
Guesthouse holiday rentals in Siena
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Top-rated Guesthouses in Siena
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A charming Tuscan retreat
Villa Pianelli is a traditional farmhouse dating from the 1500's and consists of 2 structures. The main house where I live, always available to ensure your stay runs smoothly and the Garden apartment. Both are completely independant with separate entrances. The Garden apartment is composed of 5 rooms on ground level, the interiors have retained the Tuscan characteristics with brick ceilings and chestnut beams and terracotta floors. There are 2 double bedrooms, 1 bathroom with shower, 1 lounge with a wood burning stove and open plan kitchen - dining area. The kitchen is equipped with fridge,oven and ceramic hob. From the lounge you access the spa room with sauna and from there onto a terraced garden complete with b.b.q. The swimming pool is 8mx16m and is open May through September, furnished with sun loungers,a b.b.q area and a large covered pergola with dining tables and chairs. Villa Pianelli is secluded in a quiet corner of the Tuscan countryside, nestled in the hills of Arezzo, surrounded by vineyards, olive groves and oak forests.We can offer our guests a dimension of peace and quiet whilst ensuring various possibilities of entertainment in wineries, restaurants,shopping etc just a few kilometres away in Arezzo. Please note that the house has two bedrooms but if the booking is for two people only one bedroom will be provided.If required there is an additional cost of 50 euro per night for the second bedroom.

Appartment 1 surrounded by Tuscan Nature
This detached appartment has 55 mp with kitchen, bathroom, bedroom, and terrace. It is built in the traditional tuscan style with stone and wood. Its 20 minutes drive to the sea,1 hour to Siena, 2 hours to Rome and Florence, 5 minutes to Caldana city Center where you have all amenities (groceries, bank, Postoffice,3 restaurants..) You will find a lot of activities like horseriding,excursions of history and plants,winetasting and kilometers of wonderfull beaches, watch the birds and wild animals.

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Cosy apartment with terrace and pool
Set in the beautiful Tuscan countryside in the heart of the famous wine district of Chianti Classico, you find this newly refurbished apartment with private terraces. On the property there is a large pool and gardens. The perfect getaway for those who want to escape, or an ideal base from which to visit Siena, Florence and Arezzo Walking distance of a few hotels, wineries and restaurants. Only a few kilometres away there are the famous Chianti villages; Gaiole, Radda and Castellina.

Casale Santa Barbara - Exclusive Apartment
At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

Alice's stop
La nostra piccola guest-house è perfetta perché situata in un punto strategico della val d’Orcia a 7 km da la località storica e termale di Bagno Vignoni e 8 km dalle terme di Bagni san Filippo, Pienza dista solamente 20km. Circondati da meravigliose camminate e punti panoramici, ottime per passeggiate o per fermate durante il pellegrinaggio. Vicino a noi si trovano attività di noleggio biciclette elettriche oppure se uno preferisce anche una bella passeggiata a cavallo

The Orion Villa
Welcome to Orion at Colle sul Lago. This independent villa on the property boasts 3 bedrooms and 2 full bathrooms (one bedroom is ensuite). There is a large kitchen and an outdoor terrace, both with dining tables. Wake up in true Italian style and enjoy your cappuccino looking out over Lake Montepulciano. Take a stroll through our private forest, or a dip in the beautiful pool. Adventures await as you set off to discover all the magic of Tuscany and Umbria!

Beautiful Apartment with Pool in Maremma
Art & Garden offers apartments with swimming pool in Tuscany for weekly stays. Immersed in the typical Tuscan landscape, in the ancient medieval village of Monte Antico, five beautiful apartments with pool and an elegant private villa, ideal for families with children, are available for guests who want to enjoy a vacation in Tuscany. Spend a vacation dedicated to relaxation and nature, immersed in one of the most enchanting landscapes of Italy.

La Rondine Sea-view Cottage. Tuscany
Welcome to Il Baciarino, a rustic agriturismo in the green hills of Maremma, Tuscany’s wild and less-traveled coastal region. Our property offers unique, handcrafted cottages with sea views, privacy, and direct contact with nature. Set within 19 acres of hillside wilderness in the charming Etruscan town of Vetulonia, Il Baciarino is the perfect place to escape the city, slow down, and enjoy unspoiled landscapes, fresh seafood, and good wine.

LA CASINA: Your tiny house in Tuscany
Cozy cottage rests within garden of architect-restored farmhouse. LA CASINA di Malabiccia is proud to offer year-round hospitality in a unique location amidst the rolling hills of Tuscany. Italian materials and quirky details create an unforgettable charm and comfort. Guests enjoy ample garden space, a fully equipped kitchen and daytrips to Montalcino, Montepulciano, Pienza, Arezzo, Siena, Cortona and more.

Secret Haven
The dépendance, fully immersed in the green of the Tuscan countryside, is located in the heart of Valdichiana. The large outdoor spaces and the pool are the ideal place to spend pleasant days among the countryside scents. The house has a double bedroom and a sofa bed in the living room so it can accommodate a maximum of two adults and one child. A baby crib will be made available to guests upon request.

Apartment "Cerbaia" in rural house with pool
Welcome to Villa Xavante della Solaia – a large rural house in the Tuscan countryside. The house has 4 apartments and apartment "Cerbaia" has entrance from the street. The house includes a pool, a beautiful garden with nice patios – and not least a great view of the Tuscan hills. The property is around 30 minutes' drive from Sienna (36 km).
Popular amenities for Siena guesthouses
Family-Friendly guesthouses

The Orion Villa

Tuscan cottage with an heavenly view

Il Giglio Relax in Castellina in Chianti

Appartment 1 surrounded by Tuscan Nature

Podere Rachele - Ghiandaia House

Podere Rachele - Owl's House

Apartment "Cerbaia" in rural house with pool

A charming Tuscan retreat
Guesthouses with a patio

The Orion Villa

Small, charming pool house - country house

San Gimignano Relaxation

nikki’s room

Apartment "Cerbaia" in rural house with pool
Other guest house holiday rentals

The Orion Villa

Tuscan cottage with an heavenly view

Il Giglio Relax in Castellina in Chianti

Appartment 1 surrounded by Tuscan Nature

Podere Rachele - Ghiandaia House

Podere Rachele - Owl's House

Apartment "Cerbaia" in rural house with pool

A charming Tuscan retreat
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- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Cala Violina
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- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
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