
House holiday rentals in Guardistallo
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Top-rated house rentals in Guardistallo
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House rentals with a pool

dependance in villa Toscana
My wife and I stayed at Marco’s for a week for our honeymoon. We both loved it. Pool was beautiful and peaceful. The property is fantastic the pictures don’t do it justice. As amazing as it looks in the photos it is 1000 times better in person. The front gate made everything feel so secure. Walking up the steps to the guest house we were hit with a nice floral smell with all the daisies growing everywhere. Such a peaceful and beautiful property. The view was stunning looking over the mountains. The place was perfect. The kitchen was everything we needed and more, the pull out couch allowed us to relax and watch tv at the end of the night. The patios were perfect for coffees and meals. And the bed was nice and comfortable. Marco left a flower pedal heart on the bed for us which was a nice personal touch. We met his parents (who stay in the main house) they were very kind and gave us our privacy. There was lots of information about the area and things to do. Wish we stayed longer

beautifull detached former country
A real little paradise. A warm welcome from Manuela. I highly recommend it!!! We just left and dream of going back!

Iris Residence "Casa vista mare-giardino-piscina"
We had a wonderful vacation time in this very nice apartment. The location in the small village up in the hills of Tuscany is so authentic and typically Italian. The pool and the view are a dream. The rooms are very clean, large and nicely furnished. The bed was amazing. I haven't slept this well in a long time. The kitchen is well equipped. The only thing missing was a nice salad bowl and a toaster. The location of the apartment is ideal for exploring Tuscany. The well-known white beaches can be reached in 20 minutes by car. Parking is available everywhere. Shopping is possible in the small village at the bakery and in the corner shop or down in the city at Lidl and Coop, etc. Restaurants are within walking distance. We loved the snack bar opposite the butcher's shop in the village. You sit idyllically in the square in the middle of the village. Thank you for the nice time.

farm Lupina: green corner between the sea and the hills
This was the second time for us staying at this beautiful little house. It’s been just as lovely as it was the first time around: the pool, the garden, the playground, the fresh herbs, and our favorite: the terrace, where we spend many hours eating, drinking, chatting. Daniele and his family are so friendly and helpful and we very much enjoyed our vacation there. Thank you once again!

Villino Isotta (exclusive private villa)
Villino Isotta is a breathtaking accommodation, super in every aspect: location, cleanliness, all bedrooms are air-conditioned, kitchens and bathrooms are fully equipped, free parking is just a few steps away and a café is open until late in the evening. Outside, there is a patio overlooking the hills, a barbecue, and a swimming pool equipped with every comfort (hot shower, hot tub, sun loungers, wifi, etc.). Last but not least, the host Andrea, whom I thank for the incredible and constant attention to his guests from the first moment (welcoming us with a welcome aperitif) to the last. Always present but never intrusive, always available with advice to make your stay unforgettable, a person with an immense heart who manages this accommodation with passion and seriousness. It was hard to go home, we will definitely see each other again!

Collina Power
Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!

casa delle acque-casedigello
This was an amazing stay. The grounds were beautiful, serene, and the air was fresh. The residence was charming, rustic and comfortable. Giselle and Elmar were so gracious and kind. The pool was amazing with an unforgettable view. This ended up being our favorite part of our entire Italy trip. Relaxing stay, close to various wine regions and unique cities (we went to Bolgheri and Volterra and they were both about 30 minutes away). Highly recommend to anyone looking for a little slice of heaven in Tuscany! We will be back!

Paluffo Stillo House
Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!
Weekly house rentals

Montecatini Alto Art View
We loved staying in Carolina’s house in Montecatini Alto. It was a lovely welcoming place to wake up in and return to at the end of the day. The view from the windows and the patio is extraordinary and sitting out enjoying it was one of the best parts of the holiday. The house had all we needed. Carolina was a wonderful host; friendly, quick to reply and extremely helpful. The village is a lovely quiet place to stay and we wouldn’t look anywhere else if we return to the area.

"Il Frassino" Country House
Our stay was perfect all around! We immediately felt at home. The accommodation is not only convincing because of the great location and surroundings, it was also wonderfully furnished and nothing was missing. We would like to especially highlight Ranieri's warm hospitality. He was always available and helpful. We would come back.

Conte Martini House
Andrea en Simone, Are very welcoming, the location is a smal walk but with good directions easy to find. Palaia and the accommodation has amazed us, with a amazing home away from home. Great facilities, terrace, jacuzzi, pool, and not to forget amazing views. As a base to explore there is alot of interesting places to go to witin a hour drive. big cities, smaller towns, wineries, and with a tiny bit extra travelling time the sea. We had a great stay with our friends and made some great memories. would recommend the accommodation, as well as the hosts, and would definitely stay again. Kind Regards, Boyd and Naomi

La Loggia – Casine al Sole
Spontaneously booked. And can easily arrange everything necessary at short notice. Federico is calmly communicative and can refine the stay with good recommendations. The location is special. The place has a good effect on the body and mind. WeiläuAbout but not far for shopping or restaurants. A beautiful pool. Tasteful spaces. Wifi junckies could sometimes hate something with the net, but the overall picture is not diminished. Everything else necessary is on site or will be promptly provided by Federico. A wonderful starting point for Visit in Florence or Chianti. Lots of rustic trattorias,winemakers and olive farmers nearby.

Agriturismo Podere San Martino (apartment for two)
Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!

Stunning Casa with Pool & Views
We loved the peaceful environment and the home itself. We were close to restaurants and grocery stores.

Cottage in the Cecina countryside
Our stay at Fernanda's house was very nice. The place looks like the photos. You are absolutely private, despite the proximity to the hosts' house. The road is close but didn't bother us at all. At night, there are also hardly any cars. The house is small but nice, you have everything you need and a wonderful terrace with garden. You have to get used to the shower briefly, but this is also quick. We rented bicycles in the village and were able to drive to the beach or to the village quickly and easily. Great starting point for excursions in the area. Fernanda also gave us a great restaurant recommendation for our wedding anniversary (thanks again, it was so beautiful!!) and there was a homemade cake. Fernanda and her husband are incredibly warm and helpful. You can only speak Italian but thanks to modern technology no problem if you don't understand everything. Highly recommend the house and would book it again anytime!!

Il Palagio
Outstanding accommodation. Pristine, spacious yet very cozy. Very helpful host. 10/10 would come again
Private house rentals

Volare
We had a beautiful stay in Alessandro’s home for one week in May 2025. The location was perfect to visit Pisa, Lucca and Florence as day trips. We were in the outskirts of old San Miniato - walking distance to restaurants and cafes, a short drive to the supermarket yet remote enough to be peaceful. We enjoyed the well appointed apartment which had everything we needed for our stay. We loved having dinner in our private garden amongst the olive trees and relaxing by the pool. We travelled with our bicycles and the areas surrounding San Miniato is just about the most beautiful riding I’ve ever found in Europe. Alessandro is clearly a very kind and welcoming gentleman, who enjoys hosting his guests, and we were grateful for his tips on what to visit and where to eat. We are sure we will be back again.

The house in the Castle and the secret garden
A beautiful place. You can see and feel it is not just a random vacation rental but feels like someones home and someone has put a lot of detail and love in the place. Once you talk with Diana, you understand even better: as the owner, so the home :) The house offers all you need to stay there (with your whole family) also for longer than only a few nights. The village is very cute and offers all you need, plus charming bars and restaurants. On top it is a great starting point to go and explore the area/ medieval towns/ nature parcs/ beaches. By car it felt like everything is reachable in max 20minutes. Further you can explore by bike and even start from the town on hikes so: if you get a chance to book, stop searching - hit the button and enjoy your time :)

apartment in farmhouse
We absolutely loved our wonderful stay at Susanna's and Carlo's. The apartment was well equipped, comfortable bed, welcoming interior, the views were stunning. It was really calm and it felt like home. Especially because Susanna and Carlo were such great hosts, friendly, helpful with good advice, they even organised to rent bikes for us. Also, the dog Peppe, gave us so much love, such a sweet dog, we really miss him. We witnessed the arrival of two cute cats and how they met Peppe. It was hard to leave. We absolutely recommend to stay there! Grazie mille per tutto, Susanna, Carlo and Peppe!

Balconevisi Elegant Home
We loved staying here! the views out of the terrace and even the bathroom window were something I’ve never seen before, right out of a movie. About a 15 minute drive to the closest city, San Miniato, which has great restaurants. This was such a charming & peaceful place to stay in Tuscany, and the visits from the neighborhood cats on the terrace was a bonus! :)

Podere Quercia al Santo [Quercia al Santo Estate]
Antonio and Carmela were both exceptional hosts and made us feel right at home. Despite the language barrier, both of them were incredibly warm and invited us into their home for a home-made Italian dinner that included three different pizzas, focaccia and salad. The views and vibes of the area were truly beautiful and we would highly recommend this place to everyone, even if only for one night.

"IRIS" Secret Nature Retreat
The place was just great. We felt comfortable right away and all our needs were recognized directly without asking. As soon as the sun was shining, there were two loungers ready. The two were very warm and you can see how much attention to detail they renovated the house. Really unique. The property is very idyllically surrounded by lots of nature. A dream to just shut down.

La Stallina
Another perfect time in the same place. We love this house, everything is perfect: calm, silent, possibilities. Special thanks to owner, Raffaello. Best host. Thank You.

Chianti House Stunning view 20 min. from Florence
Tommaso was very responsive and fantastic! Check in was a breeze. The pool was great. Overall, it was a great stay for our trip in Tuscany!
Quick stats about house rentals in Guardistallo
Total rentals
50 properties
Nightly prices starting at
$51 SGD before taxes and fees
Total number of reviews
530 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool
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- Elba
- Santa Maria Novella
- Duomo di Firenze
- Piazza del Duomo (Pisa)
- Gorgona
- Basilica of Santa Maria Novella
- Gulf of Baratti
- Ponte Vecchio
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Spiaggia di Capo Bianco
- Piazzale Michelangelo
- Mercato Centrale
- Spiaggia Di Sansone
- Kite Beach Fiumara
- Marina di Grosseto beach
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Spiaggia di Marina Di Campo
- Cavallino Matto