
Holiday Homes in Tuscany
Find and book unique holiday homes on Airbnb
Top-rated Holiday Homes in Tuscany
Guests agree: These holiday homes 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 farm stay 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 companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!

Home Luxury - Greek and marine style apartment
Greek and marine style apartment finished renovating in July 2023. Furnished in a simple and elegant way, the white color and wood will make you feel immediately on vacation as soon as you enter the large living room. You will feel like you are on an island in Greece, with the false ceiling of beams and reeds, the concrete double bed as well as the TV cabinet and bathrooms. A simple but valuable home equipped with all possible amenities that can be managed through Alexa. A magnificent apartment!

Tuscan Country house with panoramic pool
Old stone Country House located on the top of an uncontaminated hill in a secluded atmosphere, with stunning 360° panoramas over the hills and the Arno river. Surrounded by private olives grooves, the accommodation offers an ideal mix between peaceful relaxation and opportunities for outdoor activities. With easy access to Florence (18 km) and major arts sites of Tuscan region such as Siena, San Gimignano, Pisa, Lucca, the wine Chianti area and many others landscaping or trekking attractions.

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.

Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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

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.

Romantic stay, where Tuscany meets the sky!
The property is located on top of a very panoramic hill, near the medieval village of Sillico where is located also a very good restaurant. Perfect accommodation for romantic couples, families with children with their dogs. Perfect place to relax but also suitable for guests who like active holiday with many exiting trekking, canyoning, mtb and horse riding excursions. Nice panoramic pool and view on the entire valley. Welcome where Tuscany meets the sky!

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.

In Tuscany Rooms
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

La Loggia. House with pool and stunning view
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.

[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 Tuscany holiday homes
Family-Friendly holiday homes

Linearis apt B (4+2) Toscana

Experience rustic off-grid life in the wilderness

Margherita Tuscan home apartment

Breathe in Tuscany: 180° view of the hills

"IL FIENILE" rustic stone house

Villa Incanto in Tuscany, swimming pool, Wi-Fi, parking

Elegant farmhouse overlooking Pienza

Tuscan House with Private Jacuzzi in Chianti
Holiday home rentals with a patio

The Eagle and the Olive Tree

Casa Isla, near Orvieto, amazing views + pool

Tuscan Cottage - I' Cipresso di Mirro

the oasis of the foxes

Tuscany Country House, Central Chianti, Pano Views

Unique & Historic Getaway: Dreamy Garden

Glicini 1, holiday home and pool 30' from Florence

Tower House
Holiday home rentals with a washing machine and dryer

[Florence hills] Tuscan house with parking space

Tuscan Nature Views From Casa Gave

Torretta House - cin: IT046017c2XQY33MML

4BR • Luxury Palazzo • Iconic Views • Pitti Palace

Podere Docciolino Vacation Home

La Trinità Comfort & Parking in the Historic Centre

Villino Anna house surrounded by greenery near the sea

Chianti Panorama | House with 3 En-Suite Bathrooms
Destinations to explore
- Villa rentals Tuscany
- Condo rentals Tuscany
- Bungalow rentals Tuscany
- Chalet rentals Tuscany
- Lakehouse rentals Tuscany
- Rentals with an accessible height toilet Tuscany
- Aparthotel rentals Tuscany
- Bed and breakfasts Tuscany
- Mansion rentals Tuscany
- Nature eco lodge rentals Tuscany
- Apartment rentals Tuscany
- Guesthouse rentals Tuscany
- Barn rentals Tuscany
- Rentals with beach access Tuscany
- Rentals with lake access Tuscany
- Campsite rentals Tuscany
- Earth house rentals Tuscany
- Cabin rentals Tuscany
- House rentals Tuscany
- Rentals with breakfast Tuscany
- Private suite rentals Tuscany
- Rentals with pools Tuscany
- Beach house rentals Tuscany
- Beachfront rentals Tuscany
- Rentals with a sauna Tuscany
- Cottage rentals Tuscany
- Loft rentals Tuscany
- Pet-friendly rentals Tuscany
- Family-friendly rentals Tuscany
- Boutique hotels Tuscany
- Farmstay rentals Tuscany
- Serviced apartment rentals Tuscany
- Hostel rentals Tuscany
- Tiny house rentals Tuscany
- Resort rentals Tuscany
- Waterfront rentals Tuscany
- Hotel rooms Tuscany
- Boat rentals Tuscany
- Rentals with a hot tub Tuscany
- Ski-in/ski-out rentals Tuscany
- Rentals with a kayak Tuscany
- Luxury rentals Tuscany
- RV rentals Tuscany
- Townhouse rentals Tuscany
- Rentals with an accessible height bed Tuscany
- Castle rentals Tuscany
- Tower rentals Tuscany
- Tent rentals Tuscany
- Holiday home rentals Italy
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Tastings Tuscany
- Workouts Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Cooking Italy
- Food tours Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy
- Landmarks Italy





