
Luxury rentals in San Gimignano
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Top-rated luxury vacation rentals in San Gimignano
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Other great luxury vacation rentals in San Gimignano
Luxe

Villa in Buonconvento
5 out of 5 average rating, 6 reviewsPodere Maiano
AnthonyRating, 5 stars26 months ago
Villa di Montesoli was an amazing experience for our entire multigenerational family. Our group consisted of 9 adults and 4 children including an 18 month infant. Pietro and the entire staff were beyond accommodating to all of us the entire week. The accommodations were fantastic with plenty of space for the entire family, with bonus spa room (hot tub, sauna and pool table). Outdoors we enjoyed family bocce. We were not in season to use the pool but it would be ideal for a summer stay. The location of the Villa is perfect for a memorable Tuscan vacation. The property expands many acres with fantastic views of hills and valleys within Val d’Orcia. We were able to visit Pienza, Montalcino, Montepulciano, Cortona, Siena and even Florenece from the Villa, in addition to a local farm, olive oil producer and wineries for tastings/tours all within our 7 day stay. We took advantage of breakfast and dinner each day at the Villa and the house cooks Giovanna and Daniela were wonderful and the food was amazing- true home cooked italian meals. They were also helpful shopping on our behalf at the local COOP for anything that we may require during the stay. We also enjoyed a fun and delicious pizza night with Ciro at the Villa - he was awesome. Pietro was very attentive during our stay and also had great communication prior to our trip. If you are looking for a true Tuscan experience, in an ideal location with a fabulous host look no further than Villa di Montesoli.
Luxe

Villa in Radicondoli
Dimora storica San Lorenzo a Montalbano
RonniRating, 5 stars2 months ago
Perfect stay in the beautiful Tuscan countryside! The Villa is newly renovated and impeccably decorated. Each bedroom has its own bathroom, all beautifully decorated with very comfortable beds. The kitchen is enormous and well equipped to entertain a large group. The pool and garden are truly gorgeous, facing out into the countryside for a fabulous view. Finally, our hosts were amazing, They provided us with tons of recommendations, arranged for a local chef and even got us into a winery for a last minute tasting. I cannot recommend this property and the Villa Med hosts enough! We will be reaching out to them for our next trip!
Luxe

Apartment in Centro Storico
4.96 out of 5 average rating, 48 reviewsBarone Achille -La Dimora degli Affreschi Florence
AlannaRating, 5 stars2 months ago
We had a fantastic stay in Florence—the apartment was extremely spacious for 3 travelers, it was clean, comfortable, and in the perfect location. The host was extremely responsive. Can’t wait to book again soon.
Luxe

Apartment in Centro Storico
4.97 out of 5 average rating, 36 reviewsDon Tommaso - Dimora degli Affreschi Florence
LisaRating, 5 stars2 months ago
This apartment is magnificent. It is beautiful, clean, quiet, updated, in a great location and full of amenities. Cecilia is a wonderful and responsive host. We would absolutely stay here again if we return to Florence!
Luxe

Private room in Tavarnelle Val di Pesa
Castellare de' Sernigi
SandraRating, 5 stars44 months ago
Outstanding Villa with outstanding owners! Our two weeks were a dream come true! Definitely would come back again!
Luxe

Villa in Monteroni d'Arbia
San Gerolamo
BrunaRating, 5 stars32 months ago
We rent and travel very often, all around the world, and we never had such a great service and welcome as we did at San Gerolamo. Such a beautiful place, kitchen well equipped, wood fired oven, beautiful rooms, perfect pool. The Housekeeper Lucia made everything so perfectly clean every day, she is lovely and trusted. The gardener Michele is always there when needed, and Francesco the house manager as well. They were always there when we were in need of something, and we could tell at San Gerolamo they do it with real pleasure. our best stay in a rented villa for sure! The property is charming. We felt like home from the first night, and we slept like never before Thank you so much
Luxe

Villa in Palaia
5 out of 5 average rating, 4 reviewsValle
MichaelRating, 5 stars23 months ago
We had an awesome experience. We were a group of 3 families and we found the location to be great - near Florence, Pisa and Luca. The villa is very well kept and furnished. Daria, the manager, was super responsive. The winery is a great touch to experience the Tuscan region. Highly recommend this Tuscan home away from home!
Luxe

Home in Buonconvento
Villa di Montesoli
Laurel LeeRating, 5 stars2 weeks ago
This is the greatest place on earth. It is more beautiful than the pictures even show. Every room is truly enormous and so beautifully designed. The view from every room is a dream - and from the outdoor dining and lounge area just heaven. We couldn’t stop saying it doesn’t look real. We were here on a work retreat from NYC and there is so much room for everyone to have privacy. It’s also more luxury than I even realized with really nice huge brand new bathrooms. The host helped us with everything and every recommendation was excellent. We hired the local chefs that were recommended and they were perfect - pizza in the outdoor pizza oven, delicious pasta and meats from local nonnas. Some of us came by the train from Florence and it was so easy into Buonconvento. Others drove (beautiful!!) and others took the recommended driver who took us at all hours to Rome and Florence airports - use him he’s great. The food at the local town is so good and easy to get to. Magical!!
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cavallino Matto
- Spiaggia Libera
- Teatro Verdi
- Palazzo Vecchio
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