
Vacation rentals in Castiglion Fiorentino
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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 G$8,367 GYD per night before taxes and fees

Verified guest reviews
Over 1,920 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 60 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
90 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!
Top-rated vacation rentals in Castiglion Fiorentino
Guests agree: these stays are highly rated for location, cleanliness, and more.

Farmhouse Fattoria La Parita
Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Cortona’s Rooftop Nest
L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

The walnut tree view, Montepulciano
The walnut tree view ( castoldi apartments site) is our new apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 1 double rooms (king ) 1 bathroom with large shower and a large kitchen-living room with a nice terrace overlooking the hills. From summer 26 a wine tasting will be available in the new garden for all the guests from 7 pm Old private wine cellar available Guests will park close the apartment

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 - Villa Senaia
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

Casa Dolce Toscana | Panoramic Suite with a View
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.

Tuscan Villa Luigina with Pool & Panoramic View
If you want to live in a postcard .... Villa Luigina is the ideal place, all the rooms have a panoramic view, a dining room with a view ... a breakfast room with a view, or you can eat outside in the garden in front of the house and enjoy the spectacular view of the old town!! In the fascinating Tuscan hills, among olive trees and vineyards, a stone villa in perfect harmony with the environment in a strategic position to discover the secrets of Tuscany and Umbria. CIN:IT051012C2129WHTZX

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

Modern apartment in the heart of Tuscany
A few steps from Castiglion Fiorentino train station. Ideal for exploring not only this charming medieval city but also other beautiful Tuscan cities, such as Arezzo, Cortona and Siena. The apartment has 1 bathroom and 5 beds, ideal for families or groups of friends. There is also an additional sofa bed for extra guests. It also has a small loggia for relaxing. Its central location allows you to easily find services such as shops, restaurants and bars nearby.

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.

Casale Santa Barbara - Exclusive Apartment
Your private Tuscan retreat between Pienza and Montepulciano. A spacious 100 m² apartment for two, with exclusive access, a large private garden and breathtaking views over the Val d’Orcia hills. Elegance, calm and authenticity — just you… and Tuscany.
Popular amenities for Castiglion Fiorentino vacation rentals
Other great vacation rentals in Castiglion Fiorentino

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When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$22,591 GYD | G$20,499 GYD | G$20,708 GYD | G$24,055 GYD | G$25,938 GYD | G$25,101 GYD | G$27,193 GYD | G$22,591 GYD | G$24,055 GYD | G$29,075 GYD | G$23,637 GYD | G$22,800 GYD |
| 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
What are the best places to stay in Castiglion Fiorentino?
Stays near the town center provide easy access to cafés, markets, and historic sites. Countryside villas and renovated farmhouses are frequently suggested for those wanting extra privacy and scenic views.
What are the best things to do in Castiglion Fiorentino with kids?
Children can join creative workshops, enjoy playgrounds, and participate in seasonal town festivals. Interactive museum exhibits and countryside walks are often recommended for families.
What are some of the best things to do in Castiglion Fiorentino?
Explore the historic old town, visit hillside churches, and take in local art at galleries. Walking through medieval streets and enjoying Tuscan cuisine are frequently suggested activities.
How is the weather in Castiglion Fiorentino?
Castiglion Fiorentino has cool, rainy winters around 33–49°F (0–9°C), and warm, dry summers near 82–89°F (28–32°C). Spring and autumn bring milder temperatures and changing foliage.
When is the best time to visit Castiglion Fiorentino?
Late spring and early autumn are frequently suggested for milder temperatures near 66–74°F (19–23°C) and cultural events. The town’s landscape is especially lively during festival seasons.
What are the best places to visit in Castiglion Fiorentino?
Explore the old town center, climb to historic towers, and visit local churches. The area has traditional markets, artisan workshops, and an archaeological museum.
What are some hiking trails in Castiglion Fiorentino?
The area has countryside trails that lead through olive groves, woodland paths, and scenic hilltops. Walks frequently include historical ruins and views of the surrounding valley.
What are some family activities we can do in Castiglion Fiorentino?
Families often explore local parks, enjoy hands-on workshops in pottery, and attend community festivals. Visiting museums or taking part in guided nature walks around town are frequently suggested.
What are some of the best day trip ideas from Castiglion Fiorentino?
Nearby hill towns known for Renaissance history, vineyards, and artisan shops are popular day trip choices. Exploring local farms or visiting larger cities with museums and galleries is often recommended.
Are there any pet friendly accommodations available in Castiglion Fiorentino?
Castiglion Fiorentino has a selection of pet friendly vacation rentals. Many hosts welcome pets, especially in countryside areas and within town, making it easier to explore with your companion.
What are some local tips for visiting Castiglion Fiorentino?
Locals often suggest starting mornings at a café, wearing comfortable shoes for cobbled streets, and visiting regional markets for fresh produce. Try learning a few Italian phrases to connect with residents.
What is Castiglion Fiorentino known for?
Castiglion Fiorentino is known for medieval architecture, hillside panoramas, and vibrant cultural traditions. It also has historic churches and regional agricultural fairs.
What are the best foods to try in Castiglion Fiorentino?
Castiglion Fiorentino has locally rooted Tuscan fare, such as handmade pasta, hearty ribollita soup, and pecorino cheese. Olive oil from nearby groves and rustic breads are frequently suggested additions.
What should I bring for a trip to Castiglion Fiorentino?
Bring comfortable walking shoes, layers for changing temperatures, and a travel adapter. A light jacket for evenings and sunscreen during warmer months come in handy.
What is the nightlife in Castiglion Fiorentino like?
Castiglion Fiorentino has a relaxed evening scene, with local wine bars, cafés, and occasional live music. Social gatherings in historic squares are common, especially during festivals.
What are the most popular events or festivals in Castiglion Fiorentino?
Castiglion Fiorentino hosts medieval reenactments in late spring, a historic Palio festival, and seasonal fairs celebrating local food and crafts. Community gatherings and music events are often popular throughout the year.
Are there family friendly vacation rentals in Castiglion Fiorentino?
Castiglion Fiorentino has a variety of family friendly accommodations, including larger apartments and countryside homes with outdoor space. Hosts often share tips for nearby family activities and local dining.
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.
Destinations to explore
- Villa rentals Castiglion Fiorentino
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- Family-friendly rentals Castiglion Fiorentino
- Apartment rentals Castiglion Fiorentino
- Pet-friendly rentals Castiglion Fiorentino
- House rentals Castiglion Fiorentino
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- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mercato Centrale
- Stazione Santa Maria Novella
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Centro Storico Orvieto
- Medici Chapel
- Basilica of Santa Croce
- Stadio Artemio Franchi





