
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.

Stone House with Exclusive Pool Codilungo in Chianti
Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

Eleutherìa: Cozy Cottage in the heart of Tuscany
Eleutherìa is a recently refurbished cottage, located on the top of the hill surrounded by the stunning Tuscan countryside. It is right in the middle of trekking tracks crossing centuries-old woods and wild nature, those who walk along can feel nature and discover to belong to it.. Offering a 75 sqm (800 sqft) area with patio overlooking the garden to unwind your senses. Just about 18 Km (11 Mi) from the medieval city of Siena, it’s a strategic location to the major Tuscan’s attractions.

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.

Il Fienile, Cottage in the country with Jacuzzi
Surrounded by wineyards, close to Florence, a charming accomodation in a cozy cottage with heated jacuzzi at your exclusive use. Rooms sanitized by health protocols. Perfect starting point to discover Florence and Siena. Kitchen, wide living room, bathroom, two double bedroom (one with an extra single bed). In the living room a sofa bed for other 2 people. Tasteful furniture, Air Conditioning, barbecue, private parking. Partnership for: bike rental, private chef, private driver

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.

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.

Casa La Misura in the heart of Chianti
La Misura house is part of Borgo Montecastelli, a beautiful rural complex located right on the border between the provinces of Siena and Florence. Due to its strategic position, straddling two valleys, Borgo Montecastelli enjoys a magnificent panorama from its summit towards the villages that surround it: Panzano, Radda in Chianti, Castellina in Chianti, as well as farmhouses, churches, and towers.

Lovely countryhouse on Chiant hills
Lovely view on the valley, sweet relax in the smelling garden under a very old tree tasting a good wine and then to visit Firenze, Pisa, Siena only 30 km far from here and medieval castles,little churchs ,winery,across the beautiful Chianti road.....

Countryside Cottage With View - Le Rondini 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.
Popular amenities for cottage rentals in Siena
Cottage rentals with a hot tub

Romantic House in Tuscany with jacuzzi

"Rosso Poggiolo" farmhouse with swimming pool.

NEW Leccino home pool&Jacuzzi a Fontanaro Property

Tuscany Villa Girasole

Independent cottage with private spa

Tuscan country house with pool+garden by Vacavilla

Farmhouse in the Tuscan countryside "Stars" apartment

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

Romantic lake view cottage (2/4),Tuscany/ Umbria,

Tuscan Countryside Holiday Home with Pool

Il Seccatoio - a stone house with panoramic views

Casa degli ulivi, live Chianti with swimming pool

villa in a typical Tuscan farmhouse

House in Sogna

Villetta Belvedere

QuarterApartment for 6P Agriturismo Quarantallina
Private cottage rentals

Old Chianti chapel-style cottage

Il Fienile, characteristic stone cottage for 2

dependance mandriola

Crete Senesi - Asciano Cavoni Hut

Angalia Guesthouse

Typical Tuscan house

Loft & patio under the vineyard

Grove Cottage, Immersed in nature & close to town
Quick stats about cottage rentals in Siena

Nightly prices starting at
Siena holiday rentals start at $207 SGD per night before taxes and fees

Verified guest reviews
Over 80 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Siena rentals

4.9 Average rating
Siena stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Bed and breakfasts Siena
- Rentals with an EV charger Siena
- Family-friendly rentals Siena
- Rentals with a patio Siena
- Flat rentals Siena
- Rentals with a fireplace Siena
- Apartment rentals Siena
- Hotel rentals Siena
- Serviced apartment rentals Siena
- Boutique hotel rentals Siena
- Holiday home rentals Siena
- Rentals with pools Siena
- Rentals with breakfast Siena
- Smoking-friendly rentals Siena
- House rentals Siena
- Fitness-friendly rentals Siena
- Pet-friendly rentals Siena
- Villa rentals Siena
- Rentals with a hot tub Siena
- Rentals with a firepit Siena
- Rentals with a washing machine and dryer Siena
- Rentals with outdoor seating Siena
- Cottage rentals Siena
- Cottage rentals Tuscany
- Cottage rentals Italy
- 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
- Gulf of Baratti
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazzale Michelangelo
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Mugello Circuit
- Kite Beach Fiumara
- Spiagge bianche
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Medici Chapels
- Spiaggia Marina di Cecina
- Stadio Artemio Franchi
- Things to do Siena
- Art and culture Siena
- Tours Siena
- Nature and outdoors Siena
- Sightseeing Siena
- Food and drink Siena
- Things to do Siena
- Food and drink Siena
- Art and culture Siena
- Nature and outdoors Siena
- Tours Siena
- Sightseeing Siena
- Things to do Tuscany
- Sightseeing Tuscany
- Wellness Tuscany
- Art and culture Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Nature and outdoors Tuscany
- Tours Tuscany
- Sports activities Tuscany
- Things to do Italy
- Food and drink Italy
- Wellness Italy
- Art and culture Italy
- Sightseeing Italy
- Sports activities Italy
- Nature and outdoors Italy
- Tours Italy
- Entertainment Italy

