
Vacation rentals in Siena
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Top-rated vacation rentals in Siena
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Apartment in Tuscan farm house.
Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.
Medieval Tower experience with Panoramic Rooftop
If you are looking for a memorable experience, this is the right place for you! With its 42 mt high, the Salvucci Tower is one of the famous towers of San Gimignano and today the only one turned into a vertically-spread apartment divided into 11 floors, for a total of 143 steps. A unique and timeless place, ideal to experience something never tried before. The tower can hosts couples or small groups up to 3 people. Its panoramic rooftop boasts an incredibly breathtaking view all over the town.

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.

Capannacce more than a Farmhouse: La Casetta
Capannacce is a special place for us. Farm, but not only. It is home. For us and for the animals that live here, horses, chickens, cows, felines and canids. Indeed, the heart of the farm is the breeding of racehorses, English thoroughbreds. And of the Pontremolese cow, a native heritage breed. We are immersed in the Crete Senesi, where every summer sunset is a delight. The countryside made of quietness that soothes, but not far from the town of Rapolano Terme and all related comforts.
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.

Villa di Geggiano - Perellino Suite
The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Mascagni Farmhouse in Val d'Orcia, Pienza
Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

House at Gianni - Olmo
Hi, we're Cristina & Carmelo! We invite you to discover the rustic charm and authenticity of "Casa al Gianni," our farmhouse in the heart of the Tuscan countryside, 20 minutes from Siena. After a recent renovation, our accommodations are ready to welcome you with all modern comforts without losing the essence of tradition. In the Olmo Apartment, brand new beds await you, a promise of peaceful and regenerating sleep, a new kitchen and a new bathroom.

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.

Romantic Garden in Historic San Gimignano
Enjoy a romantic stay in the heart of San Gimignano, inside the medieval walls.The apt features a private garden, a rare and peaceful corner where you can have breakfast, relax after exploring the town or enjoy a glass of wine in the evening. Perfect for couples looking for charm, history and quiet retreat in one of Tuscany's most beautiful villages.

A BALCONY ON THE PIAZZA OF THE PALIO
Three windows with balcony overlooking Piazza del Campo that allows access to an exclusive terrace with breathtaking views of the Piazza del Palio and the Palazzo Pubblico. One bedroom, large super-equipped kitchen. Sofa bed available to comfortably accommodate up to 4 people

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.
Popular amenities for Siena vacation rentals
House rentals in Siena

StageROOM03 - Idyllic Chianti cottage near Siena

Love in Chianti

Charming converted Hayloft overlooking the Chianti Hills

Charming Apartment in City Center

[Duomo 8 min. walk] Luxury Home • Self Check-in

Domus Nannini - Loggia Salimbeni SPA

Infinity view

Piazza del Campo, nothing will be so central
Apartment rentals in Siena

CasaZappa - apartment and parking

CASA WOW panoramic terrace * . *

House with a terrace overlooking the rooftops and green spaces in the Duomo area

Luce in Provenzano

A view from the gate, Montepulciano.

Stuart White Tea Central Panoramic & Garden

Renovated flat 50 meters from Piazza del Campo

Luxury frescoed apartment in the historical center
Boutique hotels in Siena

Sleeping on Siena roof

AM Collection Florence

Single Room

Romantic Medieval Village with pool

Charming Room one step from Duomo 3

Sant'ansano Suite

The Villino Fiorentino, superior king room

Spirit of Florence -2 bedroom SUITE Quadruple Room
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$21,619 GYD | G$20,149 GYD | G$23,088 GYD | G$25,816 GYD | G$27,496 GYD | G$28,545 GYD | G$27,705 GYD | G$28,125 GYD | G$26,866 GYD | G$26,236 GYD | G$23,927 GYD | G$25,816 GYD |
| 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 |
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 G$2,099 GYD 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!
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- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Marina di Cecina
- Del Chianti
- Basilica of Santa Maria Novella
- Mercato Centrale
- Cala Violina
- Eremo Di Camaldoli
- Fortezza da Basso
- Spiagge Bianche
- Uffizi Gallery
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Pitti Palace
- Cascate del Mulino
- Parco delle Cascine
- Mugello Circuit
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