
Holiday houses in Chianni
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Top-rated holiday rentals in Chianni
Guests agree: these stays are highly rated for location, cleanliness and more.

Casa al Gianni - Hut
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

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.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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.

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.

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.

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 Castle of Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

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.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Casa Dante – Authentic Chianti Stay | Views & Relaxation
Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.
Popular amenities for Chianni holiday rentals
Other great holiday rentals in Chianni

Villa la scuderia quiet luxury private garden pool

Venere's Paradise Cabine - Le Fraine Glamping

Rosa: Tuscan Views & Pool, Walk to Town

Luxury 4BR Chianti Tuscany Home Pool Ensuite Baths

Villa of the Hydrangeas

Tower dating back to 1212 in the heart of Tuscany

Air Suite at Villa Santa Lucia Nuova

Wine Loft in the vineyards
Frequently Asked Questions
Are there pet-friendly vacation rentals in Chianni?
Four-legged friends are welcome in Chianni. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there Chianni vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chianni, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in Chianni?
Chianni has more than 20 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 Chianni?
Experience the best of Chianni with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Chianni have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Chianni. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chianni have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Chianni. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chianni have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Chianni. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Chianni?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Chianni

Total holiday rentals
Explore 30 holiday rentals in Chianni

Nightly prices starting at
Chianni holiday rentals start at $69 NZD per night before taxes and fees

Verified guest reviews
Over 440 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Wi-Fi availability
30 of Chianni holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chianni rentals

4.8 Average rating
Chianni stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Piazza del Duomo (Pisa)
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Pisa Centrale Railway Station
- Mercato Centrale
- Fortezza da Basso
- Piazza della Repubblica
- Uffizi Gallery
- Del Chianti
- Gorgona
- Spiaggia Di Sansone
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Parco delle Cascine
- Boboli's Garden
- Spiagge Bianche
- Spiaggia di Capo Bianco
- Gulf of Baratti
- Basilica of Santa Croce





