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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Castelfiorentino vacation rentals

An arched entrance with a lantern above, flanked by two potted plants.

1. 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
$215 nightly
The price is $241
Oct 6 - Oct 7
Total with taxes and fees
Villa il Fedino
An open wooden door leading to an outdoor patio with a table and chairs.

2. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 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
$132 nightly
The price is $151
Oct 30 - Oct 31
Total with taxes and fees
Palazzo al Torrione 2
A view from a window overlooking a rural landscape with fields and a distant mountain range.

3. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
$128 nightly
The price is $147
Oct 18 - Oct 19
Total with taxes and fees
B&B Palazzo Tortoli
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
$73 nightly
The price is $82
Oct 13 - Oct 14
Total with taxes and fees
Chianti Village Morrocco
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

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, (87 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
$118 nightly
The price is $134
Oct 7 - Oct 8
Total with taxes and fees
B&B La Fonte del Machiavelli
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

6. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
$47 nightly
The price is $55
Oct 22 - Oct 23
Total with taxes and fees
Camping Boschetto Di Piemma
A garden with a stone pathway, wooden benches, and various potted plants.

7. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (86 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
$138 nightly
The price is $158
Oct 18 - Oct 19
Total with taxes and fees
Antico Borgo il Cardino
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

8. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (170 reviews)
"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."
United Kingdom
Jacqui
$106 nightly
The price is $130
Oct 29 - Oct 30
Total with taxes and fees
I Parigi Corbinelli
A swimming pool with lounge chairs and a flag.

9. Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (265 reviews)
"Great location easy access to Firenze"
Canada
Donnie
$77 nightly
The price is $100
Oct 26 - Oct 27
Total with taxes and fees
Fattoria il Milione Agriturismo
A water park with a pool, slides, and a wooden deck area.

10. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (108 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
$41 nightly
The price is $48
Oct 13 - Oct 14
Total with taxes and fees
hu Firenze Certosa camping in town
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

11. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (268 reviews)
"Very friendly and clean."
United States
Mohamed
$140 nightly
The price is $158
Oct 21 - Oct 22
Total with taxes and fees
Relais Villa Olmo
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
$158 nightly
The price is $178
Oct 24 - Oct 25
Total with taxes and fees
La Locanda di Pietracupa
A modern house with glass walls and a patio area.

13. 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
$207 nightly
The price is $241
Oct 22 - Oct 23
Total with taxes and fees
Marignolle Relais and Charme
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

14. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 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 $126
Oct 31 - Nov 1
Total with taxes and fees
Palazzo Pacini
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, (877 reviews)
"great staff. Very accessible and close to very good restaurants and gelaterias."
Canada
Melika
$231 nightly
The price is $268
Oct 28 - Oct 29
Total with taxes and fees
Relais Piazza Signoria
A hotel room with a bed, a bedside table, a heater, a mirror, and a bathroom with a sink.

16. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,741 reviews)
"Love this place, came back twice. Literally had all you need . The shuttle downtown is amazing, exploring with families can be chaotic this helped. The pool gets a bit crowded during peak season but still worth a visit."
United States
Ama
$62 nightly
The price is $77
Oct 27 - Oct 28
Total with taxes and fees
Hu Firenze Camping In Town
A modern bedroom with a wooden ceiling, a bed with a white headboard, a beige sofa, and a glass-enclosed shower area with marble walls.

17. Residenza La Musa Amarcord

Residenza La Musa Amarcord
Historic Centre of Florence
9.8 out of 10, Exceptional, (178 reviews)
"Very good place. Walkable distance to every where. Clean and large room. Very comfortable."
United States
Yujia
$165 nightly
The price is $195
Oct 26 - Oct 27
Total with taxes and fees
Residenza La Musa Amarcord
A wooden door with a sign, a large potted plant, and a view of a historic building.

18. La Casa del Garbo - Luxury Rooms & Suite

La Casa del Garbo - Luxury Rooms & Suite
Historic Centre of Florence
9.6 out of 10, Exceptional, (308 reviews)
"It was a wonderful place to stay. I would highly recommend it to anyone."
United States
Salvatore
$187 nightly
The price is $220
Oct 27 - Oct 28
Total with taxes and fees
La Casa del Garbo - Luxury Rooms & Suite
A balcony with a view of a historic building with a dome and bell tower, surrounded by traditional buildings.

19. Firenze Rentals

Firenze Rentals
Historic Centre of Florence
9.2 out of 10, Wonderful, (464 reviews)
"Stayed at this location for four nights for our first visit to Florence - wonderful location for the tourist attractions, as well food scene. The apartment was spacious, clean and well maintained - with a wonderful air conditioner. Will be staying here again for our next visit."
Canada
Lauren
$187 nightly
The price is $242
Oct 31 - Nov 1
Total with taxes and fees
Firenze Rentals
A courtyard with outdoor seating, a building with shutters, and lush greenery.

20. Numa Florence Palazzo San Niccolò

Numa Florence Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (210 reviews)
"Very nice place, backing onto the mountain and quiet. Clean and spacious. Comfortable beds. Only complaint which is not a great one is that it was too digital - the front door & room key were down for most of a day (creating an hassle because of the lack of onsite staff) and the wifi was down for 2 days, leading to inconvenience. Otherwise good place in a good location."
Canada
Dante
$187 nightly
The price is $220
Oct 27 - Oct 28
Total with taxes and fees
Numa Florence Palazzo San Niccolò
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

Italiana Hotels Florence

Italiana Hotels Florence

8/10 Good
"Greta place and friendly staff. Pool closed early in the month due to rain that was disappointing"
Jodie 2-night trip
Posted 6 hours ago
Italiana Hotels 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 $48 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.