
Family-friendly holiday rentals in Guardistallo
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Guardistallo

Total holiday rentals
Explore 130 holiday rentals in Guardistallo

Nightly prices starting at
Guardistallo holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 920 verified reviews to help you choose

Pet-friendly accommodation
Find 80 rentals that welcome pets

Holiday rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
110 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
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 historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills, and vineyards with unique sunsets.

Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Tuscan cottages in an ancient villa with a garden
The Cottage is part of a property owned by the Bernocchi family, which was already on maps of the area in the 1500s and is located right on an ancient Roman road that crossed the Calvana Mountains. About 9 km from Prato and 20 km from Florence. The Cottage, open on three sides, is situated in a panoramic position surrounded by a private park, ideal for walking and sports. A real home fitted with kitchen, living room, bedroom and bathroom. Large outdoor spaces, garden, and botanical garden.

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

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.

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

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!

House at Gianni - Leccio
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!

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!

[SAN LORENZO-DUOMO] Prestigious Historic Residence
Make your stay a unique experience and give yourself an emotion that will last for life. Located in the heart of Florence, this magnificent historic residence is the ideal solution for those looking for an exclusive and prestigious location to combine with a central position, perfect for easily visiting the main sites of interest, reachable in less than 10 minutes on foot. The apartment enjoys exclusive views of the Medici Chapels, offering a unique view.

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

A Big Dream in a Little Tower.

Beautiful renovated barn in Tuscany

Agriturismo La Villa - L'Olivo, Pool & Hot Tub

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Country home near Florence and Pisa

Nada Home

Farm in the Tuscan hills

Tuscan Villa Florence, pool, hot tub e tennis
Family- and pet-friendly home rentals

I 9 Cipressi – Tuscan Retreat with Pool & View

In the Tuscan countryside, Podere I Luoghi with swimming pool Ap3

2+2 apartment in beautiful residenc

Rosa: Tuscan Views & Pool, Walk to Town

Gorgona - cozy apartment in farmhouse

The Cottage to relax and enjoy

Apartment with swimming pool and garden

Borgo Ripostena – No. 8 Casa Vecchia
Family-friendly home rentals with a pool

Podere La Sterza The barn

Luxury Villa in Chianti • Private Natural Pool

Michelangelo apt ~ wild Tuscany Hills ~ Le Fraine

Podere Tignano, 4-bedroom villa in the Chianti!

Countryside Dream farm in Tuscany

Two-room apartment with exclusive pool, large garden, sea

Beautiful vacation home with infinity pool

Superior Lodge with 2 bedrooms and outdoor tub
When is the best time to visit Guardistallo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $366 NZD | $370 NZD | $304 NZD | $275 NZD | $261 NZD | $292 NZD | $325 NZD | $385 NZD | $280 NZD | $294 NZD | $298 NZD | $366 NZD |
| 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 |
Destinations to explore
- Rentals with pools Guardistallo
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- Rentals with an EV charger Guardistallo
- Rentals with a hot tub Guardistallo
- Rentals with outdoor seating Guardistallo
- Smoking-friendly rentals Guardistallo
- Rentals with a patio Guardistallo
- Pet-friendly rentals Guardistallo
- Rentals with a washing machine and dryer Guardistallo
- Rentals with a fire pit Guardistallo
- Rentals with a fireplace Guardistallo
- Condo rentals Guardistallo
- Family-friendly rentals Pisa
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Elba
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Mercato Centrale
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Spiagge Bianche
- Piazza della Repubblica
- Gulf of Baratti
- Parco delle Cascine
- Spiaggia Di Sansone
- Piazzale Michelangelo
- Gorgona
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio





