Best Vacation Homes in Siena
915 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £129/Night
For 7 Nights GB £902
520.26 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
GB £138/Night
For 7 Nights GB £968
1130 ft²
7 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £182/Night
For 7 Nights GB £1,277
2153 ft²
10 Guests
4 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Spa
GB £528/Night
For 7 Nights GB £3,693
861 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
GB £132/Night
For 7 Nights GB £927
915 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
GB £247/Night
For 7 Nights GB £1,726
Siena Luxury Rentals
58125 ft²
100 Guests
49 Bedrooms
49 Bathrooms
Family Friendly
Villa
- Private Pool
- Spa
- Fireplace/Heating
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4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
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8073 ft²
50 Guests
20 Bedrooms
22 Bathrooms
Group Friendly
Other
- Fireplace/Heating
- Pool
- Parking
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10764 ft²
22 Guests
10 Bedrooms
9 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Spa
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16146 ft²
36 Guests
18 Bedrooms
20 Bathrooms
Family Friendly
Villa
- Private Pool
- Spa
- Fireplace/Heating
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22 Guests
11 Bedrooms
11 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
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60 Guests
27 Bedrooms
22 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Spa
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38 Guests
16 Bedrooms
13 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Spa
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Siena Pet Friendly Vacation Rentals
603 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
GB £121/Night
For 7 Nights GB £848
1291.67 ft²
9 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- Pet Friendly
- Parking
GB £55/Night
For 7 Nights GB £385
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Breakfast
- Pet Friendly
- Kitchen
GB £160/Night
For 7 Nights GB £1,117
12 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
GB £216/Night
For 7 Nights GB £1,510
914.93 ft²
18 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
GB £111/Night
For 7 Nights GB £775
37674 ft²
15 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
GB £810/Night
For 7 Nights GB £5,670
2476 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Fireplace/Heating
- Pool
- Ocean View
GB £473/Night
For 7 Nights GB £3,314
1238 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Cottage
- Private Pool
- Fireplace/Heating
- Pool
GB £150/Night
For 7 Nights GB £1,052
Siena Large Vacation Homes
4844 ft²
12 Guests
6 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Spa
GB £1,334/Night
For 7 Nights GB £9,341
670.95 ft²
11 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- View
- Breakfast
GB £55/Night
For 7 Nights GB £387
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
GB £147/Night
For 7 Nights GB £1,030
2153 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
GB £419/Night
For 7 Nights GB £2,934
498.73 ft²
27 Guests
11 Bedrooms
12 Bathrooms
Free Cancellation
Bed & Breakfast
- Oceanfront
- Fireplace/Heating
- Pool
GB £190/Night
For 7 Nights GB £1,333
2368 ft²
9 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
GB £627/Night
For 7 Nights GB £4,392
2153 ft²
9 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
GB £485/Night
For 7 Nights GB £3,398
2691 ft²
12 Guests
5 Bedrooms
6 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
GB £582/Night
For 7 Nights GB £4,071
Why Choose Rent By Owner for your Siena 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 Siena
When should you plan your Vacation Rentals stay?
Choosing the best time to visit can enhance your experience here, as the region offers different charms depending on the season, making it essential to consider weather and local events when planning your stay in Siena, Tuscany.
Peak Season Highlights
Spring (April to June)
During this period, the area's scenery is in full bloom, making it an ideal time to explore at a comfortable pace. The weather is pleasantly warm, perfect for outdoor activities and cultural sightseeing.
Average Temperature Daytime: 20°C - 24°C - Nighttime: 10°C - 14°C
Early Fall (September to October)
This peak season offers warm temperatures and fewer crowds, creating a more relaxed atmosphere to enjoy local festivals and events. It’s the perfect time to experience authentic regional culture while benefiting from pleasant weather.
Average Temperature Daytime: 22°C - 26°C - Nighttime: 12°C - 16°C
Off-Season Highlights
Winter (December to February)
During the winter months, you'll find fewer visitors in this destination, allowing for a more tranquil experience. The cooler weather is suitable for exploring indoor attractions and enjoying cozy accommodations.
Average Temperature Daytime: 8°C - 12°C - Nighttime: 0°C - 4°C
Late Fall (November)
As the region transitions into winter, the landscape takes on a quieter, more subdued charm. This is an ideal time for budget-conscious travelers seeking lower rates and a peaceful environment.
Average Temperature Daytime: 10°C - 15°C - Nighttime: 3°C - 7°C
Weekly Weather Forecast for Siena
How to Book Your Siena 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 Siena
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 a private outdoor terrace or patio perfect for relaxing and taking in the scenic views of the region’s rolling hills.
- Make the most of a well-maintained garden area that provides a peaceful setting amidst the natural beauty of Tuscany.
- Utilize an outdoor dining space ideal for savoring local cuisine under the sun or stars.
- Take advantage of a swimming pool, whether shared or private, to cool off during warm summer days.
- Relax in a shaded gazebo or pergola, offering comfort while appreciating the outdoor surroundings.
- Benefit from outdoor grilling facilities to enjoy authentic Tuscan barbecues with family and friends.
- Stroll along scenic pathways and landscaped grounds that showcase the area's natural charm and tranquility.
Top Attractions Around Siena
What attractions are nearby?
Within this charming destination, you can explore local art galleries, indulge in authentic Tuscan cuisine, or take leisurely strolls through historic streets, all just moments from your Siena vacation rental in the heart of Tuscany.
Family Activities
- Exploring Siena’s historic city center: Wander through the UNESCO World Heritage site, discovering medieval streets, piazzas, and awe-inspiring architecture that tell stories of this area's rich history.
- Visiting the Siena Cathedral: Experience the stunning Gothic design and intricate artworks within the cathedral, offering an educational and memorable outing for families in the region.
- Enjoying family-friendly outdoor activities at Piazza del Campo: Relax and play in the famous shell-shaped square, where you can partake in local events or simply soak up the lively atmosphere and scenic views.
- Participating in traditional Tuscan cooking classes: Discover authentic regional cuisine suited for all ages, making it a delightful and interactive way to immerse your family in local culture here.
Adult Activities
- Exploring Siena’s historic Piazza del Campo: You can immerse yourself in the vibrant atmosphere of this iconic square, renowned for its medieval architecture and lively markets.
- Wine tasting in the Chianti region: Indulge in renowned Tuscan wines within vineyards close to here, experiencing the region's rich viticultural heritage firsthand.
- Visiting Siena Cathedral: Admire the stunning Gothic architecture and intricate artworks within this religious monument that defines the city’s skyline.
- Enjoying a guided walking tour of Siena’s medieval streets: Discover hidden alleys, local artisan shops, and historical landmarks as you stroll through the area's well-preserved ancient center.
Other Places to Stay in Siena
Tuscany
Val d'Elsa
Colle di Val d'Elsa
Val di Chiana
Siena City Centre
Siena Historical Center
Val d'Orcia
Crete Senesi
San Gimignano
San Gimignano City Centre
Montepulciano
Siena Travel Tips
How Can You Make the Most of Your Stay?
- Explore the local cuisine: Take advantage of the region's renowned culinary scene by sampling traditional dishes at local markets and trattorias to truly embrace the area’s authentic flavors.
- Visit historic sites early in the day: Arrive at popular attractions before peak hours to enjoy a more intimate experience and avoid crowds, making your stay more relaxed.
- Stroll through scenic streets and viewpoints: Wander through cobblestone pathways and discover panoramic vistas that showcase the region's beauty, perfect for memorable photography and quiet reflection.
- Plan day trips to nearby towns: Use the area's convenient location to explore charming neighboring villages and countryside, enriching your experience beyond the city center.
Transportation Options
- Walking: Exploring the historic streets on foot allows you to fully immerse yourself in the charm and architecture of Siena, making it an ideal option for discovering this area’s hidden gems.
- Public Transit: Buses operate regularly within the region, offering a convenient and economical way to navigate between key areas and attractions here.
- Rental Cars: Renting a car provides the flexibility to explore the surrounding Tuscan countryside at your own pace, perfect for day trips from this destination.
- Taxis and Ride-Sharing: Taxis and ride-sharing services are readily available, providing a comfortable and efficient transportation method for getting around Siena and its nearby regions.
Local Customs Options
- Palio di Siena: Participating in or witnessing this historic horse race offers a unique glimpse into the area's vibrant local traditions and community spirit.
- Traditional Tuscan Cuisine: Savoring authentic dishes like pici pasta and ribollita soup allows you to experience the region's rich culinary heritage firsthand.
- Religious Celebrations: Attending local festivals, especially during the feast of the Holy Mary of Provenzano, immerses you in age-old customs cherished here.
- Artisan Craftsmanship: Exploring markets and workshops reveals the region’s dedication to handcrafted goods, reflecting its enduring artistic traditions.
Frequently Asked Questions About Siena?
1. What are the top vacation rentals in Siena?
There are a lot of options in Siena. If you plan on staying in the Siena area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Siena:
- Typical Tuscan Farmhouse, Superb View on Lucca, private garden/parking.WIFI.
- Typical Tuscan house.Great view on Lucca.Private parking/garden.WIFI
- Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
- Antica fattoria 25 km a Siena di fronte a Montalcino con piscina/lezione di cucina
- Farmhouse in the heart of the real chiantishire
- Agriturismo Humile
- Panoramic and Charming Villa with Private Garden in Tuscany
- Tenuta CorteDomina
- Typical Tuscan Country House
- Castello Banfi - Il Borgo - Relais et Chateaux
2. How many vacation rentals have private pools in Siena?
There are 2899 vacation rentals with private pools near Siena. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Siena are best for families?
If you are looking for a family-friendly vacation home in Siena, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Siena:
4. How many Rentbyowner vacation rentals are available in Siena?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 15033 in the Siena 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 Siena.
5. What is the cancellation policy for booking a vacation rental here?
Cancellation policies vary depending on the individual property listing. You should review the specific policy outlined in the rental details or contact the property owner directly to understand any fees or restrictions related to cancellations.
6. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning charges, security deposits, or service fees are typically listed in the property description. Be sure to read the entire listing or reach out to the owner for clarification before confirming your reservation.
7. How do I confirm my reservation and what is the process for checking in?
Reservation confirmation is completed through the booking platform once payment is processed. Check-in procedures, including key collection or access details, are provided by the host after booking. Be sure to communicate with the owner if you have any specific arrival requests.
8. Can I modify or extend my stay after booking?
Modifications or extensions depend on the availability and the host’s policies. Contact the property owner directly through the booking platform to request changes and confirm whether they can accommodate your plans.
9. What amenities are generally included in vacation rentals in this destination?
Properties typically offer amenities like Wi-Fi, kitchen facilities, air conditioning, and linens. For specifics on what each rental includes, review the amenities list in the property details or ask the owner directly.
Siena Top Rated Vacation Rentals
753 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Other
- Private Pool
- Fireplace/Heating
- Pool
GB £156/Night
For 7 Nights GB £1,089
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
GB £749/Night
For 7 Nights GB £5,243
3444 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Other
- Private Pool
- Hot Tub
- Fireplace/Heating
GB £390/Night
For 7 Nights GB £2,732
1076 ft²
5 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
GB £120/Night
For 7 Nights GB £843
GB £207/Night
For 7 Nights GB £1,447
GB £162/Night
For 7 Nights GB £1,133
2422 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Fireplace/Heating
- Pool
- Ocean View
GB £343/Night
For 7 Nights GB £2,404
1076 ft²
5 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
GB £428/Night
For 7 Nights GB £2,994
