
House vacation rentals in Castiglion Fiorentino
Find and book unique houses on Airbnb
Top-rated house rentals in Castiglion Fiorentino
Guests agree: these houses are highly rated for location, cleanliness, and more.

Charming converted Hayloft overlooking the Chianti Hills
Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

Da nonna Ornella - nest in Val d'Orcia
Spectacular views and relaxation guaranteed in this romantic studio in the heart of the Val d'Orcia, province of Siena, immersed in the beautiful Tuscany. Ideal for couples. It has a living area, equipped kitchen, bathroom, heating, courtyard, private parking and a large and panoramic garden with sun loungers and hammock. Close to iconic destinations: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d'Orcia, Radicofani, Castiglione d'Orcia and Monte Amiata. Unforgettable!

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.

Montalcino Townhouse with Private Garden & Spa
A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

Italian Interior
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.

Poggiodoro, your charming villa in Tuscany
Welcome to Poggiodoro, our 16th century stones' villa located in the countryside of Anghiari. The House offers stunning views, charming and furnished interiors providing all type of comforts: a beautiful fireplace that will keep the ambient warm even in winter, a big private garden where you can enjoy the open air and have lunch under the shade of pergola, with BBQ, fantastic in the warm seasons, a panoramic pool to spend great moments with friends, to be shared with the hamlet guests

La Perla del Lago Holiday home
Forget all your worries in this oasis of serenity. Let yourself be soothed by our amazing views and the sunsets that the lake offers us every evening The Holiday Home La Perla del Lago overlooks Lake Trasimeno. 8 minutes away is the highway from which you can easily reach Florence, Perugia,Gubbio, Spoleto, Norcia and many others In the village, there are bars, food restaurants, a pharmacy, an ATM, a small playground, and a beautiful swimming pool 2 km away for the hottest days.

Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni
Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Jenny's Barn
The ancient barn, now finely restored, is located in the heart of the Valdichiana a few steps from the characteristic medieval village of Scrofiano. From the house you can enjoy a breathtaking view of the green Sienese hills where centuries-old olive trees and vineyards alternate from which the prestigious Chianti is obtained. Ideal for 2 people looking for a relaxing stay away from the chaos of the city. On request it is possible to add a baby bed and a cot.

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.

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
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!
Popular amenities for Castiglion Fiorentino house rentals
House rentals with a pool

Casa Lucy

Cottage surrounded by nature

Family Forest - Pool in the Crete Senesi

Apt. Elena - Villa Augusto Estate

Casa di Lyndall - Entire house with exclusive pool

House Rigomagno Siena

Casa dei 5 Sensi - Trasimeno view

Wonderful panoramic view, Florence
Weekly house rentals

The View

Villa with panoramic lakeview "RenzosOlivengarten"

Fantastic Apartment in the Heart of Toscana

Little Corticellitta in Tuscany

Breathtaking Views + Terrace/Central yet Quiet

Villa Medici Donnini Superior Apartment

the oasis of the foxes

Private Tuscan cottage with a view near Cortona
Private house rentals

Casa il Cipresso

The Biricocolo Cottage

Casaletto di Monsigliolo 3 bedrooms 4 bathrooms

The Terrace of Victory

Villa le Scope 5*

Beautiful barn among the olive trees

Il Pollaio guests house

V&E • Hot tub • Gym
Quick stats about house rentals in Castiglion Fiorentino

Total vacation rentals
Explore 10 vacation rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino vacation rentals start at $70 CAD per night before taxes and fees

Verified guest reviews
Over 210 verified reviews to help you choose

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

Wifi availability
10 of Castiglion Fiorentino vacation rentals include wifi 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
- Provence Vacation rentals
- Rome Vacation rentals
- Molfetta Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Florence Vacation rentals
- Venice Vacation rentals
- Francavilla al Mare Vacation rentals
- Naples Vacation rentals
- Cannes Vacation rentals
- Italian Riviera Vacation rentals
- Bologna Vacation rentals
- Rentals with a patio Castiglion Fiorentino
- Villa rentals Castiglion Fiorentino
- Pet-friendly rentals Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
- Rentals with outdoor seating Castiglion Fiorentino
- Family-friendly rentals Castiglion Fiorentino
- Smoking-friendly rentals Castiglion Fiorentino
- Apartment rentals Castiglion Fiorentino
- Rentals with a washer and dryer Castiglion Fiorentino
- House rentals Arezzo
- House rentals Tuscany
- House rentals Italy
- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazzale Michelangelo
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Medici Chapels
- Tenuta Le Velette
- Stadio Artemio Franchi
- Basilica di Santa Croce
- Basilica of St Francis
- Palazzo Vecchio
- Castiglion del Bosco Winery
- Teatro Verdi