A vineyard with rows of grapevines, a clear sky, and distant mountains.

Calzaiolo Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Calzaiolo holiday rentals

An arched entrance with a lantern above, flanked by two potted plants.

1. 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 S$230
includes taxes & fees
23 Nov - 24 Nov
Villa il Fedino
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

2. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (274 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is S$133
includes taxes & fees
29 Nov - 30 Nov
Relais Villa Olmo - Place of Charme
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

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, (93 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is S$168
includes taxes & fees
3 Nov - 4 Nov
B&B La Fonte del Machiavelli
A water park with a pool, slides, and a wooden deck area.

4. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (123 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is S$72
includes taxes & fees
3 Nov - 4 Nov
hu Firenze Certosa camping in town
A modern house with glass walls and a patio area.

5. 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 S$201
includes taxes & fees
22 Nov - 23 Nov
Marignolle Relais and Charme
A hotel room with a bed, a bedside table, a heater, a mirror, and a bathroom with a sink.

6. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,798 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is S$80
includes taxes & fees
2 Dec - 3 Dec
Hu Firenze Camping In Town
A dining area with a table set for two, featuring a view of greenery through a window.

7. 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 S$209
includes taxes & fees
7 Nov - 8 Nov
La Locanda di Pietracupa
A stone building with a wooden door, a grill outside, and a stone wall.

8. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is S$495
includes taxes & fees
10 Nov - 11 Nov
Teranga in Chianti - Parking & Garden 3 BR
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

9. 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 S$386
includes taxes & fees
6 Nov - 7 Nov
Terre di Baccio
A room with a dining table, a vase of flowers, a lamp, and a view of a historic building through a window.

10. 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 S$204
includes taxes & fees
17 Nov - 18 Nov
Mamo Florence - Le Farine Della Signoria Apartments
A narrow stone corridor with a brick floor, a metal gate, and a brick archway leading to another room.

11. Il Frantoio delle Grazie

Il Frantoio delle Grazie
Florence
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place, picturesque country setting. Next time we stay here we will consider renting a car. The walk to the bus or train is only about a mile and it wasn’t too hot out. The kids really enjoyed the pool."
United States
Emily
Il Frantoio delle Grazie
A terrace with a table set for breakfast, a chair, and a large umbrella.

12. 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 S$168
includes taxes & fees
3 Dec - 4 Dec
Villa La Stella - Casa per Ferie
An open wooden door leading to an outdoor patio with a table and chairs.

13. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is S$163
includes taxes & fees
8 Nov - 9 Nov
Palazzo al Torrione 2
A balcony with a glass table, white curtains, and a bottle of champagne.

14. 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 S$125
includes taxes & fees
24 Nov - 25 Nov
Dimora Bandinelli Firenze
A modern bedroom with a wooden ceiling, a bed with a white headboard, a beige sofa, and a glass-enclosed shower area with marble walls.

15. Residenza La Musa Amarcord

Residenza La Musa Amarcord
Historic Centre of Florence
10.0 out of 10, Exceptional, (181 reviews)
"The staff was super friendly and helped us with recommendations, acquiring a taxi, and booking dinner reservations! The room was very clean and had lovely Firenze charm. Definitely would stay again."
United States
Lauren
The price is S$146
includes taxes & fees
18 Nov - 19 Nov
Residenza La Musa Amarcord
A rooftop pool with a clear view of historic buildings and mountains in the background.

16. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (152 reviews)
"Great property!"
United States
Jahzier
The price is S$260
includes taxes & fees
8 Nov - 9 Nov
Teatro Luxury Apartments Firenze - Starhotels Collezione
An open balcony with a table and chairs, a view of a tiled roof, and a door leading to the interior.

17. Bob W Florence Ponte Vecchio

Bob W Florence Ponte Vecchio
Historic Centre of Florence
9.0 out of 10, Wonderful, (281 reviews)
"Great location"
United States
Hatem
The price is S$100
includes taxes & fees
1 Dec - 2 Dec
Bob W Florence Ponte Vecchio
A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

18. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (891 reviews)
"The people were all extremely nice and helpful, location was amazing, exactly what we were after having never been to Florence !!"
United States
David
The price is S$171
includes taxes & fees
17 Nov - 18 Nov
Relais Piazza Signoria
An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs along the side.

19. Forte16 View & Spa

Forte16 View & Spa
Santissima Annunziata
9.6 out of 10, Exceptional, (1,040 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 S$162
includes taxes & fees
1 Dec - 2 Dec
Forte16 View & Spa
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 Calzaiolo Hotel Reviews

Hotel Albani Firenze

Hotel Albani Firenze

8/10 Good
"A lovely old hotel. We were upgraded to a large suite. As the seasons were changing, the cooling system was no longer functioning and it was very stuffy. Its location close to the main train station meant that it was very noisy all night and our window was very close to the street with loud talking and loud cars all night long. Other than that, I would say that the accommodations were superior. The breakfast was very good with high quality offerings and a variety of items from which to choose."
Richard 1-night trip
Posted 2 hours ago
Hotel Albani Firenze

Frequently asked questions

Can I find holiday rentals in Calzaiolo?

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

Villa La Stella - Casa per Ferie: This holiday home rental outside of Calzaiolo 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’s there to see and do in Calzaiolo?

While exploring the area, visit family-friendly sights like Chianti Observatory, or get outside and enjoy nature at Boboli Gardens. Other popular places to visit in the area include Piazza di Santa Maria Novella and Piazza del Duomo.

What’s a holiday rental in Calzaiolo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Calzaiolo. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.