Calzaiolo Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Calzaiolo vacation rentals

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is CA $182
CA $208 total
includes taxes & fees
May 5 - May 6
Antico Borgo il Cardino

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is CA $155
CA $174 total
includes taxes & fees
May 4 - May 5
Palazzo Pacini

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (35 reviews)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
The price is CA $176
CA $199 total
includes taxes & fees
May 18 - May 19
Tenuta Sant'Ilario

DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (1 review)
"Kjempefint rom, nydelig utsikt og hyggelig vertsskap. Anbefales. "
Norway
Karen
The price is CA $122
CA $138 total
includes taxes & fees
May 19 - May 20
DomuS Miniato

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.4 out of 10, Exceptional, (36 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is CA $218
CA $247 total
includes taxes & fees
May 2 - May 3
La Locanda di Pietracupa

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is CA $2,063
CA $2,276 total
includes taxes & fees
May 11 - May 12
Terre di Baccio

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is CA $280
CA $315 total
includes taxes & fees
Apr 29 - Apr 30
Villa il Fedino

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.2 out of 10, Very good, (68 reviews)
"Wonderful staff and great amenities!"
Canada
Chenjin
The price is CA $63
CA $74 total
includes taxes & fees
May 6 - May 7
hu Firenze Certosa camping in town

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.4 out of 10, Very good, (238 reviews)
"The accommodations are rustic, clean and comfortable, and the grounds are beautiful. The on-site restaurant was very good too. Would definitely stay there again."
United States
Antone
The price is CA $109
CA $143 total
includes taxes & fees
May 3 - May 4
Fattoria il Milione Agriturismo

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (165 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is CA $131
CA $163 total
includes taxes & fees
May 3 - May 4
I Parigi Corbinelli

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, (82 reviews)
"The hostess Sonia was fabulous."
United States
Kim
country house with garden ,pool,children's play area ,Tuscany,15 from Florence

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (238 reviews)
"We had an excellent stay, the staff is very friendly, stunning location and easy but windy road into Florence "
United States
Juliana
The price is CA $252
CA $282 total
includes taxes & fees
Apr 30 - May 1
Relais Villa Olmo

Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,646 reviews)
"Place is beautiful, staff friendly and a very nice restaurant "
United States
Ricardo
The price is CA $102
CA $123 total
includes taxes & fees
Apr 30 - May 1
Hu Firenze Camping In Town

Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (68 reviews)
"Pet friendly and clean"
United Kingdom
Nancy
The price is CA $91
CA $105 total
includes taxes & fees
May 12 - May 13
Camping Village Il Poggetto.

Camping Village Panoramico Fiesole

Camping Village Panoramico Fiesole
3.0 star property
Fiesole
8.4 out of 10, Very good, (122 reviews)
"A wonderful two night stay in a cabina near the restaurant. Really nice to come back to after a long day in the city. "
United Kingdom
Dave
The price is CA $68
CA $81 total
includes taxes & fees
May 3 - May 4
Camping Village Panoramico Fiesole

Home in Florence

Home in Florence
Historic Centre of Florence
9.0 out of 10, Wonderful, (74 reviews)
"Lovely room and the people running the place were friendly and efficient "
United Kingdom
Thomas
The price is CA $230
CA $272 total
includes taxes & fees
May 11 - May 12
Home in Florence

Sapiti Modern by Mmega

Sapiti Modern by Mmega
Historic Centre of Florence
9.4 out of 10, Exceptional, (11 reviews)
"The room was spacious for 5 of us. Nice, well equipped kitchen. Room was very clean and communication was good leading up to our stay and during. We had a miscommunication with check in time, but they were very quick to get to us (5 minutes) so all was well. Neighbourhood was great, close to everything we wanted to see and a couple great restaurants and yummy gelato place. We’d love to stay here again. "
Canada
Jeremy
The price is CA $128
CA $288 total
includes taxes & fees
May 11 - May 12
Sapiti Modern by Mmega

Appartamenti degli Artisti by Mmega

Appartamenti degli Artisti by Mmega
Historic Centre of Florence
8.6 out of 10, Excellent, (36 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Would definitely stay again"
United States
Diana
The price is CA $129
CA $288 total
includes taxes & fees
May 28 - May 29
Appartamenti degli Artisti by Mmega

B&B Mia Palace

B&B Mia Palace
Oltrarno
8.4 out of 10, Very good, (117 reviews)
"Room was clean, great position to the center. Awesome and kind lady during breakfast! 😇"
United Kingdom
Petr
The price is CA $185
CA $223 total
includes taxes & fees
Apr 30 - May 1
B&B Mia Palace

Palazzo Lombardo

Palazzo Lombardo
Santissima Annunziata
8.8 out of 10, Excellent, (153 reviews)
"nice location"
United States
Octavio
The price is CA $128
CA $160 total
includes taxes & fees
Apr 30 - May 1
Palazzo Lombardo
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.
Save an average of 15% on thousands of hotels when you're signed in

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 Uffizi Gallery and Piazza di Santa Maria Novella.

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.