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Castiglioni 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 Castiglioni 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, (87 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is CA $167
CA $190 total
includes taxes & fees
Oct 4 - Oct 5
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 CA $308
CA $345 total
includes taxes & fees
Oct 6 - Oct 7
Villa il Fedino
A table with breakfast items and a view of rolling hills.

3. 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 CA $103
CA $117 total
includes taxes & fees
Oct 12 - Oct 13
Chianti Village Morrocco
An open wooden door leading to an outdoor patio with a table and chairs.

4. 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
The price is CA $151
CA $215 total
includes taxes & fees
Oct 1 - Oct 2
Palazzo al Torrione 2
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

5. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (268 reviews)
"Very friendly and clean."
United States
Mohamed
The price is CA $199
CA $223 total
includes taxes & fees
Oct 21 - Oct 22
Relais Villa Olmo
A view from a window overlooking a rural landscape with fields and a distant mountain range.

6. 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
The price is CA $171
CA $196 total
includes taxes & fees
Oct 21 - Oct 22
B&B Palazzo Tortoli
A swimming pool with lounge chairs and a flag.

7. 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
The price is CA $109
CA $142 total
includes taxes & fees
Oct 26 - Oct 27
Fattoria il Milione Agriturismo
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

8. 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 CA $439
CA $490 total
includes taxes & fees
Oct 22 - Oct 23
Terre di Baccio
A modern house with glass walls and a patio area.

9. 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 CA $294
CA $343 total
includes taxes & fees
Oct 18 - Oct 19
Marignolle Relais and Charme
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

10. 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
The price is CA $151
CA $185 total
includes taxes & fees
Oct 26 - Oct 27
I Parigi Corbinelli
A dining area with a table set for two, featuring a view of greenery through a window.

11. 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 CA $227
CA $256 total
includes taxes & fees
Oct 6 - Oct 7
La Locanda di Pietracupa
A water park with a pool, slides, and a wooden deck area.

12. 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
The price is CA $61
CA $72 total
includes taxes & fees
Oct 12 - Oct 13
hu Firenze Certosa camping in town
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

13. 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 traveller
The price is CA $67
CA $79 total
includes taxes & fees
Oct 5 - Oct 6
Camping Boschetto Di Piemma
A room with a dining table, a vase of flowers, a lamp, and a view of a historic building through a window.

14. 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)
"Amazing property with excellent views. "
United States
Karl
The price is CA $189
CA $332 total
includes taxes & fees
Oct 28 - Oct 29
Mamo Florence - Le Farine Della Signoria Apartments
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

15. Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca
Historic Centre of Florence
9.2 out of 10, Wonderful, (840 reviews)
"Beautiful rooms and great location"
Canada
Taylor
The price is CA $485
CA $556 total
includes taxes & fees
Oct 28 - Oct 29
Palazzo Alfieri Residenza d’epoca
Room

16. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.2 out of 10, Wonderful, (332 reviews)
"Great location easy to park car with car service they offer"
United States
Joanna
The price is CA $240
CA $286 total
includes taxes & fees
Oct 22 - Oct 23
La Torre Del Cestello
A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

17. 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
The price is CA $327
CA $379 total
includes taxes & fees
Oct 28 - Oct 29
Relais Piazza Signoria
A terrace with a table set for breakfast, a chair, and a large umbrella.

18. Villa La Stella - Casa per Ferie

Villa La Stella - Casa per Ferie
Le Cure
8.6 out of 10, Excellent, (256 reviews)
"The location and staff were decent. It’s an older property that could use some upgrades."
Canada
Connor
The price is CA $192
CA $224 total
includes taxes & fees
Oct 28 - Oct 29
Villa La Stella - Casa per Ferie
A modern bedroom with a large bed, a desk with chairs, and a bathroom visible through an open door.

19. Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,180 reviews)
"Great location"
United States
Diana
The price is CA $341
CA $398 total
includes taxes & fees
Oct 9 - Oct 10
Palazzo Mannaioni Suites
A terrace with a table set for dining, overlooking a cityscape with historic buildings and a prominent dome.

20. Palazzo Graziani

Palazzo Graziani
Historic Centre of Florence
9.2 out of 10, Wonderful, (691 reviews)
"Would stay here every time. Best rooftop in the city as well."
United States
Matthew
The price is CA $296
CA $348 total
includes taxes & fees
Oct 29 - Oct 30
Palazzo Graziani
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 Castiglioni 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 2 hours ago
Italiana Hotels Florence

Find out more about Castiglioni

Everything you need to know about Castiglioni 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 Castiglioni vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 Castiglioni vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Castiglioni vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castiglioni. 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 Castiglioni vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castiglioni vacation rentals we have selected for you start as low as CA $72 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Castiglioni rentals

At Expedia, we put the best Castiglioni 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 Castiglioni 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 Castiglioni 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 Castiglioni. 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 vacation rentals in Castiglioni?

Yes, we offer vacation rentals close to the most popular attractions in Castiglioni, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Castiglioni has to offer?

Villa La Stella - Casa per Ferie: This vacation home rental near Castiglioni 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.

What’s there to see and do in Castiglioni?

While exploring the area, visit family-friendly sights like Hidron, or get outside and enjoy nature at Cascine Park. You’ll find favorite places to visit like Piazza di Santa Maria Novella and Piazza del Duomo in the larger area.

What’s a vacation rental in Castiglioni like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Castiglioni. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.