Guide)
- [Car rentals near San Gimignano Pro Loco Association ](https://www.expedia.ca/Car-Rentals-In-San-Gimignano-Pro-Loco-Association.d553248635974599856.Car-Rental-Guide)
- [Car rentals near Val d'Elsa ](https://www.expedia.ca/Car-Rentals-In-Val-DElsa.d6047917.Car-Rental-Guide)

- [Barberino Val d'Elsa Vacation Rentals ](https://www.expedia.ca/Barberino-Val-DElsa-Vacation-Rentals.d6046188.Travel-Guide-VacationRentals)

- [Things to do in Certaldo ](https://www.expedia.ca/Things-To-Do-In-Certaldo.d603153.Travel-Guide-Activities)
- [Things to do in Colle di Val d'Elsa ](https://www.expedia.ca/Things-To-Do-In-Colle-Di-Val-DElsa.d4935.Travel-Guide-Activities)
- [Things to do in Pancole ](https://www.expedia.ca/Things-To-Do-In-Pancole.d6361505.Travel-Guide-Activities)
- [Things to do in Ulignano ](https://www.expedia.ca/Things-To-Do-In-Ulignano.d6342128.Travel-Guide-Activities)
- [Things to do in Val d'Elsa ](https://www.expedia.ca/Things-To-Do-In-Val-DElsa.d6047917.Travel-Guide-Activities)

- [Book Villas in San Gimignano on Expedia.it ](https://www.expedia.it/San-Gimignano-Ville.d11091-aaVille.Guida-Viaggi-Alloggi)