
Cottage vacation rentals in Siena
Find and book unique cottages on Airbnb
Quick stats about cottage rentals in Siena

Nightly prices starting at
Siena vacation rentals start at G$37,656 GYD per night before taxes and fees

Verified guest reviews
Over 90 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!
Top-rated cottage rentals in Siena
Guests agree: these cottages are highly rated for location, cleanliness, and more.

FAETOLE typical Tuscan country house near FLORENCE
My cottage is hidden in Tuscan countryside among olive groves, vineyards and woodland. Nevertheless, downtown Florence is only 16km away! While away, spend your time by relaxing in the garden, where you will find a barbecue and an outdoor shower to cool down while sunbathing. Discover the beauty of surrounding countryside with a hike and unwind with a view of picture-perfect vineyards! One can also easily go for day trips to many tiny medieval towns scattered on the hills of Tuscany from here!

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.

Cottage Vittoria - 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), Cappero (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.

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.

From Simone, podere santi Lucia and Pietro
Recently inaugurated, the property is a portion of a Tuscan farmhouse with an independent entrance immersed in the Sienese countryside just 10 minutes from the historic center of Siena. The apartment consists of two double bedrooms, a bathroom with shower and bathtub, a living room, and a kitchen. A 60*120 cm crib with safety rails is available upon request. Outside there is a common farmyard. The price is for the entire apartment. Accommodation tax €1.5/person

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.

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. 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

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).

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.
Popular amenities for Siena cottage rentals
Cottage rentals with a hot tub

Podere Coreno / Authentic Tuscan Peace & Relaxation

Romantic House in Tuscany with jacuzzi

Cottage in the countryside with private jacuzzi and swimming pool

"Rosso Poggiolo" farmhouse with swimming pool.

NEW Leccino home pool&Jacuzzi a Fontanaro Property

Tuscany Villa Girasole

Hut at S. Carlo in Buonconvento

Detached Cottage with Private Spa
Pet-friendly cottage rentals

Stunning cottage on the Tuscan hills

Tuscan countryside vacation home with pool

Cottage in the south of Tuscany

Casa degli ulivi, live Chianti with swimming pool

Villetta Belvedere

Private pool nature Hideway

Tuscan Barn Apartment for 6 with panoramic pool

La Casa del Frantoiano - Pari -
Private cottage rentals

Castagnatello Country House – Walnut Cottage

Old Chianti chapel-style cottage

Il Fienile, characteristic stone cottage for 2

Crete Senesi - Asciano Cavoni Hut

Angalia Guesthouse

Stone cottage in beautiful Umbrian countryside

Loft & patio under the vineyard

Chianti Loft (AC & Pool)
Destinations to explore
- Provence Vacation rentals
- Rome Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Venice Vacation rentals
- Florence Vacation rentals
- Francavilla al Mare Vacation rentals
- Naples Vacation rentals
- Marseille Vacation rentals
- Italian Riviera Vacation rentals
- Cannes Vacation rentals
- Bologna Vacation rentals
- Pet-friendly rentals Siena
- Rentals with breakfast Siena
- Apartment rentals Siena
- Boutique hotels Siena
- Family-friendly rentals Siena
- Rentals with a fireplace Siena
- Rentals with outdoor seating Siena
- Smoking-friendly rentals Siena
- Vacation home rentals Siena
- Rentals with a fire pit Siena
- Bed and breakfasts Siena
- Fitness-friendly rentals Siena
- Serviced apartment rentals Siena
- Villa rentals Siena
- Hotel rooms Siena
- Rentals with a hot tub Siena
- Rentals with a washer and dryer Siena
- Condo rentals Siena
- Rentals with a patio Siena
- Rentals with pools Siena
- Rentals with an EV charger Siena
- House rentals Siena
- Cottage rentals Siena
- Cottage rentals Tuscany
- Cottage rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Lake Trasimeno
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Fortezza da Basso
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Del Chianti
- Mugello Circuit
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Boboli's Garden
- Spiagge Bianche
- Parco delle Cascine
- Gulf of Baratti
- Basilica of Santa Croce
- Medici Chapel
- Stazione Santa Maria Novella
- Things to do Siena
- Art and culture Siena
- Sightseeing Siena
- Food and drink Siena
- Nature and outdoors Siena
- Things to do Siena
- Sports activities Siena
- Nature and outdoors Siena
- Art and culture Siena
- Food and drink Siena
- Tours Siena
- Sightseeing Siena
- Things to do Tuscany
- Entertainment Tuscany
- Sports activities Tuscany
- Sightseeing Tuscany
- Art and culture Tuscany
- Tours Tuscany
- Nature and outdoors Tuscany
- Food and drink Tuscany
- Things to do Italy
- Sightseeing Italy
- Art and culture Italy
- Food and drink Italy
- Tours Italy
- Sports activities Italy
- Entertainment Italy
- Nature and outdoors Italy
- Wellness Italy







