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Guesthouse holiday rentals in Siena

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Top-rated Guesthouses in Siena

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

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Guest favourite
The outdoor area features a large swimming pool surrounded by lush greenery, including trees and shrubs. Sun loungers are positioned nearby for relaxation. The rustic farmhouse is visible in the background, showcasing traditional Tuscan architecture with terracotta accents.
Guesthouse in Antria
4.92 out of 5 average rating, 137 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
The image captures a stone exterior of an apartment at sunset, with a large tree providing shade. Rays of golden sunlight filter through branches, illuminating a grassy area and distant hills. A paved stone path leads towards the entrance, enhancing the connection to nature.
Guesthouse in Caldana
4.8 out of 5 average rating, 191 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
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 195 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
4.8 out of 5 average rating, 25 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
An exterior view of a charming Tuscan house featuring warm stone walls. The surrounding garden includes manicured grass and potted plants. A spacious patio with a table for outdoor dining is visible, alongside a stone pathway leading to the entrance.
Guesthouse in Montefollonico
4.97 out of 5 average rating, 112 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 Gallina
4.67 out of 5 average rating, 6 reviews

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

Superhost
An independent villa is showcased, featuring a rustic brick exterior with a green door. Two wooden tables and chairs are arranged on the terrace, surrounded by well-maintained greenery. The property is accentuated by a rustic fence and various potted plants.
Guesthouse in Binami
5 out of 5 average rating, 6 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!

An open living area with exposed wooden beams and brick arches is visible. A rustic dining table is centered, complemented by wooden chairs. A cozy seating nook with floral upholstery and a light fixture enhances the space, while a kitchenette can be seen in the background.
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
4.67 out of 5 average rating, 6 reviews

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.

Top Guest favourite
A cozy bedroom features a spacious bed with soft linens, positioned under wooden beams. Natural light filters through a glass door, illuminating the room. A stylish wooden ladder leans against the wall, while a small table with a flower vase adds a touch of color.
Guesthouse in Petroio
4.96 out of 5 average rating, 137 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.

An outdoor area is shown, featuring a round table set with two glasses of wine. Beyond the table, a pool is visible, surrounded by grassy landscaping. The rustic buildings, adorned with flowering plants, are positioned in the background, creating a relaxed atmosphere.
Guesthouse in Croce
4.86 out of 5 average rating, 64 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
The rustic stone exterior of the two-story villa is complemented by multiple windows with wooden shutters. A spacious patio features a large clay pot and a table with chairs, ideal for outdoor gatherings. Sunlight filters through the clouds, enhancing the welcoming ambiance.
Guesthouse in Solaia
4.95 out of 5 average rating, 40 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).

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