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

Calzaiolo Vacation Rentals

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Our top choices for Calzaiolo vacation rentals

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 CA $223
CA $252 total
includes taxes & fees
Nov 28 - Nov 29
Villa il Fedino

2. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (275 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is CA $127
CA $144 total
includes taxes & fees
Nov 23 - Nov 24
Relais Villa Olmo - Place of Charme

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 CA $162
CA $185 total
includes taxes & fees
Nov 5 - Nov 6
B&B La Fonte del Machiavelli

4. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (125 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is CA $67
CA $79 total
includes taxes & fees
Nov 16 - Nov 17
hu Firenze Certosa camping in town

5. 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 CA $169
CA $227 total
includes taxes & fees
Nov 5 - Nov 6
country house with garden ,pool,children's play area ,Tuscany,15 from Florence

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 CA $184
CA $221 total
includes taxes & fees
Nov 22 - Nov 23
Marignolle Relais and Charme

7. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,799 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is CA $72
CA $90 total
includes taxes & fees
Nov 22 - Nov 23
Hu Firenze Camping In Town

8. 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 CA $203
CA $229 total
includes taxes & fees
Nov 7 - Nov 8
La Locanda di Pietracupa

9. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
Teranga in Chianti - Parking & Garden 3 BR

10. 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 CA $363
CA $406 total
includes taxes & fees
Nov 6 - Nov 7
Terre di Baccio

11. 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 CA $105
CA $236 total
includes taxes & fees
Nov 26 - Nov 27
Mamo Florence - Le Farine Della Signoria Apartments

12. 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
The price is CA $149
CA $303 total
includes taxes & fees
Nov 7 - Nov 8
Il Frantoio delle Grazie

13. 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 CA $158
CA $187 total
includes taxes & fees
Nov 29 - Nov 30
Villa La Stella - Casa per Ferie

14. 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 CA $120
CA $178 total
includes taxes & fees
Nov 8 - Nov 9
Palazzo al Torrione 2

15. 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 CA $114
CA $144 total
includes taxes & fees
Nov 25 - Nov 26
Dimora Bandinelli Firenze

16. 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 CA $129
CA $160 total
includes taxes & fees
Nov 18 - Nov 19
Residenza La Musa Amarcord

17. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (154 reviews)
"Great property!"
United States
Jahzier
The price is CA $242
CA $285 total
includes taxes & fees
Nov 15 - Nov 16
Teatro Luxury Apartments Firenze - Starhotels Collezione

18. Bob W Florence Ponte Vecchio

Bob W Florence Ponte Vecchio
Historic Centre of Florence
9.0 out of 10, Wonderful, (282 reviews)
"Great location"
United States
Hatem
The price is CA $110
CA $139 total
includes taxes & fees
Nov 19 - Nov 20
Bob W Florence Ponte Vecchio

19. 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 CA $154
CA $188 total
includes taxes & fees
Nov 17 - Nov 18
Relais Piazza Signoria

20. Forte16 View & Spa

Forte16 View & Spa
Santissima Annunziata
9.6 out of 10, Exceptional, (1,041 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 CA $145
CA $178 total
includes taxes & fees
Dec 1 - Dec 2
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

Find out more about Calzaiolo

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Calzaiolo. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Calzaiolo?

Yes, there are vacation rentals close to popular attractions in Calzaiolo, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Calzaiolo?

Villa La Stella - Casa per Ferie: This vacation 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 vacation 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 vacation rental in Calzaiolo like?

A vacation rental is a private property where you can stay for short or long periods in Calzaiolo. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.