Gaiole in Chianti vacation rentals

We found 1,287 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Gaiole in Chianti by choosing from 32 houses, 37 apartments, and other vacation rentals. Vacation homes offer the best amenities for your family, friends, or furry companion, such as WiFi and a pool. At the end of the day, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

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Find out more about Gaiole in Chianti

Why visit Gaiole in Chianti

  • Stunning Scenery: Experience breathtaking views of the picturesque Chianti hills and rolling vineyards.
  • Historic Landmarks: Explore charming churches, castles, and palaces that showcase the rich cultural heritage of the region.
  • Outdoor Adventures: Enjoy a variety of outdoor activities, perfect for nature lovers and adventure seekers.
  • Luxurious Accommodations: Stay in opulent villa rentals that offer a lavish and relaxing getaway experience.
  • Charming Atmosphere: Immerse yourself in the friendly and romantic vibe of this enchanting Tuscan village.

Popular types of accommodation in Gaiole in Chianti

Discover the charm of Gaiole in Chianti with our selection of vacation rentals, including stunning villas, cozy apartments, and spacious private homes. Whether you're seeking a romantic getaway or a family retreat, you’ll find the perfect Chianti villa to suit your needs. Explore our Gaiole in Chianti vacation rentals and enjoy the beauty of Tuscany while experiencing transparency, savings, and reassurance in your booking.

  • Apartments: The top choice for visitors to Gaiole in Chianti, offering comfortable living spaces with essential amenities for a delightful stay.
  • Villas: A luxurious option, these spacious properties provide beautiful surroundings and often come with private pools and gardens.
  • Houses: Ideal for families or groups, these homes offer a home-like atmosphere with more privacy and flexibility.
  • Caravan Parks: A unique choice for those seeking an adventurous experience, providing a chance to enjoy the outdoors in a community setting.
  • Cottages: Quaint and cozy, these charming accommodations are perfect for a romantic getaway or a peaceful retreat.**

Top attractions near Gaiole in Chianti

Gaiole in Chianti offers a romantic and entertaining getaway, perfect for outdoor enthusiasts. Explore stunning churches, castles, and historic palaces that reflect the rich culture of the area. Don't miss the picturesque Chianti hills and consider staying in opulent villa rentals for a luxurious experience. Whether you seek romance or a vibrant city atmosphere, Gaiole in Chianti has something for every traveler to enjoy.

  • Castello di Albola: A charming castle located 4 miles from Gaiole in Chianti, Castello di Albola offers a romantic ambiance and rich cultural experiences, with stunning views of the surrounding vineyards and countryside.
  • Piazza del Campo: Situated 12 miles away, this iconic square is the heart of Siena, known for its vibrant culture and lively atmosphere, perfect for enjoying local cuisine and people-watching.
  • Siena Cathedral: Also 12 miles from Gaiole, this magnificent cathedral showcases remarkable Gothic architecture and intricate art, providing a deep cultural insight into the region's history.

Things to do recommended for couples

Ready for a romantic getaway in Gaiole in Chianti? Explore the enchanting Castle of Brolio and indulge in wine tasting at Cantalici Winery. For a touch of luxury, visit the Villa a Sesta Polo Club, just 9 miles away. Enjoy unforgettable experiences together in this charming Tuscan paradise.

Things to do recommended for families

Your family vacation in Gaiole in Chianti will be filled with excitement. Enjoy thrilling karting at the Siena Circuit, catch a game at the Siena Stadium, or cheer on your favorite team at Stadio Artemio Franchi, all located about 11 miles away, offering plenty of sports fun for everyone.

Things to do recommended for groups

Your group can enjoy a performance at the Vittorio Alfieri Theater, indulge in local wines at Enoteca Italiana, and embark on an adventurous hike along the scenic Sentierelsa Trail, all within a short drive from Gaiole in Chianti.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Gaiole in Chianti

If you're traveling with a group, with family, bringing your pets along, or planning an extended stay, be sure to use the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Gaiole in Chianti with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor space for group get-togethers. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Gaiole in Chianti with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Gaiole in Chianti: For many families, a getaway wouldn't feel complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Gaiole in Chianti: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Gaiole in Chianti

Gaiole in Chianti offers a captivating blend of romance and adventure in the heart of Tuscany. Explore charming Italian villas and vacation homes nestled in the stunning Chianti countryside. The area boasts magnificent scenery and a friendly atmosphere, perfect for outdoor enthusiasts and those seeking a relaxing getaway. Discover the historical charm of nearby towns, and immerse yourself in the luxurious vibes that make Gaiole in Chianti a truly unforgettable destination.

  • Villa: Located about 3 miles from Gaiole in Chianti, Villa is a charming village that offers a romantic outdoor experience for travelers. Visitors can explore the local market and enjoy guided tours, immersing themselves in the authentic Tuscan lifestyle. The village is surrounded by beautiful landscapes, with nearby attractions including a historic castle, a serene lake, and even a beach for those looking to relax by the water. Villa’s mix of entertainment and natural beauty makes it an ideal spot for a memorable getaway.
  • San Sano: Nestled in the heart of the Gaiole in Chianti area, San Sano captivates visitors with its rich cultural heritage. This village is perfect for those seeking a romantic and entertaining atmosphere, complete with historic landmarks such as a grand castle and an art museum. The quaint streets invite leisurely strolls, where travelers can soak in the local culture and history. San Sano provides an enriching experience that is not to be missed on your Tuscan adventure.
  • Lecchi in Chianti: Situated within the Gaiole in Chianti area, Lecchi in Chianti is a picturesque village that offers a blend of romance, culture, and entertainment. Visitors can wander through historic sites, including a stunning monument and an impressive historic palace. The village's charming ambiance and cultural attractions make it an excellent destination for those looking to delve into the region's history while enjoying the scenic surroundings. Lecchi in Chianti promises an unforgettable experience filled with exploration and discovery.

Best time to go to Gaiole in Chianti

If you're planning a trip to Gaiole in Chianti, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnyLowSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyLowSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No Rain (Dry)SunnyHighSlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnyHighSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyHighAverage
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you hoping to save on your next vacation? Staying flexible with your travel dates can really help, as prices can vary. Additionally, if you opt for a longer stay, you often unlock significant savings. To discover the perfect Vrbo rental that fits your budget, be sure to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best deal.

Save more with One Key

Plan your group trip by booking an eligible Vrbo and receive all the OneKeyCash associated with your reservation. Being the organizer has its perks. When you join our travel rewards program, One Key, you'll gain immediate access to member savings and can earn and redeem OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board is designed to help you plan your journeys effortlessly. Whether you're starting a new trip, refining your existing plans, or managing your bookings, this tool is here to assist you. Your saved or booked properties are conveniently organized into categories: Potential, Upcoming, or Current Trips. To dive into your Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Head to the rustic city of Gaiole in Chianti

The area's wineries and monuments are just a few of the reasons to vacation in Gaiole in Chianti. One of the city's many top draws is its spas. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Sightseeing in and around Gaiole in Chianti

Do you want to find attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Gaiole in Chianti has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Badia a Coltibuono (2 mi / 3.2 km)
  • Cantalici Winery (2.1 mi / 3.4 km)
  • Le Miccine (3.7 mi / 6 km)
  • Castello di Radda Winery (3.8 mi / 6.2 km)
  • Castello di Albola (3.9 mi / 6.3 km)
  • Borgo di Vescine - Tenute di Castelvecchi (5.2 mi / 8.4 km)

Exploring the natural landscape of Gaiole in Chianti

Whether you're an active traveler or just want to appreciate the scenery, Gaiole in Chianti is a great place to get outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Chianti Sculpture Park (5.8 mi / 9.3 km)
  • Terme Antica Querciolaia (14.8 mi / 23.9 km)
  • Arno River (22.4 mi / 36.1 km)
  • Val di Merse (22.7 mi / 36.5 km)
  • Enoteca Italiana (11.4 mi / 18.4 km)
  • Riserva Naturale Regionale Valle dell'Inferno e Bandella (11.5 mi / 18.4 km)

How to get to and around Gaiole in Chianti

The nearest airport is in Florence Airport, Peretola (FLR), located 25.9 mi (41.7 km) from the city center.

Frequently asked questions

What is the best area to stay in Gaiole In Chianti when booking a vacation rental?
When considering a vacation rental in Gaiole in Chianti, a popular area to stay is the historic center. This charming neighborhood offers a delightful blend of rustic Tuscan architecture and vibrant local culture. You'll be within walking distance of top attractions such as the beautiful Church of San Sigismondo, which dates back to the 14th century, and the stunning Castello di Brolio, a magnificent castle that provides breathtaking views of the Chianti landscape. The historic center is also home to quaint shops, local eateries, and wine bars where you can sample the region's famous Chianti wines.

Another appealing area is the outskirts of Gaiole, where you can find spacious properties surrounded by lush vineyards and olive groves. This setting allows for a tranquil escape while still being a short drive from the town's amenities. Here, you can explore the scenic Chianti landscape, take part in wine tours, or visit nearby attractions like the enchanting village of Radda in Chianti. Both areas offer a variety of vacation rentals, with the historic center providing a more bustling atmosphere and the outskirts offering a peaceful retreat.
How much does it cost to rent a vacation home in Gaiole In Chianti?
Prices for vacation rentals in Gaiole In Chianti 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 Gaiole In Chianti 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 Gaiole In Chianti vacation house rentals?
You can find great discounts on house rentals in Gaiole In Chianti 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.
What is the most popular type of vacation rental accomodation in Gaiole In Chianti?
In Gaiole In Chianti, villas are the most popular vacation rental option, with about 112 available throughout the picturesque region. These villas often feature spacious layouts, multiple bedrooms, private gardens, and outdoor dining areas, making them superb for families or groups seeking a tranquil retreat in the heart of Tuscany's wine country. Additionally, around 89 apartments provide a cozy alternative, typically equipped with full kitchens, comfortable living areas, and some with balconies to enjoy the stunning Chianti landscape. For those looking for a more rustic experience, several cottages are also available, offering a charming and authentic stay.
Are there any family house rentals in Gaiole In Chianti?
In Gaiole In Chianti, Tuscany, families will be pleased to find a variety of vacation rentals—approximately 97 options throughout the area. This charming locale is surrounded by stunning vineyards and rolling hills, making it an ideal destination for family gatherings. Many of the homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor terraces great for enjoying the picturesque views.

Visitors can expect amenities such as private pools, game rooms for entertainment, and even barbecue facilities for those warm Tuscan evenings. The proximity to local attractions, including vineyards that welcome tours and tastings, as well as the beautiful Chianti landscape, ensures there's plenty to explore.

Families can also venture to nearby towns like Radda in Chianti and Castellina in Chianti, both rich in history and local culture. These areas offer additional dining options, markets, and outdoor activities like hiking and biking in the scenic countryside.
Can I rent a vacation home with a pool or hot tub in Gaiole In Chianti?
In Gaiole In Chianti, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 230 options to choose from. This picturesque area in Tuscany offers a serene countryside atmosphere, great for relaxation and exploration. Travelers can expect many of these properties to include outdoor swimming pools, private hot tubs, and beautifully landscaped gardens, ideal for enjoying the stunning views of the Chianti hills.

Additionally, many rentals come equipped with amenities such as spacious living areas, fully equipped kitchens, and outdoor dining spaces, making them great for families or groups. The charming village atmosphere and proximity to vineyards and local attractions enhance the experience, allowing guests to immerse themselves in the rich culture and gastronomy of the region.
Can I find long-stay vacation rentals in Gaiole In Chianti?
A long-stay vacation rental in Gaiole In Chianti 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 pet-friendly house rentals in Gaiole In Chianti?
In Gaiole In Chianti, travelers will find a wealth of pet-friendly house rentals, with around 140 options available. This picturesque area in Tuscany is known for its stunning landscapes, vineyards, and historic charm, making it a delightful destination for both pets and their owners. Many of the vacation rentals feature amenities such as spacious outdoor areas, private gardens, and fully equipped kitchens, allowing guests to enjoy a comfortable stay while exploring the beautiful surroundings.

The region is dotted with quaint villages and scenic countryside, making it superb for leisurely walks with pets. Nearby, the Chianti Classico Wine Route offers numerous opportunities to visit local wineries, many of which are pet-friendly and welcome guests to bring their furry companions along.
Are there any remote work vacation rentals in Gaiole In Chianti?
In Gaiole In Chianti, there are numerous remote work vacation rentals available, with around 237 options to choose from. This picturesque area in Tuscany is renowned for its stunning landscapes, vineyards, and charming medieval villages, making it an excellent choice for those looking to blend work and leisure. Many properties come equipped with essential remote work amenities such as Wi-Fi, dedicated desks, comfortable desk chairs, and even spaces designed for office setups, including safe storage and computer monitors.

Travelers can expect to find a variety of accommodations, from rustic villas with sweeping views of the Chianti hills to cozy apartments in the heart of the village. These rentals often feature additional comforts like fully equipped kitchens, outdoor terraces, and beautiful gardens, providing a serene environment to work while enjoying the tranquil Tuscan countryside. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Gaiole In Chianti vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Gaiole In Chianti 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.
What are popular rental amenities in Gaiole In Chianti?
In Gaiole In Chianti, popular vacation rental amenities include WiFi, kitchens for preparing meals, and various pool options. Travelers can expect private pools at some properties, offering a secluded space to relax, while others feature shared pools for a more communal atmosphere.
When is the best time to visit Gaiole In Chianti for a vacation rental?
April is an excellent time to visit Gaiole In Chianti, as the region begins to awaken from winter, showcasing its stunning landscapes and vibrant vineyards. During this month, the weather is pleasantly mild, with temperatures ranging from the mid-40s to low 70s Fahrenheit, making it ideal for outdoor activities such as hiking through the rolling hills and exploring local wineries.

The peak tourist season in Gaiole In Chianti stretches from July to September, when visitors flock to the area to enjoy the warm summer weather and the lively atmosphere of local festivals. This is the superb time for travelers who appreciate bustling markets, exquisite dining, and the chance to participate in grape harvest activities. However, if you prefer a more tranquil experience, visiting in April allows you to enjoy the beauty of the countryside with fewer crowds, while still taking advantage of outdoor sightseeing and leisurely strolls through charming villages.

For those looking for a more economical visit, December can be a great option. Although it's considered low season, the holiday spirit brings a unique charm to the area, with festive decorations and local traditions that enrich the experience.
How early should I book a Gaiole In Chianti vacation rental?
Book your Gaiole In Chianti 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 Gaiole In Chianti?
In Gaiole In Chianti, visitors can experience firsthand the picturesque Tuscan landscape and explore a variety of attractions. The historic town center features charming streets and local shops, where travelers can discover artisan products and enjoy authentic Italian cuisine. Nearby, the medieval Castello di Brolio offers stunning views and a glimpse into the region's winemaking history, with opportunities for wine tasting and guided tours.

Additionally, the surrounding Chianti region is renowned for its vineyards and olive groves, superb for those interested in agritourism. The scenic countryside is ideal for hiking and cycling, with numerous trails that allow visitors to appreciate the natural beauty of the area.
Can I change or cancel my Gaiole In Chianti home rental booking on Vrbo?
To find Gaiole In Chianti 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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Gaiole In Chianti vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCareℱ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCareℱ, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCareℱ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCareℱ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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