
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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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

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.

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.

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.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

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

Chianti La Pruneta, Raphael 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.

Explore nature in the center of Vigneti Chianti
Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Podere Guidi
Appartamento in Villa panoramica tra Firenze e Siena, nel cuore del Chianti, in un borgo incantevole. Piscina aperta da maggio a fine settembre. La piscina è aperta dal 1 Maggio al 30 settembre, dalle ore 9 alle 13, con utilizzo esclusivo per gli ospiti in questo orario.

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2
Beautiful charming 1 bedroom ground floor apartment in the Le Miccine villa. Surrounded by vines and nature. Ideal location for visiting Tuscany or relaxing by the pool. Wine tasting on site and helpful staff. We are classified as a 4 Sunflower Agriturismo.
Popular amenities for Gaiole in Chianti rentals with a pool
House rentals with a pool

Ancient Barn in Chianti with Pool

House “il colle”.nice house surrounded by vineyard

Explore Chianti from a Charming Stone House

Casetta Melograno – Cozy farmhouse in Chianti

Leonardo - Chianti/Siena, Firenze, San Gimignano.

loft in the heart of Tuscan Chianti

Romantic cosy flat - Toscana Italy

Paluffo Stillo House
Apartment rentals with a pool

Stone House in Chianti with pool

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa

Casa Rebecca with a small private pool

House between Firenze, Arezzo, chianti e Siena

Vintage apartment with swimming pool in Chianti

Ginestra: Private Pool Overlooking Florence

Manuela apartment with pool in farmhouse
Home rentals with a private pool

Poggio Cuccule by Interhome

Sole by Interhome

Ambrogetta by Interhome.

Stone House with Exclusive Pool Codilungo in Chianti

Melograno by Interhome

La Salciaia by Interhome

Casa Luigi Suite with exclusive pool

Casa 360 by Interhome
Quick stats about holiday rentals with a pool in Gaiole in Chianti

Total holiday rentals
Explore 10 holiday rentals in Gaiole in Chianti

Nightly prices starting at
Gaiole in Chianti holiday rentals start at $130 SGD per night before taxes and fees

Verified guest reviews
Over 180 verified reviews to help you choose

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

Wifi availability
10 of Gaiole in Chianti holiday rentals include wifi access

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

4.6 Average rating
Gaiole in Chianti stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Family-friendly rentals Gaiole in Chianti
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- Santa Maria Novella
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Mugello Circuit
- Spiaggia Marina di Cecina
- Palazzo Vecchio
- Stadio Artemio Franchi
- Basilica di Santa Croce
- Castiglion del Bosco Winery
- Golf Club Toscana




