
Holiday rentals with a pool in Casole d'Elsa
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Quick stats about holiday rentals with a pool in Casole d'Elsa

Total holiday rentals
Explore 10 holiday rentals in Casole d'Elsa

Nightly prices starting at
Casole d'Elsa holiday rentals start at $89 SGD per night before taxes and fees

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Over 270 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Wifi availability
10 of Casole d'Elsa holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Casole d'Elsa rentals

5 Average rating
Casole d'Elsa stays are highly rated by guests – averaging 5 out of 5!
Top-rated rentals with a pool in Casole d'Elsa
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

La Casetta
“La Casetta”, is a new restored enchanting apartment immersed in the splendid Tuscan countryside, only 2 kms from the medieval village of Casole d'Elsa in Siena province. Situated in a old farm complex with private entrance, large private garden, and access to the communal swimming pool. Furnished with utmost care down to the finest detail. Ideal for a relaxing, regenerative week with family or friends, emerged in an uncontaminated natural landscape. Possibility of excursions on foot and by bicycle in an evocative natural setting of lush forests and gentle hills of rare beauty. One can enjoy local dishes of the wonderful Tuscan tradition in many of the nearby restaurants or organize splendid home-cooked meals with the barbecue in the garden. Ideally situated for visits the many nearby towns and cities rich in art and beauty: 30 mins to Siena, 1 hour to Florence ,30 mins to San Gimignano and Volterra, 45 mins to the Chianti area. La Casetta is the ideal place to regenerate your body and mind. (We are the same owners of “La Senesina" apartment near Siena check out our rating on the web! Our 5 stars ratings are your warranty for a great stunning vacation)
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Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.
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Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.
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Girasoli apartment with pool in farmhouse
After climbing 17 steps, you will be accommodated in an apartment located on the second floor with a separate entrance. Consisting of a kitchen, bathroom with shower, and double bedroom with 2 windows overlooking the town of Casole d'Elsa and the swimming pool. Mosquito nets on the windows. Small terrace shared with the Manuela apartment IT IS MANDATORY TO PAY THE ACCOMMODATION TAX AT CHECK-IN €1 per person in cash USE of heating from November 1 to April 15 (Regional Law) €15.00 per day.
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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.
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Villa Gourmet Food, Pizza, Chef, Pool and Nature
Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services
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Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.
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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.
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Villa L'Olivo w/Private pool (Close San Gimignano)
Villa L'Olivo is located in the Tuscan countryside, about 10 kilometers from San Gimignano and a few minutes from the supermarkets and various services in Poggibonsi. Our Villa is a great starting point to discover all the beauty of Tuscany, but it is also an ideal place for those who love to take a break from the hectic life of the city. At Villa L'Olivo, you can book a dinner with a private chef, directly in the villa, to enjoy a Tuscan dinner in peace. Write to us for info!
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La Villa Farmhouse - Chestnut, Pool & Garden
Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.
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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.
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Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
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Popular amenities for Casole d'Elsa rentals with a pool
House rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views
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Explore Chianti from a Charming Stone House
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Infinity pool in Chianti 1
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Collina Power
LocationFamilyPets

SuiteLouise.pool, Hot Tub,homeGym & private Garden
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Palazzo Monaci - Pool in the Crete Senesi
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Ancient Barn in Chianti with Pool
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Open space surrounded by nature
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Apartment rentals with a pool

Charming Tuscan home with pool, garden & Air-Con
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Apt. Panzanello-Panzano in Chianti
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Scenic Stilish Country
LocationFamilyParking

Adalberto Apartment inside the Manor of Fulignano
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House between Firenze, Arezzo, chianti e Siena
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Casa Luna-Splendida overlooking the pool and Tuscan nature
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Poggiolieto Studio - on hills 10' from city center
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Bel Canto Lari, exclusive, rural, Tuscan retreat
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Home rentals with a private pool

TREEhouse / casaBARTHEL
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Casa Luigi Suite with exclusive pool
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Historic villa x8 with exclusive pool
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Villa Fonteintanata Ground floor
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Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





