Lodging Image

Calzaiolo Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Calzaiolo vacation 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, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is ￥36,507
￥40,869 total
includes taxes & fees
Oct 7 - Oct 8
Villa il Fedino
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

2. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ￥23,687
￥26,410 total
includes taxes & fees
Oct 6 - Oct 7
Palazzo Pacini
A table with breakfast items and a view of rolling hills.

3. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is ￥11,805
￥13,341 total
includes taxes & fees
Oct 6 - Oct 7
Chianti Village Morrocco
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

4. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (87 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is ￥18,412
￥20,964 total
includes taxes & fees
Oct 6 - Oct 7
B&B La Fonte del Machiavelli
An open wooden door leading to an outdoor patio with a table and chairs.

5. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is ￥16,677
￥23,675 total
includes taxes & fees
Oct 8 - Oct 9
Palazzo al Torrione 2
A view from a window overlooking a rural landscape with fields and a distant mountain range.

6. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is ￥19,471
￥22,306 total
includes taxes & fees
Oct 20 - Oct 21
B&B Palazzo Tortoli
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

7. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (90 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is ￥7,841
￥9,158 total
includes taxes & fees
Oct 7 - Oct 8
Camping Boschetto Di Piemma
A dining area with a table set for two, featuring a view of greenery through a window.

8. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (39 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is ￥22,823
￥25,817 total
includes taxes & fees
Oct 8 - Oct 9
La Locanda di Pietracupa
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, (80 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 ￥43,026
￥48,039 total
includes taxes & fees
Oct 16 - Oct 17
Terre di Baccio
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

10. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (268 reviews)
"Very friendly and clean."
United States
Mohamed
The price is ￥20,579
￥23,170 total
includes taxes & fees
Nov 2 - Nov 3
Relais Villa Olmo
A water park with a pool, slides, and a wooden deck area.

11. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (108 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is ￥7,097
￥8,340 total
includes taxes & fees
Oct 7 - Oct 8
hu Firenze Certosa camping in town
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

12. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (170 reviews)
"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."
United Kingdom
Jacqui
The price is ￥12,036
￥15,372 total
includes taxes & fees
Nov 1 - Nov 2
I Parigi Corbinelli
A swimming pool with lounge chairs and a flag.

13. Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (267 reviews)
"Great location easy access to Firenze"
Canada
Donnie
The price is ￥9,521
￥12,960 total
includes taxes & fees
Nov 5 - Nov 6
Fattoria il Milione Agriturismo
A modern house with glass walls and a patio area.

14. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (93 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 ￥32,422
￥37,796 total
includes taxes & fees
Oct 21 - Oct 22
Marignolle Relais and Charme
A pool area with a water slide and a stage for performances.

15. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (333 reviews)
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."
United Kingdom
Katie
Hu Norcenni Girasole Village
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

16. Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca
Historic Centre of Florence
9.2 out of 10, Wonderful, (842 reviews)
"Beautiful rooms and great location"
Canada
Taylor
The price is ￥39,466
￥45,899 total
includes taxes & fees
Nov 1 - Nov 2
Palazzo Alfieri Residenza d’epoca
Reception

17. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (131 reviews)
"Book this for our honeymoon and will definitely come back"
Canada
Kerby
The price is ￥30,848
￥36,065 total
includes taxes & fees
Nov 1 - Nov 2
Teatro Luxury Apartments Firenze - Starhotels Collezione
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

18. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (75 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is ￥16,378
￥18,282 total
includes taxes & fees
Oct 29 - Oct 30
Relais Villa Belvedere
A market with a sign reading "BAR IL POGGETTO MARKET".

19. Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (80 reviews)
"Nice property, very reasonable price"
United States
Alex
The price is ￥6,832
￥7,781 total
includes taxes & fees
Nov 1 - Nov 2
Camping Village Il Poggetto.
Room

20. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.2 out of 10, Wonderful, (338 reviews)
"Great location easy to park car with car service they offer"
United States
Joanna
The price is ￥17,442
￥21,673 total
includes taxes & fees
Nov 4 - Nov 5
La Torre Del Cestello
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Calzaiolo Hotel Reviews

The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

10/10 Excellent
"The overall concept of the hub is excellent and really different from other hotels and properties. The staff need to be more engaging as well as the house keeping needs to be a little better .. such as when they come to clean the room and change towels they also need to make sure to fill other pantry items such as creamers coffee pods etc. Also you need to look into some exhaust issues in the showers as it all fogs up and the drains need to be cleared on regular basis too much clogging"
Kushwant 3-night trip
Posted less than an hour ago
The Social Hub Florence Belfiore

Find out more about Calzaiolo

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

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

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

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.