
Holiday rentals with a pool in Montaione
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Top-rated rentals with a pool in Montaione
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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.

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

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!

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.

Cercis - La Palmierina
E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

Lovely house in a scenic and paiceful location
This beautiful house is nestled in a quiet and panoramic location, making it the perfect spot to get away from it all. With three bedrooms, three bathrooms, and room for up to six guests, this is the perfect place for a group of friends or a large family to call home while exploring Tuscany. Spend your days hiking the picturesque landscape, wandering through charming villages, or simply relaxing in the lovely gardens of the house.

La Casa di Nada - Suite
From every window of my home there are wonderful views of the Tuscan hills, a charm that will accompany every moment of your stay. My kitchen is fully equipped and the rooms are comfortable and bright, with a private bathroom for each room. In the living room I have a beautiful fireplace all for you. A practical laundry completes this refuge in the Heart of Chianti

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Countryside Dream farm in Tuscany
Great place in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Podere Guidi
Apartment in a panoramic villa between Florence and Siena, in the heart of Chianti, in a charming village. Pool open from May until the end of September. From 2026, the pool will be open from 9 am to 1 pm with exclusive use for guests during this time.

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
Popular amenities for Montaione rentals with a pool
House rentals with a pool

Volare

I Limoni Apartment in Tuscany

Ancient Barn in Chianti with Pool

Casa Bada - Barn

Explore Chianti from a Charming Stone House

Old barn The Nepitella

Antico Borgo Ripostena – n. 8 Old House

Casa Luigi Suite with exclusive pool
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa

VILLA LE PERGOLE - Florence

House between Firenze, Arezzo, chianti e Siena

Vintage apartment with swimming pool in Chianti

Ginestra: Private Pool Overlooking Florence
Home rentals with a private pool

Sole by Interhome

Tuscan Villa Featured Conde Nast Best Villas Italy

Tassinaia by Interhome

The Leccio by Interhome

Podere San Lorenzo by Interhome

Charming villa in the Chianti hills

Santa Margherita by Interhome

Casa 360 by Interhome
Quick stats about holiday rentals with a pool in Montaione
Total rentals
20 properties
Nightly prices starting at
€ 60 before taxes and fees
Total number of reviews
140 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
- Santa Maria Novella
- Duomo di Firenze
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Ponte Vecchio
- Cala Violina
- Gulf of Baratti
- Uffizi Gallery
- Mugello Circuit
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Spiagge bianche
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- Spiaggia Libera
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Marina di Cecina
- Stadio Artemio Franchi
- Medici Chapels