Vacation 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 favorite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 196 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

Guest favorite

Villa in San Leolino

5 out of 5 average rating, 105 reviews

Poggio del Fattore-Villa with pool,hilltop,Chianti

Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Guest favorite

Home in Lecchi in Chianti

4.96 out of 5 average rating, 135 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 8 metre pool is private & located on the top terrace of the olive grove, has a child proof fence, and 4 sun lounges.

Guest favorite

Home in Rietine

4.85 out of 5 average rating, 206 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.

Superhost

Home in Gaiole In Chianti

4.86 out of 5 average rating, 248 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.

Guest favorite

Home in Castellina in Chianti

4.98 out of 5 average rating, 104 reviews

StageROOM03 -Chianti Idillic Country living

This beautiful country house is located in the Borgo di Tuopina, a hamlet overlooking the Chianti hills, only 10 mins drive from Siena and Castellina in Chianti. This original Tuscan country house has been completely renovated in 2019 and boasts 2 bedrooms, 2 bathrooms, TV, a fully equipped kitchen with a dishwasher, two fridges and a washing machine. The outdoor marble hot-tub allows you to fully relax while enjoying the amazing views of the surroundings.

Guest favorite

Castle in Ferrano

4.99 out of 5 average rating, 182 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.

Guest favorite

Cottage in Lucardo

4.99 out of 5 average rating, 238 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).

Guest favorite

Loft in Siena

4.95 out of 5 average rating, 219 reviews

Siena Country Loft Hideway

Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town

Guest favorite

Tower in Fiesole

4.94 out of 5 average rating, 181 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.

Guest favorite

Villa in Cavriglia, Arezzo

4.99 out of 5 average rating, 128 reviews

Villa Poggio a Mandria in Chianti

Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.

Guest favorite

Farm stay in Gaiole in Chianti

4.94 out of 5 average rating, 225 reviews

Il Piccolo Nido alla Pieve Marsina

Stonewalls and the small romantic fireplace, the iron and wood staircase which brings you to the big double bedroom, the private outdoor area with iron pergola, table and deckchairs characterize the apartment Nido. The best accommodation for couples seeking an unforgettable romantic escape immersed in the Chianti hills. Ideal also for couple with a little baby.