Discover a selection of 2,000 vacation rentals in Siena, IT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $86 per night, and houses and villas are popular options for a stay in Siena. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Siena
Destination guide

Siena is one of Italy's most beautiful cities

There's no doubt about it, Siena is one of Italy's most scenic cities. It's small enough to explore by foot, but large enough to have plenty of attractions, eateries and nightlife to keep you busy for your whole stay. Its heart is the Piazza del Campo, which is perhaps best known for the annual horse race. If you've nabbed a Siena vacation rental, you'll realize why this city's center was designated a UNESCO World Heritage Site. So, what are you waiting for? Pull up a chair in the sunny piazza, grab a cappuccino and soak up the Italian ambiance.

Things to do

Start your visit to Siena at the Piazza del Campo

Your best introduction to Siena's attractions is the Piazza del Campo. If you're here in early July or mid-August, you can immerse yourself in the Palio Horse Race, which sees riders pitted against each other on laps of the square. Any other time of the year, it still buzzes with local life. You should save some time to amble around the Cathedral, dive into the Baptistery and discover Siena's other architectural gems that date back centuries. If you think your knees will cope, you can climb the 400 plus steps to the top of Torre del Mangia, for fine views across the city.


A typical day in Siena

A day in Siena could look something like this. Awake in your Siena vacation rental for spectacular views across the terracotta-tiled rooftops of this Medieval city. For breakfast, you could dive into one of the cafes for a little coffee and pastry, before hitting the boutique shops for some serious retail therapy. If you're a foodie, spend the afternoon digging into tasty Tuscan bites like pappardelle, wild boar sausage or local cheeses. In the evening, you can take your pick of the nightlife, from buzzy wineries to trendy clubs.


Walk the sunny streets of Siena in summer

When the summer season hits the throngs of crowds begin to drift into the city, booking up Sienna vacation rentals and ambling around the Medieval streets with gelatos in hand. With bright blue skies and balmy evenings, it's a wonderful time to visit, but does come with the highest price tag. If you have the time, consider bagging a rental in late spring or early fall, when the weather can still be bright and warm and the queues at the attractions are not half as long, not to mention the serious drop in prices.

Natural features

Tuscan woodland at its best in Siena

If you fancy a break from the city, you can hop in your rental car and drive out southwest to the Riserva Naturale Alto Merse, which hugs the Merse River just a few miles from the city. The dense woodland of chestnut and oak trees provides habitat for an impressive list of wildlife. While you're there, look out for wild boar rustling around the forest floor, shy deer darting past the trails and tawny owls which hoot from dusk till dawn from the deciduous treetops. Just be sure to bring your camera: your Instagram feed would never forgive you if you didn't.

How to get there

Transportation options to and around Siena

The nearest airport is in Florence Airport, Peretola (FLR), located 34.1 mi (54.8 km) from the city center.

If you're traveling by train, you can make your way to Siena Station.

What are the top vacation rentals in or near Siena?

Whether you're looking for a cozy escape for you and your love or someplace spacious to fit all your friends, you'll find some top vacation rentals in and around Siena. Here are a couple to get you inspired:

  • Around 11 miles from the center of Siena, you'll love staying at "Farmhouse In The Heart Of The Real Chiantishire". It has 2 bedrooms and handy features including a living room and a microwave oven.
  • "La Casina Toscana - Near Center" is another winner, offering 3 bedrooms, a water park, WiFi and more. It's around 30 miles from Siena.

For even more great options, use the search bar at the top of the page to find the perfect Siena vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Siena?

Your working week will be much easier to endure if you've got something wonderful organized for the weekend. Give yourself something to look forward to by locking in one of these top weekend getaways in or near Siena:

  • Book a few nights or longer at "Apartment With Unique View", around 0.1 miles to the west of Siena, and you've got yourself the best kind of weekend escape. You'll have outdoor attractions like Riserva Naturale Regionale Valle dell'Inferno e Bandella and Torrenieri Montalcino Station nearby and amenities like air conditioning and a balcony to make the most of.
  • "Il Mangia Nest 2 + 2 Bd Just Under The Mangia Tower" is also perfect for a whirlwind getaway. About 0.1 miles to the east of Siena, this vacation rental comes with amenities like air conditioning and a microwave oven. Garden of Daniel Spoerri and San Giovanni d'Asso Station should be on your itinerary if you stay here.

Can I find studio apartments for rent in and around Siena?

Studio apartments are difficult to beat when it comes to convenience and location. Choose one of these studio apartments for rent in or near Siena and take in the vibrant local culture:

  • Make "Apartment With Unique View" your home away from home. This fantastic property comes with amenities including WiFi and a hair dryer.
  • Another appealing option is "Il Mangia Nest 2 + 2 Bd Just Under The Mangia Tower". Make use of a stovetop, a microwave oven and other convenient amenities during your stay.

There are loads of sights around Siena to put on your to-do list. Feed the culture vulture within with a visit to Palazzo Piccolomini and Palazzo Comunale.

Can I find short term rentals in or near Siena?

Short-term rentals abound in and around Siena. Chill out for a night or two in a cool condo, a resort-style apartment or a roomy home. Whatever type of rental you're after, you'll have plenty to select from with Vrbo. Here are a few top picks:

  • "Lenzi Palace - Piccolomini Suite" is close to the heart of Siena, which means you'll have lots of things to do and see. Explore interesting attractions like Monte Oliveto Maggiore Abbey and La Porta Gallery when you're not making the most of your cozy pad.
  • "Farmh. Podere Cunina 25 Km Sud Siena Di Fronte Al Montalcino Prendendo Lezioni Di Cucina" is another tempting option. Consider adding Museum of Sacred Art in Val d’Arbia and Museo della Mezzadria to your itinerary when it's time to sightsee.

What are the best romantic weekend getaways in or near Siena?

Nothing says "I love you" quite like a romantic weekend together. If you're longing to spend a couple of nights away with your significant other, we've got some romantic getaways in and around Siena that will sweep you off your feet:

  • Put on some soft tunes and chill together at "Farmhouse In The Heart Of The Real Chiantishire". Around 11 miles from Siena, this property has everything you need for a romantic weekend away, including beauty services and winery tours.
  • "La Casina Toscana - Near Center" is another wonderful option that'll woo you. It's about 30 miles from Siena and has winery tours and beauty services.

Are there mansions for rent in or near Siena?

Nothing says "best vacation evvv-er" like staying in a mansion. Treat your loved ones to an unforgettable escape at one of these mansions for rent in or near Siena:

  • Around 25 miles to the southeast of Siena is "Ginepro - Suite Of The Shell Mansion". Along with its awe-inspiring design, you'll also love its first-class amenities, such as winery tours and a separate dining area.
  • Alternatively, score Brownie points with your crew and spend a week at "Apartment "la Mansion" In The Chianti Region". It's located about 6 miles to the north of Siena and offers amenities like golf, a separate dining area and more.

What are the best large group vacation rentals in or near Siena?

Share your stay and have more fun. Whether you're planning an epic escape with your best friends or an overdue family reunion, there's no shortage of large group vacation rentals in and around Siena:

  • A wide array of amenities including a swimming pool and a kitchen make "Villa With Unique View Of Siena" a standout. This sprawling getaway has 7 bedrooms and sleeps up to 12 people. From the heart of Siena, it's around 1 mile away to the northeast.
  • Invite as many as 12 of your friends to "Casa Arcobaleno In Siena - Free Parking" and fill the place with laughter and love. This option has 3 bedrooms and is around 1 mile to the northwest of central Siena. It's packed with features to keep a large group occupied, including a garden and a kitchen.

What are the best houses for rent with a pool in or near Siena?

A pool is often a necessity when deciding where to stay on vacation, particularly if you're bringing the kids along. Check out these houses with a pool in or near Siena and spend your days splish-splashing around:

  • Round up your crew and enjoy a memorable stay at "San Domenico House - Two Bedroom Apartment". There's plenty to love about this retreat apart from its pool, such as a TV and a dishwasher.
  • "Charming House Siena, Large, Panoramic" is the kind of place you go to get away from the everyday and enjoy your surroundings, starting with its inviting pool. A dishwasher and a microwave oven are also on hand to make your stay as comfortable as possible.

Unsure how to pack your bags for your Siena getaway? This popular destination has a humid subtropical climate. In the summertime, you can expect average temperatures ranging from 60 ºF to 85 ºF. Scroll through our selection of Siena vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more inspiration on where to stay.

What are the best large family vacation rentals in or near Siena?

You'll always have more fun sharing the good times with the ones closest to your heart. Whether you're planning a family break or taking time out with close friends, we'll have a large vacation rental that suits you. Here are two of our best in and around Siena:

  • Sleeping as many as 8 guests in 4 bedrooms, "Penthouse With Roof Terrace: Enchantment And Relaxation Among The Beauties Of Siena" is the ideal place to spend time together. This getaway is 0.1 miles to the northwest of Siena and has creature comforts that include cable/satellite TV services and a nearby laundromat.
  • Another great choice is "Villa Terral - Pollensa". This property is 0.1 miles west of Siena and comes with nearby ecotour services, a porch and more. With 4 bedrooms accommodating up to 10 people, you won't have to leave anyone off your invitation list.

If you're after family-friendly attractions in the area, you're spoiled for choice. Palazzo Pubblico, Palazzo Piccolomini and Monteriggioni Castle promise lots of fun for young and old.

What are the best large houses to rent with indoor pools in or near Siena?

Nothing says "deluxe getaway" like having a pool inside your house. Pack your favorite swimwear and splash around in the privacy of one of these roomy vacation homes in or near Siena:

  • Invite your loved ones over for a refreshing swim at "Villa I Cipressini Tuscany Private Luxury Heated Pool Spa Gym Pienza Siena". This home has space to spare, with 5 bedrooms comfortably sleeping up to 10 people. A garden and a sauna are other things your team will love about this place.
  • Another top option is "Private Villa With Sauna, A/c, Wifi". With 13 bedrooms accommodating up to 26 people, you can invite your entire crew to stay with you and swim. A swimming pool and a sauna are other amenities your guests can enjoy here.

Use the search bar at the top of the page and adjust the filters to find more wonderful Siena vacation rental options for your next big getaway.