
Vacation rentals in Castiglion Fiorentino
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Top-rated vacation rentals in Castiglion Fiorentino
Guests agree: these stays are highly rated for location, cleanliness, and more.

Fontarcella, H&R- mediterranean home with jacuzzi
Situata nelle colline a cavallo tra Montepulciano,Castiglione del Lago e Cortona, Fontarcella si presenta come una villetta indipendente immersa nel verde, che offre jacuzzi e parcheggio privati; Scoprirete un luogo senza tempo, per condividere momenti preziosi. La struttura, arredata in stile mediterraneo, dispone di climatizzazione e wi-fi gratuita. Il giardino, interamente recintato, offre vari comfort. A pochi minuti dalle autostrade, Fontarcella è facilmente raggiungibile dai viaggiatori.

Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Tuscan charm of villa - countryside
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Interno Italiano
Knock on the door of this house, and an inspiring world will open up to you. The modern design, now luxurious, now fun, blends beautifully with the structures and airiness of the 18th-century rural complex, and offers a breathtaking panoramic window. The house is located within a residence, and use of the pool is shared with other guests in the complex. Surrounded by green hills, offers an ideal accommodation for families looking for a relaxing stay. The house is ideal for four people.

Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Pendici 15, piccolo appartamento
Accogliente appartamento all’interno di un casolare in pietra dove godere dell’atmosfera della campagna toscana ed allo stesso tempo della vicinanza al centro storico di Castiglion Fiorentino. Ideale per coppie, famiglie e viaggiatori con amici a quattro zampe, è il punto di partenza ideale per visitare la Toscana. L’alloggio coniuga il fascino rustico delle case in pietra con i comfort moderni, offrendo un soggiorno rilassante in un contesto silenzioso e panoramico.

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.

Tofanello Turquoise Luxury 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 orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Casa del Passerino
Appartamento inserito all'interno di un palazzo storico di Cortona, collocabile nel 1500, con vista sulla piazza principale della città... La nostra struttura, pur condannando la guerra, si dissocia da tutti i comportamenti razzisti verso la popolazione russa e bielorussa. A Casa del Passerino le persone di queste nazionalità sono ben accette e saranno considerate alla stregua di tutte le altre. Vi aspettiamo in Toscana!

Esplora la natura al centro di Vigneti Chianti
Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.
Popular amenities for Castiglion Fiorentino vacation rentals
Other great vacation rentals in Castiglion Fiorentino

Casale La Cedrina(Il Melograno)

Villa Degli Olivi

Casa Tòrta - comfort room

Fantastic Apartment in the Heart of Toscana

Agriturismo Via della Stella | Casa le Rose

Romantic Tuscan Holiday House

Il Giardino degli Ulivi | Casa Ippocastano

Gli sterpi
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ342 | ﺩ.ﺇ312 | ﺩ.ﺇ331 | ﺩ.ﺇ422 | ﺩ.ﺇ455 | ﺩ.ﺇ441 | ﺩ.ﺇ477 | ﺩ.ﺇ397 | ﺩ.ﺇ422 | ﺩ.ﺇ360 | ﺩ.ﺇ393 | ﺩ.ﺇ400 |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Castiglion Fiorentino?
Yes! Work meets play with ease at over 30 vacation rentals in Castiglion Fiorentino featuring dedicated workspaces. Stay connected and productive in your home away from home.
What types of vacation rentals are available in Castiglion Fiorentino?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Castiglion Fiorentino. From over 30 apartment rentals to over 10 house rentals, we've got you covered.
Are there Castiglion Fiorentino vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Castiglion Fiorentino, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Castiglion Fiorentino?
Four-legged friends are welcome in Castiglion Fiorentino. Choose from more than 50 vacation rentals for guests traveling with pets.
How much does it cost to stay in condo rentals in Castiglion Fiorentino?
Experience the best of Castiglion Fiorentino with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Castiglion Fiorentino?
Castiglion Fiorentino has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Castiglion Fiorentino have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Castiglion Fiorentino have free parking?
Absolutely! We offer over 10 house rentals with free parking in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Castiglion Fiorentino have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Castiglion Fiorentino have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Castiglion Fiorentino

Total vacation rentals
Explore 90 vacation rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 1,740 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
80 of Castiglion Fiorentino vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Castiglion Fiorentino rentals

4.8 Average rating
Castiglion Fiorentino stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Villa rentals Castiglion Fiorentino
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- Smoking-friendly rentals Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- Apartment rentals Castiglion Fiorentino
- Rentals with a patio Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Rentals with a washer and dryer Castiglion Fiorentino
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- Family-friendly rentals Castiglion Fiorentino
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- Santa Maria Novella
- Piazza della Signoria
- Mercato Centrale
- Ponte Vecchio
- Santa Maria Novella
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Salvatore Ferragamo Museum
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Del Chianti
- Siena Cathedral
- Basilica of Santa Maria Novella
- Piazzale Michelangelo
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Boboli's Garden
- Parco delle Cascine
- Eremo Di Camaldoli
- Palazzo Vecchio
- Medici Chapel




