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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Castelfiorentino and around

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Relax by the serene pool surrounded by a well-maintained walkway and picturesque views.

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

10.0 out of 10, Exceptional, (96)
"Outstanding lodging and within 10 minutes from the San Gimignano City/Center. Side trips were enjoyable and easy to explore. The accommodations in a country villa were very comfortable and our host Alessandro Martini was great to work with. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Relax by the serene pool surrounded by lush greenery and mature trees.

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany

10.0 out of 10, Exceptional, (80)
"Great place. Great host Driveway….needs work "
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Villa Boccaccio
Terrace/patio

Villa Boccaccio

2.0 out of 10, (1)
"Keiner Vor-Ort gewesen. Es war kein Check In möglich trotz Buchungsbestätigung"
The price is €154
includes taxes & fees
10 Aug - 11 Aug
Villa Boccaccio
Montecarlo, 1.5 acres, private pool, walk to restaurants. WIFI Close Lucca
Relax by the serene pool surrounded by lush greenery and a pergola offering shade.

Montecarlo, 1.5 acres, private pool, walk to restaurants. WIFI Close Lucca

9.6 out of 10, Exceptional, (20)
"Beautiful Villa , great location , wonderful Pool and very friendly host"
Montecarlo, 1.5 acres, private pool, walk to restaurants. WIFI Close Lucca
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Enjoy the serene view of rolling hills and a distant hilltop structure from this charming balcony.

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (107)
"We had a lovely stay at the villa. The villa was comfortable, well furnished and had a beautiful view of San Gimignano. The owner was very helpful and responsive. We will definitely stay there again if we visit San Gimignano."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Villa Le Balze Large Private Pool, WiFi
Relax in a Mediterranean-style villa surrounded by lush greenery and scenic views.

Villa Le Balze Large Private Pool, WiFi

9.8 out of 10, Exceptional, (19)
"An excellent choice for a worry-free and comfortable stay."
Villa Le Balze Large Private Pool, WiFi
Villa Poggio Scalette: Elegance meets Comfort amidst ancient olive trees
Outdoor pool

Villa Poggio Scalette: Elegance meets Comfort amidst ancient olive trees

10.0 out of 10, Exceptional, (9)
"Villa Poggio Scalette was truly a dream place to stay on our vacation. The pictures cannot do this beautiful home justice - you have to see it for yourself!! The view, the amazing property, the Tuscan touches in the decorating with all the modern amenities - we already cannot wait to go back!!! We slept so comfortably and had everything we needed at the house for some relaxing afternoons and evenings enjoying wine, good food, and the view :) Our host Simone was very communicative and so helpful...
Villa Poggio Scalette: Elegance meets Comfort amidst ancient olive trees
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Relax by the serene pool surrounded by lush greenery and olive trees.

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

9.6 out of 10, Exceptional, (22)
"The villa was a beautiful home to send our our time in Tuscany, Italy. We enjoyed having our own bedrooms and baths. We had a special meal cooked by a local chef, Rachel. The kitchen worked well for the cooking, and for our breakfasts. The scenery was just breathtaking, and it is just as pictures in books looked like. We very much enjoyed our stay."
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Historic Villa Tuscany
Cozy attic bedroom with a television, framed portrait, and comfortable seating area.

Historic Villa Tuscany

2.0 out of 10, (2)
The price is €147
includes taxes & fees
10 Aug - 11 Aug
Historic Villa Tuscany
Luxury Villa Basilio Chianti
Seasonal outdoor pool

Luxury Villa Basilio Chianti

Luxury Villa Basilio Chianti
TUSCANY - VILLA - MAX PRIVACY - PISCINA CON VISTA PANORAMICA
Relax by the serene pool surrounded by lush green hills and a soothing water feature.

TUSCANY - VILLA - MAX PRIVACY - PISCINA CON VISTA PANORAMICA

10.0 out of 10, Exceptional, (118)
"We had another wonderful stay in Buti. Thank you again Marco."
TUSCANY - VILLA - MAX PRIVACY - PISCINA CON VISTA PANORAMICA
Your panoramic house in Tuscany between vineyards and olive groves.
Surrounded by lush greenery and vineyards, this house offers a tranquil environment.

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (39)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Standalone residence with a traditional Mediterranean architectural style, surrounded by lush greenery.

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (53)
"The house was fantastic and had more than enough space for our large family. What was particularly great was the large table where we always ate before we went to the very large swimming pool."
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Relais Badia a Passignano
Land view from property

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Surrounded by lush greenery, this property features a large rectangular pool and traditional buildings.

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

10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
The price is €2,277
includes taxes & fees
16 Aug - 17 Aug
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Beautiful Villa With Panoramic Views near San Gimignano
Relax by the serene pool surrounded by lush greenery and distant hills.

Beautiful Villa With Panoramic Views near San Gimignano

9.6 out of 10, Exceptional, (73)
"Nice area! We enjoyed the terasse and the pool a lot "
Beautiful Villa With Panoramic Views near San Gimignano
Villa Casa al Sole Large Private Pool, WiFi
Relax by the serene pool surrounded by lush greenery and trees.

Villa Casa al Sole Large Private Pool, WiFi

9.8 out of 10, Exceptional, (20)
"Thank you for a fantastic experience - everything was just right."
Villa Casa al Sole Large Private Pool, WiFi
Exclusive Farmhouse Pool & View of San Gimignano
Enjoy a romantic dinner for two in this charming outdoor dining area with a round table and wicker chairs.

Exclusive Farmhouse Pool & View of San Gimignano

10.0 out of 10, Exceptional, (1)
Exclusive Farmhouse Pool & View of San Gimignano
Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14
Relax by the serene pool surrounded by lush greenery and mature trees.

Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14

9.8 out of 10, Exceptional, (7)
"My family and I stayed here for almost a full week in the spring, and had an amazing time. The host was extremely responsive about the check-in process leading up to the stay, during the stay whenever we had any issues, and even after our stay when we needed to recover an item that was left behind. There were some slight hiccups with the house during our stay (garage door opener was out of batteries one time and the shower drain clogged one time), but the host was proactive as can be and quick...
Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14
Authentic Tuscan country house, dating back to around the year 1000
Enjoy a casual meal with a panoramic view of lush greenery and distant hills from this elevated outdoor dining area.

Authentic Tuscan country house, dating back to around the year 1000

9.6 out of 10, Exceptional, (53)
"We spent our last week of our 3 weeks in Italy in Marila’s home and are so happy we did! The location was fantastic, the home was perfect for us and Marilia was a warm and gracious host. We asked her to help with booking a chef to come in to teach a class, a wine tour and restaurant suggestions and all were fantastic. We would love to go back again!!"
Authentic Tuscan country house, dating back to around the year 1000
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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Top Castelfiorentino Hotel Reviews

Grand Hotel Cavour

Grand Hotel Cavour

10/10 Excellent
"We are staying in a suite for 3 people. I don’t think there is an upgrade to it available."
Joseph 1-night trip
Posted 10 hours ago
Grand Hotel Cavour