
House holiday rentals in Guardistallo
Find and book unique houses on Airbnb
Top-rated house rentals in Guardistallo
Guests agree: These houses are highly rated for location, cleanliness and more.

Garden House
"Casa del giardino" ...... a blooming oasis within the medieval walls.. The owners Mario and Donella would like to offer you a unique vacation in San Gimignano. You can enjoy the wonderful garden, an extraordinary oasis of peace and silence, in the city center, for the exclusive use of those who rent the apartment. Thus, reading a book, relaxing in the sun, sipping an excellent glass of Chianti or having breakfast surrounded by greenery and among the flowers of this garden will be a memorable experience!

The Chianti Classico Sunset
Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Collina Power
Collina is an ancient stone farmhouse, the house is surrounded by fields and olive groves. It has a large garden with swimming pool and a terrace where you can have pleasant lunches and dinners. A barbecue and garden furniture are available. The road to get to the house in the last stretch is not paved and is therefore not suitable for sports cars or particularly low ones. The route lends itself to pleasant walks during the day, while at night we recommend using a car because it is not lit.

House with a breathless view in Tuscany
Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

Open space surrounded by nature
Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

Podere Quercia al Santo [Quercia al Santo Estate]
Portion of farmhouse, located in the hills of Lajatico overlooking the Teatro del Silenzio. The perfect place for those who want to spend a refreshing vacation, in contact with nature, in tranquility, but at the same time love to visit nearby villages and cities. Suitable for couples, families with kids and 4-legged friends. The house, surrounded by a beautiful garden, has a double bedroom, a bedroom, a living room with a sofa and an equipped kitchen. Parking lot and the private garden

Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Cottage in the Cecina countryside
In the Cecina countryside, along the road leading to the medieval village of Casale Marittimo, a private park with parking, the 30 sqm studio overlooks a veranda equipped for outdoor dining even with the use of the barbecue. Convenient to services (town and shopping center). The beautiful pine forest of Marina di Cecina and the sea can be reached by car or bicycle. Nearby are beautiful villages and very well-known locations. For additional fees, see the House Manual

Infinity pool in Chianti area
On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Cercis - La Palmierina
E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.
Tuscan Counrtry Detached House. Wi-Fi Free
Update: Air conditioning starting June 1st, 2025. Enjoy the summer with a cool breeze! Do you want to spend your holiday in a typical Tuscan barn? This is your place! Charming renovated barn for families / groups. Located in the heart of the Tuscan countryside at 2km from Poggibonsi. Ideal for a relaxing holiday and in a great location for visiting San Gimignano (13km), Siena (25km), Florence (35km).

Casa Al Poggio & Chianti view
Casa al Poggio is a typical country house of Chianti area is spread in 145 square meters on two floors, the ground floor is a large living area, with kitchen and sofa ,fireplace ,up stairs there is 2 large double bedrooms and a sofa bed in the middle open room , always setable as 2 singles or a double bed bed and a relaxing bathroom with shower and bath with Chianti view.
Popular amenities for Guardistallo house rentals
House rentals with a pool

Design loft with private SPA in Tuscany

Villa Casabella near Siena

Ancient Barn in Chianti with Pool

Private villa/swimming pool in Tuscany

Vacation in an authentic farmhouse 10 km from the city

Tenuta Tegolaia

Le Porrine IV

Ancient villa, panoramic pool by Vacavilla
Weekly house rentals

Romantic Tuscan Town house with Breathtaking Views

The house in the Castle and the secret garden

Large Apartment with private garden, barbecue, A/C

Oasi Marina – Sea View, 500m from the Beach

Elegant House in Rosignano: 2.5 km from the Sea

Il Corbezzolo

Relaxing Tuscan country house with amazing views

At the pace of a boat
Private house rentals

Alma Tuscany House

Apartment in country house with panoramic view

Historic Loft Overlooking the Hills of Florence

Three-room apartment on the sea with garden

Tuscany,Bolgheri, Cottage

villa n/florence with fireplace, cozy fall escape

Casina La Bandita

Olivo, a cottage with many flowers in the Valley.
Quick stats about house rentals in Guardistallo

Total holiday rentals
Explore 60 holiday rentals in Guardistallo

Nightly prices starting at
Guardistallo holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 530 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Guardistallo holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Guardistallo rentals

4.6 Average rating
Guardistallo stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Rentals with pools Guardistallo
- Rentals with outdoor seating Guardistallo
- Rentals with an EV charger Guardistallo
- Villa rentals Guardistallo
- Rentals with a patio Guardistallo
- Apartment rentals Guardistallo
- Smoking-friendly rentals Guardistallo
- Rentals with a fireplace Guardistallo
- Condo rentals Guardistallo
- Rentals with a fire pit Guardistallo
- Rentals with a washing machine and dryer Guardistallo
- Pet-friendly rentals Guardistallo
- Family-friendly rentals Guardistallo
- House rentals Pisa
- House rentals Tuscany
- House rentals Italy
- Elba
- Santa Maria Novella
- Piazza della Signoria
- Mercato Centrale
- Ponte Vecchio
- Santa Maria Novella
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Salvatore Ferragamo Museum
- Cathedral of Santa Maria del Fiore
- Marina di Cecina
- Del Chianti
- Siena Cathedral
- Porta Elisa
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Piazza dei Cavalieri
- Cala Violina
- Piazzale Michelangelo
- Cattedrale di San Francesco
- Gorgona
- Piazza del Duomo (Pisa)
- Uffizi Gallery
- Fortezza da Basso




