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

Castelfiorentino Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Castelfiorentino vacation rentals

An outdoor dining area with a table set for breakfast, surrounded by greenery and a flowering bush.

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

Agriturismo “Fattoria Bellosguardo”, 'mangiatoia' apartment
Castelfiorentino
$187 nightly
The price is $190
Oct 13 - Oct 14
Total with taxes and fees
Agriturismo “Fattoria Bellosguardo”, 'mangiatoia' apartment
Holiday Home Swimming Pool

2. Farmhouse in Castelfiorentino with Pool

Farmhouse in Castelfiorentino with Pool
Castelfiorentino (FI)
9.8 out of 10, Exceptional, (6 reviews)
"This was a beautiful location and the host Patrizia was friendly and responsive. The pool was refreshing and the view was outstanding. We had a 3 bedroom apartment in the main building and it was quite large and ideal for our grandson as apart from the main stairs it was mostly all one level so he could easily crawl around. Please note that basic amenities are not provided. You will need toilet paper, hand soap, dish soap, dish cloths etc. We arrived late so were a bit surprised to be without...
Canada
Lori G.
Farmhouse in Castelfiorentino with Pool
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, (89 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
$116 nightly
The price is $132
Oct 16 - Oct 17
Total with taxes and fees
B&B La Fonte del Machiavelli
An arched entrance with a lantern above, flanked by two potted plants.

4. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
$210 nightly
The price is $235
Oct 26 - Oct 27
Total with taxes and fees
Villa il Fedino
An open wooden door leading to an outdoor patio with a table and chairs.

5. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
$117 nightly
The price is $134
Nov 8 - Nov 9
Total with taxes and fees
Palazzo al Torrione 2
A table with breakfast items and a view of rolling hills.

6. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
$84 nightly
The price is $95
Oct 18 - Oct 19
Total with taxes and fees
Chianti Village Morrocco
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

7. 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
$47 nightly
The price is $55
Oct 12 - Oct 13
Total with taxes and fees
Camping Boschetto Di Piemma
A narrow alleyway with brick walls, wooden barrels, and potted plants.

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, (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.
$166 nightly
The price is $171
Oct 14 - Oct 15
Total with taxes and fees
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.

9. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (117 reviews)
"Friendly staff!"
United States
larisa
$42 nightly
The price is $50
Oct 12 - Oct 13
Total with taxes and fees
hu Firenze Certosa camping in town
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

10. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.4 out of 10, Exceptional, (269 reviews)
"Very friendly and clean."
United States
Mohamed
$138 nightly
The price is $155
Nov 8 - Nov 9
Total with taxes and fees
Relais Villa Olmo - Place of Charme
A room with two beds, a wooden dresser, a painting, and a door.

11. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
$376 nightly
The price is $385
Oct 17 - Oct 18
Total with taxes and fees
Teranga in Chianti - Parking & Garden 3 BR
A dining area with a table set for two, featuring a view of greenery through a window.

12. 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
$129 nightly
The price is $147
Nov 11 - Nov 12
Total with taxes and fees
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.

13. 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.
$2,158 nightly
The price is $2,163
Nov 1 - Nov 2
Total with taxes and fees
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A modern house with glass walls and a patio area.

14. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (93 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
$164 nightly
The price is $194
Nov 10 - Nov 11
Total with taxes and fees
Marignolle Relais and Charme
Reception

15. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (138 reviews)
"Book this for our honeymoon and will definitely come back"
Canada
Kerby
$173 nightly
The price is $203
Nov 9 - Nov 10
Total with taxes and fees
Teatro Luxury Apartments Firenze - Starhotels Collezione
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

16. 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
$283 nightly
The price is $316
Oct 19 - Oct 20
Total with taxes and fees
Terre di Baccio
Room

17. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.2 out of 10, Wonderful, (344 reviews)
"Great location easy to park car with car service they offer"
United States
Joanna
$89 nightly
The price is $113
Nov 9 - Nov 10
Total with taxes and fees
La Torre Del Cestello
A hotel room with a bed, a bedside table, a heater, a mirror, and a bathroom with a sink.

18. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,785 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
$52 nightly
The price is $65
Nov 8 - Nov 9
Total with taxes and fees
Hu Firenze Camping In Town
A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

19. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (885 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
$124 nightly
The price is $149
Nov 8 - Nov 9
Total with taxes and fees
Relais Piazza Signoria
A balcony with a glass table, white curtains, and a bottle of champagne.

20. 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
$76 nightly
The price is $97
Nov 10 - Nov 11
Total with taxes and fees
Dimora Bandinelli Firenze
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 Horto Convento

Hotel Horto Convento

8/10 Good
"Beautiful place and room was nice and clean. Breakfast in the morning was nice also (coffee was surprisingly bad). We were booked in their other hotel - Horto Convento. Upon our arrival we were strongly encouraged (coerced?) to move to this hotel - Della Calza. In hind sight, I’m not sure I would have moved - Della Calza is a further walk from the sights of Florence, not as pretty and, while in Florence, we had little interest in the spa."
Peter 3-night trip
Posted 23 hours ago
Hotel Horto Convento

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 $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 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 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.