
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 €61 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)
4.93 out of 5 average rating, 197 reviews
Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
5.0 out of 5 average rating, 142 reviews
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.
4.97 out of 5 average rating, 161 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic 17th-century property located in the beautiful Chianti hills of Tuscany, with the option of arranging a private shuttle and local experiences directly with our family. 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.
5.0 out of 5 average rating, 352 reviews
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
4.98 out of 5 average rating, 127 reviews
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.
4.98 out of 5 average rating, 218 reviews
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.
4.99 out of 5 average rating, 138 reviews
Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.
4.99 out of 5 average rating, 137 reviews
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.
4.98 out of 5 average rating, 222 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 107 reviews
Farmhouse in Chianti with Swimming Pool
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.
4.99 out of 5 average rating, 516 reviews
Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
4.96 out of 5 average rating, 146 reviewsPopular amenities for Casole d'Elsa rentals with a pool
House rentals with a pool

Collina Power
4.93 out of 5 average rating, 203 reviews
Explore Chianti from a Charming Stone House
4.98 out of 5 average rating, 123 reviews
Relaxation and charm in the Chianti hills
4.99 out of 5 average rating, 114 reviews
Open space surrounded by nature
4.96 out of 5 average rating, 137 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
4.91 out of 5 average rating, 128 reviews
Ancient Barn in Chianti with Pool
4.89 out of 5 average rating, 125 reviews
Casa Giulia di Sopra Farmhouse
4.95 out of 5 average rating, 106 reviews
Villetta La Colombaia Farm
4.95 out of 5 average rating, 163 reviewsApartment rentals with a pool

Apt. Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 282 reviews
Charming Tuscan home with pool, garden & Air-Con
4.88 out of 5 average rating, 100 reviews
House between Firenze, Arezzo, chianti e Siena
4.84 out of 5 average rating, 302 reviews
Scenic Stilish Country
4.88 out of 5 average rating, 136 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Casa Luna-Splendida overlooking the pool and Tuscan nature
4.97 out of 5 average rating, 151 reviews
The House in Chianti - IlVillinoFarmhouse
4.78 out of 5 average rating, 246 reviews
Bel Canto Lari, exclusive, rural, Tuscan retreat
4.97 out of 5 average rating, 105 reviewsHome rentals with a private pool

TREEhouse / casaBARTHEL
4.88 out of 5 average rating, 821 reviews
Casa Luigi Suite with exclusive pool
4.95 out of 5 average rating, 122 reviews
Luxe Estate nr Florence. Vineyard, Pool, Privacy
4.97 out of 5 average rating, 73 reviewsHistoric villa x8 with exclusive pool
4.87 out of 5 average rating, 46 reviews
Villa Fonteintanata Ground floor
4.8 out of 5 average rating, 75 reviewsDestinations 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)
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mugello Circuit
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





