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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Villas in Castelfiorentino and around

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

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

10.0 out of 10, Exceptional, (84)
"Alessandro was a fantastic host! He always made us feel right at home. Addressing all of our questions regarding the local area. The property was exactly what we expected. The surrounding area was magnificent. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Outdoor pool

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

10.0 out of 10, Exceptional, (95)
"Our host was responsive to our questions and needs. He also arranged a women to come to the property and prepare dinner for us on two separate nights.To our host, thank you."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Outdoor pool, a heated pool

Luxury converted barn with hilltop views in chianti wine region, Tuscany

10.0 out of 10, Exceptional, (87)
"I wish we could have stayed longer; such a beautiful location. The villa was very nice and comfortable. We enjoyed meals prepared by Serena twice during our visit; she cooked multi-course dinners that were delicious. Highly recommend the property and Serena’s cooking. We look forward to going back!"
Luxury converted barn with hilltop views in chianti wine region, Tuscany
CountryHouse con Piscina Privata 5 min dal centro
Point of interest

CountryHouse con Piscina Privata 5 min dal centro

9.8 out of 10, Exceptional, (8)
"These accomodations were wonderful! So convenient to take the tram to downtown! Host extremely responsive and helpfull."
The price is €448
includes taxes & fees
18 Feb - 19 Feb
CountryHouse con Piscina Privata 5 min dal centro
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Outdoor pool

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
LA QUERCIA ESTATE, QUINTESSENTIAL ITALIAN EXPERIENCE
Outdoor pool, pool loungers

LA QUERCIA ESTATE, QUINTESSENTIAL ITALIAN EXPERIENCE

10.0 out of 10, Exceptional, (45)
"This is such a lovely property that I enjoyed with my family for a special birthday celebration. Our host Margherita is as beautiful as the property is magnificent. She was so gracious and helpful. We so enjoyed taking a cooking class with her and her mother Veronica, who learned traditional Tuscan cooking from her grandmother. They also made a delicious dinner for us one evening. The rooms are beautifully appointed in neutral shades and very comfortable. We highly recommend this fabulous...
LA QUERCIA ESTATE, QUINTESSENTIAL ITALIAN EXPERIENCE
Historic Villa Tuscany
3 bedrooms, bed sheets

Historic Villa Tuscany

2.0 out of 10, (2)
The price is €147
includes taxes & fees
18 Feb - 19 Feb
Historic Villa Tuscany
Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center
Outdoor pool, a heated pool, pool loungers

Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center

10.0 out of 10, Exceptional, (96)
"We had a fantastic stay at this lovely villa. We were a group of two families with four adults and four kids ages 5 to 13. Cate, the hostess, was extremely attentive and helped us arrange various activities during our stay. She helped us arrange a cooking class at the villa, a bike tour through Chianti region with a private wine tasting, and a chef cooking a Thanksgiving meal for us (we opted for Tuscan - not American food). We also got to tour a working olive mill. In addition, upon hearing...
The price is €1,120
includes taxes & fees
19 Feb - 20 Feb
Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center
Luxury Villa in the Florentine hills
Fridge, microwave, oven, stovetop

Luxury Villa in the Florentine hills

9.8 out of 10, Exceptional, (133)
"Fantastic location near Florence. In driving distance to Florence yet it feels secluded and private. The view from the bedrooms and backyard is stunning. The house was in immaculate condition with all amenities for a wonderful stay. The host David was extremely responsive and professional. We highly recommend this property for anyone looking for a house with character in the countryside yet accessible to the main city centres."
The price is €272
includes taxes & fees
18 Feb - 19 Feb
Luxury Villa in the Florentine hills
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
View from property

Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.

9.6 out of 10, Exceptional, (17)
"Our 2-wk. reservation (Oct. 5-19) was actually increased by a week Sept. 28-Oct. 5, making it a 3-wk reservation, however, due to a medical issue, we had to return to the USA 10 days early. Gabriella was a wonderful property manager assisting us with seeking medical and hospital care. Lovely property and location."
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Beautiful Villa With Panoramic Views near San Gimignano
Outdoor pool

Beautiful Villa With Panoramic Views near San Gimignano

9.6 out of 10, Exceptional, (70)
"We had a wonderful stay and this property provided a nice central location from which to explore the region. Information from Steve was timely and extremely helpful. "
Beautiful Villa With Panoramic Views near San Gimignano
Typical Tuscan villa with pool, near Lucca. Beautiful panoramic terrace
Exterior

Typical Tuscan villa with pool, near Lucca. Beautiful panoramic terrace

9.8 out of 10, Exceptional, (41)
"This was our second time staying at the property. Lido and Massimo are fantastic hosts, so kind, helpful and quick to sort any issues. Montecarlo is a beautiful place and the house is an excellent base to explore more of the area. Would definitely recommend! "
Typical Tuscan villa with pool, near Lucca. Beautiful panoramic terrace
Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.
Fridge, microwave, oven, stovetop

Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.

Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.
New 2 bed villa with large panoramic pool 40min to beaches
Outdoor dining

New 2 bed villa with large panoramic pool 40min to beaches

10.0 out of 10, Exceptional, (34)
"My wife and I had a fantastic week at the villa, we are very grateful to Mrs Consuelo for the hospitality and everything she did for us, what a fantastic lady!!! A great thank you to Mr Marcello for the free wine and fresh salad from the allotment, again thank you very much from Antonio & Louise from London"
New 2 bed villa with large panoramic pool 40min to beaches
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
Outdoor pool

- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi

10.0 out of 10, Exceptional, (98)
"The entire experience (pre-booking, booking, and our stay) was positive. Barbara quickly responded to my inquiries before and after booking and greeted us upon arrival. Plus, she prepared two delicious meals for our group that we enjoyed at the outside dining area—from which we had gorgeous views of the San Gimignano skyline. There are uninterrupted views of San Gimignano from inside, too: from the kitchen, the living room, and one of the bedrooms. We savored those views our entire stay. The...
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Outdoor pool

Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly

9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Exclusive Tuscan Villa with Black Pool & Jacuzzi
Outdoor pool

Exclusive Tuscan Villa with Black Pool & Jacuzzi

9.4 out of 10, Exceptional, (71)
"Luca is a very hospitable and friendly host! The house is exactly as in the pictures with a private entry gate and parking. The jacuzzi is heated and very relaxing. We really enjoyed the late night BBQs next to the pool. The house is perfect for 2-9 people. If you would like a relaxing holiday with privacy and luxury this is the perfect spot for you!"
Exclusive Tuscan Villa with Black Pool & Jacuzzi
Villa with view and private pool
Outdoor pool

Villa with view and private pool

10.0 out of 10, Exceptional, (20)
"We loved the villa and the location. We couldn’t have asked for a better view giving us a wonderful feeling of Tuscany. The closeness to Volterra, coupled with the great supermarket and lovely pizzerias made it special. Guilia was very responsive and helpful at all times. We would come back in a heartbeat. "
Villa with view and private pool
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool
Interior

Villa Franchetti - Luxurious Florentine Villa with Swimming Pool

10.0 out of 10, Exceptional, (11)
"We enjoyed this beautiful property It was just like in the pictures!!! Everything worked perfect"
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool
Luxury villa, infinity pool, chef, pizzaiolo, massages, yoga, grocery delivery
Outdoor pool

Luxury villa, infinity pool, chef, pizzaiolo, massages, yoga, grocery delivery

10.0 out of 10, Exceptional, (132)
"My family and I spent the last week at the villa and had a wonderful time despite some rainy weather. The villa is in a beautiful location, well maintained and extremely clean. We booked an onsite chef who prepared a fabulous dinner, we also booked the pizza chef who created the best pizza we had on the trip, he is a true artist! Valerio is an excellent host, very accessible and quickly responds to any questions or requests. We would not hesitate to stay here in the future. I highly...
Luxury villa, infinity pool, chef, pizzaiolo, massages, yoga, grocery delivery
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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Other property types in Castelfiorentino

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

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

9.6 out of 10, Exceptional, (50)
"Beautiful place and a very friendly and helpful host. Authentic Tuscan farmhouse with no frills. Lovely views all round, especially from the terrace. Excellent bar/ restaurant within walking distance. It was very hot when we were there, so the location of the pool across the road was a problem. Otherwise,great."
Authentic Tuscan country house, dating back to around the year 1000
Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.
Pool

Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.

9.8 out of 10, Exceptional, (59)
"My wife and I had a wonderful time. Our host Marilia is lovely and gave very helpful recommendations for vineyards, restaurants and cooking classes in the area. The view and surrounding area is breathtaking!"
Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.
Palazzo Mannaioni Suites
Interior detail

Palazzo Mannaioni Suites

4.0 star property
9.2 out of 10, Wonderful, (961)
"My mom and I loved our stay at the Palazzo Mannaioni in Florence. Roberto made us feel safe the minute we entered the Mannaioni and was very knowledgable of the area and accommodated anything we needed. The suites were in a great location, and the place was pristine. "
Palazzo Mannaioni Suites
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.