
Holiday houses in Guardistallo
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Top-rated holiday rentals in Guardistallo
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The Casale Hills & Sea Tuscany Barn
In the heart of the medieval village of Casale Marittimo Il Fienile di Casale is a beautifully restored old hayloft that keeps all the authentic Tuscan charm. With its brick vaulted ceilings, wooden beams and stone walls it offers a warm and welcoming atmosphere. From the living room you can enjoy a breathtaking view over the rolling hills, vineyards and olive groves of the Etruscan Coast stretching all the way to the sea. Perfect for those looking for relaxation wine tourism and nearby beaches.

1500 Stone house a corner of paradise in Chianti
Welcome to Agriturismo Podere Tegline your gateway to a true unforgettable Tuscan holiday. Immerse yourself in the secrets of Chianti Classico Wine as you reside in a meticulously restored ancient farmhouse from the 1500s. Here we strive to offer an authentic experience that resonates with the charm of the past, within a breathtaking natural oasis as a little heaven. 2005-2026 We have been hosting for 21 years and guests have come from 67 different countries.We have been Superhost for 11 years.

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

Countryside apartment in villa close to the beach
Montescudaio, one of the most beautiful villages in Italy and located in the Val di Cecina, is the setting for the Agriturismo Il Polveraio, located in the open countryside and in the middle of an olive grove, with a view of the nearby Tyrrhenian Sea and the Tuscan Archipelago. The agriturismo offers various accommodations located in the main house, dating back to the 11th century AD, and in two outbuildings and will allow you to experience a stay in total peace and tranquillity.

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.

Cosimo Charme in Chianti
An authentic corner of Tuscany in the heart of Chianti Let yourself be captivated by the charm of our apartment, a small jewel with a unique style, finely renovated and set inside a historic building in the center of the medieval village of Barberino Val d'Elsa. Here, every detail tells a story and offers an authentic experience of Tuscan beauty. The location is ideal for those who want to explore the nearby wonders, we are only 30 km from Florence and 35 km from Siena

Casa al Gianni - Hut
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Live the Tuscany Experience 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 greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

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.

Open Space Piscina e Giardino
La mia casa è immersa nella campagna toscana, tra olivi e vigne, nel cuore del Chianti. Intorno, panorami meravigliosi e un’atmosfera di pace e relax. Il giardino è uno spazio speciale, ideale per momenti da vivere all’aperto. Per chi lo desidera, è possibile – su richiesta – condividere esperienze legate alla cucina e alla convivialità, come cene preparate con cura, da gustare insieme, anche a lume di candela, in un contesto intimo e accogliente.

Tuscan Luxury Villa • Natural Pool & Privacy
Immagina di svegliarti in totale privacy, circondato dalle colline del Chianti, con la tua piscina naturale, la spiaggia e il chiringuito. Non è solo un soggiorno, ma una vera “private luxury experience” toscana. Tenuta Virgilio nel Chianti è una villa immersa nella natura, perfetta per chi cerca relax, silenzio ed esclusività in Toscana. Oltre 3 ettari di uliveto e totale privacy: nessuno spazio condiviso, solo la tua esperienza in Toscana.
Popular amenities for Guardistallo holiday rentals
Other great holiday rentals in Guardistallo

AnticaVista, Luxury Apartment with Tower Views

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

Montaleo 4 by Interhome

ASTOR - "La Dolce Vita" the Tuscan way

"La Cavina" Vacation Home

Luxury Medieval Tower • Exclusive Chianti Stay

Il Pietraio

In the Castle
When is the best time to visit Guardistallo?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $224 AUD | $194 AUD | $168 AUD | $166 AUD | $166 AUD | $171 AUD | $175 AUD | $194 AUD | $159 AUD | $175 AUD | $180 AUD | $215 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 serviced apartment rentals in Guardistallo?
Experience the best of Guardistallo with our serviced apartment rentals, starting at about $170 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 vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 130 vacation homes 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 serviced apartment rentals in Guardistallo have a kitchen?
Absolutely! We offer over 10 serviced apartment rentals with a kitchen in Guardistallo. Enjoy a tailored experience with all the comforts you desire.
Do serviced apartment rentals in Guardistallo have wifi?
Absolutely! We offer over 10 serviced apartment rentals with wifi in Guardistallo. Enjoy a tailored experience with all the comforts you desire.
Do serviced apartment rentals in Guardistallo have free parking?
Absolutely! We offer over 10 serviced 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 80 homes with free parking, over 100 homes with wifi, over 60 homes with air conditioning, over 120 homes with a kitchen, 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
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- 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
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Stazione Santa Maria Novella
- Del Chianti
- Piazza della Repubblica
- Spiagge Bianche
- Gorgona
- Piazzale Michelangelo
- Spiaggia Di Sansone
- Parco delle Cascine
- Gulf of Baratti
- Pitti Palace
- Piazza della Signoria
- Boboli's Garden





