
Family-friendly vacation rentals in Guardistallo
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Top-rated family-friendly rentals in Guardistallo
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Podere Vergianoni immerso nelChianti con piscina
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.

Giglio Blu Charming Loft
The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

House with a breathless view in Tuscany
Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

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

Farmhouse with pool in Chianti
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

Monteriggioni Castello, holiday house in Tuscany
Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

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!

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.

Casa del Poggio, with a beautiful sea view
The Casa del Poggio (house at the hill) is located in the hills of Castagneto Carducci and is part of our organic farm. It is immersed in a peaceful countryside surrounded by olive groves, vineyards and woodland and enjoys a beautiful view of the sea and the castle of Castagneto Carducci. At the same time its position allows you to reach the village in just 10 minutes by foot and the beaches of Marina di Castagneto in 10 minutes by car or bus.

Casa al Gianni - Capanna
Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Michelangelo: entire space in the heart of Tuscany
Come and take a vacation at our beautiful apartment in Peccioli, Tuscany! Enjoy a renovated space, beautifully decorated, with new appliances and furniture, Air conditioner in all spaces, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.
Popular amenities for Guardistallo family-friendly rentals
Family-friendly home rentals with a hot tub

Infinity pool in Chianti area

Il Fienile, Cottage in the country with Jacuzzi

[Near Florence] Nautilus loft

"Sunflower" apartment with view of Siena

Beautiful renovated barn in Tuscany

Il Fienile di Tigliano (former barn in Vinci-Florence)

Villa di Geggiano – Guesthouse

Farmhouse , pool, 13 px. Lucca 10km
Family- and pet-friendly home rentals

Belforti Tower

Casa Al Poggio & Chianti view

Countryside apartment in villa close to the beach

Apartment with swimming pool and garden

Antico Borgo Ripostena – n. 8 Old House

Piazzale Michelangelo among the olive trees

Countryside Cottage With View - Le Rondini apt

Stunning Tuscan apartment for 2
Family-friendly home rentals with a pool

Farmhouse (for 4 pp Tuscan Maremma

In the Tuscan countryside, Podere I Luoghi with pool Ap1

2+2 beautiful apartment in residenc

Amazing view, pool and relax, 5 adults

The Cottage to relax and enjoy

Tuscan countryside, peace and relaxation 10 minutes from Siena

Farmhouse in Chianti

TUSCANY farm house SWIMMING POOL
Quick stats about vacation rentals that are family-friendly in Guardistallo
Total rentals
120 properties
Nightly prices starting at
€ 34 before taxes and fees
Total number of reviews
930 reviews
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
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- Elba
- Santa Maria Novella
- Duomo di Firenze
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Gorgona
- Gulf of Baratti
- Uffizi Gallery
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Spiaggia Di Sansone
- Spiaggia di Capo Bianco
- Spiagge bianche
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- Kite Beach Fiumara
- Spiaggia Di Barbarossa
- Spiaggia Libera
- The Boboli Gardens