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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Castelfiorentino vacation rentals

Outdoor dining

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

Agriturismo “Fattoria Bellosguardo”, apartment 'mangiatoia'
Castelfiorentino
$193 nightly
The price is $197
Aug 17 - Aug 18
Total with taxes and fees
Agriturismo “Fattoria Bellosguardo”, apartment 'mangiatoia'
Exterior

2. DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (2 reviews)
"Super clean, felt brand new with a beaaautiful view on the terrace! Quite a few stairs (heavy luggage :D) but definitely worth it! Sadly we only stayed two nights"
United Kingdom
Celesta
$99 nightly
The price is $111
Sep 1 - Sep 2
Total with taxes and fees
DomuS Miniato
Garden view

3. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (47 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
$109 nightly
The price is $127
Sep 13 - Sep 14
Total with taxes and fees
Villa San Filippo
View from room

4. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (116 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$90 nightly
The price is $102
Aug 23 - Aug 24
Total with taxes and fees
Chianti Village Morrocco
Balcony

5. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (110 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
$122 nightly
The price is $140
Sep 15 - Sep 16
Total with taxes and fees
Palazzo al Torrione 2
Property grounds

6. san gimignano apartment in historical center, courtyard and fast free wifi

san gimignano apartment in historical center, courtyard and fast free wifi
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.
$197 nightly
The price is $203
Sep 3 - Sep 4
Total with taxes and fees
san gimignano apartment in historical center, courtyard and fast free wifi
Property amenity

7. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very Good, (97 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
$49 nightly
The price is $58
Sep 6 - Sep 7
Total with taxes and fees
hu Firenze Certosa camping in town
Terrace/patio

8. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$113 nightly
The price is $127
Sep 2 - Sep 3
Total with taxes and fees
Palazzo Pacini
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

9. Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.4 out of 10, Very Good, (260 reviews)
"Nice inn on a working farm located deep in the hills of suburban Florence."
United States
Allan
$97 nightly
The price is $123
Aug 25 - Aug 26
Total with taxes and fees
Fattoria il Milione Agriturismo
Courtyard

10. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (168 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
$96 nightly
The price is $120
Aug 21 - Aug 22
Total with taxes and fees
I Parigi Corbinelli
Exterior

11. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
$156 nightly
The price is $177
Sep 6 - Sep 7
Total with taxes and fees
Antico Borgo il Cardino
Restaurant

12. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (261 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
$140 nightly
The price is $158
Aug 30 - Aug 31
Total with taxes and fees
Relais Villa Olmo
Superior Double Room, 1 King Bed | Premium bedding, down comforters, in-room safe, desk

13. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (292 reviews)
"Exceptionally friendly service staff that helped us. Location was also very convenient and accessible. Super clean room with strong AC that worked well during summer."
Singapore
Justin
$88 nightly
The price is $113
Aug 16 - Aug 17
Total with taxes and fees
La Torre Del Cestello
Breakfast, lunch and dinner served

14. La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.6 out of 10, Exceptional, (38 reviews)
"Charming and very original. Great warmth from the staff and very helpful. Enjoyed the room and restaurant at and surrounding towns."
Australia
Con
$174 nightly
The price is $196
Aug 22 - Aug 23
Total with taxes and fees
La Locanda di Pietracupa
Apartment | City view

15. Mamo Florence - Le Farine Della Signoria Apartments

Mamo Florence - Le Farine Della Signoria Apartments
Historic Centre of Florence
8.6 out of 10, Excellent, (10 reviews)
"Amazing property with excellent views. "
United States
Karl
$168 nightly
The price is $191
Aug 20 - Aug 21
Total with taxes and fees
Mamo Florence - Le Farine Della Signoria Apartments
Exterior

16. Il Castello di San Ruffino

Il Castello di San Ruffino
Casciana Terme Lari
9.2 out of 10, Wonderful, (36 reviews)
"Really cool experience to stay at a castle. Perfect destination for celebrations."
United States
daniel
$107 nightly
The price is $122
Aug 26 - Aug 27
Total with taxes and fees
Il Castello di San Ruffino
Terrace/patio

17. Numa Florence Palazzo San Niccolò

Numa Florence Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (202 reviews)
"We had a good, clean room.Staff was helpful"
United States
Luisiana
$99 nightly
The price is $123
Aug 23 - Aug 24
Total with taxes and fees
Numa Florence Palazzo San Niccolò
Exterior detail

18. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.4 out of 10, Exceptional, (23 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
$185 nightly
The price is $185
Aug 18 - Aug 19
Total with taxes and fees
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Garden

19. Serristori Palace Residence

Serristori Palace Residence
Historic Centre of Florence
9.6 out of 10, Exceptional, (224 reviews)
"Everything was great Thank you"
United States
aleksandar
$99 nightly
The price is $123
Aug 21 - Aug 22
Total with taxes and fees
Serristori Palace Residence
Family Apartment | Living area | 40-inch flat-screen TV with digital channels, TV

20. Appartamenti degli Artisti by Mmega

Appartamenti degli Artisti by Mmega
Historic Centre of Florence
8.6 out of 10, Excellent, (44 reviews)
"We stayed with our children and the space was excellent and the location was close enough to walk to everything. "
United States
Juliet
$163 nightly
The price is $184
Aug 16 - Aug 17
Total with taxes and fees
Appartamenti degli Artisti by Mmega
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 Calimala Florence

Hotel Calimala Florence

10/10 Excellent
"From the time we walked through the front door and left the staff was amazing! Extremely helpful, from helping with an early check in, to snagging tickets to see the David, staff made it easy to ask for help! As if they truly enjoyed it! Thanks for the memorable stay."
Colby 2-night trip
Posted less than an hour ago
Hotel Calimala Florence

Find out more about Castelfiorentino

Everything you need to know about Castelfiorentino 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 Castelfiorentino 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 Castelfiorentino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castelfiorentino vacation 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 low season months. For more hustle and bustle, you may prefer to visit Castelfiorentino 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 $71 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 Castelfiorentino rentals

At Expedia, we put the best Castelfiorentino 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 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 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 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.

Explore a world of travel with Expedia

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 10 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 popular places to visit in the area include Piazza di Santa Maria Novella and Cathedral of Santa Maria del Fiore.

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.