
Cottage holiday rentals in Siena
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Siena
Guests agree: these cottages are highly rated for location, cleanliness and more.

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Cottage Cappero - Masseto In Chianti
MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Vittoria (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

Monteriggioni Castello, holiday house in Tuscany
Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Country cottage C&M surrounded by greenery, love Tuscany
Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

EcoLodge – modern design in a peaceful panoramic location
The EcoLodge, modern, ecological, comfortable, is in the middle of nature in a peaceful, fertile cultural landscape on Monte Amiata in the quiet southern Tuscany. It belongs to an old farmhouse with plenty of space, beautiful views, many old fruit, chestnut, olive trees and our vineyard. It's an ideal location. From here you can explore world-famous sights, do a lot and enjoy the tranquility of Tuscan country life away from the hordes of tourists.

La Dolce Vita Romantic 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.

Cottage "Girasole" in Tuscany
A lovely cottage in the old farmhouse "Podere Maltaia" that overlooks the Unesco's Heritage protected area Orcia Valley, surrounded by large farmyards and 3 hectares of private land that includes an outdoor swimming pool (opened seasonally, based on outside temperature - please ask to know the dates for the upcoming or ongoing summer season), garden, outdoor dining area, BBQ and parking area (not-covered, free of charge).

Lovely apartment with garden and views near Siena
At just 18km from Siena, the apartment is part of a traditional Tuscan farmhouse, Santa Barbara, tucked away in the scenic rolling hills of Tuscany. The uniquely positioned grounds dominate the valley, allowing for stunning views with the most enchanting sunsets, or sunrises for those early birds! The apartment allows for a relaxing and recharging break, as well as being in the perfect location to go out and explore.

Countryside Cottage With View - Le Papere apt
The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany. A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers. Warm and cozy atmosphere that makes you feel instantly at home. For those who wish to live the experience of the Tuscan countryside as it is lived by the locals.

Charming cottage in Tuscany
Charming cottage located on a hill with 360-degree views. An oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ Area Inside there is a bedroom with a French bed, a living room with a sofa bed, a bathroom, a kitchenette and an indoor and outdoor dining area. Ideal for couples and families with one/two children. Crib available
Popular amenities for cottage rentals in Siena
Cottage rentals with a hot tub

Podere Coreno / authentic Tuscan peace & relaxation

Romantic House in Tuscany with jacuzzi

From Simone, podere santi Lucia and Pietro

Cottage in the countryside with private jacuzzi and swimming pool

"Rosso Poggiolo" farmhouse with swimming pool.

Casale con Piscina Privata Salata • Montepulciano

Hut at S. Carlo in Buonconvento

Luxury Cottage Spaccasole - Pool W/Cortona
Pet-friendly cottage rentals

Castagnatello Country House – Walnut Cottage

Stunning cottage on the Tuscan hills

Tuscan countryside vacation home with pool

Cottage in the south of Tuscany

Il Seccatoio - a stone house with panoramic views

Private pool nature Hideway

Tuscan Barn Apartment for 6 with panoramic pool

La Casa del Frantoiano - Pari -
Private cottage rentals

Old Chianti chapel-style cottage

Peaceful modern eco house in the Tuscan hills

Cottage in the Tuscan countryside

La Loggia, cozy stone cottage for 2 with terrace

Crete Senesi - Asciano Cavoni Hut

Podere Grignano, beautiful Tuscany

Casa Roberta: a beautiful view of the Crete!

Angalia Guesthouse
Destinations to explore
- Rentals with a firepit Siena
- Rentals with a hot tub Siena
- Castle rentals Siena
- Apartment rentals Siena
- Rentals with lake access Siena
- Flat rentals Siena
- Smoking-friendly rentals Siena
- House rentals Siena
- Boutique hotels Siena
- Hotel rooms Siena
- Townhouse rentals Siena
- Tiny house rentals Siena
- Bed and breakfasts Siena
- Villa rentals Siena
- Rentals with breakfast Siena
- Rentals with a sauna Siena
- Fitness-friendly rentals Siena
- Holiday home rentals Siena
- Tent rentals Siena
- Rentals with a fireplace Siena
- Rentals with a patio Siena
- Rentals with an accessible-height bed Siena
- Rentals with a cinema Siena
- Rentals with beach access Siena
- Nature eco lodge rentals Siena
- Rentals with a balcony Siena
- Luxury rentals Siena
- Serviced apartment rentals Siena
- Rentals with an EV charger Siena
- Guest house rentals Siena
- Loft rentals Siena
- Family-friendly rentals Siena
- Barn rentals Siena
- Rentals with outdoor seating Siena
- Farm stay rentals Siena
- Pet-friendly rentals Siena
- Waterfront rentals Siena
- Private suite rentals Siena
- Rentals with pools Siena
- Rentals with a washing machine and dryer Siena
- Cottage rentals Tuscany
- Cottage rentals Italy
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Mercato Centrale
- Parco Regionale Della Maremma
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Stazione Santa Maria Novella
- Del Chianti
- Piazza della Repubblica
- Piazzale Michelangelo
- Parco delle Cascine
- Pitti Palace
- Piazza della Signoria
- Boboli's Garden
- Palazzo Vecchio
- Cascate del Mulino
- Basilica of Santa Croce
- Things to do Siena
- Sightseeing Siena
- Food and drink Siena
- Art and culture Siena
- Tours Siena
- Nature and outdoors Siena
- Sports activities Siena
- Things to do Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sightseeing Tuscany
- Entertainment Tuscany
- Things to do Italy
- Sightseeing Italy
- Entertainment Italy
- Food and drink Italy
- Tours Italy
- Sports activities Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy





