
Vacation rentals with a pool in Gaiole in Chianti
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Gaiole in Chianti
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Podere Vergianoni immerso nelChianti con piscina
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.

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. A/C in the bedrooms
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.

Wonderful Loft in Villa with Pool in Chianti
Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

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.

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.

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
Apartment in a panoramic villa between Florence and Siena in the heart of Chianti in a charming village. The swimming pool is open from May 1st to September 30th, from 9 a.m. to 1 p.m. with exclusive use for guests during this time. For different needs, ask the host.

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

Casa Bada - Barn

Explore Chianti from a Charming Stone House

Antico Borgo Ripostena – n. 8 Old House

loft in the heart of Tuscan Chianti

Nada Home

Casa Luigi Suite with exclusive pool

Romantic cosy flat - Toscana Italy
Condo rentals with a pool

Loggiato 3 apartment in Tuscany near Siena

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa

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

Garden & SPA -FlorArt Boutique Apartment
Home rentals with a private pool

Poggio Cuccule by Interhome

Sole by Interhome

La Felcaia by Interhome

Stone House with Exclusive Pool Codilungo in Chianti

Melograno by Interhome

Historic home with exclusive pool

La Salciaia by Interhome

Villa il Palagio in the Tuscan countryside
Quick stats about vacation rentals with a pool in Gaiole in Chianti

Total vacation rentals
Explore 10 vacation rentals in Gaiole in Chianti

Nightly prices starting at
Gaiole in Chianti vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

Verified guest reviews
Over 180 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of Gaiole in Chianti vacation rentals include wi-fi 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
- Rentals with a washer and dryer Gaiole in Chianti
- Family-friendly rentals Gaiole in Chianti
- Apartment rentals Gaiole in Chianti
- Rentals with a patio Gaiole in Chianti
- House rentals Gaiole in Chianti
- Villa rentals Gaiole in Chianti
- Pet-friendly rentals Gaiole in Chianti
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Boboli's Garden
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapel
- Palazzo Vecchio
- Stadio Artemio Franchi
- Spiaggia Marina di Cecina
- Mugello Circuit
- Castiglion del Bosco Winery
- Basilica of Santa Croce
- Golf Club Toscana




