
Family-friendly vacation rentals in Guardistallo
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Guardistallo
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

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

La casa dei remi, discover Tuscany near the sea
My house is located in Livorno, in the characteristic Antignano district, close to the center and a stone's throw from the beautiful coves of the Lungomare, perfect for a dip and sunbathing. Ideal base for discovering the treasures of our city and the famous Tuscan art cities. You can enjoy our sea and cuisine based on fresh fish. Coffee, tea, herbal teas, milk and cookies are offered. The quiet and picturesque neighborhood is a 10-minute drive or 20-minute bike ride from the Center.

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.

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

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!

Wonderful Loft in Villa with Pool in Chianti
Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

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!
Popular amenities for Guardistallo family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

[Near Florence] Nautilus loft

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

Japan Apartment Port Area with Balcony and Jacuzzi

Nada Home

Farmhouse , pool, 13 px. Lucca 10km

La Casetta

Casa Luna-Splendida overlooking the pool and Tuscan nature
Family- and pet-friendly home rentals

Farmhouse (for 4 pp Tuscan Maremma

In the Tuscan green, Podere I Places with swimming pool Ap1

2+2 beautiful apartment in residenc

CaFrada, a medieval village in Guardistallo, Tuscany

Podere Guidi

Casa Al Poggio & Chianti view

Countryside apartment in villa close to the beach

Il Corbezzolo
Family-friendly home rentals with a pool

Infinity pool in Chianti area

A barn in Chianti

Podere La Castellina - No. 1 COTTAGE

Amazing view, pool and relax, 5 adults

La Fabbrichina

FIENILE VILLACOLLE Tuscan hill

Manuela apartment with pool in farmhouse

Cipressini 1 - Swimming pool and stunning view
When is the best time to visit Guardistallo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $260 CAD | $262 CAD | $245 CAD | $222 CAD | $210 CAD | $235 CAD | $262 CAD | $310 CAD | $226 CAD | $158 CAD | $264 CAD | $264 CAD |
| 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 |
Quick stats about vacation rentals that are family-friendly in Guardistallo

Total vacation rentals
Explore 120 vacation rentals in Guardistallo

Nightly prices starting at
Guardistallo vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 930 verified reviews to help you choose

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
90 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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- Elba
- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Spiagge bianche
- Cala Violina
- Gorgona
- Uffizi Gallery
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Pitti Palace
- Spiaggia Di Sansone
- Spiaggia di Capo Bianco
- Parco delle Cascine
- The Boboli Gardens
- Kite Beach Fiumara
- Spiaggia Libera
- Spiaggia Di Barbarossa
- Spiaggia della Padulella




