Holiday rentals with a pool in Gaiole in Chianti

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Top-rated rentals with a pool in Gaiole in Chianti

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Guest favourite

Villa in Castellina in Chianti

4.92 out of 5 average rating, 167 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

31 Oct – 7 Nov

€ 492 per night

Guest favourite

Apartment in Noce

5.0 out of 5 average rating, 129 reviews

Vergianoni estate nestled in the Chianti with a pool

Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale dell'antica Toscana : travi in legno, pavimenti in cotto e arredamenti curati ed artigianali che vi faranno vivere un soggiorno unico. Nel grande cortile esterno troverete a vostra disposizione una grande piscina su terrazza panoramica con stupenda vista sulle colline e vigneti con tramonti unici.

7–14 Jan

€ 136 per night

Guest favourite

Home in Lecchi in Chianti

4.96 out of 5 average rating, 115 reviews

Casa di Lyndall - Entire house with exclusive pool

Welcome to “Casa di Lyndall” My home is located in the medieval village of Lecchi in Chianti, set in rolling hills, castles, vineyards & olive groves, & provides a view that extends nearly 50 kms. It’s a perfect choice for a family or group of four people. My home is built in typical Tuscan style with exposed chestnut beams, fireplace, and a well appointed kitchen. The new 8 metre pool is private & located on the top terrace of the olive grove, has a child proof fence, and 4 sun lounges.

31 Oct – 7 Nov

€ 193 per night

Guest favourite

Home in Rietine

4.85 out of 5 average rating, 186 reviews

Gaiole in Chianti Poggio Casabianca

We invite you in the heart of Chianti area. Poggio Casabianca is a little family homestead located in the Chianti Classico region exactly in the hearth of Tuscany. The owners live here and they offer at their guests an apartment with a big living room-kitchen with a big door that open directly to the garden, a bathroom with shower and a confortable doublebed room. Outside in the garden ther is a pool, shared with the owner, where you can refreshing and relaxing during the summer.

14–21 Apr

€ 117 per night

Superhost

Home in Gaiole In Chianti

4.85 out of 5 average rating, 223 reviews

Charming estate with views

The estate finely restored in 2016 is accessorized with all the confort you need for an holiday dedicated to the relax or to excursions The Breathtaking view on the Chianti Classico's vineyards give to the estate a unique feature perfect for a romantic holiday, small group of friend or a little family. The estate is provided of external Jacuzzi, private garden and we can arrange for you bike or hike excursions. The Village of Gaiole in Chianti is just 5 minutes away by car.

18–25 Feb

€ 159 per night

Guest favourite

Flat in Panzano in Chianti (FI)

4.96 out of 5 average rating, 204 reviews

Apt. Panzanello-Panzano in Chianti

The apartment offers all the comforts and tranquility of the Tuscan countryside. Enjoy the wonderful panorama that you can admire from your private terrace, a perfect place to spend moments of peace and serenity and accompanied by a glass of Panzanello wine. Access to the apartment is private and free parking is available. The kitchen is equipped with everything you need to prepare delicious meals. We don't have a restaurant but we'll help you book in Panzano.

7–14 Nov

€ 122 per night

Guest favourite

Castle in Ferrano

4.99 out of 5 average rating, 163 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.

4–11 Mar

€ 282 per night

Guest favourite

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)

17–24 Feb

€ 167 per night

Guest favourite

Cottage in Lucardo

4.99 out of 5 average rating, 216 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).

26 Jan – 2 Feb

€ 251 per night

Guest favourite

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.

30 Nov – 7 Dec

€ 152 per night

Guest favourite

Farm stay in Cavriglia

4.88 out of 5 average rating, 143 reviews

Chianti La Pruneta, Caravaggio apartment

A Jewel of an apartment in the heart of Tuscany. Stunning views over cypress and olive trees. Beamed ceilings, marble floors, all recently refurbished. The apartment includes an antique wooden bed and Venetian lights. You can relax and eat 'Al Fresco' in your own private garden where sun loungers a BBQ and a shaded eating area are all provided, enjoying the beautiful views. Breakfast is included, not served.

14–21 Dec

€ 105 per night

Guest favourite

Tower in Fiesole

4.95 out of 5 average rating, 154 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.

23–30 Sep

€ 783 per night