
House holiday rentals in Castiglione dei Pepoli
Find and book unique houses on Airbnb
Top-rated house rentals in Castiglione dei Pepoli
Guests agree: these houses are highly rated for location, cleanliness and more.

Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Love in Chianti
Welcome to the delightful cottage of Riccardo and Pauline, a small corner of love where colors and details are designed to give peace and quiet. You will find yourself immersed in the green Tuscan hills, in a breathtaking landscape where the renowned Chianti Classico wine is born. The area is ideal for walking and cycling. You will be close to the cities of art, such as Florence, Siena and Arezzo. Upon request and according to availability, we offer a paid shuttle service. We look forward to seeing you ❤️

The MOONLIT & SUNNY COTTAGE near Florence
IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence and Mugello is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients such as bio vegetables, eggs or cheese.

Il Cerro Country House
You can Relax and recharge yourself in this oasis of quiet and elegance, in the sunny hill of Cerreto you can find the "Dimora il Cerro", harmoniously inserted in the Tuscan landscape. It is a portion of a farmhouse surrounded by green olive trees, with a magnificent views of the city . this is an excellent starting point for visiting Tuscany, a suitable destination for those who love active holidays and for those interested in culture. From here you can easily reach cities such as Florence.

TREEhouse / casaBARTHEL
casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the florentine Duomo. Come and live with us; enjoy the olive trees, the kitchen garden, our horse Astro and our family life style, away from the working rhythm. By providing wifi only in the communal courtyard we suggest to take a break from been connected with elsewhere and enjoy the 'here and now' . But if you need to work you can rent a portable private connection from us.

Sunset on Chianti Classico
Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Tuscan cottages in an ancient villa with a garden
The Cottage is part of a property owned by the Bernocchi family, which was already on maps of the area in the 1500s and is located right on an ancient Roman road that crossed the Calvana Mountains. About 9 km from Prato and 20 km from Florence. The Cottage, open on three sides, is situated in a panoramic position surrounded by a private park, ideal for walking and sports. A real home fitted with kitchen, living room, bedroom and bathroom. Large outdoor spaces, garden, and botanical garden.

Home with a view in nature_ 2
A cozy stone and wood chalet with amazing views of the Apennines, surrounded by nature with a large garden where you can relax and enjoy the spectacular sunsets. We will be happy to host you on the ground floor which is dedicated to the B&B. The warm and welcoming rooms have independent entrances and lead onto the garden. Fantastic location between Bologna and Florence, 10' from the motorway exit and 30' from Bologna airport. Don't miss the sunset, even better with a good glass of wine!

House nestled in the Apennines
The house is near the path of the gods and the wool and silk roads. The 120 sqm house, consisting of a kitchen with dining room, bathroom, dining room, laundry room, 2 double bedrooms (with 4-door wardrobe), single bedroom (with 4-door wardrobe), laundry room and garden. Immersed in the green of the Emilian Tuscan Apennines, about 45 km from Bologna and Florence, with a breathtaking landscape and perfect for those who want to walk and get away from the weariness of the city.

Courtyard apartment with stunning views
Beautiful courtyard apartment set in over 20 acres - the location is just right for relaxing, and eating some of the best food in Italy. If you love mountain biking or hiking this is perfect. We are 40 minutes from Bologna airport. Our nearest town is Vignola, rich in history and famous for its cherries. You can explore the region of Emilia Romagna, and return each evening and watch the sun go down with a chilled glass of wine. (2 nights stay in Winter when requested)

"La limonaia" - Romantic Suite
Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

Casale La Quercia - Tuscany country house
Casale La Quercia is an elegant country house nestled in the Tuscan hills. Surrounded by oak and cypress forests, it is located at an altitude of almost 500 meters, which gives it an enchanting view of the entire valley. In the wonderful farmyard adjacent to the house, guests can enjoy the silence of nature or take advantage of the masonry barbecue for a charming dinner under the stars.
Popular amenities for house rentals in Castiglione dei Pepoli
House rentals with a pool

dependance in villa Toscana

Vacation immersed in the Tuscan countryside 'Canaiolo'

the Rossino windmill

Private villa/swimming pool in Tuscany

Casa Nespolo – Cozy farmhouse in Chianti

Ancient Tuscan Rural Residence

La Lucertola Pisa/Lucca - Pool, Views LeaningTower

Infinity view
Weekly house rentals

1800s house & garden close to the Spa GrottaGiusti

Torretta Apartment
Gorgeous Villa with Postcard Views in Historical Florence

Costalmandorlo, a rustic home in the heart of Tuscany

Gigallino, in the countryside, close to Firenze

[Lungarno] Prestigious apartment with a view

Il Fienile di Tigliano (former barn in Vinci-Florence)

Tuscan Villa 15 min from Florence, Parking, Garden
Private house rentals

Casetta 42

"Il Campanile" House

I Palpiti - Dream Villa in the heart of Florence

Bright house with garden and mountain views

The Clock Tower View Loft

Lucia's barn

Sunset over Tuscany

The Cannicciaia
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Bologna Center Town
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Bologna Fiere
- Piazza del Duomo (Pisa)
- Mugello Circuit
- Stadio Renato Dall'Ara
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Stazione Santa Maria Novella
- Del Chianti
- Piazza della Repubblica
- Centrale
- Autodromo Enzo e Dino Ferrari
- Piazzale Michelangelo
- Parco delle Cascine
- Unipol Arena
- Appennino Tosco-emiliano National Park





