
Holiday rentals with a patio in Castiglion Fiorentino
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Top-rated rentals with patio in Castiglion Fiorentino
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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.

Incredible Views & Pool in the Tuscan Hills
Fuggite nel cuore della Toscana e vivete un soggiorno immersi in dolci colline, una bellezza senza tempo e panorami indimenticabili. La casa offre l'accesso a una splendida piscina in comune e a tranquilli spazi esterni, perfetti per rilassarsi al sole o godersi serate serene. All'interno, troverete comfort, stile, tutto il necessario per un soggiorno memorabile. Ideale per coppie, famiglie o gruppi di amici che desiderano vivere un'autentica esperienza toscana a breve distanza in auto da Siena.

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

Breathtaking views: Historic House w/Terrace & BBQ
Welcome to our longtime family home — an elegant, light-filled space in the heart of Cortona. Set in a quiet historical square just steps from the main piazza. Enjoy spectacular views of the valley, lake and city. This elegant house blends the character of Tuscany with warmth and comfort. Antique terracotta beamed ceilings floors, a terrace with panoramic views, a house that tells a story. It's a space for travelers who appreciate beauty, stillness, and the atmosphere of an authentic home.

Elegant farmhouse overlooking Pienza
Podere Fonte Bernardi is an authentic Tuscan country house. Surrounded by the nature of the Val d'Orcia, an ideal place to relax. Located a few km from the most beautiful places in Tuscany such as Pienza, the medieval village of Monticchiello, the thermal site of Bagno Vignoni and the homeland of Montepulciano wine. Perfect for taking long walks and discovering local wines and food. You will be able to enjoy the most beautiful sunset over Pienza in the silence of the most authentic nature.

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.

Tuscany Villa Mammi
Grande villa in pietra ristrutturata tra i boschi di Castiglion Fiorentino, vicono a Cortona, Arezzo e Siena. Un paradiso di privacy con piscina, idromassaggio panoramico con vista mozzafiato sulla valle e ping pong. Godetevi serate magiche sotto le stelle grazie all'autentico barbecue in pietra e al forno a legna per la pizza. Il rifugio ideale per chi cerca relax, natura e comfort nel cuore della Toscana, perfetto per famiglie o gruppi che sognano una vacanza davvero indimenticabile.

Luxury Medieval Tower • Exclusive Chianti Stay
Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

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?

Open Space Piscina e Giardino
La mia casa è immersa nella campagna toscana, tra olivi e vigne, nel cuore del Chianti. Intorno, panorami meravigliosi e un’atmosfera di pace e relax. Il giardino è uno spazio speciale, ideale per momenti da vivere all’aperto. Per chi lo desidera, è possibile – su richiesta – condividere esperienze legate alla cucina e alla convivialità, come cene preparate con cura, da gustare insieme, anche a lume di candela, in un contesto intimo e accogliente.

Holiday Home with Pool in Tuscany – La Roccia
Modern villa with private pool, waterfall, large garden and relaxation area, private bathroom and refreshment corner; Apartment with 2 bedrooms, equipped kitchen and bathroom in elegant white faux marble. Perfect for families and groups up to 6. Features American BBQ, panoramic gazebo, ping pong, outdoor dining area and poolside shower. Steps from Cortona, Arezzo, Montepulciano, Siena and the Crete Senesi. A tranquil oasis in the heart of Tuscany.

I Tramonti di Eramo, central Montepulciano.
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.
Popular amenities for rentals with patio in Castiglion Fiorentino
Flat rentals with a patio

Melo in fiore Apartment - Mulino del Cilone

Colle ai Lecci: Design Apartment in Tuscany

Charming apartment with small gardens, pool access

Experience an ancient island with a garden by the lake

Casa Crociani - Amazing Pool & Free Parking

Resort Panoramic view - Free parking

Chianti Patio Apartment

Luxury Penthouse with Incredible View & A/C 300mq
House rentals with a patio

18th-century farmhouse in Cortona, with garden and 4 bathrooms

The Terrace of Victory

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Casa San Ripa: Relax Oasis with Private Pool

Live the Tuscany Experience in Our Country House

Villa Medici Donnini Superior Apartment

Poggiolo

Original Tuscan Experience in the Heart of Chianti
Apartment rentals with a patio

Sogno Toscano in Fonterutoli, between Siena and the Chianti region

Casa Biancospino Crete Senesi | Podere Fossaccio

Tuscany | Apartment in farm with restaurant & pool

Amazing Apartment near Piazza Grande w/ Terrace

Corso Italia 189-Apartment [Historic Center]

Il TramontO

Agriturismo Poggio Bonelli, 4 people apartment

Solengo Apartment in Podere Capraia
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £81 | £70 | £90 | £101 | £93 | £119 | £123 | £79 | £104 | £129 | £190 | £152 |
| 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 |
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 £37 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!
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- Rentals with a patio Arezzo
- Rentals with a patio Tuscany
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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
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Stazione Santa Maria Novella
- Del Chianti
- Piazza della Repubblica
- Piazzale Michelangelo
- Parco delle Cascine
- Basilica of St Francis
- Pitti Palace
- Piazza della Signoria
- Boboli's Garden
- Palazzo Vecchio
- Centro Storico Orvieto
- Basilica of Santa Croce
- Stadio Artemio Franchi
- Medici Chapel





