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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.

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Top Guest favourite
An open-plan living area features a white dining table surrounded by chairs, complemented by greenery from house plants. A modern kitchen is visible in the background, with minimalist cabinetry and a decorative light fixture hanging above. Light streams in from windows, creating a bright atmosphere.
Holiday home in Massa

Home Luxury - appartamento stile greco e marino

Appartamento in stile greco e marino finito di ristrutturare a luglio 2023. Arredato in maniera semplice ed elegante, il colore bianco e il legno vi faranno sentire subito in vacanza appena entrerete nell'ampio salone. Vi sembrerà di essere su un'isola della Grecia, con il controsoffitto di travi e canniccio, il letto matrimoniale di cemento così come il mobile tv ed i bagni. Una casa semplice ma di pregio dotata di tutti i comfort possibili gestibili tramite Alexa. Un appartamento magnifico!

LocationFamilyTV

5.0 out of 5 average rating, 108 reviews
Guest favourite
An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.
Holiday home in Poggibonsi

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.

FamilyLocationCheckout

4.94 out of 5 average rating, 205 reviews
Top Guest favourite
A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.
Holiday home in San Gimignano

Respira la Toscana: vista a 180° sulle Colline

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. inVivi la tua esperienza a San Gimignano con una splendida vista sulle colline toscane! Nel cuore di San Gimignano, vivi la città con ingresso indipendente, primo piano e panorama mozzafiato sulle colline toscane. Disponibile su richiesta il posto auto privato. Ingresso, salotto, 2 camere matrimoniali, cucina e ampio bagno. city tax da aggiungere al prezzo, 2,5€ per ogni persona per ogni notte.

FamilyValueDecor

4.98 out of 5 average rating, 165 reviews
Top Guest favourite
An aerial view captures the historic castle surrounded by lush green hills and vineyards. The impressive structure features tall towers and ornate architecture, set amid manicured gardens and tree-lined pathways, reflecting the beauty of the Chianti landscape.
Holiday home in Badia a Passignano

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

ValueLocationAccuracy

5.0 out of 5 average rating, 123 reviews
Guest favourite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Holiday home in Sovicille

Podere La Castellina - N°1 COTTAGE

Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

ValueLocationDecor

4.97 out of 5 average rating, 161 reviews
Top Guest favourite
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Holiday home in loc. Simignano

Casa al Gianni - Quercia

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

FamilyLocationWalkability

4.93 out of 5 average rating, 245 reviews
Top Guest favourite
Holiday home in Petrignano

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.

ValueFamilyBiking

4.98 out of 5 average rating, 168 reviews
Top Guest favourite
Holiday home in Sillico

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!

LocationFamilyWalkability

4.98 out of 5 average rating, 175 reviews
Top Guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home in Monticchiello

In Toscana Camere

**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.

LocationValueCheck-in

4.96 out of 5 average rating, 137 reviews
Top Guest favourite
An expansive window offers a breathtaking view of rolling hills and valleys, extending into the distant horizon. A small table with a laptop is positioned in front, accompanied by a white chair. Soft light fills the inviting space, emphasizing the serene landscape outside.
Holiday home in Rosennano

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.

FamilyLocationCondition

4.99 out of 5 average rating, 103 reviews
Guest favourite
A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.
Holiday home in Castelnuovo Berardenga

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property

LocationFamilyLong stay

4.91 out of 5 average rating, 100 reviews
Guest favourite
A spacious living area features a light-colored sofa with a decorative throw, complemented by wooden beams overhead. The open kitchen with modern appliances is visible in the background, alongside large windows that provide natural light and a view of the exterior.
Holiday home in Peccioli

Michelangelo: entire space in the heart of Tuscany

Come and take a vacation at our beautiful apartment in Peccioli, Tuscany! Enjoy a renovated space, beautifully decorated, with new appliances and furniture, Air conditioner in all spaces, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.

ValueLocationKitchen

4.87 out of 5 average rating, 263 reviews

Popular amenities for Tuscany holiday homes

Family-Friendly holiday homes

Holiday home rentals with a washing machine and dryer

Guest favourite
A stone-paved courtyard features a rustic house with weathered yellow walls and green shuttered windows. A small table with chairs is set under the sun, surrounded by potted plants, creating an inviting outdoor space for guests to enjoy the fresh air.
Holiday home in Fiesole

[Colline di Firenze] Casa toscana con posto auto

ValueLocationHeating

4.92 out of 5 average rating, 148 reviews
Guest favourite
The two-story rural home is situated on a gently sloping landscape, surrounded by lush greenery and vibrant flowers. Stone accents adorn the exterior, with a terracotta roof and a porch area framed by trees. Various shrubs and plants enhance the natural setting.
Holiday home in Lucca

Torretta House - cin: IT046017c2XQY33MML

ValueLocationHeating

4.87 out of 5 average rating, 140 reviews
Top Guest favourite
Holiday home in Viterbo

La Trinità-Comfort e Parcheggio in Centro Storico

ValueFamilyDecor

4.98 out of 5 average rating, 233 reviews
Top Guest favourite
A paved pathway leads to a charming outdoor seating area under a canopy, surrounded by low shrubs and greenery. The house features a mix of neutral-colored walls with green shutters, providing a cozy retreat in a tranquil setting.
Holiday home in Pistoia

Podere docciolino casa vacanze

ValueFamilyDecor

4.98 out of 5 average rating, 166 reviews
Guest favourite
A spacious living area is highlighted by large windows, allowing natural light to fill the room. Elegant furnishings include a comfortable gray sofa, a round dining table with four chairs, and a cozy reading nook, creating a welcoming atmosphere for relaxation and socializing.
Holiday home in Florence

Melarancio Residence

FamilyValueAir conditioning

4.91 out of 5 average rating, 360 reviews
Top Guest favourite
A panoramic view captures a hillside town featuring a historic tower, surrounded by lush greenery and rolling vineyards. The landscape displays a blend of trees, fields, and distant hills under a clear sky, showcasing the natural beauty of the Tuscan countryside.
Holiday home in Montespertoli

Chianti Panorama | House with 3 En-Suite Bathrooms

FamilyLocationTV

4.95 out of 5 average rating, 146 reviews
Guest favourite
Holiday home in Ripa- Pozzi-Ponterosso

Villino Anna casa immersa nel verde vicina al mare

ValueLocationGetting around

4.89 out of 5 average rating, 168 reviews
Guest favourite
An inviting living space features a terracotta sofa alongside a wooden dining table with four white chairs. A television is mounted on the wall, and natural light illuminates the room. Decorative elements include a hanging light and a plant in the corner.
Holiday home in Florence

Zen Island downtown Florence, new apartment for 6

FamilyLocationAmenities

4.94 out of 5 average rating, 102 reviews

Destinations to explore