San Filippo Holiday Rentals

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Our top choices for San Filippo holiday rentals

Residence in Barberino Tavarnelle

Villa San Filippo
4.0 star property
8.4 out of 10, Very good, (40 reviews)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
Villa San Filippo
The price is AU$135
includes taxes & fees
11 Mar - 12 Mar
Blue Room 'Borghetto San Filippo' with Shared Pool, Wi-Fi and Air Conditioning
The price is AU$122
includes taxes & fees
11 Mar - 12 Mar
Yellow Room 'Borghetto San Filippo' with Shared Pool, Wi-Fi and Air Conditioning
The price is AU$122
includes taxes & fees
11 Mar - 12 Mar
Green Room 'Borghetto San Filippo' with Shared Pool, Wi-Fi and Air Conditioning
The price is AU$107
includes taxes & fees
11 Mar - 12 Mar
Lilla Room 'Borghetto San Filippo' with Shared Pool, Wi-Fi & Air Conditioning

Townhouse in San Casciano in Val di Pesa

Villa il Fedino
9.6 out of 10, Exceptional, (99 reviews)
"Great people, great location great service"
Canada
James
The price is AU$212
includes taxes & fees
14 Mar - 15 Mar
Villa il Fedino

Townhouse in Ravacciano

Domus il Palio B&B
9.2 out of 10, Wonderful, (83 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
Domus il Palio B&B

Townhouse in Florence

Marignolle Relais and Charme
9.2 out of 10, Wonderful, (91 reviews)
"I stayed here June 2025 and was most delighted in the property and staff. They were incredibly kind and accommodating and the property is beautiful. Would stay here again!"
Canada
Shelley
Marignolle Relais and Charme

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (429 reviews)
"Nice place!"
United States
Pavel
The price is AU$165
includes taxes & fees
11 Mar - 12 Mar
Siena Vip

Townhouse in Siena City Centre

B&B Il Corso
9.8 out of 10, Exceptional, (194 reviews)
"Great location"
United Kingdom
Mina
B&B Il Corso

Residence in Siena City Centre

La Terrazza Sul Campo Rooming House
9.8 out of 10, Exceptional, (239 reviews)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House

Apartment in Siena City Centre

Regis Condo
9.4 out of 10, Exceptional, (68 reviews)
"Adequate basic clean room in a beautiful area."
United States
Margaret
The price is AU$359
includes taxes & fees
2 Apr - 3 Apr
Regis Condo

Townhouse in Siena City Centre

PALAZZO DEL PAPA
9.6 out of 10, Exceptional, (97 reviews)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is AU$238
includes taxes & fees
13 Mar - 14 Mar
PALAZZO DEL PAPA

Residence in Colle di Val d'Elsa

Palazzo Pacini
9.8 out of 10, Exceptional, (99 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is AU$236
includes taxes & fees
12 Mar - 13 Mar
Palazzo Pacini

Apartment in Siena

ApartHotel Anghel
8.4 out of 10, Very good, (335 reviews)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
ApartHotel Anghel

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is AU$185
includes taxes & fees
16 Mar - 17 Mar
Palazzo al Torrione 2

Townhouse in Gambassi Terme

Tenuta Sant'Ilario
9.4 out of 10, Exceptional, (34 reviews)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario

Camping in San Gimignano

Camping Boschetto Di Piemma
3.0 star property
8.8 out of 10, Excellent, (85 reviews)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."
United States
Martha
Camping Boschetto Di Piemma

Residence in Barberino Tavarnelle

Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco

Residence in Impruneta

Relais Villa Olmo
9.4 out of 10, Exceptional, (229 reviews)
"Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!"
United States
Cameron
Relais Villa Olmo
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.

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Top San Filippo Hotel Reviews

Find out more about San Filippo

Everything you need to know about San Filippo holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Filippo holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Filippo holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

San Filippo holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Filippo. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Filippo holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Filippo holiday rentals we have selected for you start as low as AU$115 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on San Filippo rentals

At Expedia, we put the best San Filippo holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top San Filippo rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Filippo holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Filippo. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in San Filippo?

Yes, there are holiday rentals close to the most popular sights in San Filippo, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that San Filippo has to offer?

Borgo Argiano: This holiday home rental outside of San Filippo is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. You can relax into your holiday with a garden and a library.

How many holiday rentals will I find in San Filippo?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your San Filippo stay.

What’s there to see and do in San Filippo?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Sentierelsa Trail. Casa Sola - Chianti Winery and Isole e Olena Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in San Filippo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Filippo. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family getaway.