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

Holiday Rentals in Castelfiorentino

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Our top choices for Castelfiorentino holiday rentals

1. La Coccinella - Relaxation, Private Courtyard

La Coccinella - Relaxation, Private Courtyard
Dogana
La Coccinella - Relaxation, Private Courtyard

2. New Listing

New Listing
Dogana
New Listing

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

Agriturismo “Fattoria Bellosguardo”, 'mangiatoia' apartment
Castelfiorentino
Agriturismo “Fattoria Bellosguardo”, 'mangiatoia' apartment

4. Palazzo Brunelleschi

Palazzo Brunelleschi
Castelfiorentino
Palazzo Brunelleschi

5. 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 €118
includes taxes & fees
3 Nov - 4 Nov
B&B La Fonte del Machiavelli

6. 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 €161
includes taxes & fees
23 Nov - 24 Nov
Villa il Fedino

7. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (123 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is €50
includes taxes & fees
5 Nov - 6 Nov
hu Firenze Certosa camping in town

8. 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, (44 reviews)
"P. Buonaccorsi is a unique property that is centrally located in San Gimignano. It is well maintained and restored and a very beautiful residence. Senora and Bianca were perfect hosts. The town was perfectly located in Tuscany and within easy day-trips to Florence, Siena, and Massa Marittima."
United States
Glenn
The price is €148
includes taxes & fees
3 Nov - 4 Nov
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

9. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (274 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is €93
includes taxes & fees
29 Nov - 30 Nov
Relais Villa Olmo - Place of Charme

10. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is €350
includes taxes & fees
7 Nov - 8 Nov
Teranga in Chianti - Parking & Garden 3 BR

11. 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 €149
includes taxes & fees
3 Nov - 4 Nov
country house with garden ,pool,children's play area ,Tuscany,15 from Florence

12. 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 €146
includes taxes & fees
7 Nov - 8 Nov
La Locanda di Pietracupa

13. 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 €141
includes taxes & fees
22 Nov - 23 Nov
Marignolle Relais and Charme

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 €1,397
includes taxes & fees
1 Dec - 2 Dec
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

15. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,798 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is €58
includes taxes & fees
22 Nov - 23 Nov
Hu Firenze Camping In Town

16. 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 €284
includes taxes & fees
15 Nov - 16 Nov
Terre di Baccio

17. 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 €92
includes taxes & fees
24 Nov - 25 Nov
Dimora Bandinelli Firenze

18. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (153 reviews)
"Great property!"
United States
Jahzier
The price is €182
includes taxes & fees
15 Nov - 16 Nov
Teatro Luxury Apartments Firenze - Starhotels Collezione

19. 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 €143
includes taxes & fees
17 Nov - 18 Nov
Mamo Florence - Le Farine Della Signoria Apartments

20. 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 €120
includes taxes & fees
30 Nov - 1 Dec
Relais Piazza Signoria
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

Find out more about Castelfiorentino

Everything you need to know about Castelfiorentino holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castelfiorentino holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Castelfiorentino holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Castelfiorentino holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castelfiorentino holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castelfiorentino holiday rentals we have selected for you start as low as €50 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Castelfiorentino rentals

At Expedia, we put the best Castelfiorentino holiday 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 Castelfiorentino 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 Castelfiorentino holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castelfiorentino. 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 a holiday rental in Castelfiorentino?

Yes, there are holiday rentals close to the most popular sights in Castelfiorentino, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Castelfiorentino has a good selection of restaurants. Make sure you have time to check out the theatres and wineries during your trip.

What are some of the best holiday rentals that Castelfiorentino has to offer?

Villa La Stella - Casa per Ferie: This holiday 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 holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Castelfiorentino?

Expedia has 9 holiday 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 holiday rentals like in Castelfiorentino?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castelfiorentino. Holiday rentals feature extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip or a small group gathering.