Vacation rentals in Castellina in Chianti

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Castellina in Chianti

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Panzano In Chianti

4.98 out of 5 average rating, 354 reviews

Old farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

Mar 23 – 30

R2,082 ZAR per night

Guest favorite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 166 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

Apr 13 – 20

R11,539 ZAR per night

Guest favorite

Condo in Noce

5.0 out of 5 average rating, 125 reviews

Vergianoni estate nestled in the Chianti with a pool

Podere Vergianoni is located in the beautiful hills of Chianti. The apartment is furnished in perfect traditional style of ancient Tuscany : wooden beams, terracotta floors and unique, handcrafted furniture. Inside you will find a large living room with kitchen ,sofa bed , a bathroom and a bedroom with double bed. In the large outdoor courtyard you will find at your disposal a swimming pool on a breathtaking terrace where you can enjoy a wonderful view of the view with unique sunsets!

Jan 22 – 29

R2,517 ZAR per night

Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 109 reviews

Villa di Geggiano - Guesthouse

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 idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. 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.

Mar 25 – Apr 1

R9,407 ZAR per night

Guest favorite

Cottage in Monteriggioni

4.97 out of 5 average rating, 173 reviews

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.

Feb 11 – 18

R2,756 ZAR per night

Guest favorite

Guest suite in Greve in Chianti

4.94 out of 5 average rating, 381 reviews

Selvabella in Chianti B&B. Suite Lo Scricciolo

Lo Scricciolo is located in the tower, the highest building of the house. By a separate entrance from the main house, through a loggia overlooking the Tuscan countryside, you access the first floor. Here are the living room with wooden ceiling and a small bathroom. From the living room, an old stone staircase leads to the upper floor where there is a large double bedroom. Lo Scricciolo has an efficient system of heating for the cold season.

Oct 13 – 18

R2,316 ZAR per night

Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 311 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Nov 30 – Dec 7

R3,077 ZAR per night

Guest favorite

Apartment in Greve in Chianti

4.99 out of 5 average rating, 115 reviews

The Nest in the Chianti

We would like to inform you that for this emergency we are doing everything we can to help and protect our guests by adopting a detailed and strict cleaning, disinfecting and sanitizing all parts of the house. Cozy apartment, finely renovated in the heart of the historic center on the second floor overlooking the beautiful Piazza di Greve in Chianti. On its condominium terrace you can spend beautiful moments of relaxation.

Feb 13 – 20

R1,973 ZAR per night

Guest favorite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 202 reviews

"Red Rose" apartment with a view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located in the Villas di Corsano, just 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Mar 26 – Apr 2

R2,494 ZAR per night

Guest favorite

Home in Monticchiello

4.97 out of 5 average rating, 135 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Jan 20 – 27

R6,063 ZAR per night

Guest favorite

Farm stay in Pari

4.98 out of 5 average rating, 226 reviews

TUSCANY farm house SWIMMING POOL

Our little farm is a beautiful location for a relaxing vacation with a private swimming pool. We are close to the naturally occurring hot springs of Petriolo and 30 km. far from Siena. We are only two km. from Pari, an ancient medieval village.

Apr 20 – 27

R1,876 ZAR per night

Guest favorite

Home in Radda in Chianti

4.92 out of 5 average rating, 104 reviews

Casa Dante

Casa Dante is in the heart of Chianti, a stone's throw from the historic center of Radda in Chianti, an hour from Florence and halfanhour from Siena. Located in a panoramic position in the Chianti hills, it allows you to enjoy a beautiful view.

Oct 28 – Nov 4

R3,492 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Castellina in Chianti vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Castellina in Chianti's top sights

Gelateria di Castellina10 locals recommend

Osteria Rosticceria Il Re Gallo6 locals recommend

Antica Trattoria la Torre20 locals recommend

Taverna Squarcialupi4 locals recommend

Il Fondaccio Dai Dottori9 locals recommend

Pizzeria il Fondaccio4 locals recommend

Other great vacation rentals in Castellina in Chianti

Superhost

Apartment in Castellina in Chianti

4.81 out of 5 average rating, 258 reviews

Relax Chianti. Apartment with pool and garden

Mar 9 – 16

R2,084 ZAR per night

Guest favorite

Farm stay in Siena

4.97 out of 5 average rating, 231 reviews

Authentic Tuscan Country House WITH A/C

Feb 9 – 16

R2,237 ZAR per night

Guest favorite

Apartment in Monticchiello

4.99 out of 5 average rating, 299 reviews

Romantic Tower's dating 1200

Nov 1 – 8

R4,476 ZAR per night

Guest favorite

Guest suite in Greve in Chianti

4.93 out of 5 average rating, 164 reviews

House with garden in a medieval village

Nov 8 – 15

R2,200 ZAR per night

Guest favorite

Villa in Ambra

4.98 out of 5 average rating, 107 reviews

Chianti Villa in Tuscany near Siena & Arezzo

Jan 18 – 25

R15,734 ZAR per night

Guest favorite

Apartment in Castellina in Chianti

5.0 out of 5 average rating, 45 reviews

Apartment "Gardenia"

Oct 22 – 29

R2,183 ZAR per night

Guest favorite

Home in Castellina in Chianti

4.91 out of 5 average rating, 64 reviews

Casanuova Pietrafitta farm stay

Jan 23 – 30

R2,679 ZAR per night

Guest favorite

Home in Castellina in Chianti

4.97 out of 5 average rating, 79 reviews

StageROOM03 -Chianti Idillic Country living

Dec 2 – 9

R8,985 ZAR per night

Show all

Quick stats about vacation rentals in Castellina in Chianti

Total rentals
50 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
670 reviews
Nightly prices starting at
R742 ZAR before taxes and fees

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 20 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 10 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 30 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 Castellina in Chianti?
Experience the best of Castellina in Chianti 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 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 villa rentals in Castellina in Chianti have wifi?
Absolutely! We offer over 10 villa rentals with wifi 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 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Castellina in Chianti

Top-rated vacation rentals in Castellina in Chianti

Vacation rentals for every style

Apartments

Hotels

Unique stays

Popular amenities for Castellina in Chianti vacation rentals

Stay near Castellina in Chianti's top sights

Other great vacation rentals in Castellina in Chianti

Apartment in Castellina in Chianti

Farm stay in Siena

Apartment in Monticchiello

Guest suite in Greve in Chianti

Villa in Ambra

Apartment in Castellina in Chianti

Home in Castellina in Chianti

Home in Castellina in Chianti

Quick stats about vacation rentals in Castellina in Chianti

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Castellina in Chianti?

Are there vacation rentals with a dedicated workspace in Castellina in Chianti?

Are there Castellina in Chianti vacation rentals on Airbnb with pools?

Are there family-friendly vacation rentals in Castellina in Chianti?

How much does it cost to stay in apartment rentals in Castellina in Chianti?

Do apartment rentals in Castellina in Chianti have air conditioning?

Do villa rentals in Castellina in Chianti have wifi?

What are the most popular amenities for Apartment Rentals in Castellina in Chianti?

Destinations to explore