Compare Chianti Region Vacation Rentals

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Chianti Region Rentals

Relais Villa Olmo

Relais Villa Olmo

Via Imprunetana Per Tavarnuzze 19 Impruneta FI
12.05 mi from city center
A local mainstay since 1500, Relais Villa Olmo features a winery, a seasonal outdoor pool, and coffee in a common area. You can take advantage of free parking, along with an airport shuttle (available 24 hours) for EUR 185 per vehicle one-way. The front desk has multilingual staff that can help with securing valuables, tours or tickets, and dry cleaning/laundry. Other amenities at this golf residence include a terrace, laundry facilities, and a banquet hall.
Pool
Breakfast included
hu Firenze Certosa camping in town

hu Firenze Certosa camping in town

Via San Cristofano 2 Impruneta FI
14.94 mi from city center
Guests of hu Firenze Certosa camping in town enjoy access to free WiFi in public areas, a seasonal outdoor pool, and coffee in a common area. Free parking is available if you drive. The 24-hour front desk has staff always at the ready.
Pool
Pet friendly
Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Castellina in Chianti Tuscany
5.19 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Chianti Village Morrocco

Chianti Village Morrocco

3 out of 5
Strada Morrocco 36/A Barberino Tavarnelle FI
Free Cancellation
Reserve now, pay when you stay
8.18 mi from city center
Guests of Chianti Village Morrocco enjoy an outdoor pool, free WiFi in public areas, and conference space. For transportation, you can make use of an airport shuttle for a fee (available on request), as well as limo/town car service. The front desk has multilingual staff that can help with tours or tickets, securing valuables, and luggage storage. Other amenities at this family-friendly residence include a business center, a seasonal outdoor pool, and a terrace.
Pool
Kitchen
Relais Villa Belvedere

Relais Villa Belvedere

Via Aretina per San Donato 1 Figline e Incisa Valdarno FI
Free Cancellation
Reserve now, pay when you stay
9.99 mi from city center
$100 nightly
The price is $112 total per night
$112 total
Jan 10 - Jan 11, 2026
Total with taxes and fees
At Relais Villa Belvedere, guests have access to an outdoor pool, a rooftop terrace, and free WiFi in public areas. There's free parking, and an airport shuttle (available 24 hours) for EUR 60 per vehicle one way. Front-desk staff can assist with tours or tickets, dry cleaning/laundry, and securing valuables. Additional amenities include a seasonal outdoor pool, a terrace, and laundry facilities.
Pool
Kitchen
Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

Siena Tuscany
9.37 mi from city center
At this vacation home, guests have access to an outdoor pool, laundry facilities, and a living plant wall. Other amenities at this family-friendly vacation home include barbecue grills and a garden.
Pool
Kitchen
Villa with concierge service & heated pool at 20 minute from Florence center

Villa with concierge service & heated pool at 20 minute from Florence center

impruneta Toscana
11.44 mi from city center
$1,086 nightly
The price is $1,091 total per night
$1,091 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
Guests of this villa enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. Transportation is made easy with limo/town car service. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this golf villa include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Kitchen
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Castellina in Chianti Siena
5.9 mi from city center
Guests of this villa enjoy features like an outdoor pool, a gym, and a library. Transportation is made easy with limo/town car service. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this family-friendly villa include a terrace, laundry facilities, and barbecue grills.
Pool
Kitchen
Villa Il Palagio

Villa Il Palagio

Via Il Palagio 59 Rignano sull'Arno FI
12.01 mi from city center
Guests of Villa Il Palagio have access to a nightclub, an outdoor pool, and free WiFi in public areas. There's free parking, and an airport shuttle (available 24 hours) for EUR 120 per vehicle one-way. Multilingual staff at the 24-hour front desk can assist with concierge services, securing valuables, and luggage storage. Other amenities at this family-friendly apartment building include meeting rooms, a business center, and a seasonal outdoor pool.
Pool
Parking included
Castello di Montegufoni

Castello di Montegufoni

Via Montegufoni, 18 Montespertoli FI
16.64 mi from city center
At Castello di Montegufoni, guests have access to an outdoor pool, a rooftop terrace, and free WiFi in public areas. You can take advantage of free parking if you drive. Front-desk staff can assist with tours/tickets and luggage storage. Additional amenities include a seasonal outdoor pool, a meeting room, and a terrace.
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Ruffoli Toscana
2.87 mi from city center
Guests staying at this apartment have access to a garden and barbecue grills.
Kitchen
Pet friendly
Your panoramic house in Tuscany between vineyards and olive groves.

Your panoramic house in Tuscany between vineyards and olive groves.

Barberino Val d'Elsa
8.64 mi from city center
Guests staying at this villa enjoy an outdoor pool, a terrace, and laundry facilities. Additional amenities include barbecue grills and a garden.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chianti Region Large Group Rentals

How to Book Vacation Rentals in Chianti Region



🏠 What is the best price for Chianti Region vacation rentals?

Chianti Region vacation rentals range in price, starting at $112 per night.


🏠 What types of vacation rentals in Chianti Region can I rent?

Orbitz offers a wide range of Chianti Region rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Chianti Region condo rentals.


🏠 Is it free to cancel my Chianti Region vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Chianti Region vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Chianti Region. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Chianti Region?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Chianti Region apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Chianti Region?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Chianti Region package deals will get you even more savings.

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