
Villa vacation rentals in Guardistallo
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Top-rated villa rentals in Guardistallo
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Popular amenities for Guardistallo villa rentals
Private villa rentals

Villa Via Francigena
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.

The pinewood for wine lovers with AC
Beautiful House and super friendly host.

Exclusive Farmhouse Pool & View of San Gimignano
This property exceeded our expectations with spectacular views and peaceful, natural surroundings! The host was friendly and responsive. The proximity to San Gimignano and other Tuscan destinations was convenient. Each day felt magical! Just sitting on the patio was amazing! An unforgettable destination and experience!

Villa sii felice
We had an unforgettable stay at this villa for our bachelorette getaway! The host was incredibly responsive and made everything smooth from start to finish. The views were absolutely breathtaking — even better than in the pictures! The villa had everything we needed to set the perfect atmosphere: fully stocked kitchen with plates and glasses, plenty of towels, and thoughtful details throughout. We loved picking fresh lemons from the garden and finding peaceful spots around the property to read and relax. It’s incredibly private and serene — the perfect escape. While the drive-up can be a bit tricky at first, it quickly becomes second nature and is well worth it.This place exceeded all of our expectations. Highly, highly recommend — we'd come back in a heartbeat!

Tuscan farmhouse with private pool and views
Incredible! We had such an amazing time staying here. Charly & Ann have done it up so beautifully. The views are incredible and it’s so peaceful. They went above and beyond answering any questions and recommended an amazing winery to visit! Would highly recommend a visit to this beautiful home. Thank you Charly & Ann

Private Villa with semi-Olympic pool and Tennis
absolutely amazing!! Francesca made us feel right at home. the place was amazing and we definitely want to come back. the property is beautiful and great if you want to play tennis , ping pong, or swim… super fun. Francesca was so sweet, gave us great recommendations, and helped us with all our questions. She even graciously helped our grandma get a doctor to see her when she sick. 10/10 amazing !

Campo Alle Lucciole: Entire Tuscan Stonehouse
This place is so private and beautiful. Quiet and the perfect place to return after a busy day of sightseeing. We enjoyed a wonderful dinner at our host’s family restaurant one night. The town is so lovely too. Delightful stay.

Sestuccia
This was the most magical place so spend a week in Chianti! The villa is exceptionally beautiful, and has everything you could need for a comfortable stay. The grounds were spectacular, with many things to do and different areas to sit and enjoy. My toddler especially loved picking strawberries from the small garden and collecting eggs from the chickens for breakfast. The hosts were lovely and helpful with any questions we had, and took great care of us. The town of Gaiole in Chianti is very close and with great restaurants and things to do. A perfect spot I can’t recommend highly enough!
Luxury villa rentals

Luxury Villa on Chianti Wine Estate
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.

Casa Pineta Elba, a short walk from the sea
We enjoyed a perfect family holiday on Elba Island in the perfect family home. The outdoor kitchen/dinning/sitting area was ideal to unwind after a day or exploring beautiful beaches, trekking amazing mountain trials and of course eating our way the many traditional Italian restaurants. If you want the perfect Italian holiday this is the perfect family home, you will not be disappointed. Claudia is the super host.

Villa Barsocchini intera
Thankyou Brian (and family) for what was an unforgettable magical experience. The villa far surpassed all our expectations. The villa is beyond beautiful and oozes rustic charm, perfect for a large group. Rooms were clean and with beautiful views (on the top floor) to wake up to, so much so that it felt like a dream. Bathrooms were lovely and higher spec than expected for such an old building. swimming pool serves it's purpose, but it's in a gorgeous garden amongst olive groves....stunning. Brian and family were the perfect balance of keeping in touch and ensuring we had everything we needed whilst ensuring that we felt we had the place to ourselves, a perfectly ran operation. We arranged a dinner one evening in the house cooked by Brian's mother which was an amazing experience to enjoy such a wonderful setting with friends. thank you Brian! we already hope to return in future.

Romantic Villa with private pool and fabulous view
Our stay felt like something out of a movie. Janine has decorated the home with love and attention to detail. We loved the pool and decided to spend a day doing nothing but lazing by the pool eating home cooked food in the amazing kitchen. Memories were made here and we will 100%. Return for a longer stay as you will not beat the view from Janine’s villa anywhere in Tuscany.

Borgometato – Farm
It was an adventurous and absolutely breathtakingly beautiful accomadation. We loved everything about it. The host was very helpful, the donkeys were very cute, the view was amazing, the interiour design was spot on, the dinner they prepared was delicious and communication with host was absolutely perfect! Thank you very much for having us!

La Dolce Vita - Tuscan experience
We had a wonderful stay, the house really felt like a home and was instantly relaxing. The whole booking and check in process was very straightforward and Giuseppe who met us to show us around the property and hand over the keys was very welcoming, kind and informative. The house has wonderfully peaceful location, with beautiful views. It has been furnished with excellent taste, and so adds to the feeling of being in a real home rather than a rental. The gardens and pool are delightful and evenings on the loggia will be remembered for a long time, we cant wait to return!

Luxury Villa w/Tennis Court, Pool, Jacuzzi & Gym
Wonderful stay at Villa Vittoria, surrounded by greenery at the gates of Lucca, a wonderful city. We really enjoyed the tennis court and gym area with hot tub, perfect for relaxing. We didn't use the soccer field and the pool, but the latter is really beautiful and well maintained. Maximum privacy and tranquility: ideal for unwinding. The villa is taken care of in detail and the outdoor spaces are spacious and quiet. A perfect place to rejuvenate, which we recommend without hesitation.

Podere la Pompa
I stayed with my family at Maria's beautiful house in the countryside north of Grosseto. The property is idyllic, tucked away between the trees with virtually no line of sight to other houses or buildings. The home is modern (although the architecture is very traditional) and the furnishings are of very high quality. The outdoor pool area is perfect for an evening cocktail or just to lounge during the day. I cannot recommend Maria's home highly enough and I look forward to visiting again!
Villa rentals with a pool

Villa Angiolina
Laura was an amazing host and made sure we knew all the details of the house and was very responsive if we had a question. The house itself is gorgeous and so are the surroundings. Highly recommend staying here as a home base in the Tuscany area! We visited many surrounding cities as well as a winery 40 minutes south. We would also recommend the restaurant Nuevo Ranch right done the street! Wonderful!

CASA SCIACOL - Entire apartment with pool
Great accommodation, well maintained, lots of natural feeling, facilities were extensively furnished and accommodating

Villa Le Panteraie - located between Florence and Pisa
A beautiful villa with exceptional views to the hills and valley. Various oudoor areas. Private location however close to sights and amenities. Cafes and restaurants not far however not walking distance, best accessed by own car. Electric bikes were available for sightseeing. Fantastic host, always responsive and helpful. Can warmly recommend.

Old renovated mill in the Tuscan hills
You can stop looking now! This is probably the most perfect place to stay and with the best host in all of Tuscany. This is said by a very travel and quite picky family from Sweden that this time went with three sons 16, 18 and 22 and the eldest son's fiancée. The host Lorenzo is absolutely amazing both before and during the stay: quick responses, incredibly helpful and very accommodating. You live in a renovated mill (two super-fresh separate buildings one of which is newly built) in the small village of Montefoscoli, with wonderful views of the landscape and sun location from morning till night. Large patio with barbecue and pool for lovely meals and relaxing. Inside there is everything you need and more: full equipped kitchen, dishwasher, washing machine, ironing equipment, ac in each bedroom. Good wifi and TV box. Excellent little bakery 50 meters from the residence. A small Coop shop 5 minutes walking distance from the residence with everything you need. We've already told friends and acquaintances about this home — it won't be better!

Villa "Il Grillo" Private pool Panoramic view Privacy
The villa was beautiful! Very peaceful and a great base for exploring the region. Lorenzo was very helpful before we got there and while we were there. The entry road is steep, so follow his directions on the type of car to get. Once you drive it the first time you’ll be fine!

Villa Casa al Povero
I don’t even know where to begin describing this place. It was the most amazing place I have ever stayed. If you are looking for a peaceful and private villa with incredible views, then stop looking. This is it !! All of the reviews we read before we arrived talked about how amazing the views are and that you must take up the offer if Paola and Alessandro offer to cook a meal for you. Both recommendations are spot on. The sliced beef was one of the best meals I have ever had, and I often found myself wandering around outside the villa looking at the 360 degree views in all directions. We all felt so sad to leave this magic place. Paola and Alessandro were perfect hosts. Always friendly and with a smile on their faces. It’s a long way from Australia but I really hope we get an opportunity one day to return to this majestic place.

la Balza
We loved our time at La Balza - such a picturesque, peaceful and relaxing stay! Alessandro and his parents were a pleasure to deal with and answered all of my questions very quickly. They were very hospitable and accommodating. The area surrounding Radda in Chianti is absolutely beautiful and we loved the easy access to so many different cities and small villages. Would definitely recommend. A+

Leo's Romantic House
We had a great week at the Belforte. The place was spacious with many retreats and a great overgrown garden. Everything was very well maintained and the amenities were great. Communication with Leo was always hassle-free and friendly. We will be happy to come back. 👍🏼
Quick stats about villa rentals in Guardistallo
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ404 before taxes and fees
Total number of reviews
160 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Osteria BardoVino, Locanda Le Volte, and L'Osteria del Pinzagrilli e B e B Il sogno del Pinzagrilli
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- Elba
- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Gorgona
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Marina di Grosseto beach
- Kite Beach Fiumara
- Spiaggia di Capo Bianco
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Spiaggia Di Sansone
- Giardino Bardini
- Medici Chapels
- Spiaggia di Marina Di Campo