
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.

Casa al Gianni - The Simignano Barn
Converted from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this little slice of paradise!

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.

Captain's House | Monte Grosso, Elba
The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

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

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.

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

The Loggia
Country house located in Radda, the heart of the Chianti, within walking distance from the historical center and other services such as; Coffee shops, Post Office,grocery stores and restaurants. The house is composed of a full equipped kitchen, living room with a sofa bed, bedroom, loggia and bathroom. The property is surrounded by a garden and there is a nice wooden table in the garden to eat in an open space and another lounge spot to enjoy the magnificent landscape.

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.

House with a breathless view in Tuscany
Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

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.

"La limonaia" - Romantic Suite
Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

Casa Dante – Authentic Chianti Stay | Views & Relaxation
Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.
Popular amenities for house rentals in Guardistallo
House rentals with a pool

Antico Borgo Ripostena – n. 5 Garage

SuiteLouise.pool, Hot Tub,homeGym & private Garden

The Porrine Ferienhaus IV

Villa of the Hydrangeas

Beautiful vacation home with infinity pool

Casa Luigi Suite with exclusive pool

La Moraiola - Characteristic Tuscan barn

Lovely house in a scenic and paiceful location
Weekly house rentals

I Palpiti - Dream Villa in the heart of Florence

Dream villa in Chianti with panoramic garden

Castel San Giorgio

Beachfront Tuscany

Villetta Rio surrounded by greenery

Dalu Home

Golden View - Dream Farmhouse in Tuscany

La Bandita Dependance
Private house rentals

Villa Due Pini Marti with private pool

"Il Campanile" House

Design loft with private SPA in Tuscany

"Apartment Antiche Fonti"

Le Piccole Scalette "Under the Tuscan Sun"

Elegant House in Rosignano: 2.5 km from the Sea

Villa Vestra in Vinci holiday home

Podere Livrone with Pool - Tombolo
Quick stats about house rentals in Guardistallo

Total holiday rentals
Explore 80 holiday rentals in Guardistallo

Nightly prices starting at
Guardistallo holiday rentals start at £44 per night before taxes and fees

Verified guest reviews
Over 540 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
60 of Guardistallo holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi 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 a patio Guardistallo
- Rentals with a fireplace Guardistallo
- Rentals with a washing machine and dryer Guardistallo
- Villa rentals Guardistallo
- Rentals with a firepit Guardistallo
- Rentals with pools Guardistallo
- Rentals with an EV charger Guardistallo
- Rentals with a hot tub Guardistallo
- Smoking-friendly rentals Guardistallo
- Family-friendly rentals Guardistallo
- Flat rentals Guardistallo
- Rentals with outdoor seating Guardistallo
- Pet-friendly rentals Guardistallo
- Apartment rentals Guardistallo
- House rentals Pisa
- House rentals Tuscany
- House rentals Italy
- Elba
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Marina di Cecina
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Strozzi Palace
- Porta Elisa
- Del Chianti
- Pisa Centrale Railway Station
- Cala Violina
- Mercato Centrale
- Basilica Di San Miniato A Monte
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Piazzale Michelangelo
- Pitti Palace
- Gorgona
- Spiaggia Di Sansone
- Parco delle Cascine




