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Holiday rentals in Guardistallo

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Top-rated holiday rentals in Guardistallo

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Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment in Noce
5 out of 5 average rating, 318 reviews

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.

Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 150 reviews

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.

Guest favourite
Home in Montescudaio
4.96 out of 5 average rating, 126 reviews

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

Top guest favourite
The image features a rustic stone house surrounded by lush greenery, with a wooden door and shuttered windows. A set of stairs leads to a raised outdoor area, partially enclosed by a stone wall, providing a serene view of the surrounding nature.
Holiday home in San Gimignano
4.97 out of 5 average rating, 63 reviews

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.

Superhost
A spacious glass-enclosed veranda provides views of the garden and surrounding countryside. The wooden ceiling features exposed beams, complemented by black seating and a glass table. Potted plants add a natural touch, enhancing the tranquil atmosphere of the space.
Farm stay in Montescudaio
4.72 out of 5 average rating, 90 reviews

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.

Top guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 129 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 207 reviews

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.

Top guest favourite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Apartment in San Gimignano
5 out of 5 average rating, 39 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Top guest favourite
A modern kitchen and dining area feature sleek cabinetry and a spacious dining table. White chairs surround the table, complemented by a vase of flowers. Large windows enhance the room's brightness, while neutral-colored tiles create a clean and inviting atmosphere.
Flat in Montescudaio
4.93 out of 5 average rating, 167 reviews

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!

Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.92 out of 5 average rating, 255 reviews

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!

Guest favourite
A white umbrella provides shade over a small round table, which holds a potted cactus. In the background, rolling hills and olive trees are visible, accompanied by a swimming pool reflecting the sky. Lush greenery surrounds the area, enhancing the peaceful countryside ambiance.
Guest suite in Casale Marittimo
4.83 out of 5 average rating, 111 reviews

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 within easy reach. A half-hour drive from Volterra. The furnishings are completely new. Garden and swimming pool with sea view available for guests.

Top guest favourite
A sunlit terrace features a wooden dining table with chairs, surrounded by vibrant red flowers in pots. An awning provides shade, and a view of nearby buildings is visible. The tiled flooring adds to the rustic charm of this outdoor space.
Home in Guardistallo
4.94 out of 5 average rating, 36 reviews

Da 7 Cervelli

The XIXth century house is in a small village in Tuscany, 10 km to the Tyrrhenian Sea, 25km to Volterra, 20 km to Bolgheri, 80 km to Siena and 100 km to Florence. The train station (Cecina) it's 9km away. Slow life, excellent wine and food, historical heritage, this part of Tuscany it's a great choice for your holidays. For your stay you can find a private parking and a beautyful country garden.

Popular amenities for Guardistallo holiday rentals

When is the best time to visit Guardistallo?

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Avg. price$179 SGD$145 SGD$159 SGD$149 SGD$149 SGD$154 SGD$157 SGD$174 SGD$142 SGD$157 SGD$161 SGD$193 SGD
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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 $38 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    220 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

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