
Holiday rentals with a patio in Castiglion Fiorentino
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Top-rated rentals with patio in Castiglion Fiorentino
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Apt. Elena - Villa Augusto Estate
The property is located in a residential area 3/4 km from the center of Cortona. Surrounded by greenery, a true paradise of tranquility. Independent and cozy accommodation with large spaces furnished with antique furniture and objects, equipped kitchen, 2 bedrooms (double and 2 single), 2 bathrooms. Air-conditioned rooms. Outdoor space equipped with table, chairs and sun loungers. Large park with many shaded areas and large swimming pool (14x7) surrounded by greenery, shared with other guests of the estate.

The Eagle and the Olive Tree
At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Da nonna Ornella - nest in Val d'Orcia
Spectacular views and relaxation guaranteed in this romantic studio in the heart of Val d 'Orcia, province of Siena, immersed in 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.

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Luxurious Medieval Tower & Private Concierge
It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

"Dimora Valinda" Montepulciano Piazza Grande + A/C
Welcome to Montepulciano, a historical gem! Our apartment, located in the heart of the historic center, offers the perfect location to experience the authenticity of this unique place: just a few steps from Piazza Grande, excellent restaurants, shops, and all the main attractions. Whether you come to explore the wineries, for a romantic getaway, or to learn about the history and culture of Montepulciano, here you will find the perfect place for an unforgettable experience.

Ancient Tuscan farmhouse in the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is on the first floor of the main farmhouse, with independent access and a tree-lined garden. Furnishings in the classic Tuscan style, with wooden beamed ceilings, terracotta floors that give a characteristic touch.

Mascagni Farmhouse in Val d'Orcia, Pienza
Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Resort Panoramic view - Free parking
Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Buffet di dolci gratuiti. Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

I Tramonti di Eramo, Montepulciano city center.
Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

Pendici 15, small apartment
Cozy apartment inside a stone farmhouse where you can enjoy the atmosphere of the Tuscan countryside and at the same time the proximity to the historic center of Castiglion Fiorentino. Ideal for couples, families and travelers with four-legged friends, it is the ideal starting point to visit Tuscany. The accommodation combines the rustic charm of stone houses with modern comforts, offering a relaxing stay in a quiet and panoramic setting.

Poggio dell'orso.Traditional Casale. Amazing views
Fantastic, recently restored, 150 years old Casale in Tuscany with amazing views. Two bed rooms, a spacious living room with a double sofa bed, a 85" smart TV, a corner with a desk and a fully equipped kitchen. Outside a stone table, a huge garden, a gazebo, a state of art warmed Jacuzzi (optional if available) a fantastic 6 x 12 infinity pool . All the property is fenced. Pet friendly.
Popular amenities for rentals with patio in Castiglion Fiorentino
Flat rentals with a patio

A terrace in the historic center

Relax a few steps from the Campo

suite with Jacuzzi tub

Casa Crociani - Amazing Pool & Free Parking

Chianti Patio Apartment

Luxury Attic in Tuscany+Incredible view and A/C

The Farmhouse in Chianti-IlVillinoFarmhouse

2 King Bed-2 Full Bath Apartment in Umbria/Tuscany
House rentals with a patio

Tuscan Casale near Cortona

Tuscany House with pool and courtyard

Holiday Home with Pool in Tuscany – La Roccia

The Terrace of Victory

Casa San Ripa: Relax Oasis with Private Pool

Breathtaking Views + Terrace/Central yet Quiet

Villa le Scope 5*

"Hortus Conclusus" House
Apartment rentals with a patio

Tuscan charm in Fonterutoli Exposed beams & relaxation

Charming Castle

Romantic cottage in Tuscany with pool and garden

Casa Piccola

Casa Granaio | Ground floor 1-bedroom apartment (2

Casa Biancospino Crete Senesi | Podere Fossaccio

Reggello - Pendolino Agritourism

Penelope's Canvas
Quick stats about holiday rentals with a patio in Castiglion Fiorentino

Total holiday rentals
Explore 30 holiday rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Castiglion Fiorentino holiday rentals include wifi access

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

4.9 Average rating
Castiglion Fiorentino stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Family-friendly rentals Castiglion Fiorentino
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- Flat rentals Castiglion Fiorentino
- Pet-friendly rentals Castiglion Fiorentino
- Villa rentals Castiglion Fiorentino
- Rentals with outdoor seating Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Rentals with a washing machine and dryer Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
- Rentals with a patio Arezzo
- Rentals with a patio Tuscany
- Rentals with a patio Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Del Chianti
- Basilica of Santa Maria Novella
- Mercato Centrale
- Eremo Di Camaldoli
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Pitti Palace
- Parco delle Cascine
- Palazzo Vecchio
- Boboli's Garden
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapel




