
House holiday rentals in Castiglion Fiorentino
Find and book unique houses on Airbnb
Quick stats about house rentals in Castiglion Fiorentino

Total holiday rentals
Explore 10 holiday rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino holiday rentals start at $105 NZD per night before taxes and fees

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Over 240 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Wi-Fi availability
10 of Castiglion Fiorentino holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Castiglion Fiorentino rentals

4.7 Average rating
Castiglion Fiorentino stays receive an average rating of 4.7 out of 5 from guests
Top-rated house rentals in Castiglion Fiorentino
Guests agree: These houses are highly rated for location, cleanliness and more.

La Perla del Lago Holiday home on Lake Trasimeno
La Perla del Lago: your refuge at Trasimeno Rediscover your harmony in this oasis of absolute peace. Let yourself be enchanted by our magical view and the sunsets that the lake offers every evening. The La Perla del Lago Holiday Home overlooks the mirror of Lake Trasimeno. 8 minutes away you will find the highway to visit towns such as Florence, Perugia, Gubbio, Spoleto, Norcia and many others. In the village, you will find bars, restaurants, a market, a pharmacy, an ATM, and children's play areas. There is a swimming pool 3 km away where you can relax in the summer.
4.98 out of 5 average rating, 206 reviews
The small tower
The proposed farmhouse is a typical terratetto made of characteristic Tuscan stone, ideal for those who want to spend relaxing holidays immersed in the green hills of Castiglione that surround the small valley of Chio. The turret-style building is arranged over three levels: the usable portion of the building is located on the first floor, with a living/dining room and an equipped kitchen, and on the second floor, with a double bedroom, a twin bedroom, and a bathroom with a shower, all furnished with period-style furniture.
4.95 out of 5 average rating, 108 reviews
Casa Lucy
House located on the Cortonese hill, completely renovated, consisting of 3 double bedrooms, 2 bathrooms and an open space kitchen and dining room. It is located 5 minutes from the historic center of Cortona and in an excellent position to reach the most beautiful and characteristic places of Tuscany and Umbria such as Pienza, Montepulciano, Castiglione del Lago up to cities that are cradles of art such as Florence, Arezzo, Siena and Perugia. Mandatory tourist tax to be paid on site (€2.50 per person for 4 days)
4.95 out of 5 average rating, 109 reviews
La Lisa: country house surrounded by fields
La Lisa is a traditional farm house that has been wisely restored. It is surrounded by Tuscan countryside hills, in a quiet, out of time atmosphere. At the same time it is well connected with the A1 motorway and the highway Siena – Perugia (6 km). A large yard with a barbecue and pizza oven, is ideal for evenings under the stars. There's also a tavern with kitchen, living and dining room can host up to 30 people. During warm season enjoy the HEATED POOL equipped with loungers and umbrellas.
4.94 out of 5 average rating, 135 reviews
Casa Dolce Toscana | Panoramic Suites & Views
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.
4.98 out of 5 average rating, 184 reviews
House Rigomagno Siena
Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.
4.96 out of 5 average rating, 125 reviews
Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.
4.98 out of 5 average rating, 145 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.
4.9 out of 5 average rating, 135 reviews
Conca d'Oro villa with private pool, sleeps 4
Just 2 km from the village, cozy typical Tuscan farmhouse, tastefully furnished and equipped. The farmhouse is located in a panoramic position immersed in the peaceful Tuscan countryside. Guests have access to a beautiful infinity pool for their exclusive use, equipped with sun loungers, and a lovely garden with a patio furnished for outdoor dining and enjoying fantastic sunsets. A strategic location for tourists. Free high-speed satellite Wi-Fi
4.92 out of 5 average rating, 173 reviews
PoggiodoroLoft, Tuscan dream e relax
Welcome to Poggiodoro Loft, 16th century stones' villa located in the countryside of Anghiari. Stunning views, charming and furnished interiors providing all type of comforts, the relaxing sauna, the private garden where you can enjoy the open air and lunch under the pergola, BBQ, fantastic in the warm seasons, lounge with brazier a panoramic swimming pool to spend great moments with friends, to be shared with the hamlet guests.
4.87 out of 5 average rating, 167 reviews
Cottage surrounded by nature
"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.
4.99 out of 5 average rating, 111 reviews
Casa del Passerino
Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!
4.94 out of 5 average rating, 225 reviewsPopular amenities for Castiglion Fiorentino house rentals
House rentals with a pool

Il Vecchio Mulino
4.91 out of 5 average rating, 114 reviews
Palazzo Monaci - Pool in the Crete Senesi
4.96 out of 5 average rating, 142 reviews
Villa Lolù with private heated swimming-pool
4.98 out of 5 average rating, 160 reviews
Infinity view
4.88 out of 5 average rating, 203 reviews
The lemon house
4.9 out of 5 average rating, 103 reviews
Hidden gem in Tuscany
5.0 out of 5 average rating, 56 reviews
Villa BellaVista of Mammi
5.0 out of 5 average rating, 6 reviews
Villa with Private Pool in the Tuscan Countryside
5.0 out of 5 average rating, 23 reviewsWeekly house rentals

Domus Nannini - Loggia Salimbeni SPA
4.96 out of 5 average rating, 156 reviews
Charming converted Hayloft overlooking the Chianti Hills
4.97 out of 5 average rating, 307 reviews
Secret Garden Siena
4.98 out of 5 average rating, 220 reviews
Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni
4.99 out of 5 average rating, 232 reviews
The Garden under the Tower
5.0 out of 5 average rating, 12 reviews
Gorgeous, light studio in Tuscan hilltown
4.88 out of 5 average rating, 56 reviews
Breathtaking views: Historic House w/Terrace & BBQ
5.0 out of 5 average rating, 26 reviews
Casa Primo Stylish-townhouse w/ patio & jetted tub
5.0 out of 5 average rating, 75 reviewsPrivate house rentals

Casale Toppello on Lake Trasimeno
4.99 out of 5 average rating, 69 reviews
House in farmhouse with amazing views
4.94 out of 5 average rating, 16 reviews
Spacious Tuscan Home – 2 Connected Apts, 4BR/4BA
5.0 out of 5 average rating, 9 reviews
Due Torri, Umbrian elegance
5.0 out of 5 average rating, 27 reviews
Beautiful barn among the olive trees
5.0 out of 5 average rating, 65 reviews
Fantastic Apartment in the Heart of Toscana
4.65 out of 5 average rating, 99 reviews
"La Ginestra" Farmhouse - "Lavanda" Apartment
4.9 out of 5 average rating, 78 reviews
Country charm walking distance from Cortona centre
4.93 out of 5 average rating, 54 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Stadio Artemio Franchi
- Medici Chapel





