
Vacation home rentals in Casentino
Find and book unique vacation home rentals on Airbnb
Top-rated vacation home rentals in Casentino
Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.

Casa al Gianni - Oak
Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!

Romantic stay at a bio-agritourism in Florence
Escape the crowd and hot of the towns. We are 40 min away from the centre of Florence (consider driving the last 3 km on a narrow winding beautiful countryside road). Be ready for an authentic rural Tuscan lifestyle experience, here the deers graze the fields near the house, you can hear the wild boars grunting and the crickets singing. Healthy food, good wine, a bio sauna and a jacuzzi in the oliveyards; a real re-charge and re-connection in Nature in an eco-friendly and cozy accommodation .

Vittoria Chianti Vacations 🍇🍷
Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Chianti Craft House Badia a Passignano
Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

SMN Luxury Secret Garden View
Welcome to the central part of Florentine charm! This extraordinary apartment, located just 50 meters from Piazza Santa Maria Novella, offers you an unparalleled experience in the historic heart of Florence. Imagine crossing the threshold of a Renaissance Palace, a jewel of inestimable artistic and historical value, and being welcomed by an atmosphere that speaks of history and elegance. Two bedrooms, two complete bathrooms, living room with fully equipped kitchen.

La casina sulle Mura with garden
La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

Fontarcella, H&R- mediterranean home with jacuzzi
Located in the hills between Montepulciano, Castiglione del Lago, and Cortona, Fontarcella is a detached villa surrounded by greenery, offering a private jacuzzi and parking. You'll discover a timeless place to share precious moments. The property, furnished in Mediterranean style, features air conditioning and free Wi-Fi. The fully fenced garden offers a variety of amenities. Just minutes from the highways, Fontarcella is easily accessible for travelers.

Experience rustic off-grid life in the wilderness
This ancient rustic farmhouse lies within a national park in one of the largest areas of forests in Europe. Solar power, wood stoves, the bumpy road and the lack of phone signal offer an authentic off-grid experience. A rare privilege to go into the wild and take a break from urban life and modern conveniences. Hike to the monastery of St.Francis and the sacred forests of La Verna...or simply sit and enjoy the peace of this magical remote place.

Barrel Suite Tuscany • Hot Tub • Vineyard View
Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.

Casa Manu
CHARACTERISTIC TUSCAN HOUSE in stone nestled in the hills of the province of Arezzo. Close to Siena, Florence, Cortona, Perugia, Sansepolcro and the Casentino Forests. Ideal for trekking, food and wine tourism (some of the best wineries in Tuscany are just a few kilometers away), for art and culture enthusiasts. A large, very private panoramic terrace is available exclusively for guests. We will welcome you with a welcome gift.

THE WINE CELLAR OF THE WISTERIA
The apartment is an annex of the main house – originally the winery of the nearby 19-century villa –composed of sitting room, kitchen, double bedroom with attached bathroom. In the living area there is a French-size sofa bed, only suitable for family or close friends (no independent access to the bathroom). Uncovered private parking. About 300 mt of dirt road from the main road. Tourist tax: 1,5 Euros per person per night.

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment
Nestled in a medieval village in the heart of Chianti, this exclusive historical apartment blends Tuscan charm with refined contemporary design. Enjoy a panoramic pool overlooking the hills, multiple terraces, and a unique hot tub Jacuzzi suite and bathroom carved in travertine. Designed for two, it’s the perfect place to slow down, reconnect, and experience Tuscany in total peace.
Popular amenities for Casentino vacation home rentals
Family-friendly vacation home rentals

House in Tuscany with swimming pool "La casetta di Ghiora"

PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶

Fienile Santa Teresa

Apartment in Anghiari

Tuja

"Baldacchini" (Canopies) 4/6p, pool, garden, view

Ancient stone farmhouse with park and pool

Stuart Jasmine central, panoramic top location
Vacation home rentals with a patio

Pian'D'olmo, an ancient farmhouse in the heart of Tuscany

Unique & Historic Getaway: Dreamy Garden

Romantic cottage with Jacuzzi and large garden - 2p.

Tuscan Suite Amiata in Villa Q Dimorae Adults Only

★ Romantic apartment & stunning view of Tuscany ★

City Centre Patio - 10 mins to Duomo

Cenerentola chianti 1 apartment - near Panzano

Tuscany Country House, Central Chianti, Pano Views
Vacation home rentals with a washer and dryer

Antico Casale Tiravento - Apartment with balcony

Apartment in historic Villa in Siena_"LE CONTRADE"

Melarancio Residence

Florence Elegant Suite

Azzurro, history and family in Florence

Podere Docciolino Vacation Home

TOSCANELLA APT. AMBRA

Casa Vitiolo - left section
Destinations to explore
- House rentals Casentino
- Rentals with lake access Casentino
- Apartment rentals Casentino
- Condo rentals Casentino
- Rentals with an EV charger Casentino
- Rentals with a washer and dryer Casentino
- Rentals with breakfast Casentino
- Farmstay rentals Casentino
- Bed and breakfasts Casentino
- Rentals with a fireplace Casentino
- Cottage rentals Casentino
- Fitness-friendly rentals Casentino
- Rentals with pools Casentino
- Rentals with a sauna Casentino
- Family-friendly rentals Casentino
- Smoking-friendly rentals Casentino
- Villa rentals Casentino
- Rentals with a hot tub Casentino
- Pet-friendly rentals Casentino
- Rentals with outdoor seating Casentino
- Rentals with a fire pit Casentino
- Rentals with a patio Casentino
- Vacation home rentals Arezzo
- Vacation home rentals Tuscany
- Vacation home rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Lake Trasimeno
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Fiera Di Rimini
- Mercato Centrale
- Uffizi Gallery
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Pinarella Di Cervia
- Fortezza da Basso
- Mugello Circuit
- Misano World Circuit
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Boboli's Garden
- Palacongressi Della Riviera Di Rimini
- Parco delle Cascine
- Mirabilandia
- Medici Chapel





