Calzaiolo Vacation Rentals from $50: Search Short-Term Rentals

Q: 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.

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Our top choices for Calzaiolo vacation rentals

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

1. Villa il Fedino

San Casciano in Val di Pesa

Lori

$226 nightly

Oct 8 - Oct 9

Total with taxes and fees

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

2. Palazzo Pacini

Colle di Val d'Elsa

John

$137 nightly

Nov 3 - Nov 4

Total with taxes and fees

A table with breakfast items and a view of rolling hills.

3. Chianti Village Morrocco

Tavarnelle Val di Pesa

Winonah

$75 nightly

Oct 6 - Oct 7

Total with taxes and fees

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

4. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

James

$117 nightly

Oct 6 - Oct 7

Total with taxes and fees

An open wooden door leading to an outdoor patio with a table and chairs.

5. Palazzo al Torrione 2

San Gimignano City Centre

Angela

$131 nightly

Oct 30 - Oct 31

Total with taxes and fees

A view from a window overlooking a rural landscape with fields and a distant mountain range.

6. B&B Palazzo Tortoli

San Gimignano City Centre

Harold

$127 nightly

Oct 18 - Oct 19

Total with taxes and fees

A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

7. Camping Boschetto Di Piemma

San Gimignano

Anonymous traveler

$47 nightly

Oct 7 - Oct 8

Total with taxes and fees

A dining area with a table set for two, featuring a view of greenery through a window.

8. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

$151 nightly

Nov 5 - Nov 6

Total with taxes and fees

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

9. Terre di Baccio

Greve in Chianti

Gage

$283 nightly

Oct 15 - Oct 16

Total with taxes and fees

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

10. Relais Villa Olmo

Impruneta

Mohamed

$126 nightly

Oct 21 - Oct 22

Total with taxes and fees

A water park with a pool, slides, and a wooden deck area.

11. hu Firenze Certosa camping in town

Impruneta

Jessica

$43 nightly

Oct 6 - Oct 7

Total with taxes and fees

A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

12. I Parigi Corbinelli

Florence

Jacqui

$76 nightly

Nov 1 - Nov 2

Total with taxes and fees

A swimming pool with lounge chairs and a flag.

13. Fattoria il Milione Agriturismo

Florence

Donnie

$54 nightly

Nov 5 - Nov 6

Total with taxes and fees

A modern house with glass walls and a patio area.

14. Marignolle Relais and Charme

Florence

Honey

$194 nightly

Nov 5 - Nov 6

Total with taxes and fees

A pool area with a water slide and a stage for performances.

15. Hu Norcenni Girasole Village

Figline e Incisa Valdarno

Katie

A terrace with outdoor seating, a view of the city, and a clock tower in the background.

16. Palazzo Alfieri Residenza d’epoca

Historic Centre of Florence

Taylor

$266 nightly

Nov 5 - Nov 6

Total with taxes and fees

17. Teatro Luxury Apartments Firenze - Starhotels Collezione

Historic Centre of Florence

Kerby

$195 nightly

Nov 1 - Nov 2

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

18. Relais Villa Belvedere

Figline e Incisa Valdarno

Janet

$100 nightly

Oct 18 - Oct 19

Total with taxes and fees

A market with a sign reading "BAR IL POGGETTO MARKET".

19. Camping Village Il Poggetto.

Rignano sull'Arno

Alex

$43 nightly

Nov 1 - Nov 2

Total with taxes and fees

20. La Torre Del Cestello

Historic Centre of Florence

Joanna

$111 nightly

Nov 4 - Nov 5

Total with taxes and fees

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Top Calzaiolo Hotel Reviews

c-hotels Ambasciatori

8/10 Good

"The area does not feel so safe at night. A lot of by standers on the sidewalk."

Bernini Palace

10/10 Excellent

"We loved everything about this hotel. They had world class service from morning to night. We had a wonderful introduction to the hotel and a personal escort to our room. The breakfast was lovely, with a nice selection of premium products, and a beautiful dining room with china. We highly recommend Hotel Bernini, it was the perfect hotel in a perfect location."

Hotel Albani Firenze

8/10 Good

"The room was clean, however the shutters were difficult to open leaving the room dark for the duration of our stay. The staff were ok we didn't really have much to do with them Breakfast was ok, however some fresh cut fruit rather than a fruit salad would have been nicer. Good selection of hot and cold foods. The air-conditioning is excellent it kept the room comfortable for our whole stay. We loved that there was an old fashioned key to open our room door. Overall it was a good stay."

Art Hotel Villa Agape

8/10 Good

"Beautiful property. The restaurant and breakfast are great. Rooms are cozy and quaint. To consider there shuttle is only to get you to the bridge and walk or cab from there to wherever you’re going. It’s the distance from places such as stores restaurants be prepared for any extra needs of expenses such as bottled water or snacks. Make sure the wine card you prepay for self serve you return for credit it’s $10 a glass and it’s about three sips. But beautiful place and great for quiet and privacy."

IQ Hotel Firenze

10/10 Excellent

"Laundry was very important while traveling. Room was clean, hotel was clean and well kept. Breakfast was good. The staff was the best part, the hotel had kind and helpful persons at all points of contact. Front desk was staffed with kind and welcoming people. The pool bar we encountered 2 different people during our 3 day stay. Both were exceptional. Daniel and a woman whose name I don't recall but started with a V. are the kind of employees who reflect very well on your facility and I hope they are recognized as such."

Find out more about Calzaiolo

Everything you need to know about Calzaiolo vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Calzaiolo vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Calzaiolo vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Calzaiolo vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Calzaiolo. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Calzaiolo in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $50 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Calzaiolo rentals

At Expedia, we put the best Calzaiolo vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Calzaiolo rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Calzaiolo vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Calzaiolo. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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Check prices for these dates

Our top choices for Calzaiolo vacation rentals

1. Villa il Fedino

2. Palazzo Pacini

3. Chianti Village Morrocco

4. B&B La Fonte del Machiavelli

5. Palazzo al Torrione 2

6. B&B Palazzo Tortoli

7. Camping Boschetto Di Piemma

8. La Locanda di Pietracupa

9. Terre di Baccio

10. Relais Villa Olmo

11. hu Firenze Certosa camping in town

12. I Parigi Corbinelli

13. Fattoria il Milione Agriturismo

14. Marignolle Relais and Charme

15. Hu Norcenni Girasole Village

16. Palazzo Alfieri Residenza d’epoca

17. Teatro Luxury Apartments Firenze - Starhotels Collezione

18. Relais Villa Belvedere

19. Camping Village Il Poggetto.

20. La Torre Del Cestello

Find vacation rentals that suit your style

Top Calzaiolo Hotel Reviews

c-hotels Ambasciatori

Grand Hotel Baglioni

Hotel Paris

Bernini Palace

Hotel Albani Firenze

The Social Hub Florence Belfiore

Radisson Blu Hotel, Florence

Art Hotel Villa Agape

IQ Hotel Firenze

Find out more about Calzaiolo

Frequently asked questions

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