
House vacation rentals in Casole d'Elsa
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Quick stats about house rentals in Casole d'Elsa

Nightly prices starting at
Casole d'Elsa vacation rentals start at G$27,197 GYD per night before taxes and fees

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Over 110 verified reviews to help you choose

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 house rentals in Casole d'Elsa
Guests agree: these houses are highly rated for location, cleanliness, and more.

Domus Nannini - Loggia Salimbeni SPA
Apartment of 200 sqm furnished with precious classical furniture and very spacious rooms: 13 windows overlooking the old town, each window offers a unique view of the city. Big and spacious lounge with peerless view on the begin of Banchi di Sopra, Piazza Salimbeni and the headquarter of the Monte dei Paschi, formed by the noble palaces Tantucci, Salimbeni and Spannocchi. Second lounge with library, sofa-bed and the same exclusive view. 2 large bedrooms with city-views and king-size beds. 3 bathrooms one with jacuzzi and one with shower. A long corridor that crosses the apartment, spacious entrance and private terrace on the internal courtyard. Third lounge with sofa-bed and city-view. Dining room with panoramic views of the Duomo of Siena and Basilica of San Domenico which stand out over the medieval roofs of Siena a few meters from us. Fully equipped kitchen with laundry area. It occupies the entire second floor our 1600's palace and offers unique and privileged views of Siena and its architectural wonders. We are on Banchi sopra Sopra, the main course of the historical center of Siena, below the house you will find the best shops in the center with all the brands of high fashion, lots of restaurants; Wineries, Bars and Supermarkets with typical Tuscan products.
ValueFamilyParking
4.96 out of 5 average rating, 156 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.
FamilyValueIndoor spaces
5.0 out of 5 average rating, 141 reviews
Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
LocationValueLong stay
4.97 out of 5 average rating, 194 reviews
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.
ValueFamilyOutdoor spaces
4.99 out of 5 average rating, 113 reviews
Casa Panorama
Welcome to Casa Panorama! A cozy apartment situated in the wonderful Tuscan countryside just a stone's throw away from the medieval town of Casole d'Elsa.Casa Panorama is in between some of the most beautiful locations such as Siena,Monteriggioni,Florence,San Gimignan,Volterra and many other hidden hilltop Tuscan jewels.Our house is situated less than 1 km from the center of the very romantic town of Casole d'Elsa where there are restaurants and much to see as far as culture and art is concerned
LocationFamilyOutdoor spaces
4.99 out of 5 average rating, 111 reviews
Borgo Ripostena – n.10 Capanna
Charming cottage in the heart of Tuscany on a peaceful property. It is surrounded by a big private garden and has a marvelous panoramic terrace with stunning views over San Gimignano and the Chianti Hills. PRIVACY: EACH APARTMENT HAS A PRIVATE ENTRANCE AND TERRACE FOR TOTAL PRIVACY CLEANING: APARTMENTS ARE DISINFECTED WITH CERTIFIED EQUIPMENT BEFORE EACH ARRIVAL POOL: EACH APARTMENT HAS A DESIGNATED SPACE RESERVED AT THE POOL. SMART SERVICES: WEB CHECK-IN AND GUEST ASSISTANCE VIA SMARTPHONE APP
LocationFamilySleep quality
4.91 out of 5 average rating, 99 reviews
Collina Power
Collina is an ancient stone farmhouse, the house is surrounded by fields and olive groves. It has a large garden with swimming pool and a terrace where you can have pleasant lunches and dinners. A barbecue and garden furniture are available. The road to get to the house in the last stretch is not paved and is therefore not suitable for sports cars or particularly low ones. The route lends itself to pleasant walks during the day, while at night we recommend using a car because it is not lit.
FamilyValueWifi
4.93 out of 5 average rating, 201 reviews
Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.
FamilyValueIndoor spaces
5.0 out of 5 average rating, 232 reviews
The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of Chianti Classico, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a dominant position with a breathtaking view, where you can enjoy stunning sunsets. The total independence of the house, the cozy garden, and the large loggia allow you to spend your stay in total peace of mind. Our reviews are your best guarantee.
LocationValueKitchen
4.98 out of 5 average rating, 242 reviews
The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.
LocationFamilyBathroom
4.9 out of 5 average rating, 133 reviews
Nada Home
3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷
LocationValuePets
4.87 out of 5 average rating, 215 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.
FamilyValueWifi
4.96 out of 5 average rating, 144 reviewsPopular amenities for Casole d'Elsa house rentals
House rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views
FamilyLocationParking
4.99 out of 5 average rating, 136 reviews
Palazzo Monaci - Pool in the Crete Senesi
ValueFamilyAccess
4.96 out of 5 average rating, 138 reviews
Ancient Barn in Chianti with Pool
ValueLocationGetting around
4.89 out of 5 average rating, 125 reviews
Casa Giulia di Sopra Farmhouse
LocationFamilyPool
4.95 out of 5 average rating, 103 reviews
Lovely house in a scenic and paiceful location
ValueLocationLayout
4.93 out of 5 average rating, 122 reviews
Open space surrounded by nature
LocationFamilySleep quality
4.96 out of 5 average rating, 137 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
LocationFamilyBathroom
4.91 out of 5 average rating, 124 reviews
TREEhouse/casaBARTHEL
FamilyValuePets
4.88 out of 5 average rating, 820 reviewsWeekly house rentals

Casa Al Poggio in Chianti Shire
FamilyLocationHospitality
4.96 out of 5 average rating, 330 reviews
The House in the Alley – Colle di Val d'Elsa
LocationFamilyBreakfast
4.99 out of 5 average rating, 133 reviews
Next to castle of Villa-Siena. heart Francigena
FamilyLocationParking
4.83 out of 5 average rating, 157 reviews
Raffaella's House nel Chianti
LocationFamilyBreakfast
4.99 out of 5 average rating, 479 reviewsTuscan Counrtry Detached House. Wi-Fi Free
ValueFamilyParking
4.9 out of 5 average rating, 290 reviews
Costalmandorlo, a rustic home in the heart of Tuscany
ValueLocationSleep quality
4.91 out of 5 average rating, 126 reviews
Private House for 4P – La Capanna Di Azzurra
ValueLocationIndoor spaces
4.96 out of 5 average rating, 23 reviews
Beautiful farmhouse in the Chianti panoramic garden
FamilyLocationSleep quality
4.96 out of 5 average rating, 47 reviewsPrivate house rentals

Relax in a Jacuzzi in Tuscany
LocationPoolPets
4.95 out of 5 average rating, 98 reviews
Casa La Selva
FamilyLocationLong stay
5.0 out of 5 average rating, 28 reviews
La Paiolina: pool, Jacuzzi & sauna
ValueFamilyHospitality
4.98 out of 5 average rating, 57 reviews
Villa delle Ortensie
ValueLocationAir conditioning
4.98 out of 5 average rating, 43 reviews
Cottage with jacuzzi in Tuscany
LocationFamilyWalkability
4.98 out of 5 average rating, 45 reviews
Fienile House
LocationAccuracyCleanliness
4.8 out of 5 average rating, 5 reviews
Design loft with private SPA in Tuscany
ValueLocationSleep quality
5.0 out of 5 average rating, 74 reviews
Margherita: Tuscany views, Pool & Walk to Village
LocationFamilySleep quality
4.88 out of 5 average rating, 34 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)
- Cala Violina
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





