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Vacation rentals in Guardistallo

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Top-rated vacation 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.
Condo in Noce
5 out of 5 average rating, 316 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
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 100 reviews

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.

Guest favourite
A charming stone cottage is surrounded by lush greenery and tall trees. Two white lounge chairs are positioned on the manicured lawn, accompanied by a small round table. A sun umbrella offers shade, while large windows reflect natural light, showcasing the inviting interior.
Home in Montescudaio
4.96 out of 5 average rating, 125 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

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
The living area features a striped sofa paired with a round coffee table and a wooden dining table. Exposed wooden beams line the ceiling, and natural light brightens the space through a window. A warm, terracotta tile floor complements the traditional furnishings.
Condo in Montescudaio
4.95 out of 5 average rating, 78 reviews

Casina del Fabbro Hills and Sea Views Tuscany

Casina del Fabbro is a 45 sqm apartment above old blacksmith Nonno Mario's workshop, right in Montescudaio's center, Costa degli Etruschi. Step into the village and open the windows to an uninterrupted view: green hills, vineyards, olive groves and the sea on the horizon. 15 minutes from beaches, dreamy sunsets. Warm original terracotta floors, full kitchen, comfy double bed, air conditioning, fast Wi-Fi. Perfect for two seeking real Tuscany, peace and DOC wine. Welcome!

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.
Apartment in Montescudaio
4.93 out of 5 average rating, 166 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, 249 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, 110 reviews

The cypress

A new building of 30 sqm located in the context of a property with a main detached house immersed in the beautiful Tuscan countryside 12 km from the sea and close to centres of cultural interest. You can easily reach the beautiful villages of Bolgheri and Castagneto Carducci. Halfan hour's 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.

Guest favourite
Apartment in Montescudaio
4.92 out of 5 average rating, 79 reviews

The Borgo Suite

Comfortable and charming two-room apartment, newly renovated, located in the heart of the historic center of Montescudaio. The Suite has the use of a large terrace that offers a breathtaking view from the hills to the sea overlooking the islands of the Tuscan archipelago. Strategically located both for enjoying a beach vacation and for relaxing in the tranquility of a medieval village

Top guest favourite
A solitary tree stands prominently in the foreground, framed against a vast landscape. Below, the coastline stretches toward the horizon, with the sea shimmering in the distance. The view includes a charming town nestled among the lush greenery of the surrounding hills.
Farm stay in Castagneto Carducci
4.99 out of 5 average rating, 114 reviews

sea view villa with private infinity pool

RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.

Popular amenities for Guardistallo vacation rentals

When is the best time to visit Guardistallo?

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Avg. price$195 CAD$158 CAD$173 CAD$162 CAD$162 CAD$168 CAD$172 CAD$190 CAD$155 CAD$172 CAD$176 CAD$211 CAD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Guardistallo?

    Guardistallo has more than 120 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Guardistallo?

    Experience the best of Guardistallo with our apartment rentals, starting at about $30 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 140 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 50 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 house rentals in Guardistallo have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Guardistallo. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Guardistallo have a kitchen?

    Absolutely! We offer over 10 villa rentals with a kitchen in Guardistallo. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Guardistallo have wifi?

    Absolutely! We offer over 10 condo 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 Villa Rentals in Guardistallo?

    Enhance your stay in our Villa Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Guardistallo

  • Total vacation rentals

    Explore 290 vacation rentals in Guardistallo

  • Nightly prices starting at

    Guardistallo vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 140 rentals that welcome pets

  • Vacation rentals with a pool

    130 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    220 of Guardistallo vacation 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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