San Polo in Chianti Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for San Polo in Chianti holiday rentals

A villa with multiple bedrooms, a swimming pool, and a garden.

1. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (277 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is HK$732
HK$831 total
includes taxes & fees
22 Nov - 23 Nov
Relais Villa Olmo - Place of Charme
A swimming pool with people enjoying the water, a wooden deck, and a covered seating area.

2. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (128 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is HK$371
HK$435 total
includes taxes & fees
16 Nov - 17 Nov
hu Firenze Certosa camping in town
A pool area with a view of rolling hills and a clear sky.

3. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is HK$896
HK$1,020 total
includes taxes & fees
16 Nov - 17 Nov
B&B La Fonte del Machiavelli
An outdoor dining area with multiple tables and chairs, surrounded by plants and hanging lights.

4. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,809 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is HK$398
HK$498 total
includes taxes & fees
22 Nov - 23 Nov
Hu Firenze Camping In Town
A stone building with a covered patio, a table with chairs, and a hanging plant.

5. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is HK$2,094
HK$2,338 total
includes taxes & fees
28 Nov - 29 Nov
Terre di Baccio
A rural landscape with a house surrounded by lush greenery and a small pool.

6. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (94 reviews)
"The Marignolle Relais & Charme is absolutely gorgeous. The rooms are beautifully decorated and everything is so clean. The grounds are well maintained and the pool area is stunning. We loved our two day stay and heartily recommend it. Stay here you’ll love it!!!"
Canada
Honey
The price is HK$1,004
HK$1,209 total
includes taxes & fees
9 Dec - 10 Dec
Marignolle Relais and Charme
An arched entrance with a lantern above, flanked by two potted plants.

7. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is HK$1,234
HK$1,392 total
includes taxes & fees
25 Nov - 26 Nov
Villa il Fedino
A swimming pool with clear blue water, surrounded by tall trees and a stone patio with lounge chairs.

8. Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (284 reviews)
"Great location for a Tuscany experience ."
United States
Bond
The price is HK$453
HK$620 total
includes taxes & fees
16 Nov - 17 Nov
Fattoria il Milione Agriturismo
A large, multi-story building surrounded by lush greenery and trees.

9. Villa La Stella - Casa per Ferie

Villa La Stella - Casa per Ferie
Le Cure
8.6 out of 10, Excellent, (270 reviews)
"Great location with a beautiful view."
United States
Erin
The price is HK$874
HK$1,031 total
includes taxes & fees
29 Nov - 30 Nov
Villa La Stella - Casa per Ferie
An outdoor patio with a table, chairs, and a view of a landscape.

10. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Toscana
9.8 out of 10, Exceptional, (83 reviews)
"The hostess Sonia was fabulous."
United States
Kim
The price is HK$872
HK$1,192 total
includes taxes & fees
16 Nov - 17 Nov
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
A dining area with a table set for two, featuring a view of greenery through a window.

11. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is HK$1,120
HK$1,267 total
includes taxes & fees
21 Nov - 22 Nov
La Locanda di Pietracupa
A room with a dining table, a vase of flowers, a lamp, and a view of a historic building through a window.

12. Mamo Florence - Le Farine Della Signoria Apartments

Mamo Florence - Le Farine Della Signoria Apartments
Historic Centre of Florence
8.8 out of 10, Excellent, (11 reviews)
"Great host, amazing location!"
United States
raxshaaz
The price is HK$582
HK$1,306 total
includes taxes & fees
26 Nov - 27 Nov
Mamo Florence - Le Farine Della Signoria Apartments
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

13. Palazzo Alfieri Residenza d’epoca - Place of Charme

Palazzo Alfieri Residenza d’epoca - Place of Charme
Historic Centre of Florence
9.2 out of 10, Wonderful, (874 reviews)
"This is an excellent hotel very near the historic area. They offer a wonderful breakfast."
United States
robert
The price is HK$1,134
HK$1,369 total
includes taxes & fees
16 Nov - 17 Nov
Palazzo Alfieri Residenza d’epoca - Place of Charme
A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

14. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (899 reviews)
"Amazing location lots of space and very comfortable. Would go back for sure"
Canada
Paul
The price is HK$797
HK$980 total
includes taxes & fees
3 Dec - 4 Dec
Relais Piazza Signoria
A hotel room with a large bed, a nightstand with a lamp, an air conditioner, a wardrobe, and a framed picture on the wall.

15. Quadra Key Easy Home In Florence

Quadra Key Easy Home In Florence
Florence
8.2 out of 10, Very good, (743 reviews)
"Fantastic location "
Malaysia
Mohd Mydin
The price is HK$694
HK$867 total
includes taxes & fees
22 Nov - 23 Nov
Quadra Key Easy Home In Florence
A rooftop pool with a cityscape view at sunset.

16. Forte16 View & Spa

Forte16 View & Spa
Santissima Annunziata
9.6 out of 10, Exceptional, (1,046 reviews)
"Great front desk Great perfect location Great room Great spa Great ammenties Awesome views Perfect for long stays."
United States
JENNIFER
The price is HK$793
HK$976 total
includes taxes & fees
1 Dec - 2 Dec
Forte16 View & Spa
A restaurant with a rustic interior, featuring exposed brick walls, wooden beams, and a long counter with blue upholstered chairs.

17. Residenza La Musa Amarcord

Residenza La Musa Amarcord
Historic Centre of Florence
10.0 out of 10, Exceptional, (185 reviews)
"Beautiful room and property"
United States
Amy
The price is HK$634
HK$801 total
includes taxes & fees
18 Nov - 19 Nov
Residenza La Musa Amarcord
A historic building with ornate iron gates, potted plants, and a visible staircase leading to an upper floor.

18. Signoria Collection

Signoria Collection
Historic Centre of Florence
9.8 out of 10, Exceptional, (24 reviews)
"The property location was ideal for visiting the landmarks, churches and museums."
United States
SCOTT
The price is HK$821
HK$1,007 total
includes taxes & fees
1 Dec - 2 Dec
Signoria Collection
A hotel room with a large bed, a sofa, a dining table, and a chandelier.

19. Tornabuoni Suites Collection

Tornabuoni Suites Collection
Historic Centre of Florence
9.6 out of 10, Exceptional, (353 reviews)
"Great location! Room was spacious and comfortable! Would stay again!"
United States
Bethany
The price is HK$1,006
HK$1,384 total
includes taxes & fees
13 Dec - 14 Dec
Tornabuoni Suites Collection
A sunlit room with a glass table, white curtains, a white sofa, and a view of greenery and buildings.

20. Dimora Bandinelli Firenze

Dimora Bandinelli Firenze
Oltrarno
9.8 out of 10, Exceptional, (191 reviews)
"We had a wonderful experience with hotel owners. Great hospitality, beautiful room, perfect location. Breakfast included, good selection of breakfast options. Highly recommend this place if you’re visiting Florence"
United States
Marat
The price is HK$631
HK$798 total
includes taxes & fees
22 Nov - 23 Nov
Dimora Bandinelli Firenze
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.
View all properties

Find holiday rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
Apartment image
Apartments
Apartments

Top San Polo in Chianti Hotel Reviews

A terrace with a table and chairs, potted plants, and a view of a historic tower.
Hotel Calimala Florence

Hotel Calimala Florence

Hotel Calimala Florence
Historic Centre of Florence

8/10 Good

The hotel is generally good but I was very bothered by the music and noise from a restaurant downstairs on the first night during my stay. I asked to change the room and the staff was helpful to arrange a quiet room for me on the next day. You may want to double check with the hotel on this point before you reserve if you are a light sleeper as I am.
Hong Kong SAR China
Jingyang
Reviewed February 7, 2025
Hotel Calimala Florence

Find out more about San Polo in Chianti

Search for holiday rentals in San Polo in Chianti on Expedia! You can easily find your home rentals, villas, holiday apartments in San Polo in Chianti using one of the methods below:

  • View our selection of featured holiday rentals in San Polo in Chianti
  • Use the map to find apartments and other holiday homes in the San Polo in Chianti neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in San Polo in Chianti while they last

Look no further and take a look at our great range of rental properties in San Polo in Chianti!

Frequently Asked Questions

Can I find a holiday rental in San Polo in Chianti?

Yes, there are holiday rentals close to the most popular sights in San Polo in Chianti, 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 Polo in Chianti has to offer?

Villa La Stella - Casa per Ferie: This holiday home rental outside of San Polo in Chianti is located near the airport, and has a garden, a library and air conditioning to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

What can I see and do in San Polo in Chianti?

Explore the area and family-friendly sights such as Villa Medicea di Lilliano - Malenchini, or get out into nature at a spot like Arno River. While in the area, you can also visit popular places such as Piazza del Duomo and Piazza di Santa Maria Novella.

What are holiday rentals like in San Polo in Chianti?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in San Polo in Chianti. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.