Rolling hills, vineyards, and scattered buildings in a hilly landscape.

Castelfiorentino Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Castelfiorentino vacation rentals

Holiday Home Swimming Pool

1. Apartment in Castelfiorentino with Pool

Apartment in Castelfiorentino with Pool
Castelfiorentino (FI)
9.6 out of 10, Exceptional, (14 reviews)
"An easy walk through beautiful surroundings leads you right into town or to places nearby."
United States
Anonymous traveler
Apartment in Castelfiorentino with Pool
An outdoor dining area with a table set for breakfast, surrounded by greenery and a flowering bush.

2. Agriturismo “Fattoria Bellosguardo”, 'mangiatoia' apartment

Agriturismo “Fattoria Bellosguardo”, 'mangiatoia' apartment
Castelfiorentino
The price is ￥15,983
￥30,190 total
includes taxes & fees
Oct 21 - Oct 22
Agriturismo “Fattoria Bellosguardo”, 'mangiatoia' apartment
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, (90 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is ￥18,405
￥20,955 total
includes taxes & fees
Oct 25 - Oct 26
B&B La Fonte del Machiavelli
An open wooden door leading to an outdoor patio with a table and chairs.

4. 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 ￥14,489
￥21,266 total
includes taxes & fees
Nov 8 - Nov 9
Palazzo al Torrione 2
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

5. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is ￥7,501
￥8,784 total
includes taxes & fees
Oct 21 - Oct 22
Camping Boschetto Di Piemma
A narrow alleyway with brick walls, wooden barrels, and potted plants.

6. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (42 reviews)
"Authentic 13th century building with so much character and charm. The room was very unique and opened to a lovely courtyard. The location was great, and very close to the gate. A full Italian breakfast buffet was offered at a reasonable cost. Laundry service was also available. And the hosts were very friendly and helpful."
United States
Marilyn H.
The price is ￥17,581
￥27,171 total
includes taxes & fees
Oct 21 - Oct 22
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
A water park with a pool, slides, and a wooden deck area.

7. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (121 reviews)
"Friendly staff!"
United States
larisa
The price is ￥6,713
￥7,918 total
includes taxes & fees
Oct 21 - Oct 22
hu Firenze Certosa camping in town
An arched entrance with a lantern above, flanked by two potted plants.

8. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (108 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is ￥34,620
￥38,792 total
includes taxes & fees
Oct 23 - Oct 24
Villa il Fedino
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

9. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (171 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 ￥12,031
￥15,365 total
includes taxes & fees
Nov 1 - Nov 2
I Parigi Corbinelli
A dining area with a table set for four, a wine rack, and a fireplace.

10. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is ￥15,026
￥61,669 total
includes taxes & fees
Oct 29 - Oct 30
Teranga in Chianti - Parking & Garden 3 BR
A hot tub with a bottle and glasses, surrounded by a misty outdoor area with trees and a pool.

11. Lebbiano Residence Bio Resort

Lebbiano Residence Bio Resort
3.0 star property
Scandicci
9.4 out of 10, Exceptional, (23 reviews)
"Very good service, staff are very friendly and helpful. I would defenitely come back."
Australia
R.D
The price is ￥26,815
￥34,114 total
includes taxes & fees
Nov 6 - Nov 7
Lebbiano Residence Bio Resort
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

12. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (272 reviews)
"Very friendly and clean."
United States
Mohamed
The price is ￥17,139
￥19,386 total
includes taxes & fees
Nov 15 - Nov 16
Relais Villa Olmo - Place of Charme
A dining area with a table set for two, featuring a view of greenery through a window.

13. 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 ￥21,642
￥24,517 total
includes taxes & fees
Nov 7 - Nov 8
La Locanda di Pietracupa
A dining area with a table set for four, surrounded by chairs, in front of a house with a stone facade and a wooden door.

14. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is ￥301,904
￥344,881 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

15. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
Riserva di Fizzano Residence
A modern house with glass walls and a patio area.

16. 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 ￥25,397
￥30,070 total
includes taxes & fees
Nov 14 - Nov 15
Marignolle Relais and Charme
A hotel room with a bed, a bedside table, a heater, a mirror, and a bathroom with a sink.

17. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,789 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is ￥8,173
￥10,233 total
includes taxes & fees
Nov 15 - Nov 16
Hu Firenze Camping In Town
A balcony with a glass table, white curtains, and a bottle of champagne.

18. Dimora Bandinelli Firenze

Dimora Bandinelli Firenze
Oltrarno
9.8 out of 10, Exceptional, (190 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 ￥12,983
￥16,412 total
includes taxes & fees
Nov 9 - Nov 10
Dimora Bandinelli Firenze
Reception

19. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (141 reviews)
"Book this for our honeymoon and will definitely come back"
Canada
Kerby
The price is ￥27,446
￥32,322 total
includes taxes & fees
Nov 8 - Nov 9
Teatro Luxury Apartments Firenze - Starhotels Collezione
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

20. 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 ￥43,041
￥48,056 total
includes taxes & fees
Oct 30 - Oct 31
Terre di Baccio
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 Castelfiorentino Hotel Reviews

Hotel Paris

Hotel Paris

10/10 Excellent
"We enjoyed our stay it exceeded our expectations definitely we will come back to this hotel"
Leah Giovanna 1-night trip
Posted 3 hours ago
Hotel Paris

Find out more about Castelfiorentino

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

  • View our selection of featured holiday rentals in Castelfiorentino
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  • Enter your travel dates to view the best deals on holiday rentals in Castelfiorentino while they last

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

Frequently asked questions

Can I find a vacation rental in Castelfiorentino?

Yes, we give you a choice of vacation rentals near top attractions in Castelfiorentino, or you can choose a secluded option if you want a relaxing place to stay. Our travelers say Castelfiorentino has a good selection of restaurants. Make sure you have time to check out the theaters and wineries during your trip.

What are some of the best vacation home rentals in Castelfiorentino?

Villa La Stella - Casa per Ferie: This vacation home rental outside of Castelfiorentino 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.

How many vacation rentals are there in Castelfiorentino?

Expedia has 9 vacation rentals for your stay in Castelfiorentino.

What can I see and do in Castelfiorentino?

Cultural attractions to visit include Benozzo Gozzoli Museum and Teatro del Popolo. Other places in town to visit include Castle of Oliveto and Castello di Coiano.

What are vacation rentals like in Castelfiorentino?

Vacation rentals are privately owned accommodations you can stay in for a few days or a quick weekend in Castelfiorentino. Vacation rentals offer amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.