
Holiday houses in Guardistallo
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Top-rated holiday rentals in Guardistallo
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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Case nell'aia Arco, apartment in Chianti and pool
L'appartamento Arco si trova in un tipico borgo toscano tra vigneti e oliveti. Appartamento arredato in stile rustico toscano, accogliente per farvi rilassare e visitare la zona. L'appartamento si affaccia sulla grande terrazza dove potete fare pranzi e cene all'aperto o aperitivi. Cucina, divano e punto TV, wifi, due camere matrimoniali, bagno, terrazza, piscina. Parcheggio auto nella proprietà . Ideale come punto di partenza per visitare Siena, Firenze, San Gimignano, sia in auto che in bici.

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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

Peaceful tuscan house with pool in Tuscany
An oasis of peace located in the heart of Tuscany on the wine roads! -A strategic area between Certaldo, San Gimignano, Siena and Florence. -Casa Valentina is hidden in a grove where you will enjoy fresh air, a stream with the chirping of birds -A newly renovated house that meets the historicity of the property, the comfort and the contemporaneity that makes it unique in its style - The warmth of the wood-burning fireplace - Heated whirlpool tub embraced by your own 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.

Elegant and bright apartment in Montescudaio
The apartment has been recently renovated, very bright and welcoming, the furnishings are modern and practically new. Located in the residential area of Montescudaio, quiet and peaceful from where you can easily reach the most characteristic places of Tuscany: medieval villages, enchanting hills and all the splendid historic cities (Pisa, Florence, Siena...) that make Tuscany such a popular destination. Just 20 minutes to the sea. Your vacation will be unforgettable!

Luxury Medieval Tower • Exclusive Chianti Stay
Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

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.

Enjoy Amazing View in Tuscany in Our Country House
An amazing experience between nature, flavor 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 olive groves and vineyards with an amazing view. A countryside Tuscan home, surrounded by olive’s fields And greenery, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a cozy and relaxing holiday.

The cypress
Dependance of 30 sqm new building located in the context of property with independent main house immersed in the beautiful Tuscan countryside 12 km from the sea and close to centers of cultural interest. The beautiful villages of Bolgheri and Castagneto Carducci are easily accessible. Half anhour drive from Volterra. The furniture is brand new. Garden and pool with sea view with sea view available for guests to use.
Popular amenities for Guardistallo holiday rentals
Other great holiday rentals in Guardistallo

Luxury Medieval Tower - Penthouse

PRIVATE VILLA ACQUAVIVA in Montescudaio/pool

"La Cavina" Vacation Home

Rosa: Tuscan Views & Pool, Walk to Town

Charming Olive Harmony Villa

THE VIEW - ENTIRE VILLA - SWIMMING POOL WITH SEA VIEW

Dream villa in Chianti with panoramic garden

Romantic Villa with private pool - "Il Pollaio"
When is the best time to visit Guardistallo?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $197 AUD | $159 AUD | $175 AUD | $163 AUD | $163 AUD | $169 AUD | $173 AUD | $191 AUD | $157 AUD | $173 AUD | $177 AUD | $212 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 |
Frequently Asked Questions
Are there family-friendly vacation rentals in Guardistallo?
Guardistallo has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Guardistallo?
Experience the best of Guardistallo with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Guardistallo?
Four-legged friends are welcome in Guardistallo. Choose from more than 180 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Guardistallo?
Yes! Work meets play with ease at over 60 vacation rentals in Guardistallo featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Guardistallo house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 house rentals with pools in Guardistallo, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Guardistallo have air conditioning?
Absolutely! We offer over 60 apartment rentals with air conditioning in Guardistallo. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Guardistallo have a kitchen?
Absolutely! We offer over 10 condo rentals with a kitchen in Guardistallo. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Guardistallo have wifi?
Absolutely! We offer over 100 apartment rentals with wifi in Guardistallo. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Guardistallo have free parking?
Absolutely! We offer over 80 apartment rentals with free parking in Guardistallo. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Guardistallo?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 120 homes with a kitchen, over 80 homes with free parking, over 60 homes with air conditioning, over 100 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Guardistallo

Total holiday rentals
Explore 280 holiday rentals in Guardistallo

Nightly prices starting at
Guardistallo holiday rentals start at $42 AUD per night before taxes and fees

Verified guest reviews
Over 3,160 verified reviews to help you choose

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

Pet-friendly accommodation
Find 180 rentals that welcome pets

Holiday rentals with a pool
130 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
220 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
Destinations to explore
- Apartment rentals Guardistallo
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- 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
- Fortezza da Basso
- Uffizi Gallery
- Basilica Di San Miniato A Monte
- Piazza della Repubblica
- Piazzale Michelangelo
- Pitti Palace
- Gorgona
- Spiaggia Di Sansone
- Parco delle Cascine




