
House holiday rentals in Guardistallo
Find and book unique houses on Airbnb
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 $85 AUD per night before taxes and fees

Verified guest reviews
Over 570 verified reviews to help you choose

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

Pet-friendly accommodation
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

Wi-Fi availability
60 of Guardistallo holiday rentals include Wi-Fi 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
Top-rated house rentals in Guardistallo
Guests agree: These houses are highly rated for location, cleanliness and more.

Casa al Gianni - The Simignano Barn
Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, and 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 looking for 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 outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

fabulous villa in Chianti, panoramic garden
"BADIA A PASSIGNANO DWELLING" You will enjoy a relaxing and restorative holiday in the heart of the Chianti Classico region. You will stay in a fully restored, ancient stone barn with a large fenced garden and an old gazebo, suitable for large groups and families. The rooms are comfortable and spacious for 8 people. The renovation has been carried out with great care, taking into account every aesthetic detail to allow you to experience the ancient Tuscan tradition combined with comfortable modernity.

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the Chianti Classico region, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a dominant position with an amazing view, where you can enjoy breathtaking sunsets. The complete independence of the house, the welcoming garden and the large loggia allow you to enjoy your stay in total tranquillity. Our reviews are your best guarantee.

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.

Countryside-panoramic sea Casale Marittimo Tuscany
Small apartment immersed in the tranquility of the Tuscan countryside. Ten minutes from the Etruscan Coast. Sea view. To spend a stay in the name of privacy and relaxation, but with all the attractions of the area just a short walk from here. I welcome your furry friend,JUST ONE and SMALL. From here many hiking trails and bike paths start to discover the evocative landscapes. Great typical restaurants, and wineries.!!! Enjoy your stay! Tourist tax is payable at check-out.

Breathtaking Views in Our Chianti Country House
An incredible experience between flavor, nature and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst vineyards and olive groves with an amazing view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

Nada Home
In my home, you can experience the most authentic side of Tuscany, filled with peace, warmth and family traditions. Surrounded by olive groves and vineyards in the heart of Chianti, you will have a private garden all to yourself, where you can relax in complete tranquillity. On request, you can join a cooking class in the house, preparing our family recipes handed down by Grandma Graziella, or share a special dinner in an intimate and welcoming atmosphere.

The Cottage to relax and enjoy
Detached country house – for exclusive use – in stone and glass from the 18th century; ideal for 4 people. The spacious wooden terrace at the house with a large dining table invites you to socialize. On the terrace by the saltwater pool (10m x 5m, depth 1.4m-2.4m), you can relax on the sun loungers and deckchairs. Large property with olive and fruit trees, completely self-sufficient accommodation thanks to photovoltaics. (CIN IT050012C29N4AT4OD)

Frontemare house with exclusive sea access
Casa Frontemare is a completely renovated property with direct access to the sea, from which you can enjoy a panoramic view of the sea, the Tuscan islands and wonderful sunsets. It is a perfect place for those who love a relaxing and private vacation. The proximity to the Tuscan art cities and the small typical villages means that it is also possible to discover new places and discover the flavors of Italian cuisine.
Popular amenities for Guardistallo house rentals
House rentals with a pool

TREEhouse / casaBARTHEL

Country House w/ heated Pool near the City Centre

Collina Power

Infinity pool in Chianti 1

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Borgo Ripostena – No. 8 Casa Vecchia

Ancient Barn in Chianti with Pool

Paluffo Tower House
Weekly house rentals

I Palpiti - Dream Villa in Florence

Medieval Tower House in the Historic Center

Poggiolo

The Maison on the Ponte Vecchio

Villa Carla – Florence View, Tennis & Hot Tub

Beautiful vacation home with infinity pool

Pistoia Hill, charming stone farmhouse

Chalet i Poggetti,
Private house rentals

"Il Campanile" House

La Paiolina: pool, jacuzzi & sauna

Margherita: Tuscany views, Pool & Walk to Village

[10 min from the sea] Apartment with garden + Jacuzzi

The Porrine Ferienhaus IV

Japandi apartment with a view!

Le Piccole Scalette "Under the Tuscan Sun"

Romantic Tuscan Town house with Breathtaking Views
When is the best time to visit Guardistallo?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $300 AUD | $310 AUD | $231 AUD | $229 AUD | $233 AUD | $262 AUD | $231 AUD | $200 AUD | $215 AUD | $214 AUD | $245 AUD | $249 AUD |
| Avg. temp | 7°C | 8°C | 10°C | 13°C | 17°C | 21°C | 24°C | 24°C | 21°C | 17°C | 12°C | 8°C |
Destinations to explore
- Elba
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Uffizi Gallery
- Spiagge Bianche
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Gorgona
- Piazzale Michelangelo
- Capraia
- Pitti Palace
- Palazzo Vecchio
- Piazza della Signoria
- Boboli's Garden





