
Vacation home accommodations in Siena
Find and book unique vacation houses on Airbnb
Top-rated vacation houses in Siena
Guests agree: these vacation houses are highly rated for location, cleanliness, and more.

"Lisa" apartment with fireplace
Lisa apartment is very romantic, the most peculiar of our farm.... You enter directly into a large living room with fireplace, dining table, two sofas and television. In this room there is a charming loft where the bed is located. Bathroom with bath, dressing room with closet and washing machine. Large kitchen with dining table and a view over the Chianti hills. This apartment has a private solarium with deck chairs and table.“Il Poderaccio” dates back to 13th century when its ancient building served as an outpost of Siena against the “League”. Dominating “Chiantishire” , this charming country house offers all recently refurbished, independent flats just a few minutes from Siena city centre. Perfectly integrated in the surrounding environment, the flats can host from 2 to 5 people and come complete with bed and bath linen, dishes and pottery and traditionally furnished with country furniture. Guests can swim in the 18x6-mt swimming-pool, sunbathe in the cotto sundeck surrounded by an orchard and flowers, play bowls and table tennis while children enjoy the playground in the garden or play in the beautiful park spotted with trees and flowers coming from all over the world. Garden areas are reserved for each flat together with sun chairs, garden table and chairs for a perfectly relaxing stay. Furthermore, two wooden desks are available in the shadow and perfect silence of a fenced-in grove where you can hear the birds singing … “Il Poderaccio” stretches for 32 hectares, all cultivated. This ICEA -controlled farm offers totally organic products such as wine, extra vergin olive oil and Grappa. On sale at the farm are: Chianti Colli Senesi DOCG, the “Brunaccio” a special IGT Tuscan red wine, extra virgin olive oil, and a grappa These organic products are the result of an environment- and consumer-friendly growing. “Il Poderaccio” hosts a lot of animals: horses, dogs, cats, a cow, a donkey, a kid as well as the geese, ducks and mallards swimming together in the farm pond. Horse trekking and riding can be organized upon request at a riding school renowned for its highly-qualified trainers situated near the farm. Mountain bikes rental is also available. All the flats are equipped with independent central heating thus being available all year round. NB: FOR WEEKLY STAYS THE AMOUNT OF THE HEATING WILL BE CALCULATED ON CONSUME

Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Vittoria Chianti Vacations 🍇🍷
Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Stuart Jasmine central, panoramic top location
This abode boasts 1 double and 1 single bedroom, a spacious living room with a fully equipped kitchen, and 1 bathroom with shower. Every window frames a breathtaking view, filling the space with natural light. High-speed Wi-Fi ensures comfort for both work and leisure. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.

Chianti Craft House Badia a Passignano
Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

Breathe in Tuscany: 180° view of the hills
Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.

Casa al Gianni - Oak
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

SMN Luxury Secret Garden View
Welcome to the central part of Florentine charm! This extraordinary apartment, located just 50 meters from Piazza Santa Maria Novella, offers you an unparalleled experience in the historic heart of Florence. Imagine crossing the threshold of a Renaissance Palace, a jewel of inestimable artistic and historical value, and being welcomed by an atmosphere that speaks of history and elegance. Two bedrooms, two complete bathrooms, living room with fully equipped kitchen.

Barrel Suite Tuscany • Hot Tub • Vineyard View
Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.

In Tuscany Rooms
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

La Loggia. House with pool and stunning view
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment
Nestled in a medieval village in the heart of Chianti, this exclusive historical apartment blends Tuscan charm with refined contemporary design. Enjoy a panoramic pool overlooking the hills, multiple terraces, and a unique hot tub Jacuzzi suite and bathroom carved in travertine. Designed for two, it’s the perfect place to slow down, reconnect, and experience Tuscany in total peace.
Popular amenities for Siena vacation houses
Family-friendly vacation houses

Experience rustic off-grid life in the wilderness

The Eagle and the Olive Tree

Siena house with private garden 300m from the center

Apartment in historic Villa in Siena_"LE CONTRADE"

La Dimora del Lago - Lake views of Tuscany and Umbria

Fienile Santa Teresa

Linearis apt B (4+2) Toscana

Tuja
Vacation home rentals with a patio

Tuscany Breath - Panoramic Pool & Tennis Court

★ Romantic apartment & stunning view of Tuscany ★

City Centre Patio - 10 mins to Duomo

Elegant farmhouse overlooking Pienza

The Piccola Villa of Borgo Argenina

Tuscany Country House, Central Chianti, Pano Views

Pienzalettings

cenerentola chianti 2 apartment - near Panzano
Vacation home rentals with a washer and dryer

Melarancio Residence

Rondini Blu Vacation Home - Torretta Apartment

[Florence hills] Tuscan house with parking space

Tuscany country Village near Siena

Verde, space and relax in historic Florence

Podere le Fonti - Pet Friendly - 15 min to San Gimignano

Large group house + breackfast + parking Florence

Vicolo delle Rose Apartment
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $161 CAD | $168 CAD | $214 CAD | $237 CAD | $234 CAD | $232 CAD | $227 CAD | $203 CAD | $232 CAD | $242 CAD | $207 CAD | $198 CAD |
| Avg. temp | 5 °C | 6 °C | 9 °C | 12 °C | 16 °C | 21 °C | 23 °C | 24 °C | 19 °C | 14 °C | 9 °C | 5 °C |
Destinations to explore
- Cottage rentals Siena
- Rentals with breakfast Siena
- Pet-friendly rentals Siena
- Serviced apartment rentals Siena
- Boutique hotels Siena
- Condo rentals Siena
- Family-friendly rentals Siena
- Rentals with pools Siena
- Bed and breakfasts Siena
- Rentals with a hot tub Siena
- House rentals Siena
- Villa rentals Siena
- Apartment rentals Siena
- Hotel rooms Siena
- Vacation home rentals Siena
- Vacation home rentals Tuscany
- Vacation home rentals Italy
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Parco Regionale Della Maremma
- Cala Violina
- Stazione Santa Maria Novella
- Mercato Centrale
- Spiagge Bianche
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden
- Things to do Siena
- Art and culture Siena
- Nature and outdoors Siena
- Tours Siena
- Sightseeing Siena
- Food and drink Siena
- Things to do Siena
- Sightseeing Siena
- Art and culture Siena
- Entertainment Siena
- Food and drink Siena
- Nature and outdoors Siena
- Tours Siena
- Sports activities Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Things to do Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Food and drink Italy
- Sports activities Italy
- Sightseeing Italy
- Tours Italy
- Entertainment Italy







