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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Castelfiorentino vacation rentals

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

1. 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 P7,257
P8,262 total
includes taxes & fees
Oct 15 - Oct 16
B&B La Fonte del Machiavelli
An arched entrance with a lantern above, flanked by two potted plants.

2. 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
The price is P13,909
P15,580 total
includes taxes & fees
Oct 21 - Oct 22
Villa il Fedino
An open wooden door leading to an outdoor patio with a table and chairs.

3. 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
The price is P5,713
P8,385 total
includes taxes & fees
Nov 8 - Nov 9
Palazzo al Torrione 2
A table with breakfast items and a view of rolling hills.

4. 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
The price is P5,306
P5,976 total
includes taxes & fees
Oct 15 - Oct 16
Chianti Village Morrocco
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 P3,323
P3,865 total
includes taxes & fees
Oct 26 - Oct 27
Camping Boschetto Di Piemma
A water park with a pool, slides, and a wooden deck area.

6. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (118 reviews)
"Friendly staff!"
United States
larisa
The price is P3,008
P3,519 total
includes taxes & fees
Oct 15 - Oct 16
hu Firenze Certosa camping in town
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

7. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.4 out of 10, Exceptional, (270 reviews)
"Very friendly and clean."
United States
Mohamed
The price is P8,672
P9,751 total
includes taxes & fees
Nov 13 - Nov 14
Relais Villa Olmo - Place of Charme
Outdoor dining

8. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is P6,393
P24,895 total
includes taxes & fees
Oct 24 - Oct 25
Teranga in Chianti - Parking & Garden 3 BR
A dining area with a table set for two, featuring a view of greenery through a window.

9. 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 P9,070
P10,257 total
includes taxes & fees
Nov 7 - Nov 8
La Locanda di Pietracupa
A modern house with glass walls and a patio area.

10. 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
The price is P10,850
P12,775 total
includes taxes & fees
Nov 8 - Nov 9
Marignolle Relais and Charme
Reception

11. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (139 reviews)
"Book this for our honeymoon and will definitely come back"
Canada
Kerby
The price is P10,868
P12,799 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.

12. 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 P16,958
P18,933 total
includes taxes & fees
Oct 16 - Oct 17
Terre di Baccio
Room

13. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (346 reviews)
"Great location easy to park car with car service they offer"
United States
Joanna
The price is P5,933
P7,507 total
includes taxes & fees
Nov 5 - Nov 6
La Torre Del Cestello
A hotel room with a bed, a bedside table, a heater, a mirror, and a bathroom with a sink.

14. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,787 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is P3,236
P4,052 total
includes taxes & fees
Nov 8 - Nov 9
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.

15. 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
The price is P7,768
P9,389 total
includes taxes & fees
Nov 9 - Nov 10
Relais Piazza Signoria
A balcony with a glass table, white curtains, and a bottle of champagne.

16. 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 P5,687
P7,096 total
includes taxes & fees
Nov 9 - Nov 10
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 Santa Maria Novella

Hotel Santa Maria Novella

10/10 Excellent
"Definitely will book this place on next trip to Florence. Location was perfect and place is top notch not to mention the incredible breakfast. 5 great restaurants within in 3 blocks and the church in the square is a must see."
Renee 2-night trip
Posted 9 hours ago
Hotel Santa Maria Novella

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:

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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.