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

Casa Mirella in Chianti
Nestled among the rolling Tuscan hills, our apartment is the ideal choice for those who want to experience an authentic stay in the Chianti Classico region. The terrace offers a relaxing space where you can enjoy a glass of wine while admiring the view. The location is strategic: 28 km from Siena and 45 km from Florence, in the heart of medieval villages, among renowned wineries, farms and suggestive Etruscan tombs, to be visited by those who love history and culture. Experience the most authentic Tuscany: we look forward to seeing you!

Leonardo - Chianti/Siena, Florence, San Gimignano.
Ancient stone house from the 15th century in a small renovated medieval hamlet in the heart of the Chianti Classico. Located on top of a hill between Florence, Siena and San Gimignano. TENNIS COURT+ SWIMMING POOL Splendid view over the valley. Independent entrance; On the ground floor: large living room with two sofas, dining area and open kitchen. On the 1st floor: 2 bedrooms and 1 bathroom with shower; Private garden with terrace - table and chairs for eating under the gazebo and sun loungers

Cottage Vittoria - Masseto In Chianti
MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Cappero (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

Visit Chianti, Florence, Siena, S.Gimignano
The apartment into Borgo Sicelle Residence, in Castellina in Chianti area, between Florence and Siena. It's 55 sqm, 4 guests, it has a small kitchen with sat tv, 2 double bedroom, a bathroom with shower (not bidet). It’s on the first floor. Outside, on the ground floor, there are shared tables. Heated pool up to 25°degrees in printemps and automne. In front of the property there is a restaurant, only for dinner, closed on Wednesday. Not public transport to reach the property

"Gardenia" Apartment
The apartment is located in the new “CASA VACANZE SQUARCIALUPI” building, 100 meters from the historic center of Castellina in Chianti. Attention to detail, it is finely furnished in marble, with relaxing neutral and natural colors that recall the Provencal style. Very bright and spacious, it has an area of about 42 square meters and is spread over two floors. On foot you can reach: restaurants, wine bars, bars, banks, laundry, supermarket, clothing stores, grocery stores, baker.•

Relaxation and comfort in the hills of Florence
Apartment in a typical Tuscan stone farmhouse: measuring 160 square meters, it is finished with typical Tuscan materials, pietra serena and terracotta. It consists of a large living room at the entrance, dining room, kitchen, 2 bathrooms, storage room, 3 bedrooms, and a study area. Arranged in an east-west position thanks to a large terrace, a patio and a large private garden, it allows you to enjoy the sunrise for your breakfast and the sunset for a pleasant aperitif.

Farmhouse in Chianti with Swimming Pool
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 located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.

House at Gianni - Olmo
Hi, we're Cristina & Carmelo! We invite you to discover the rustic charm and authenticity of "Casa al Gianni," our farmhouse in the heart of the Tuscan countryside, 20 minutes from Siena. After a recent renovation, our accommodations are ready to welcome you with all modern comforts without losing the essence of tradition. In the Olmo Apartment, brand new beds await you, a promise of peaceful and regenerating sleep, a new kitchen and a new bathroom.

The Pesa di Mezzo
La Pesa di Mezzo is a beautifully restored Tuscan barn set in the heart of the unspoilt Chianti countryside.The property enjoys a peaceful and secluded position on a gentle slope, offering panoramic views across the Chianti Classico landscape. Surrounded by fragrant rosemary and lavender, this is the perfect retreat for couples or honeymooners seeking privacy, charm, and an authentic Tuscan atmosphere.

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

La Terrazza sul Borgo - Montefioralle Apartment
L'appartamento "La terrazza sul Borgo" nasce all'interno di uno storico edificio nello stupendo borgo medievale di Montefioralle, uno dei borghi più belli d'Italia. La struttura, risalente a circa 1000 anni fa, è stata completamente ristrutturata nel Gennaio 2020 cercando di preservare tutte le caratteristiche originali che ne fanno un ambiente unico.

Casa Tatini your house in Chianti
Casa Tatini is in the heart of Chianti just 500 meters from Castellina in Chianti in the middle of the vines and nature, to relax in the greenery. The house, equipped with swimming pool, consists of a double bedroom, living room with kitchen and private bathroom.
Popular amenities for Castellina in Chianti holiday rentals
Other great holiday rentals in Castellina in Chianti

Tuscany jem: The Chianti Farmer's House

Leonardo Suite

Cerretino Vigna by Interhome

Podere La Castellina - No. 4 FICO

Tenuta Virgilio in Chianti · Pool & Total Privacy

Sunset Vineyard Views • Pool • Walk to Panzano

La Nicchia, our little gem

Castellin di Bocco Tuscan countryhouse with pool
When is the best time to visit Castellina in Chianti?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £93 | £91 | £98 | £125 | £126 | £135 | £132 | £133 | £139 | £128 | £115 | £114 |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Castellina in Chianti?
Four-legged friends are welcome in Castellina in Chianti. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Castellina in Chianti?
Yes! Work meets play with ease at over 20 vacation rentals in Castellina in Chianti featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Castellina in Chianti vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Castellina in Chianti, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in Castellina in Chianti?
Castellina in Chianti has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Castellina in Chianti?
Experience the best of Castellina in Chianti with our house rentals, starting at about $50 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 Castellina in Chianti have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Castellina in Chianti have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Castellina in Chianti have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Castellina in Chianti have free parking?
Absolutely! We offer over 10 house rentals with free parking in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Castellina in Chianti?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Castellina in Chianti

Total holiday rentals
Explore 60 holiday rentals in Castellina in Chianti

Nightly prices starting at
Castellina in Chianti holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
60 of Castellina in Chianti holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Castellina in Chianti rentals

4.7 Average rating
Castellina in Chianti stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Cottage rentals Castellina in Chianti
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- Chalet rentals Castellina in Chianti
- Villa rentals Castellina in Chianti
- Rentals with pools Castellina in Chianti
- Rentals with a washing machine and dryer Castellina in Chianti
- Rentals with a fireplace Castellina in Chianti
- House rentals Castellina in Chianti
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- Rentals with a patio Castellina in Chianti
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Marina di Cecina
- Del Chianti
- Basilica of Santa Maria Novella
- Mercato Centrale
- Pisa Centrale Railway Station
- Cala Violina
- Eremo Di Camaldoli
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Spiagge Bianche
- Uffizi Gallery
- Porta Elisa
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Pitti Palace




