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Holiday houses in Guardistallo

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Top-rated holiday rentals in Guardistallo

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A charming pathway leads to the entrance of the house, surrounded by lush greenery. Flower pots are positioned along the stone walkway, with a seating area visible to the side, inviting guests to enjoy the serene landscape of rolling hills in the background.
Home in Greve in Chianti
4.98 out of 5 average rating, 220 reviews

Love in Chianti

Welcome to the delightful cottage of Riccardo and Pauline, a small corner of love where colors and details are designed to give peace and quiet. You will find yourself immersed in the green Tuscan hills, in a breathtaking landscape where the renowned Chianti Classico wine is born. The area is ideal for walking and cycling. You will be close to the cities of art, such as Florence, Siena and Arezzo. Upon request and according to availability, we offer a paid shuttle service. We look forward to seeing you ❤️

Guest favourite
Apartment in Casale Marittimo
4.93 out of 5 average rating, 40 reviews

Fienile di Casale Hills & Sea Tuscany

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.

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, 151 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.

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, 107 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
Home in Montescudaio
4.96 out of 5 average rating, 128 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
An outdoor seating area is showcased on a sunlit terrace, featuring a small wooden table surrounded by colorful chairs. A terracotta pot filled with vibrant red flowers adds a touch of color against the rustic stone wall of the structure.
Home in Casale Marittimo
5 out of 5 average rating, 58 reviews

Countryside-panoramic sea Casale Marittimo Tuscany

Piccolo appartamento immerso nella tranquillità della campagna toscana. A dieci minuti dalla Costa degli Etruschi. Vista mare. Per trascorrere un soggiorno all’insegna della privacy e del relax, ma con tutte le attrattive della zona a un passo da qui.E' ben accetto il tuo amico peloso,SOLO UNO e di PICCOLA taglia. Da qui partono molti sentieri di trekking e percorsi bike per scoprire i paesaggi suggestivi.Ottimi ristoranti tipici,e cantine .!!! Buon soggiorno!Tassa soggiorno al check-out

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
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, 218 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 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
4.94 out of 5 average rating, 171 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
The rustic building features a warm ochre facade and a classic tiled roof. An expansive oak tree provides shade to the outdoor seating area, which includes wooden chairs and a small table. Lush greenery surrounds the property, contributing to the tranquil rural setting.
Farm stay in Simignano
4.92 out of 5 average rating, 271 reviews

Casa al Gianni - Fig

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
Apartment in Montescudaio
4.82 out of 5 average rating, 129 reviews

Casetta Sole View over Tuscany Hills and Sea

Casetta Sole is a cozy Tuscan home with equipped garden, at the foot of Montescudaio village, Costa degli Etruschi, a step from the countryside. View over green hills, vineyards, olive groves and sea in the valley. Super-fast Wi-Fi (ideal for smart working), free parking + EV charging station. Garden with barbecue. Few km from the sea, on the Wine Route: near Volterra and San Gimignano, perfect for relaxation, wine tours and DOC tastings. Welcome to our Tuscany!

Top Guest favourite
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home in Peccioli
4.99 out of 5 average rating, 141 reviews

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.

Popular amenities for Guardistallo holiday rentals

When is the best time to visit Guardistallo?

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Avg. price$271 NZD$235 NZD$204 NZD$201 NZD$201 NZD$208 NZD$213 NZD$235 NZD$192 NZD$213 NZD$218 NZD$261 NZD
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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 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 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 house rentals in Guardistallo have wifi?

    Absolutely! We offer over 60 house 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 120 homes with a kitchen, 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 $51 NZD 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

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