We have put together an exclusive selection of luxury villas and stylish holiday homes and apartments in Tuscany
The Tuscan countryside is characterized by rolling hills, vineyards, olive groves, cypress avenues and picturesque villages. As a guide to authentic and especially beautiful places to stay, we have taken great care to select holiday homes and self-catering vacation rentals that stand out for their tasteful decoration, unique surroundings and location. You will find a choice that ranges from inexpensive, but beautifully decorated holiday apartments in Tuscany to elegant luxury villas that make all your dreams come true. You will find charming rural country houses, architecturally spectacular design villas with a modern flair in Tuscany or rustic and remote mountain chalets for people seeking peace and a connection with nature. Let us inspire you with our handpicked selection of exceptional holiday homes and villas for a truly special escape, without losing that homely feeling.
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Hotel & Self-Catering - Medium BudgetIt is hard to know where to begin, because Locanda Rossa has it all. It is one of those places that, without trying too hard, fits almost any idea of a holiday. It suits honeymooners just as well as families with energetic children,...- Countryside
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- 37 rooms
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- from 180 EUR
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Holiday Apartments - Medium Budget- Italy
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- Tuscany
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- Siena
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- San Giovanni D'Asso
Authentic vacation homes in a historic Tuscan village. Masterfully restored, they offer modern comfort, rustic charm and panoramic views. Ideal for romantic getaways and weddings. The pool and Casale Sarageto are best suited for larger groups. An unforgettable Tuscan experience!- Countryside
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- 6 properties
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- from 210 EUR
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Bed and Breakfast & self-catering - Medium BudgetThe San Niccolò apartments have been furnished with extreme attention to detail with a mix of luxury vintage and modern decor. An incredible atmosphere that will make it difficult to leave.- City
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- 11 properties
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- from 140 EUR
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Hotel & Self-Catering - Medium BudgetVilla Campestri is a traditional hotel surrounded by nature, vineyards and olive groves. Here you will experience the beauty and tradition of the region. Enjoy the pool overlooking the Mugello Valley and the exquisite cuisine of the house. Activities such as hiking and cooking classes will complete your stay.- Countryside
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- 21 rooms
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- from 219 EUR
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Hotel & Self-Catering - Medium BudgetResidence Hilda: Charming small hotel in the heart of Florence. Perfect location, modern suites and apartments with first class service. Discover Tuscany from the comfort of your home away from home.- Historic Quarters
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- 4 rooms
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- from 140 EUR
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Holiday Apartments - Medium BudgetLa Pievuccia offers the opportunity to experience living in authentic Tuscan apartments, which have been recently renovated with great attention to detail and incorporate many characteristic features from the local region. Guests are able to...- Countryside
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- 6 properties
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- from 95 EUR
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Holiday Apartments - Low BudgetAre you looking for a calm, natural retreat? Then, the Ginestriccio is the perfect place for you. With its ivy-draped walls and tranquil and peaceful atmosphere the building feels like straight out of a fairy tale.This is, certainly, a place to in...- Countryside
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- 2 properties
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- from 119 EUR
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Bed and Breakfast & self-catering - Low Budget- Italy
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- Tuscany
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- Siena
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- Gaiole in Chianti
In a lovingly restored village in Chianti, Argenina offers self-catering country houses and elegant rooms in a charming B&B. Vineyards, stillness, homemade breakfasts and family-style cooking in one of central Italy’s most authentic regions.- Wine Country
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- 17 rooms
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- from 115 EUR
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Holiday home villa - Medium Budget- Italy
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- Tuscany
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- Siena
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- Montalcino
This design villa in Tuscany is a modern work of art surrounded by nature. With 2 bedrooms, a swimming pool, a sauna and original artworks, it offers a contemporary style and maximum comfort. Ideal for art and nature lovers.- Countryside
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- 4 people
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- from 540 EUR
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Holiday homes villas - Low Budget"Arte in Paradiso" is a fascinating vacation home surrounded by Tuscan nature with art, swimming pool and tranquillity. Ideal for 5 people, it offers creative space, a sun terrace and excursions to nearby towns and the sea. Enjoy the Tuscan way of life.- Countryside
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- 5 people
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- from 120 EUR
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Bed and Breakfast & self-catering - Medium BudgetB&B Hotel Le Due Volpi is a peaceful rural retreat in the Tuscan countryside, just 30 km from Florence. With four colourful rooms, spacious gardens and warm hospitality, it is ideal for a harmonious city and country vacation.- Countryside
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- 4 rooms
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- from 80 EUR
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Holiday home villa - Medium BudgetThe Casa Capanni Cortona is the perfect place to regain your inner balance. It´s located in a small Italian village in the heart of Tuscany, surrounded by soothing tranquility. The owners – a group of friends from the Netherlands - fulfilled th...- Countryside
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- 18 people
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- from 1300 EUR
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Bed and Breakfast & self-catering - Low BudgetThis renovated medieval farmhouse is a well-located and rural bed and breakfast in the Tuscan hills, just 30 minutes from Florence. It's a great base for exploring the countryside and nearby towns. Casa Palmira offers a truly authentic and comfortable stay.- Countryside
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- 6 rooms
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- from 100 EUR
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Holiday Apartments - Medium BudgetThe historic Castello di Bibbione in the Chianti region offers beautiful self-catering apartments. The property, surrounded by vineyards and olive trees, houses apartments with authentic charm. Enjoy the local Tuscan countryside, renovated interiors, and the opportunity to explore the region's cuisine.- Countryside
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- 12 properties
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- from 130 EUR
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Hotel & Self-Catering - Medium BudgetThe charming country hotel in the heart of Chianti, near Siena, offers 4 rustic apartments for relaxing stays. Experience the timelessness of Tuscany amidst vineyards and olive groves, surrounded by traditional flair and tranquillity.- Countryside
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- 4 rooms
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- from 85 EUR
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Hotel & Self-Catering - LuxuryDiscover understated luxury in this beautiful small hotel in picturesque Tuscany. Castello di Vicarello promises authentic charm, culinary delights and rest amidst its surrounding hills, olive groves and vineyards. Ideal for a break from your daily routine.- Countryside
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- 11 rooms
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- from 630 EUR
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Holiday home villa - Medium BudgetCostalmandorlo is an authentic Tuscan retreat, offering charming small vacation homes set amidst enchanting hills. These lodges combine comfort, nature and spectacular panoramas for a perfect vacation.- Countryside
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- 1 properties
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- from 350 EUR
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Holiday Apartments - Medium BudgetFattoria Barbialla Nuova offers modern apartments and a cosy farm stay. This is an organic farm that combines conservation, comfort and authenticity. Just ideal for a vacation in touch with nature.- Countryside
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- 9 properties
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- from 85 EUR
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Holiday home villa - Medium BudgetThe 16th century Fattoria Tregole winery in Chianti is a Tuscan-style villa. Ideally located with a garden, swimming pool and close to Castellina. Experience authentic Tuscany and relax in the heart of picturesque vineyards.- Countryside
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- 4 properties
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- from 220 EUR
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Holiday Apartments - Low BudgetThe peaceful Il Borgo degli Agrumi, with six thoughtfully designed charming apartments, offers modern comforts amidst natural beauty. Ideal for hiking and biking lovers and cultural excursions to nearby Tuscan towns.- Village
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- 6 properties
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- from 120 EUR
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Bed and Breakfast or whole Villa - Medium BudgetAn intimate Bed & Breakfast in the beautiful Santa Croce district of Florence. Four cosy rooms, Italian breakfast in Santa Croce square. Possibility of exclusive rental of the historic building. Ideal for families and groups of friends.- City
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- 3 rooms
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- from 120 EUR
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Hotel & Self-Catering - Medium BudgetExperience privacy and Tuscan charm while staying in vacation apartments at Monsignor della Casa Country Resort. Historic country estate with modern comforts, wellness, sports facilities and nature experiences. Perfect end: dinner at the hotel restaurant with excellent wine.- Countryside
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- 26 rooms
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- from 150 EUR
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Holiday Apartments - Medium BudgetLovely, charming vacation apartments in a 15th century house in a quiet, yet central location close to lots of excellent restaurants in Florence. Here rustic comfort meets modern amenities – a place to feel at home.- City
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- 8 properties
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- from 190 EUR
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Holiday home villa - High BudgetThis charming villa suitable for up to 6 people. You will be warmly welcomed with snacks and local products. The villa is located near great bars and restaurants in Cortona.- Historic Quarters
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- 6 people
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- from 795 EUR
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Holiday Apartments - Medium Budget- Italy
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- Tuscany
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- Grosseto
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- Roccatederighi
Spend authentic Tuscan vacations in Pieve di Caminino. Antique furniture and a centuries-old atmosphere await you in these charming vacation apartments. Surrounded by 11th century monastery walls, you will experience the true essence of Tuscan history and nature.- Countryside
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- 7 rooms
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- from 160 EUR
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Holiday Apartments - Medium Budget- Italy
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- Tuscany
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- Pistoia
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- Cutigliano
Sasso al Melo offers you the perfect modern vacation apartment surrounded by the beautiful Tuscan nature. The apartments are stylishly furnished, offer comfort and are ideal for families and pets. Enjoy hiking trails, an outdoor pool and proximity to charming villages.- Mountain
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- 8 properties
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- from 105 EUR
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Holiday Apartments - Medium BudgetExclusive apartments surrounded by vineyards and picturesque Italian countryside. In traditional Tuscan style and with high quality furnishings – ideal for unforgettable stays.- Countryside
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- 11 properties
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- from 170 EUR
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Holiday homes villas - Luxury"The Butterflies" is a luxury villa in Lucca with ecological awareness. An architectural jewel in the middle of nature can accommodate up to 6 people. Panoramic view, Jacuzzi, pool shared with the owner. Awarded by "National Geographic" and "EXPO STONE AWARD 2015."- Countryside
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- 2 properties
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- from 700 EUR
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Holiday home villa - High Budget- Italy
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- Tuscany
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- Pisa
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- San Miniato
Umamma is a small 16th century villa, offers a unique retreat among the Florentine hills. This loft with modern industrial style and panoramic views combines history with innovation. The highlight is a secret plunge pool in a cave. San Miniato and nearby towns are easily accessible.- Historic Quarters
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- 4 people
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- from 900 EUR
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Apartments or whole Villa - High BudgetThe beautiful romantic Villa Montanare in Cortona offers stunning panoramic views, a cosy atmosphere and an exclusive experience surrounded by Tuscan nature. Ideal for romantic weddings and vacation dreams.- Countryside
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- 2 properties
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- from 433 EUR
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Hotel & Self-Catering - High BudgetThe elegant Villa Sassolini is a charming country hotel in Tuscany, perfect for a relaxing getaway. The 10 rooms offer traditional architecture with modern elegance, and the location is ideal for exploring nearby Siena, Cortona, and San Gimignano. The on-site pool and the scent of lavender promise relaxation.- Village
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- 21 rooms
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- from 175 EUR
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Hotel & Self-Catering - Medium BudgetAn enchanting small hotel offering rural happiness in the midst of the Tuscan hills. Thoroughly renovated, still traditional and authentic self-catering apartments, handily situated close to Florence, Siena, Lucca and Pisa – and first class wine.- Countryside
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- 7 rooms
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- from 249 EUR
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Holiday home villa - High BudgetThe dreamlike villa in the middle of the Tuscan countryside offers space for 14 people, a modern pool and an in-house restaurant. Discover the beauty of San Casciano dei Bagni and enjoy the Italian dream.- Countryside
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- 6 rooms
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- from 180 EUR
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Holiday home villa - Luxury- Italy
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- Tuscany
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- Florence
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- Montespertoli
Villa Vigna, a luxury vacation home in the Tuscan hills, combines elegance, authenticity and modern design. With a private pool and proximity to the most beautiful cities of Tuscany, it is the ideal retreat for unforgettable vacation experiences.- Countryside
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- 10 people
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- from 1714 EUR
Our short listed lodgings
Below you will find some more lovely accommodations we have recently discovered and that we will publish soon. You can book them through booking.com in the meantime.
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Bed and Breakfast & self-catering - High Budget- Italy
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- Tuscany
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- Arezzo
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- Pozzo della Chiana
Borgo 69 Villas and Suites is a luxurious retreat located in Tuscany, near Cortona. Surrounded by stunning landscapes and rich cultural heritage, Borgo 69 provides easy access to medieval towns, including the village of Pozzo della Chiana, known from the film Under the Tuscan Sun. On-site amenities include a swimming pool, spa treatments, and wellness experiences.- Countryside
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- 11 rooms
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- from 380 EUR
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Bed and Breakfast & self-catering - High BudgetCanto degli Scali is housed in a restored 14th-century palazzo in Florence and consists of seven units, divided into elegant B&B bedrooms and exclusive apartments. It accents the classic charm of a Tuscan Renaissance palazzo with antique terracotta floors.- City
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- 7 rooms
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- from 189 EUR