
Holiday Homes in Siena
Find and book unique holiday homes on Airbnb
Top-rated Holiday Homes in Siena
Guests agree: These holiday homes are highly rated for location, cleanliness and more.

Podere La Castellina - No. 2 LECCETO
Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The apartment located on the ground floor can comfortably accommodate 2 people and includes: - living room with TV - kitchen with oven and electric stove - master bedroom - bathroom with large shower - private outdoor table Available to guests is a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

The Eagle and the Olive Tree
At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Fontarcella, H&R- mediterranean home with jacuzzi
Situata nelle colline a cavallo tra Montepulciano,Castiglione del Lago e Cortona, Fontarcella si presenta come una villetta indipendente immersa nel verde, che offre jacuzzi e parcheggio privati; Scoprirete un luogo senza tempo, per condividere momenti preziosi. La struttura, arredata in stile mediterraneo, dispone di climatizzazione e wi-fi gratuita. Il giardino, interamente recintato, offre vari comfort. A pochi minuti dalle autostrade, Fontarcella è facilmente raggiungibile dai viaggiatori.

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.

Breathtaking view from romantic nest in citycenter
Unique and charming attic in the middle of historic center with amazing breathtaking view on the city center. Perfect for a romantic stay in the heart of Florence. Fully windowed on 3/4 walls. Completely renewed with modern design furniture. Powerful A/C, fast wi-fi, fully equipped kitchen. Going downstairs you will immediately be absorbed in the most beautiful area of city center. Attention! Only for young-soul people: 5th FLOOR, NO LIFT, last 2 flights of stairs in a narrow spiral stair.

Barrel Suite Tuscany • Hot Tub • Vineyard View
Wooden barrel suite in Tuscany, nestled in an olive grove in Reggello: breathtaking views over hills and vineyards, total peace. One of the largest barrels in the world (3.5 m x 8 m) with a private bathroom, kitchenette, veranda and small courtyard. All barrels have a hot tub pool for your relaxation. Strategic location: Florence ~40 min, Siena and Arezzo for day trips. Private parking on the property and a welcome Tuscan cold cuts and cheese board. Close to The Mall Luxury Outlet.

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.

AM Apartment
The apartment is 10 km from the center of Siena in a very relaxing and quiet place in Chianti where you can enjoy a beautiful view, take long walks on foot and by bike or taste good wine in local companies. The house includes two bedrooms, two bathrooms, a living room with fireplace, sofa and smart TV and a large equipped kitchen. In addition, there are sheets, towels, hairdryer and free wifi

Casa al Gianni - Oak
Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Charming home Crete Senesi
Less than 15 kilometers from Siena, the terraced apartment is set in a characteristic Tuscan village on high that leads to the evocative "Site Transitoire”. The property is completed by a lovely garden overlooking Siena and a comfortable swimming pool.

Stunning Tuscan apartment for 2
This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.

Fienile Santa Teresa
For a peaceful time immerse yourself in typical rural Tuscan life at this excl. guest barn surrounded by vineyards & olives groves lying between Florence & Siena. Please ask for special offers during the off season and for long term stays!
Popular amenities for Siena holiday homes
Family-Friendly holiday homes

Fede and Romy's Nest

Podere Vittoria Apartment: Heart of Chianti

Living Siena - "Chiantigiana" Apartment

Apartment La Roccaia

Apartment in historic Villa in Siena_"IL MANGIA"

Tuja

Michelangelo: entire space in the heart of Tuscany

[Authentic StoneHouse] Garden & Viewpool Apartment
Holiday home rentals with a patio

Tuscany Breath - Panoramic Pool & Tennis Court

Unique & Historic Getaway: Dreamy Garden

★ Romantic apartment & stunning view of Tuscany ★

City Centre Patio - 10 mins to Duomo

Poderino Sole-Holiday Home NOCE

Villa with swimming pool and tennis court in Chianti

Flat, terrace, pool,Spa resort,restaurant, A/C, G1

The Piccola Villa of Borgo Argenina
Holiday home rentals with a washing machine and dryer

Luxury Secret Garden View

Tuscan Suite Amiata in Villa Q Dimorae Adults Only

Melarancio Residence

Tuscany country Village near Siena

Florence Elegant Suite

Cenerentola chianti 1 apartment - near Panzano

The Cricket's Cage <Anna Maria> (A-04)

TOSCANELLA RUBY STUDIO
Destinations to explore
- House rentals Siena
- Villa rentals Siena
- Condo rentals Siena
- Rentals with breakfast Siena
- Rentals with pools Siena
- Rentals with a fireplace Siena
- Rentals with a fire pit Siena
- Cottage rentals Siena
- Rentals with an EV charger Siena
- Bed and breakfasts Siena
- Rentals with a patio Siena
- Smoking-friendly rentals Siena
- Pet-friendly rentals Siena
- Boutique hotels Siena
- Serviced apartment rentals Siena
- Family-friendly rentals Siena
- Rentals with outdoor seating Siena
- Rentals with a washing machine and dryer Siena
- Apartment rentals Siena
- Fitness-friendly rentals Siena
- Rentals with a hot tub Siena
- Hotel rooms Siena
- Holiday home rentals Siena
- Holiday home rentals Tuscany
- Holiday home rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Mercato Centrale
- Strozzi Palace
- Ponte Vecchio
- Santa Maria Novella
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Marina di Cecina
- Del Chianti
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Piazza della Signoria
- Eremo Di Camaldoli
- Cala Violina
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Piazza della Repubblica
- Siena Cathedral
- Cascate del Mulino
- Pitti Palace
- Things to do Siena
- Art and culture Siena
- Food and drink Siena
- Nature and outdoors Siena
- Sightseeing Siena
- Things to do Siena
- Sightseeing Siena
- Food and drink Siena
- Tours Siena
- Sports activities Siena
- Art and culture Siena
- Nature and outdoors Siena
- Things to do Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Entertainment Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Things to do Italy
- Sports activities Italy
- Tours Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Entertainment Italy
- Food and drink Italy
- Sightseeing Italy






