San Gusme Vacation Rentals, Castelnuovo Berardenga: house rentals & more

Discover a selection of vacation rentals in San Gusme that are perfect for your trip. Vacation homes offer the amenities you expect for you and your friends, family, or even pets, such as a fireplace and a washer and dryer. At the end of the day, you're sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - San Gusme

Showing deals for:Oct 17 - Oct 24

Exceptional

(19 reviews)

Camparone, ArcenoRentalsClub Magnificent Chianti Villa Exclusive Pool Concierge

Castelnuovo Berardenga, Provincia di Siena

14% off

Includes all fees

The Casa Colonica is located in the hamlet of il Poggiolo.

Exceptional

(29 reviews)

Tuscan Villa with Panoramic View - near Florence, Siena & Arezzo

Bucine, Tuscany

8% off

Includes all fees

Exceptional

(86 reviews)

Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi

Castelnuovo Berardenga

5% off

Includes all fees

Exceptional

(32 reviews)

Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi

Castelnuovo Berardenga, Tuscany

14% off

Includes all fees

Very Good

(10 reviews)

Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property

Gaiole in Chianti, Toscana

9% off

Includes all fees

Exceptional

(51 reviews)

Casa Rossella - ArcenoRentalsClub Romantic flat in Chianti Wifi Concierge Pool

Castelnuovo Berardenga, Province of Siena

14% off

Includes all fees

Exceptional

(63 reviews)

Arco al Poggio, Arceno Rentals Club, Spacious Chianti Apt, Pool, Concierge, WiFi

Castelnuovo Berardenga, Toscana

14% off

Includes all fees

View of the Main House looking towards the east

Exceptional

(19 reviews)

Chianti Villa with pool far reaching views towards the sunset in woods&vineyards

Gaiole in Chianti, Tuscany

9% off

Includes all fees

Excellent

(11 reviews)

Special offer Newly renovated fine detached villa with fireplace.

Castelnuovo Berardenga, Tuscany

9% off

Includes all fees

Exceptional

(5 reviews)

Apartment for 3 guests with all comforts, private terrace and garage

Siena, Provincia di Siena

9% off

Includes all fees

Exceptional

(97 reviews)

Wonderful apartment in Piazza del Campo, the center of Siena | Palazzo Giorgi

Siena, Toscana

9% off

Includes all fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - San Gusme

Showing deals for: Oct 17 - Oct 20

XIII Century Tower with Private Panoramic Pool

Sleeps 11 · 5 bedrooms · 5 bathrooms

Includes all fees

Wonderful villa for 6 guests with WIFI, private pool, A/C, TV, patio, pets allowed and parking

Sleeps 6 · 3 bedrooms · 2 bathrooms

Includes all fees

Holiday home with private pool, WiFi, private garden, Chianti Classico, Siena

Sleeps 6 · 3 bedrooms · 3 bathrooms

Includes all fees

Top rated rentals - San Gusme

Disappointing stay

Unfortunately, our stay at this property was far from what we expected based on the listing. The house was not clean upon arrival—there was visible dirt and grime throughout, and bugs, spiders, spiderwebs, and worms were present in multiple rooms including the kitchen counter, making the space unsanitary. It felt as though it had not been inhabited for quite some time.The house was not stocked with basic supplies for a group of nine staying for five nights. There were no paper towels, hand soap, bathroom toiletries, and not enough toilet paper.The appliances were extremely outdated, which made basic tasks like cooking or making coffee difficult. Even more concerning, there was a sewage leak, which flooded part of the downstairs, and created an unpleasant smell and raised serious hygiene concerns. To make matters worse, there was no hot water towards the end of our stay in most of the bathrooms, which made showering nearly impossible.The exterior patio area and area surrounding the pool needed to be tidied as there was dirt, leaves, and rocks. Even then, the outside area enjoyment was limited and we could not spend much time outdoors due to the incessant swarming of bees and hornets. We were shocked that only one person in our group got stung while swimming. This also limited the ability to open windows on the first level of the home for ventilation as no screens were present to keep out the bugs and bees. Finally, it should be noted that this home is located in a beau

Kevin L.

Stayed Jun 2025

Premier Host

Great apartment for a family!

This apartment was perfect for our family with 2 bedrooms. Nice quiet spot with an excellent restaurant steps away. Host was very responsive and accomodating!

Erin V.

Stayed May 2025

Premier Host

Great experience except…

Our stay was great. The apartment was well maintained with the exception of one thing. The vent over the stove didn’t work. It didn’t matter to us because we ate out but it might matter to someone. Two things could be better. Instruction on how to operate the systems at the apartment would have gone a long way. The biggest thing that needs to be in every listing that say they have parking is the explanation what that means. This apartment is in the heart of Sienna. What they don’t tell you is you can’t park there. The nearest parking that won’t get you towed is 1/2 mile away walking. Not really ideal when you have a large group and tons of luggage. The place is modern and nice. We enjoyed it. We were just annoyed when they told us as we pulled up to the door that we shouldn’t be driving in the city and parking was so far away.

Yudannis R.

Stayed May 2025

Premier Host

Absolutely Epic week in Tuscany!

Absolutely Epic week in Tuscany – and all thanks to Francesca and Best of Mas! We spent a week in Siena at one of her villas. Unbelievable is the only word I can think of to describe it - from the villa itself, to the pool, the hot tub, the fireplace, the bedrooms, and the bathrooms…everything was top notch. Add in the fantastic authentic Italian dinner Francesca personally cooked for us at the villa, the tours of Montepulciano and Pienza with Pepino driving us in a Mercedes Benz, and an unforgettable wine tasking bike tour led by Enrico, and I can’t give Francesca and the Best of MAS team a high enough recommendation!

Mike T.

Stayed May 2025

Beautiful Apartment in Siena Italy

The apartment is in a great location in central Siena. It is a lovely place to stay with charming decorations. We enjoyed staying in this apartment and would recommend it highly.

Davelen F.

Stayed Apr 2025

Premier Host

Warm welcome to a stunning spot

This home is an oasis of beauty with plenty of privacy and space. Our host welcomed us with food and extras so we could settle in and not have to leave for some of the simple things like a light breakfast and snacks. Wonderful.

Kristine S.

Stayed Jan 2025

Premier Host

our favorite

Charming apartment in the center medical part of Siena. Just around to block from the big square. Great coffee shop right downstairs. The bed ice very comfortable. The hosts were terrific. This is THE place to stay in Siena!

Susan T.

Stayed Oct 2024

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Find out more about San Gusme

Travel to cozy San Gusme

Enjoy the wineries and other features of San Gusme. This city's coffeehouses, local tours and gardens attract many visitors, and its scenic and relaxing location add to the charm. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in San Gusme

Are you hoping to discover top things to see and do while you're in town? Venture out of your cozy vacation rental and experience everything that makes San Gusme a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

Villa a Sesta Polo Club (3.5 mi / 5.6 km)
Cantalici Winery (4.5 mi / 7.2 km)
Siena Circuit (5.3 mi / 8.5 km)
Badia a Coltibuono (8 mi / 12.9 km)
Le Miccine (8.1 mi / 13 km)
Terme Antica Querciolaia (8.4 mi / 13.5 km)

Exploring the natural landscape of San Gusme

Whether you're looking for adventure or just want to spend some time taking in the scenery, San Gusme is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

Chianti Sculpture Park (5.8 mi / 9.3 km)
Terme Antica Querciolaia (8.4 mi / 13.5 km)
Val di Chiana (26.4 mi / 42.5 km)
Arno River (29 mi / 46.6 km)
Riserva Naturale Regionale Valle dell'Inferno e Bandella (11.9 mi / 19.1 km)
Buriano Bridge and Penna Natural Reserve (14 mi / 22.6 km)

How to get to and around San Gusme

The nearest airport is in Florence Airport, Peretola (FLR), located 32.5 mi (52.3 km) from the city center.

Frequently asked questions

What is the best area to stay in San Gusme when booking a vacation rental?

When planning a vacation in San Gusmè, a charming village in Tuscany, the best area to consider for your stay is the historic center. This picturesque area is characterized by its quaint cobblestone streets and medieval architecture, which provide a great backdrop for a relaxing getaway. Staying in the historic center allows you to immerse yourself in the local culture and enjoy easy access to nearby attractions.

One of the top highlights in the area is the beautiful Church of San Lorenzo, which showcases stunning frescoes and offers a glimpse into the village's rich history. Additionally, the enchanting gardens and panoramic views from the surrounding hills make for a delightful experience, especially during sunset. The historic center typically features a variety of vacation rental properties, ranging from cozy apartments to charming villas, providing numerous options for travelers seeking a unique stay.

For those interested in exploring further, the nearby Castello di Brolio is a must-visit, known for its impressive vineyards and scenic landscapes.

How much does it cost to rent a vacation home in San Gusme?

Prices for vacation rentals in San Gusme vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in San Gusme to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.

Are there any discounts for San Gusme vacation house rentals?

You can find great discounts on house rentals in San Gusme on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Can I find long-stay vacation rentals in San Gusme?

A long-stay vacation rental in San Gusme is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Are there any San Gusme vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in San Gusme with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

When is the best time to visit San Gusme for a vacation rental?

April is the most popular time to visit San Gusme, as travelers flock to this charming Tuscan village to embrace the beauty of spring. During this month, the weather is pleasantly mild, with temperatures ranging from the mid-50s to low 70s Fahrenheit, creating ideal conditions for outdoor exploration. Visitors can stroll through the picturesque streets, savoring local cuisine at nearby trattorias and reveling in the vibrant colors of blooming flowers that adorn the landscape.

The peak season in San Gusme runs from July to September, drawing tourists eager to bask in the warm Italian sun and partake in various cultural festivities. This time also offers an abundance of opportunities for scenic drives and vineyard tours, making it a prime period for those looking to immerse themselves in the rich flavors of Tuscany.

If you're looking for a more budget-friendly time to visit, November presents a unique charm. As the tourist crowds thin out, you can enjoy the tranquil atmosphere and experience the authentic local lifestyle. The fall season showcases the region's stunning autumn hues, superb for leisurely walks and photography.

Ultimately, your ideal timing for a vacation rental in San Gusme will depend on whether you prefer the lively ambiance of the summer months or the peaceful serenity that November offers.

How early should I book a San Gusme vacation rental?

Book your San Gusme vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

What are the top attractions in San Gusme?

In San Gusmè, travelers can immerse themselves in the charm of a medieval Tuscan village. The historic center features well-preserved stone buildings and quaint streets, superb for leisurely strolls. Nearby attractions include the impressive Castello di Brolio, a short drive away, which offers guided tours and beautiful vineyards. The surrounding Chianti region is renowned for its wine production, and visitors can explore local wineries and partake in tastings. Additionally, the picturesque town of Radda in Chianti is close by, boasting lovely shops and restaurants, making it an ideal spot for experiencing authentic Tuscan cuisine.

Can I change or cancel my San Gusme home rental booking on Vrbo?

To find San Gusme vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.