
Villa vacation rentals in Castiglion Fiorentino
Find and book unique villas on Airbnb
Quick stats about villa rentals in Castiglion Fiorentino

Total vacation rentals
Explore 20 vacation rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino vacation rentals start at G$29,291 GYD per night before taxes and fees

Verified guest reviews
Over 480 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Wi-Fi availability
20 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 villa rentals in Castiglion Fiorentino
Guests agree: these villas are highly rated for location, cleanliness, and more.

Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas
4.9 out of 5 average rating, 241 reviews
Wine Experience Villa in Montepulciano
🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.
4.97 out of 5 average rating, 126 reviews
Charming Tuscan Villa in Val d'Orcia with a view
Luxury and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, commercial kitchen at your own use. We arrange Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!
4.97 out of 5 average rating, 130 reviews
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
4.93 out of 5 average rating, 334 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
4.95 out of 5 average rating, 146 reviews
Villa a Montepulciano con Piscina
The Villa "I Girasoli" is part of the holiday farm "Il Serraglio" which covers 17 hectares. The Villa has a total area of 220 square meters that includes two bedrooms, two bathrooms, a large living room with an antique fireplace. Free WiFi. Direct access to the pool (which can be used by our other guests too) * 2 AirCon units: 1 per bedroom * * Pool open from April to November. Circular warm pool, (36C/97F) from April 1 to October 31. Pool is shared with other guests of our property. *
4.92 out of 5 average rating, 148 reviews
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
4.8 out of 5 average rating, 110 reviews
Tuscany Villa Mammi
Large renovated stone villa in the woods of Castiglion Fiorentino, near Cortona, Arezzo, and Siena. A haven of privacy with a swimming pool, a panoramic hot tub with breathtaking views of the valley, and ping pong. Enjoy magical evenings under the stars thanks to the authentic stone barbecue and wood-fired pizza oven. The ideal retreat for those seeking relaxation, nature, and comfort in the heart of Tuscany, perfect for families or groups dreaming of a truly unforgettable vacation.
4.99 out of 5 average rating, 90 reviews
Stunning Tuscan Villa & Panoramic Infinity Pool
Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.
5.0 out of 5 average rating, 96 reviews
La Vignaccia (Farmhouse) - villa w/private pool
Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.
4.96 out of 5 average rating, 102 reviews
Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.
4.97 out of 5 average rating, 159 reviews
Villa unesco heritage, Jacuzzi & garden. BB Daria
Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant
4.98 out of 5 average rating, 183 reviewsPopular amenities for Castiglion Fiorentino villa rentals
Private villa rentals

Beautiful and cozy country-house, sleeps 11
5.0 out of 5 average rating, 25 reviews
Villa Degli Olivi
4.97 out of 5 average rating, 32 reviews
Villa La Foce
4.95 out of 5 average rating, 21 reviews
Casa Napoleone - Tuscan Villa w/ pool near Cortona
4.96 out of 5 average rating, 28 reviews
Ortaglia di Sotto Farm
4.95 out of 5 average rating, 19 reviews
Villa il Laghetto with Infinity Pool in Tuscany
4.96 out of 5 average rating, 56 reviews
Coaching House
5.0 out of 5 average rating, 67 reviews
Fabulous Farmhouse with Pool & 360 Panoramic View
4.92 out of 5 average rating, 61 reviewsLuxury villa rentals

Poggio del Fattore-Villa with pool,hilltop,Chianti
4.99 out of 5 average rating, 131 reviews
Montepulciano Central Villa – Sauna & Jacuzzi
4.85 out of 5 average rating, 153 reviews
Villa with garden. The Cardinal's Garden.
4.97 out of 5 average rating, 97 reviews
Lake View Private Villa with Pool
4.92 out of 5 average rating, 51 reviews
Villa Le Murate
4.94 out of 5 average rating, 17 reviews
Villa Pietrenta
4.93 out of 5 average rating, 14 reviews
Casale La Querce-Tuscan Farmhouse with pool & view
5.0 out of 5 average rating, 25 reviews
Villa San Martino, on the Tuscany/ Umbria border
4.9 out of 5 average rating, 59 reviewsVilla rentals with a pool

la Balza
4.93 out of 5 average rating, 128 reviews
Apt. Rolando-Tenuta VillaAugusto
4.97 out of 5 average rating, 34 reviews
Villa Eleonora
4.85 out of 5 average rating, 20 reviews
Villa Montanina - relax in esclusiva in Toscana
4.99 out of 5 average rating, 85 reviews
Terra Antica Suite & Ville - Montepulciano
5.0 out of 5 average rating, 55 reviews
Magnificent 1700's villa in Tuscany
4.81 out of 5 average rating, 68 reviews
Villa Aurora
4.97 out of 5 average rating, 67 reviews
Beautiful tuscan country house
4.88 out of 5 average rating, 24 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Stadio Artemio Franchi
- Medici Chapel





