
Cottage vacation 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.

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.

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.

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).

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.

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

Countryside, 10 min from Siena
Apartment and large garden for exclusive use. It's a must for countryside, peace and relaxation, close to major places of cultural interest, trekking, biking trails. In a hilly area characterized by beautiful oak and holm oak forests, it enjoys a quiet location and a beautiful view of Siena, which is only 7 km away. (2 km are dirt 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 Siena cottage rentals
Cottage rentals with a hot tub

Romantic House in Tuscany with jacuzzi

Luxury Cottage Spaccasole - Pool W/Cortona

Cottage in the greenery with private jacuzzi and pool

EcoLodge – modernes Design in ruhiger Panoramalage

Panoramic view & outdoor jacuzzi - Pienza

Val D’Orcia Eco Cottage - Exclusive Retreat

"Rosso Poggiolo" farmhouse with swimming pool.

Tuscany Villa Girasole
Pet-friendly cottage rentals

Castagnatello Country House – Walnut Cottage

Cottages in Tuscan Country (Spazzacamino)

Rustic retreat in the Tuscan hills

Tuscan country house with pool

Il Seccatoio – stone house with panoramic view

Casa degli ulivi, live Chianti with swimming pool

House in Sogna

Lovely apartment, pool, garden view near Siena
Private cottage rentals

A beautiful exclusive ancient Haybarn near Siena

Cottage in the south of Tuscany

Your panoramic home in Tuscany among vineyards.

Tuscan Charm of Cottage Roccaio Cortona

Toscana, Country house with exclusive pool

The Barn

Cozy country cottage with swimming pool

Villetta with private patio and shared pool
Destinations to explore
- House rentals Siena
- Smoking-friendly rentals Siena
- Tiny house rentals Siena
- Pet-friendly rentals Siena
- Waterfront rentals Siena
- Rentals with an accessible height bed Siena
- Barn rentals Siena
- Farmstay rentals Siena
- Apartment rentals Siena
- Townhouse rentals Siena
- Rentals with a firepit Siena
- Rentals with a balcony Siena
- Castle rentals Siena
- Condo rentals Siena
- Rentals with pools Siena
- Rentals with a sauna Siena
- Luxury rentals Siena
- Rentals with a hot tub Siena
- Rentals with a fireplace Siena
- Rentals with breakfast Siena
- Hotel rooms Siena
- Bed and breakfasts Siena
- Rentals with outdoor seating Siena
- Tent rentals Siena
- Villa rentals Siena
- Rentals with an EV charger Siena
- Loft rentals Siena
- Fitness-friendly rentals Siena
- Vacation home rentals Siena
- Guesthouse rentals Siena
- Boutique hotels Siena
- Rentals with a patio Siena
- Rentals with a home theater Siena
- Rentals with lake access Siena
- Private suite rentals Siena
- Nature eco lodge rentals Siena
- Serviced apartment rentals Siena
- Family-friendly rentals Siena
- Rentals with a washer and dryer Siena
- Rentals with beach access Siena
- Cottage rentals Tuscany
- Cottage rentals Italy
- Santa Maria Novella
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Kite Beach Fiumara
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Spiaggia Marina di Cecina
- Mugello Circuit
- Palazzo Vecchio
- Cala Di Forno
- Stadio Artemio Franchi
- Things to do Siena
- Art and culture Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Sports activities Siena
- Tours Siena
- Food and drink Siena
- Things to do Tuscany
- Art and culture Tuscany
- Nature and outdoors Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Wellness Italy
- Nature and outdoors Italy
- Food and drink Italy
- Sightseeing Italy
- Tours Italy
- Art and culture Italy
- Entertainment Italy
- Sports activities Italy




