Best Vacation Homes in Pienza
House
10.0(58 Reviews)
5 Bedrooms
7 Baths
10 Guests
5382 ft²
Private Pool
Hot Tub
Spa
Fireplace/Heating
US $1,172/Night
7 Nights - US $8,205
Apartment
10.0(121 Reviews)
4 Bedrooms
4 Baths
11 Guests
670.95 ft²
- Fireplace/Heating
View
Breakfast
Parking
US $74/Night
7 Nights - US $521
Apartment
10.0(57 Reviews)
2 Bedrooms
2 Baths
4 Guests
1023 ft²
- Fireplace/Heating
Balcony/Terrace- Breakfast
Kitchen
US $158/Night
7 Nights - US $1,109
Apartment
10.0(17 Reviews)
3 Bedrooms
2 Baths
6 Guests
1614.59 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Pet Friendly
US $90/Night
7 Nights - US $633
Villa
10.0(44 Reviews)
4 Bedrooms
4 Baths
13 Guests
2314 ft²
- Private Pool
- Fireplace/Heating
Pool
Ocean View
US $635/Night
7 Nights - US $4,444
Villa
10.0(26 Reviews)
5 Bedrooms
5 Baths
8 Guests
3770 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,376/Night
7 Nights - US $9,632
Villa
10.0(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
1292 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $339/Night
7 Nights - US $2,373
Pienza Luxury Rentals
House
9 Bedrooms
9 Baths
18 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $4,250/Night
7 Nights - US $29,750
House
10.0(1 Review)
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $4,092/Night
7 Nights - US $28,642
Villa
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,036/Night
7 Nights - US $14,253
Villa
9 Bedrooms
7 Baths
19 Guests
7535 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,969/Night
7 Nights - US $13,782
Villa
9 Bedrooms
9 Baths
19 Guests
4306 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,735/Night
7 Nights - US $12,143
Villa
10.0(11 Reviews)
5 Bedrooms
2 Baths
9 Guests
2500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,666/Night
7 Nights - US $11,661
Villa
10.0(1 Review)
7 Bedrooms
9 Baths
14 Guests
6458 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,502/Night
7 Nights - US $10,513
US $1,481/Night
7 Nights - US $10,364
Pienza Pet Friendly Vacation Rentals
Apartment
10.0(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
775 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $123/Night
7 Nights - US $859
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $196/Night
7 Nights - US $1,372
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Internet
US $140/Night
7 Nights - US $981
House
10.0(9 Reviews)
1 Bedroom
1 Bath
2 Guests
560 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $118/Night
7 Nights - US $826
Villa
10.0(1 Review)
5 Bedrooms
7 Baths
10 Guests
5381.95 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $786/Night
7 Nights - US $5,503
House
10.0(5 Reviews)
3 Bedrooms
3 Baths
6 Guests
2153 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $503/Night
7 Nights - US $3,521
Apartment
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $293/Night
7 Nights - US $2,052
Apartment
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1615 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $193/Night
7 Nights - US $1,354
Pienza Large Vacation Homes
Villa
10.0(1 Review)
6 Bedrooms
5 Baths
11 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $1,112/Night
7 Nights - US $7,787
House
9.9(20 Reviews)
8 Bedrooms
4 Baths
22 Guests
968.75 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
US $231/Night
7 Nights - US $1,617
Villa
9.8(27 Reviews)
4 Bedrooms
4 Baths
9 Guests
3767 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $453/Night
7 Nights - US $3,168
Villa
7 Bedrooms
9 Baths
14 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,443/Night
7 Nights - US $10,099
Villa
6 Bedrooms
6 Baths
12 Guests
3767 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $1,369/Night
7 Nights - US $9,581
Villa
6 Bedrooms
7 Baths
13 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,092/Night
7 Nights - US $7,645
Villa
6 Bedrooms
6 Baths
12 Guests
4629 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,088/Night
7 Nights - US $7,616
Why Choose Rent By Owner for your Pienza Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Pienza
When should you plan your Vacation Rentals stay?
Choosing the right time to visit ensures you experience the region’s authentic charm and enjoy your stay in this picturesque destination at its best.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy the region's mild weather and vibrant spring landscapes, making it ideal for exploring and experiencing local culture with comfortable daytime temperatures.
Average Temperature Daytime: 22°C to 26°C - Nighttime: 10°C to 14°C
Early Fall (September to October)
This season offers pleasant weather and fewer crowds, allowing you to savor the area's scenic beauty and tranquility while still enjoying warm daytime temperatures.
Average Temperature Daytime: 23°C to 27°C - Nighttime: 12°C to 16°C
Off-Season Highlights
Winter (December to February)
Visit during this quiet season to experience the region's serene charm with fewer tourists and enjoy mild winter days suitable for cozy explorations of the area’s peaceful streets.
Average Temperature Daytime: 7°C to 11°C - Nighttime: 0°C to 4°C
Late Fall to Early Winter (November and early December)
This time of year features cooler weather and a tranquil atmosphere, perfect for those seeking a more relaxed and authentic experience in the region without the peak-season crowds.
Average Temperature Daytime: 10°C to 15°C - Nighttime: 3°C to 7°C
Weekly Weather Forecast for Pienza
How to Book Your Pienza Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Pienza
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas with scenic views of the Tuscan countryside.
- Relax in private gardens or courtyards that offer tranquil settings for your stay.
- Make use of outdoor lounging spaces perfect for soaking up the sun and unwinding.
- Take advantage of terraces or balconies with panoramic vistas of rolling hills and vineyards.
- Benefit from well-maintained communal yards ideal for leisurely strolls and family activities.
- Explore nearby walking trails or paths that showcase the region’s natural beauty.
- Utilize outdoor grills or barbecue areas to enjoy authentic Tuscan cuisine al fresco.
Top Attractions Around Pienza
What attractions are nearby?
Enjoy exploring charming local wineries, savoring authentic Tuscan cuisine, and strolling through picturesque landscapes just moments from your vacation rentals in this beautiful region.
Family Activities
- Explore Pienza's charming historic center: Wander through the picturesque streets filled with Renaissance architecture, ideal for family photos and discovering local artisans.
- Visit Pienza Cathedral: Attend a family-friendly tour of this stunning religious site to appreciate its unique architecture and serene atmosphere.
- Enjoy panoramic views from the Pieve di Corsignano: Take in breathtaking vistas of the Tuscan countryside that will inspire young and old alike during your stay.
- Participate in a local cheese tasting tour: Engage the whole family with a flavorful experience at nearby farms, learning how authentic Pecorino cheese is made in the region.
Adult Activities
- Wine Tasting Tours: Discover the region’s renowned wines through guided tastings at local wineries that showcase Tuscany's rich viticultural heritage.
- Historical Sightseeing: Immerse yourself in the area's history by exploring its ancient architecture, including legendary churches and well-preserved medieval structures.
- Photographic Excursions: Capture breathtaking views of rolling Tuscan hills and charming countryside while strolling through picturesque streets and scenic viewpoints.
- Culinary Experiences: Indulge in authentic Tuscan cuisine by participating in cooking classes or enjoying meals at local trattorias that highlight regional flavors.
Other Places to Stay in Pienza
Art Studio di Adelina Quadri
RI Crea RE
Piazza Pio II
Palazzo Piccolomini
Historic Centre of Pienza
Artemisia Gallery
Enoteca Di Ghino
Palazzo Vescovile
Palazzo Borgia
Museo Diocesano
Pienza Cathedral
Monticchiello
Pienza Travel Tips
How Can You Make the Most of Your Stay?
- Explore local cuisine: Take the time to enjoy authentic Tuscan dishes at nearby restaurants and trattorias, immersing yourself in the regional flavors that define this charming area.
- Visit early or late in the day: To experience the tranquility and beauty without the crowds, plan your sightseeing excursions during the morning or late afternoon hours.
- Engage with local artisans: Discover handcrafted goods and artwork by visiting small ateliers and markets to enrich your stay with unique souvenirs from the region.
- Take scenic drives: Use your vacation rentals as a starting point for exploring picturesque countryside roads that showcase the stunning vistas characteristic of this destination.
Transportation Options
- Car Rentals: Renting a car provides the flexibility to explore the picturesque countryside and historic sites at your own pace while staying comfortably close to your vacation rentals here.
- Public Buses: The local bus services offer an economical and convenient way to navigate between Pienza and neighboring towns within this charming region.
- Taxis and Ride-Sharing: Taxis and ride-sharing options are readily available, allowing you to easily reach nearby attractions and your preferred vacation rentals without hassle.
- Bicycle Rentals: Cycling is a popular choice for exploring this area’s scenic routes, with bicycle rentals providing an eco-friendly and immersive experience of the region.
Local Customs Options
- Pienza's Local Etruscan Heritage: You will notice the area's deep-rooted Etruscan traditions reflected in its archaeological sites and local crafts, offering a glimpse into the region's ancient history.
- Celebration of the Palio di Pienza: Participating in this traditional event allows you to experience the vibrant community spirit and centuries-old customs unique to this part of Tuscany.
- Regional Gastronomy Customs: Savor the authentic flavors through local culinary traditions, including pecorino cheese production, which is celebrated throughout your stay here in the region.
- Respect for Religious Traditions: Observing local religious festivals and participating respectfully in processions provides insight into the spiritual practices cherished by the inhabitants of this destination.
Frequently Asked Questions About Pienza?
1. What are the top vacation rentals in Pienza?
There are a lot of options in Pienza. If you plan on staying in the Pienza area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pienza:
- Villa PoliFlora
- Villa I Cipressini Tuscany Private luxury pool spa
- Luxury Villa in Monticchiello, your heaven in Tuscany
- Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
- Vento d’Orcia
- Luxury Tuscan villa, spectacular views, beautiful pool and garden.
- L'Olmo
- Villa Arpicella Pienza Siena Italy Tuscany, a stunning, green, peacefull corner
- Casa Bonari
- Villa PoliFlora is a modern apartment in Monticchiello of Pienza in Tuscany.
2. How many vacation rentals have private pools in Pienza?
There are 52 vacation rentals with private pools near Pienza. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Pienza are best for families?
If you are looking for a family-friendly vacation home in Pienza, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pienza:
4. How many Rentbyowner vacation rentals are available in Pienza?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 306 in the Pienza area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pienza.
5. What is the cancellation policy for vacation rentals in Pienza, Tuscany?
Cancellation policies vary by property, so you should review the specific listing details. Many rentals offer flexible options, but it's important to check the terms directly on the property page or contact the owner for clarification.
6. How do I confirm my booking in a vacation rental here?
Booking confirmation typically involves selecting your dates, completing the required information, and receiving an email confirmation from the host. Always verify the reservation details and any additional instructions provided during the booking process.
7. Are there any specific amenities included in the vacation rentals in this area?
Amenities can differ between properties, so you'll want to review each listing carefully. Common features may include Wi-Fi, kitchen facilities, and outdoor spaces, but confirm the specifics with the owner before finalizing your stay.
8. Is it possible to modify or cancel my reservation after booking?
Modifications and cancellations depend on the individual property's policy. You should read the cancellation and modification terms listed for each rental or contact the host directly to discuss any changes.
9. How do I ensure the vacation rental meets my requirements before booking?
To ensure the property matches your needs, thoroughly review the listing details, including photos, amenities, and reviews. If you have specific questions, reaching out to the owner before booking guarantees clarity and a smooth experience.
Pienza Top Rated Vacation Rentals
Other
10.0(1 Review)
6 Bedrooms
7 Baths
12 Guests
4951 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,065/Night
7 Nights - US $7,453
US $517/Night
7 Nights - US $3,619
House
9.8(69 Reviews)
7 Bedrooms
6 Baths
13 Guests
361.67 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $100/Night
7 Nights - US $699
Other
9.8(48 Reviews)
2 Bedrooms
2 Baths
5 Guests
1184 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $351/Night
7 Nights - US $2,455
Other
9.8(28 Reviews)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $170/Night
7 Nights - US $1,187
House
9.8(18 Reviews)
7 Bedrooms
6 Baths
14 Guests
1489.01 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $618/Night
7 Nights - US $4,325
US $291/Night
7 Nights - US $2,037
Bed & Breakfast
9.7(407 Reviews)
3 Bedrooms
3 Baths
8 Guests
290.63 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $144/Night
7 Nights - US $1,008
