Siena vacation rentals

4.97 out of 5 average rating, 127 reviews

Vacation home in Porto

La Dimora del Lago - Lake views of Tuscany and Umbria

Recently and authentically restored in a small rural hamlet, located halfway between Florence and Rome and Montepulciano and Cortona in the tranquil countryside overlooking tiny Lake Chiusi - less than 2 hours drive by Autostrada or train from Florence or Rome. Forged from a 500-year-old watchtower, an authentic country house - tranquil and relaxing, it also has an excellent internet connection and Netflix. TOURIST TAX TO PAY IN CASH €0,80 per adult, per night of stay for up to 5 nights .

Apartment in Centro Storico

A dining area features a light-colored table set with decorative placemats, accompanied by four chairs. A brown leather sofa is positioned nearby, while a lush green plant adds a natural touch. Illuminated wall art complements a textured brick wall, enhancing the space's charm.

4.96 out of 5 average rating, 24 reviews

New MiK HoUsE 2025 with Netflix

Ciao Caro ospite, abbiamo arredato la nostra casa con tutto l'amore possibile per rendere il tuo soggiorno un sogno. Ogni cosa è pensata per il benessere dell'ospite. La zona è super accessibile e centrale ma lontana da locali notturni rumorosi e caos cittadino, parcheggio gratuito a 200 metri, possibilità di arrivare in macchina davanti alla casa, vicinissimo, anche a piedi, alla stazione ferroviaria principale della città. Scoprite tutti confort che abbiamo ideato per i nostri ospiti.

4.98 out of 5 average rating, 130 reviews

Home in Prato

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

4.98 out of 5 average rating, 108 reviews

Loft in Scandicci

Wonderful Loft in Villa with Pool in Chianti

Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

4.8 out of 5 average rating, 46 reviews

The living area showcases natural light streaming through large open doors, leading to a balcony adorned with wrought iron details. A wooden dining table is set for two, accompanied by a cozy chair and a colorful area rug beneath.

Condo in Centro Storico

[Free Garage] 15 Min. walk from Art

⭐ NEW LISTING! Elegant Central Apartment with BALCONY and GARAGE! &#x1F463 Perfect for exploring the UNESCO center on foot 6 min from the Garden of Gherardesca → another 6 min from the Basilica dell'Annunziata → 3 min from Michelangelo's David → 5 min to Brunelleschi's Dome, Duomo. Nearby, you'll find supermarkets, lounge bars, and typical taverns, yet enjoying a peaceful location. &#x1F9D8 The perfect balance between convenience and tranquility!

4.93 out of 5 average rating, 231 reviews

A modern living area features a minimalist kitchen with white cabinetry and a stainless-steel countertop. A flat-screen television is mounted on the wall above a sleek white fireplace. A small round dining table with transparent chairs and a potted plant is located near a large window.

Condo in Centro Storico

Ognissanti 94

My accommodation, completely and finely renovated, is close to Stazione S.M-N., Garage Europa, Porta a Prato, Ponte Vecchio, etc... You'll love it for the comforts of it and its strategic location in the heart of downtown. Located in an area full of every service, under the house you can find all the sharing cars, bars, restaurants, and everything you need. My place is good for couples, business travelers, families (with kids), and large groups.

4.91 out of 5 average rating, 23 reviews

The image depicts a panoramic view of a tranquil landscape featuring a private swimming pool surrounded by sun loungers. The rolling hills of the Valdarno valley stretch into the distance, dotted with olive trees, while a charming farmhouse is visible on the hillside.

Villa in Loro Ciuffenna

Villa with pool & view near Florence and Arezzo

Tuscan 1700 farmhouse in dominant position with a stunning view over the Valdarno valley. Features six separate apartments with 1 or 2 bedrooms each (total 7 bedrooms plus added beds), private gardens, private swimming pool (open May - September), common lounge and kitchen, WI-FI in every apartment. For groups up to 20 persons.

4.9 out of 5 average rating, 179 reviews

A charming stone exterior features large windows and arched details, surrounded by lush greenery. A path lined with lavender leads to the entrance, with outdoor seating visible under shaded umbrellas. The tranquil setting is complemented by nearby trees and rolling hills in the background.

Cottage in Volterra

Podere Grignano, beautiful Tuscany

If the calendar indicates no availability, please check our other advert through the Airbnb map (Podere Grignano, beautiful Tuscany with a dot at the end). The other house can still be free. The houses are semidetached, The 2 houses are practically identical. The reviews are of both houses.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Siena vacation rentals

Laptop-friendly workspace

Stay near Siena's top sights

B & B Siena in Centro15 locals recommend

Il Campo165 locals recommend

Santa Maria della Scala136 locals recommend

Pinacoteca Nazionale di Siena92 locals recommend

Palazzo Pubblico76 locals recommend

Coop64 locals recommend

House rentals in Siena

Home in Castiglione della Pescaia

A spacious farmhouse exterior is surrounded by lush greenery, featuring a blend of trees and ornamental plants. The structure displays a large window and a covered area beside it, providing access to the outdoors in a tranquil setting.

5 out of 5 average rating, 5 reviews

Family House Baldana

4.83 out of 5 average rating, 200 reviews

A two-story stone house is surrounded by lush greenery, featuring flowering shrubs and trees. Large windows are framed by wooden shutters, allowing natural light to brighten the interior. The tranquil garden provides a serene outdoor space for relaxation.

Home in Monte San Savino

In Tuscany between Siena Arezzo, near Chianti

4.88 out of 5 average rating, 50 reviews

A chlorine-free pool is set within a spacious garden, surrounded by lush greenery and trees. Sun loungers are placed nearby, and a charming stone house is visible in the background. The landscape offers expansive views of the Tuscan countryside under a bright blue sky.

Home in Volterra

Tuscan Villa with Privacy,Pool,near towncentre

Home in Bagno di Gavorrano

A charming stone exterior of a two-family home is displayed, featuring a covered porch adorned with potted flowers. Lush greenery surrounds the property, and a clear blue sky can be seen overhead. The entrance is framed by a low brick wall and a stony pathway.

4.66 out of 5 average rating, 38 reviews

Wisteria House

4.84 out of 5 average rating, 38 reviews

A charming red cottage is nestled under a large tree, featuring wooden shutters and a welcoming entrance. Outside, a small porch area with seating is visible, surrounded by natural elements in a peaceful setting.

Home in Pian di Rocca

Fazenda da Ido ( Cosy and Renovated Studio)

4.82 out of 5 average rating, 11 reviews

A serene outdoor space is featured, showcasing a swinging bench accompanied by two white chairs. Lush green hedges surround the area, creating a private atmosphere. Terracotta tiles provide a warm flooring, inviting guests to relax and enjoy the natural surroundings.

Home in Poggibonsi

casa palme

4.87 out of 5 average rating, 62 reviews

Home in Certaldo

Paluffo Tower House

4.94 out of 5 average rating, 32 reviews

A living area is presented with two upholstered sofas, one in dark blue and the other with a contrasting orange cushion. A small, light green coffee table occupies the center. Decorative items are displayed on a wooden shelving unit, with a large window allowing natural light to filter in.

Home in Bibbona

charming apartment a few kilometers from the sea

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Other great vacation rentals in Siena

Apartment in Centro Storico

A modern kitchen is featured with sleek white cabinets and stainless steel appliances. A glass dining table is set for breakfast, adorned with green placemats and fresh tulips in a vase. Bright orange juice and pastries complete the inviting arrangement.

4.91 out of 5 average rating, 34 reviews

Chic Apartment Macci

Apartment in Centro Storico

A cozy living area is presented with a plush green sofa facing a set of glass doors that open to a small balcony. A table and two chairs on the balcony provide a space for enjoying views of the surrounding architecture.

4.98 out of 5 average rating, 220 reviews

Art Apartment Luxury Por Santa Maria

4.8 out of 5 average rating, 5 reviews

The image depicts a spacious green lawn surrounded by vibrant flowers and shrubs. Two charming stone buildings with terracotta roofs are visible in the background, complemented by a variety of trees and under a partly cloudy sky, creating a serene outdoor atmosphere.

Villa in Poppi

Villa for 22 people w/private pool

Apartment in Mercatale Valdarno

A private outdoor space features a serene swimming pool surrounded by stone tiles. Comfortable lounge chairs are positioned near the pool. A gazebo provides shade, furnished with seating, and overlooks lush greenery, enhancing the tranquil atmosphere of the area.

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

4.81 out of 5 average rating, 31 reviews

An inviting living area features a patterned sofa and a dining table set for four. Exposed wooden beams span the ceiling, while sunlight streams through a window, illuminating the tiled floor. Artwork adorns the walls, adding character to the space.

Condo in Florence

Quiet area within walking distance of the center, AC.

Apartment in Sasso D'ombrone

Two elegant glasses of red wine are placed on a dark wooden table, accompanied by a loaf of freshly sliced bread on a wooden board. A panoramic view of rolling hills and greenery stretches in the background, under a partly cloudy sky.

4.81 out of 5 average rating, 58 reviews

"La Sartina" Vacation Home

5 out of 5 average rating, 8 reviews

A spacious outdoor area is showcased, featuring a shared swimming pool surrounded by well-maintained lawns and sun loungers. Umbrellas provide shaded seating, while the scenic countryside extends in the background, enhancing the tranquil ambiance of the agriturismo.

Farm stay in Camucia

The Garden of Olives | Casa Ippocastano