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Vacation rentals in Siena

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Top-rated vacation rentals in Siena

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 309 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top guest favorite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 472 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Top guest favorite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 206 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favorite
An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.
Loft in Montepulciano
5 out of 5 average rating, 487 reviews

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

Guest favorite
A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.
Home in Castelnuovo Berardenga
4.91 out of 5 average rating, 111 reviews

The Chianti window

A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

Top guest favorite
An open living area is shown with a dining table surrounded by black and white chairs. The ceiling displays decorative beams, and light enters through a window, illuminating the space. A fireplace is positioned against one wall, with artwork adorning the surrounding walls.
Apartment in Siena
4.96 out of 5 average rating, 296 reviews

Renovated flat 50 meters from Piazza del Campo

Apartment in the historic center of Siena, just 50 meters from Piazza del Campo. The accommodation was completely renovated in 2019. The restoration was carried out trying to keep its main features intact, but adding all the necessary equipment to today's way of life. The apartment is an ideal place for those who want to visit and experience the city; In fact, all the monuments and attractions of the historic center can be reached on foot in a few minutes.

Top guest favorite
A modern living space features a bright red sectional sofa positioned against a textured stone wall. A stylish kitchen island with seating is visible, along with minimalistic lighting fixtures and decorative plants, creating a blend of comfort and contemporary design.
Condo in Siena
4.99 out of 5 average rating, 232 reviews

Palazzo del Taja - in the center with whirlpool

Brand new apartment just renovated, located inside the historic Palazzo del Taja in the heart of Siena's historic center, a few meters from Piazza del Campo and the city's main attractions. Subjected to a renovation attentive to details, the apartment is elegant, bright, welcoming and quiet. Complete with every comfort, including a beautiful bathroom with a whirlpool tub, to offer an unforgettable stay to our customers.

Top guest favorite
A bright living area features a modern white sectional sofa and a white entertainment unit with a flat-screen TV. Stylish decor includes a potted plant and black accents against light walls and exposed wooden beams, creating a spacious and uncluttered environment.
Condo in Siena
4.96 out of 5 average rating, 128 reviews

Olympia's House

A few steps from the wonders of Siena, this apartment combines comfort and refinement. Two bedrooms, two bathrooms, studied lights, careful design and tastefully chosen materials. Outside the ZTL but close to the center, with convenient parking and escalators 500 meters away. A contemporary retreat where you can feel at home and live the authentic soul of the city, between history, beauty and harmony.

Top guest favorite
A terrace table is set with two glasses of sparkling wine and a plate of cookies, overlooking the rooftops of the city. The distant bell tower is visible against a clear blue sky, framed by the balcony's railing.
Apartment in Siena
4.96 out of 5 average rating, 388 reviews

The rooftop terrace

Bright and cozy 95 sqm apartment located on the 4th floor without elevator of a notified building in the heart of the city a few steps from Piazza del Campo, the Duomo and the major attractions of the city. A splendid view overlooking the rooftops will frame your apartment from which you can see the Torre del Mangia, the Basilica dei Servi and the wonderful Val d'Orcia.

Guest favorite
An outdoor terrace offers seating for four, featuring a table and chairs. The view captures the skyline illuminated against a twilight backdrop, showcasing notable landmarks such as the Torre del Mangia and the Duomo in the distance.
Apartment in Siena
4.88 out of 5 average rating, 161 reviews

Penthouse with a view of Siena

Next to the Basilica of San Domenico, a few steps from the Duomo and Piazza del Campo, in this splendid and elegant penthouse you can enjoy the splendid view and the convenience of walking to all the major points of interest in the city in just a few minutes.

Top guest favorite
A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.
Home in Siena
4.97 out of 5 average rating, 195 reviews

Secret Garden Siena

A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.

Top guest favorite
A serene garden path is lined with lush greenery and gravel, leading to a modern entrance. A vine-covered trellis provides partial shade, while the surrounding foliage creates a tranquil atmosphere. The nearby architecture adds character to the outdoor space.
Home in Siena
4.91 out of 5 average rating, 352 reviews

Amazing Cott. in the heart of Siena

Fantastic apartment recently renovated by a famous architect from Siena. It is sited in the garden of the manor house in the heart of the city. A corner of paradise where you can relax few steps from the main tourist attractions.

Popular amenities for Siena vacation rentals

When is the best time to visit Siena?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,715 ZARR1,599 ZARR1,832 ZARR2,048 ZARR2,182 ZARR2,265 ZARR2,198 ZARR2,232 ZARR2,132 ZARR2,082 ZARR1,899 ZARR2,048 ZAR
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

Frequently Asked Questions

  • What are the best places to stay in Siena?

    Siena has a variety of stays in the historic center, known for medieval streets and easy access to local cafes. Neighborhoods around Piazza del Campo and near the Duomo di Siena are frequently suggested for both charm and convenience.

  • What are the best things to do in Siena with kids?

    Families often explore the interactive exhibits at local museums, stroll the car-free historic center, and enjoy gelato in public squares. Parks and gardens around Siena provide space for outdoor play and picnics.

  • What are some of the best things to do in Siena?

    Siena has renowned sites like Piazza del Campo, the Duomo di Siena, and Torre del Mangia, as well as lively markets and guided walks through medieval streets. Many visitors also explore local art galleries and enjoy Tuscan cuisine in trattorias.

  • How is the weather in Siena?

    Siena experiences cool winters with temperatures from 33–49°F (0–9°C), and warm, dry summers reaching up to 89°F (31°C). Spring and autumn are mild, with occasional rainfall.

  • What are the best places to visit in Siena?

    Explore Piazza del Campo, climb Torre del Mangia for wide city views, and visit the Duomo di Siena with its striking facades. Many also enjoy time at the Pinacoteca Nazionale for regional art collections.

  • What are some hiking trails in Siena?

    Siena has gentle nature trails around the city’s hills, as well as paths passing vineyards and olive groves just outside town. Locals also suggest exploring the parks and green areas for a relaxed outdoor walk.

  • What are some family activities we can do in Siena?

    Families can join hands-on workshops in art or cooking, watch lively street performances in main squares, and wander through gardens and interactive museums. Exploring Siena’s pedestrian-friendly center is a favorite for many.

  • What are some of the best day trip ideas from Siena?

    Popular day trips include visiting nearby hill towns, exploring Tuscan vineyards, and discovering historic abbeys tucked into the landscape. Local guides frequently suggest nature reserves and traditional villages just outside the city.

  • Are there any pet friendly accommodations available in Siena?

    Many accommodations around the city center and in quieter neighborhoods welcome pets. Parks and walking trails make it convenient for travelers exploring Siena with dogs or other companions.

  • What are some local tips for visiting Siena?

    Wear comfortable shoes for cobbled streets, and consider arriving early at popular sites to enjoy calmer mornings. Locals often recommend tasting seasonal dishes at small trattorias and checking neighborhood markets for fresh ingredients.

  • What is Siena known for?

    Siena is known for its medieval architecture, vibrant traditions, and the Piazza del Campo, a unique shell-shaped square. The city’s cuisine, local art, and recurring historic festivals draw visitors from around the world.

  • What are the best hidden gems to explore in Siena?

    Exploring narrow alleys near Piazza del Campo may reveal small artisan shops and tucked-away cafes. Many seek out the Orto dei Pecci, a quiet garden just behind the city’s old walls.

  • What are the best foods to try in Siena?

    Siena has classic Tuscan flavors, including pici pasta, panforte, and ricciarelli cookies. Wild boar stew and pecorino cheese are often recommended specialty dishes in local trattorias.

  • What should I bring for a trip to Siena?

    Pack sturdy walking shoes for uneven streets, a light jacket for changing weather, and sun protection in warmer months. A refillable water bottle and a camera for city views are frequently suggested.

  • What is the nightlife in Siena like?

    Siena has a relaxed nightlife, with wine bars, small music venues, and cafes around the historic center. Evening strolls in lively squares and university hubs are popular for gathering with friends.

  • What are the most popular events or festivals in Siena?

    The Palio di Siena is a renowned horse race held in Piazza del Campo during summer months, celebrating centuries-old traditions. The city also hosts food festivals and cultural events, especially around late spring and autumn.

  • Are there family friendly vacation rentals in Siena?

    Siena has many family-friendly rentals in central neighborhoods and near public gardens. These stays often provide flexible layouts and easy access to parks, shops, and local events.

  • When is the best time to visit Siena?

    Late spring through early autumn is often recommended for pleasant weather and outdoor events. Winter has a quieter atmosphere and cooler temperatures, while fall brings colorful landscapes and cultural festivities.

Quick stats about vacation rentals in Siena

  • Total vacation rentals

    Explore 1,390 vacation rentals in Siena

  • Nightly prices starting at

    Siena vacation rentals start at R167 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 79,040 verified reviews to help you choose

  • Family-friendly vacation rentals

    550 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 520 rentals that welcome pets

  • Vacation rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    650 properties have a dedicated workspace

  • Wi-Fi availability

    1,310 of Siena vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Siena rentals

  • 4.8 Average rating

    Siena stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Siena