
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

Finest country house. 3 bed rooms and shared pool
Un de nos meilleurs séjours assurément !!!! Mattéo est un hôte très aidant et prévenant. La maison est juste un petit bijou au sommet de cette colline...une vue sur un paysage Toscan très inspirant du côté de la piscine (qui est une très jolie piscine)...bien que partagée nous avons été toujours seuls à en profiter !! La terrasse où l'on prenait nos repas est très agréable avec ces fortes chaleurs. La situation de la maison permet de rayonner dans la Toscane...Lucca, Sienna, Volterra, San Gimignano....et nous avons pu pousser jusqu'au Jardin des Tarots de Niki de Saint Phalle. Nous recommandons fortement un séjour chez Mattéo...et pensons y retourner une autre fois.
Tuscan Villa Featured Conde Nast Best Villas Italy
This 500 year old house is ideally situated in Tuscany and the Chianti region. It is a perfect place for day trips to other towns, for wine, tasting excursions, and for visiting Florence. The idyllic setting gives you a sense of country life in Italy, and the views from the patio and house are stunning. There are spectacular wineries within 5 to 10 minutes of the house. We found the house very comfortable and enjoyed our stay very very much. Rose and Pier couldn’t have been more helpful in planning our stay and excursions. We found through them fabulous restaurants, and wineries that we would not have discovered on our own. They were also incredibly responsive when we had questions. Our only confusion about the house was that the listing showed three bathrooms, but one was in the laundry room in a separate building . Just something to know. Thank you to Rose for a lovely vacation ! It was the perfect place to explore Tuscany from!

Tuscany:Stone house, private pool and garden
This house is the perfect place for two families traveling together. It’s incredibly cozy, thoughtfully designed, and fully equipped with amenities that let you truly enjoy the beauty of the Tuscan countryside. From the moment we arrived, we felt at home. The hosts went above and beyond — welcoming us with fresh fruit, traditional sweets, bottled water, coffee, milk, and a selection of Tuscan wines, which we truly appreciated. They also provided high-quality Italian hygiene products, which added a thoughtful and luxurious touch to our stay. One of the highlights for us was the host’s responsiveness. Communication was always fast, helpful, and friendly — a detail that made a big difference. We didn’t get a chance to use the private pool due to our tight schedule, but the property still gave us a real sense of independence, comfort, and safety. I 100% recommend this property. It’s a peaceful, beautiful place — perfect for relaxing, connecting with nature, and creating memories

Explore Chianti from a Charming Stone House
La récompense est au bout de quelques centaines de mètres de chemin empierré mais praticable: l'environnement de la maison est superbe et la vue sur la campagne du Chianti est magnifique. La maison n'est pas très grande mais convient pour 4 personnes. Elle est très bien entretenue et équipée. Les produits que Monica laisse gentiment à disposition dans les salles de bains sont raffinés. La piscine (commune aux différents logements du hameau) est suffisamment grande pour pouvoir se détendre en nageant, avec une vue imprenable sur la campagne toscane. A partir de Castellina, il est facile de rayonner pour découvrir Sienne (à moins d'une demi-heure de route) et toute la région du sud du Chianti. Florence est un peu plus loin (compter une bonne heure de route). Séjour magique. Et Monica est très réactive pour aider ses hôtes.

Countryhometuscany - House with Garden -
Beautiful property with warm, welcoming hosts. The bed was exceptionally comfortable, and everything is tastefully decorated The kitchen is fully equipped, perfect for cooking meals at home. The pool was a great temperature, immaculately clean, and came with stunning views of the surrounding countryside. The entire setting is peaceful and relaxing, yet only a 35-minute drive to Siena and 50 minutes to Florence. We especially loved watching the sunset at the nearby five-star Belmond hotel. We went for drinks at 7pm, enjoyed live music, and were surrounded by the heavenly scent of jasmine. There is no air conditioning but the fans were absolutely fine! Another highlight was La Speranza, a gorgeous deli serving excellent coffee, pastries, cheese, and wine. They kindly spoke English when we got stuck and made us feel so welcome.

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

La Moraiola - Characteristic Tuscan barn
Egizia’s home was the ideal place for our family’s Tuscan getaway. It had everything we needed. Egizia was an excellent host, great communicator, great recommendations. We would stay here again.
Weekly house rentals

Elegant ancient villa Lucca
From the moment we were greeted by Isabella, Massimo and their son, to the moment we said goodbye we felt right at home. The house is well located. It was nice to leave the hustle of the old city and retreat to the expansive peaceful terrace of the house for an “aperitivo” before dinner. The beds were comfortable and we all slept well after long days of touring. One of our favorite things was collecting water from the town spring, which was just a few doors away.

Montecatini Alto Art View
Wir haben 10 wunderbare Tage in Carolinas geschmackvoll eingerichtetes und perfekt ausgestattetes Haus verbracht und genossen besonders die Terrasse mit herrlichem Ausblick in die toskanische Landschaft und das malerische Städtchen Montecatini Alto mit mehreren guten und gemütlichen Restaurants. Eine Gelateria und ein kleiner Lebensmittelladen sind fast vor der Haustüre. Durch die urige Standseilbahn nach Montecatini Terme (fährt alle 30 min bis Mitternacht) und eine Buslinie zum Bahnhof sind Ausflüge auch ohne Auto möglich. Carolina ist eine perfekte Gastgeberin - immer erreichbar und sehr hilfsbereit. Wir können diese Unterkunft sehr empfehlen.

1 dive in the water the green, art
Abbiamo veramente apprezzato il nostro soggiorno. Grazie Massimo per la tua gentilezza e disponibilità, i tuoi consigli e i tuoi pensierini. Abbiamo soggiornato nell'appartamento del primo piano con terrazzone immenso. Vista meravigliosa e la ciliegina sulla torta, una bella piscina in un ambiente pulitissimo grazie alla cura costante di Massimo. Spesso la piscina era tutta per noi visto che ci sono solo tre alloggi. Raccomando al 150% a chi vuole visitare la regione e apprezza la tranquillità.

CountryHouse immersed in woodland
Samen met mijn vrouw en onze 2 kinderen van 7 en 9 jaar verbleven we een week in het huis van Antonio! Wat hebben wij genoten, echt een week om nooit te vergeten! We kunnen deze plek iedereen aanraden! De tuin is prachtig met vele mooie bloemen en planten. Het zwembad en de jacuzzi zijn nog mooier dan op de foto’s en het huis was voor ons de typische Toscaanse sfeer die wij zochten! We hebben genoten van het adembenemende uitzicht en het terras met bbq en vuurplaats waar we marshmallows met de kinderen hebben geroosterd! Antonio is erg goed bereikbaar en geeft handige tips. En zijn Engels is beter dan dat hij zegt 😉 Wij komen graag nog een terug in dit paradijsje 🤩 Antonio, grazie

Sant' Andrea con piscina privata
Unser Aufenthalt war einfach traumhaft! Die Unterkunft war wunderschön gelegen, sehr gepflegt und geschmackvoll eingerichtet. Besonders der große Pool war ein Highlight – ideal zum Entspannen und Erfrischen an warmen Tagen. Die Umgebung war ruhig und bot herrliche Ausblicke auf die toskanische Landschaft. Cristina war eine fantastische Gastgeberin – herzlich, hilfsbereit und jederzeit erreichbar. Wir haben uns vom ersten Moment an wohlgefühlt.

Casa Gloria
Die Lage und insbesondere die Aussicht ist einzigartig. Der Garten ist wunderschön angelegt und bietet viele verschiedene Sitz- und Liegemöglichleiten. Das Bett, die Matratze und die Kopfkissen sind hochwertig und bequem. Die Küche ist sehr groß, ist einfach ausgestattet und biete alles, um umfangreich kochen zu können. Das Haus ist nicht barrierefrei, sowohl im Haus, als auch um das Haus herum sind viele verwinkelte Stufen. Das WLAN ist sehr gut. Wir haben uns sehr wohl gefühlt.

incantevole appartamento a pochi km dal mare
Wir 2 Erwachsene und 4 Kinder hatten diese Wohnung als Ausgangspunkt für Meerbesuche gewählt und es war logistisch gut gelegen - Nachts leise, Autostellplatz auf dem Grundstück, mehrere Restaurants in laufweite - einzig die Betten sind für größere Menschen etwas gewöhnungsbedürftig ;-) Wir würden wieder hingehen.

"IRIS" Rifugio Segreto nella natura
Die Unterkunft war einfach super. Wir haben uns auf Anhieb wohl gefühlt und alle unsere Bedürfnisse wurden ohne zu fragen direkt erkannt. Kaum schien die Sonne standen zwei Liegen parat. Die beiden waren sehr herzlich und man sieht mit wieviel Liebe zum Detail sie das Haus saniert haben. Wirklich einzigartig. Die Unterkunft liegt sehr idyllisch umgeben von viel Natur. Ein Traum, um einfach mal abzuschalten.
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.

Scenic country house with large pool near Florence
Absolute Perfection in Fiesole!** Michael’s villa in Fiesole is nothing short of spectacular. From the moment we arrived, we were mesmerized by the breathtaking views of the Tuscan countryside and Florence in the distance. The location is ideal—peaceful, romantic, and just a short drive from the heart of Florence, making it the perfect blend of serenity and convenience. The villa itself is stunning—spacious, elegantly decorated, and equipped with every amenity you could need. The outdoor terrace was our favorite spot, where we enjoyed morning coffee with panoramic views and evening wine under the stars. The lush gardens and private pool added an extra touch of luxury to our stay. Michael was an exceptional host—attentive, welcoming, and full of great local recommendations. His hospitality truly made our experience unforgettable. If you’re looking for a dreamy Tuscan escape with world-class scenery, impeccable style, and top-notch service, this is the place. We can’t wait to

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 :)

Three bedroom historical house with the best views
We loved our stay here! The house and the views were truly as picturesque as it seems in the photos. A dream spot! The town itself is full of local flair and is beautiful too. Not touristy at all. Close enough to nearby towns though to explore more of Tuscany! Overall a great stay and Laura was a kind and responsive host.

Art Beds & Garden
Cet appartement est absolument exceptionnel ! Tout est parfaitement réuni pour un séjour mémorable dans cette région magnifique : emplacement stratégique, à proximité immédiate des thermes, de plages superbes!!! à seulement 1h30 de Sienne, Florence, et proche de Pise. Les extérieurs sont agréables, et tout est pensé pour que chacun se sente à l’aise, et même plus. Nous étions un groupe de 9 (adultes, adolescents, enfants et un bébé), et nous avons tous trouvé notre espace grâce à un aménagement optimal. L’appartement est immense et joliment décoré. Quant à Monica, elle est bien plus qu’accueillante, c’est une véritable perle ! Sa gentillesse, son accueil, sa clarté, sa compréhension et son adaptabilité ont largement dépassé toutes nos attentes. Elle a fait en sorte que nous nous sentions parfaitement bien. Je vous recommande vivement cette expérience inoubliable dans cette région merveilleuse. Merci Monica!

Casa Conte Martini
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
Spontan gebucht. Und problemlos kurzfristig alles nötige regeln können. Federico ist unaufgeregt kommunikativ und kann den Aufenthalt mit guten Empfehlungen verfeinern. Die Lage ist besonders. Der Ort hat wine gute Wirkung auf Körper und Gemüt. WeiläuAbgelegen aber nicht weit zum einkaufen oder zu Restaurants. Ein schöner Pool. Geschmackvolle Räumlichkeiten. WlanJunckies könnten manchmal mit dem netz etwas hadern aber das Gesamtbild wird dadurch nicht geschmälert. Alles was sonst nötig ist,ist vor Ort oder wird von Federico prompt besorgt. Ein wunderbarer Ausgangspunkt für Besuche in Florenz oder im Chianti. Jede Menge auch rustikale trattorias,Winzer und Oliven Bauern in der Nähe.

Stunning Casa with Pool & Views
Een fijn huis op een fijne plek. Het is erg afgelegen, dus verwacht niet binnen 10 minuten in een bruisend centrum te zijn. Binnen 10 minuten lopen ben je wil in een dorpje met leuke restaurantjes. De weg ernaartoe is de eerst keer wat uitdagend, maar daarna prima te doen. Contact met Ryann was supersnel en heel makkelijk.
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