Guesthouse vacation rentals in Siena

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouses in Siena

Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guesthouse in Antria

4.92 out of 5 average rating, 134 reviews

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.

Superhost

Guesthouse in Caldana

4.8 out of 5 average rating, 188 reviews

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.

Top guest favourite

Guesthouse in Macciano

4.97 out of 5 average rating, 178 reviews

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.

Guesthouse in San Martino al Vento

4.76 out of 5 average rating, 21 reviews

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.

Top guest favourite

Guesthouse in Montefollonico

4.97 out of 5 average rating, 105 reviews

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.

Guesthouse in Binami

5 out of 5 average rating, 5 reviews

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!

Guesthouse in Monte Antico

4.4 out of 5 average rating, 10 reviews

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.

Superhost

Guesthouse in Castiglione della Pescaia

4.5 out of 5 average rating, 4 reviews

La Rondine Sea-view Cottage with Pool. 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.

Guest favourite

Guesthouse in Petroio

4.96 out of 5 average rating, 123 reviews

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.

Guesthouse in Croce

4.86 out of 5 average rating, 63 reviews

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.

Top guest favourite

Guesthouse in Solaia

4.94 out of 5 average rating, 36 reviews

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).