Vacation rentals with a pool in Castellina in Chianti

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Castellina in Chianti

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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

R11,669 ZAR per night

Guest favorite

Condo in Noce

5.0 out of 5 average rating, 124 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!

Mar 15 – 22

R3,234 ZAR per night

Guest favorite

Castle in Ferrano

4.99 out of 5 average rating, 162 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)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.

Apr 15 – 22

R5,808 ZAR per night

Guest favorite

Cottage in Chianni

4.98 out of 5 average rating, 118 reviews

La Pietruzza - The Private Chalet with a Soul -

Detached country cottage (in exclusive use) in stone and glass dating from XVIII century ideal for 4 persons. Wide wooden veranda. EXCLUSIVE POOL with SALTED WATER ( 33 ft x 16.40 ft ) depth of the pool from 4.6 ft to 7.9 ft. The Chalet is surrounded by 6000 meters of land with fruit trees, olive trees, acacias. We care about nature and do not use herbicides. There is no gas at home because it is all electric with photovoltaic system. (CIR O5OO12LTNOOO3)

Jan 5 – 12

R3,297 ZAR per night

Guest favorite

Apartment in Panzano in Chianti (FI)

4.96 out of 5 average rating, 202 reviews

Apt. Panzanello-Panzano in Chianti

The apartment offers all the comforts and tranquility of the Tuscan countryside. Enjoy the wonderful view that you can admire from your private terrace, a perfect place to spend peaceful and serene moments and accompanied by a glass of Panzanello wine. Access to the apartment is private and free parking is available. Kitchen is equipped with everything you need to prepare delicious meals. We do not have a restaurant but we will help you book in Panzano.

Nov 7 – 14

R2,452 ZAR per night

Guest favorite

Cottage in Lucardo

4.99 out of 5 average rating, 215 reviews

Best view ever & private pool

Antique Tuscan barn made into a comfortable home with private swimming pool. Best views ever. Close to Florence, Siena and Pisa. Very quiet, yet easy to reach. Sunsets you can only dream of. Ideal Tuscan getaway for family or two couples. The house has two bedrooms and two bathrooms plus a guest bathroom on the ground floor. The pool has a panoramic edge and whirlpool section. There are two restaurants on walking distance (a few hundred meters).

Jan 24 – 31

R5,152 ZAR per night

Superhost

Apartment in Castellina in Chianti

4.81 out of 5 average rating, 256 reviews

Relax Chianti. Apartment with pool and garden

Apartment nestled in the Chianti Classico hills, in the Borgo di Tregole, 5 km from Castellina in Chianti. Casa Cinzia is a private apartment inside a typical Tuscan farmhouse. Suitable for those who want to spend a vacation immersed in nature full of relaxation and silence. Ideal starting point for visiting the most important places in Tuscany. The apartment is equipped with all comforts. Linen is included in the price. Children are welcome

Apr 4 – 11

R2,108 ZAR per night

Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 310 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

R3,044 ZAR per night

Guest favorite

Apartment in Greve in Chianti

4.88 out of 5 average rating, 162 reviews

Apartment Ramerino

Mezzomonte farmhouse is located in one of the most beautiful areas in Chianti, only 33 Km from Firenze and 30 from Siena.We are on the top of the hill ,2km of unmade road from the main street SS222 The farmhouse is immersed in a forest of chestnut and pine trees, surrounded by a completely fenced 6000m2 garden. Our apartments are completaly independent including the private space in the garden.

Mar 25 – Apr 1

R2,108 ZAR per night

Guest favorite

Farm stay in Castelnuovo dei Sabbioni

4.92 out of 5 average rating, 301 reviews

Chianti La Pruneta, Raffaello Apartment

Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.

Nov 24 – Dec 1

R2,021 ZAR per night

Guest favorite

Tower in Fiesole

4.95 out of 5 average rating, 153 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Sep 23 – 30

R16,025 ZAR per night

Guest favorite

Villa in Ambra

4.98 out of 5 average rating, 107 reviews

Chianti Villa in Tuscany near Siena & Arezzo

Villa with 5bedrooms and 10sleeps in Chianti . Land of wine, good food and old traditions. Distances from the villa to:Siena 25km,Arezzo 35km,Florence 60km,villa with swimming pool obtained from the careful restoration of an ancient stone farmhouse

Dec 16 – 23

R16,497 ZAR per night