San Filippo holiday rentals

We found 1,833 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in San Filippo that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a garden. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – San Filippo

Showing deals for:13 Nov - 20 Nov

Interior
Interior
Outdoor dining
Pool
Exceptional
(42 reviews)

VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.

Certaldo

8% off
AU$10,564
for 7 nights, 1 villa
AU$1,509 per night
includes taxes & fees
VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.
Living area
Pool
Living area
Private kitchen
Exceptional
(5 reviews)

Private villa in the heart of chianti with view of siena

Castellina in Chianti

5% off
AU$5,037
for 7 nights, 1 villa
AU$720 per night
includes taxes & fees
Private villa in the heart of chianti with view of siena
Pool
House and loggia, seen from the garden
Loggia with table dressed for family dinner
View from the kitchen
Exceptional
(58 reviews)

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

Castellina in Chianti

9% off
AU$6,722
for 7 nights, 1 villa
AU$960 per night
includes taxes & fees
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Exterior
Pool
Interior
Property grounds
Exceptional
(120 reviews)

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

San Gimignano

5% off
AU$7,114
for 7 nights, 1 villa
AU$1,016 per night
includes taxes & fees
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Interior
Property grounds
Exterior
Interior
Exceptional
(8 reviews)

The Bartaline hut

Greve in Chianti

9% off
AU$1,433
for 7 nights, 1 home
AU$205 per night
includes taxes & fees
The Bartaline hut
Interior
Exterior detail
Interior
Terrace/patio
Wonderful
(11 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti

13% off
AU$1,969
for 7 nights, 1 home
AU$281 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena
Property grounds
pool
Outdoor dining
Exterior
Exceptional
(119 reviews)

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

San Gimignano

5% off
AU$8,175
for 7 nights, 1 villa
AU$1,168 per night
includes taxes & fees
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Interior
Property grounds
Pool
Living area
Exceptional
(81 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
AU$907
for 7 nights, 1 home
AU$130 per night
includes taxes & fees
Villa with large garden in the Chianti hills

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

The rustic city of San Filippo awaits you

The countryside and other outdoor surroundings create an inviting atmosphere in San Filippo. This romantic city has many special qualities. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around San Filippo

Are you hoping to find things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes San Filippo a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Castello della Paneretta (2.3 mi / 3.7 km)
  • Castello di Monsanto (2.4 mi / 3.9 km)
  • Casa Sola - Chianti Winery (2.8 mi / 4.5 km)
  • Tenuta Torciano Winery (4.6 mi / 7.5 km)
  • Buondonno Winery (5.2 mi / 8.3 km)
  • Antinori nel Chianti Classico (6 mi / 9.7 km)

Exploring the natural features in San Filippo

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, San Filippo is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Alta Val d'Elsa River Park (9.7 mi / 15.6 km)
  • Val di Merse (24.4 mi / 39.2 km)
  • Sentierelsa Trail (7.4 mi / 11.9 km)
  • Le Caldane Thermal Baths (9.6 mi / 15.4 km)
  • Chianti Sculpture Park (14 mi / 22.6 km)
  • The SottoVico Garden (3.7 mi / 6 km)

Transport to and around San Filippo

Fly into Peretola Airport (FLR), the closest airport, located 19.1 mi (30.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in San Filippo when booking a holiday rental?
When considering a holiday rental in San Filippo, Tuscany, a popular area to stay in is the charming village centre. This area boasts a delightful selection of properties, ranging from quaint apartments to traditional Tuscan villas, offering a true taste of the local lifestyle. Staying in the village centre allows easy access to several top attractions, including the stunning thermal baths, which are a popular draw for visitors seeking relaxation and rejuvenation.Additionally, the picturesque surroundings provide ample opportunities for exploration, with scenic walking trails and vineyards just a stone's throw away. The vibrant local community, with its quaint shops and eateries, enhances the experience, allowing you to savour authentic Tuscan cuisine and hospitality.
What are the top attractions in San Filippo?
In San Filippo, Tuscany, visitors can enjoy a range of attractions that highlight the region's natural beauty and historical significance. The area is renowned for its thermal baths, with the Bagni di San Filippo offering rejuvenating hot springs set amidst stunning landscapes. This natural spa is a popular spot for both relaxation and socialising, drawing visitors looking to unwind in its mineral-rich waters.The picturesque surrounding countryside is superb for leisurely walks or cycling, allowing travellers to appreciate the charming Tuscan landscapes dotted with vineyards and olive groves. Nearby, the beautiful town of Pienza, a UNESCO World Heritage site, showcases Renaissance architecture and is famous for its pecorino cheese, making it a delightful day trip from San Filippo.Additionally, the quaint village itself features traditional Tuscan architecture and local eateries where guests can savour authentic regional cuisine.
Are all fees included in the San Filippo holiday homes prices shown on Stayz?
Stayz 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.
Are there any San Filippo holiday homes with parking?
Stayz offers a wide selection of holiday homes in San Filippo with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for San Filippo holiday homes?
You can find great discounts on holiday homes in San Filippo on Stayz, 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 change or cancel my San Filippo holiday home booking on Stayz?
To find San Filippo holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in San Filippo?
A long-stay holiday home in San Filippo is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a San Filippo holiday home?
Book your San Filippo holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in San Filippo?
Prices for holiday homes in San Filippo 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in San Filippo to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.