Skip to main content

Holiday Rentals in Castiglion Fiorentino

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Castiglion Fiorentino

The best holiday rentals in Castiglion Fiorentino

Check out our pick of great holiday rentals in Castiglion Fiorentino

Filter by:

Review score

San Lazzo Luxury Room - ROOM & PERSONAL SPA

Castiglion Fiorentino

Set in Castiglion Fiorentino, 20 km from Piazza Grande and 44 km from Terme di Montepulciano, San Lazzo Luxury Room - ROOM & PERSONAL SPA offers air conditioning. A hot tub is available for guests.

J
Julia
From
Italy
Communication was polite and prompt. Collecting the key was easy. Fabiana was incredibly helpful. Amazing property decorated immaculately. Spotlessly clean. Everything you need is provided - tea & coffee, breakfast items, fresh fruit and baked goods, bottled water etc. Coffee machine, kettle and toaster. Even a juicer! Embroidered robes and towels with slippers. Toiletries in the bathroom. A little kitchenette area with a sink, fridge and hob if you want to cook. Open log fire with everything you need - we visited in November and we were warm and cosy since there is also heating. Good wifi. TV in both the bedroom and living room areas. We did not use the sauna, but the hot tub was great with clear instructions - a real luxury retreat for a few days. Located in the old town and walking distance to some lovely restaurants and a couple of bars. Perfect for a romantic getaway.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 104 reviews
Price from
US$249.09
1 night, 2 adults

San Michele al Castello

Castiglion Fiorentino

Set within 20 km of Piazza Grande and 44 km of Terme di Montepulciano, San Michele al Castello offers rooms with air conditioning and a private bathroom in Castiglion Fiorentino.

A
Anita
From
United Kingdom
Breakfast so good . Home made cakes by marcella. Taxi service fantastic . Thank you Emilio. Massage perfection Alexandro e Sonia E Gracie Cinzia per a wonderful stay . X
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 232 reviews
Price from
US$117.56
1 night, 2 adults

Le Mura Luxury Room ROOM & PERSONAL SPA

Castiglion Fiorentino

Situated in Castiglion Fiorentino, 20 km from Piazza Grande, Le Mura Luxury Room ROOM & PERSONAL SPA provides accommodation with a sauna, a hot tub and a spa centre.

E
Einar
From
Iceland
amazing room, great restaurant under the room is also wery good, fully recommend
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 120 reviews
Price from
US$208.35
1 night, 2 adults

Suite Romantica con Giardino in Dimora Storica - Camera e Appartamento - B&B Palazzo Robicci

Castiglion Fiorentino

Featuring garden views, Suite Romantica con Giardino in Dimora Storica - Camera e Appartamento - B&B Palazzo Robicci offers accommodation with a garden and a balcony, around 20 km from Piazza Grande.

S
Samantha
From
Italy
Well organized welcome Lovely breakfast at the bar
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 36 reviews
Price from
US$122.21
1 night, 2 adults

Borgo Sant'Andrea al Pozzo

Castiglion Fiorentino

Located in Castiglion Fiorentino, 20 km from Piazza Grande and 46 km from Terme di Montepulciano, Borgo Sant'Andrea al Pozzo offers a garden and air conditioning.

A
Alex
From
United Kingdom
A lovely village. Has all the charm but still walkable to the town and its bars, restaurants and cultural sights. Also has a rail link to get to Arezzo and Florence The place was super clean. Alberto was really flexible on our check in too. Outside seating areas was lovely to sit and have a glass of wine. Alberto’s mum was so lovely too. She opened the gate for us when we left. A very sweet lady xx
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 16 reviews
Price from
US$169.94
1 night, 2 adults

Casa FONTESECCA

Castiglion Fiorentino

Offering a garden and city view, Casa FONTESECCA is set in Castiglion Fiorentino, 20 km from Piazza Grande and 46 km from Terme di Montepulciano.

C
Catherine
From
United Kingdom
Lovely spacious apartment with 2 dining areas. We'll located for an event we were attending in the town. Fabulous views. Plenty of parking. Very clean. Host very accommodating with arrival times.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 17 reviews
Price from
US$186.23
1 night, 2 adults

Tuttomio Suite con idromassaggio

Castiglion Fiorentino

Featuring a spa bath, Tuttomio Suite con idromassaggio is located in Castiglion Fiorentino.

C
Catalin
From
Romania
The property itself is a masterpiece. It’s even better than in the pictures, good quality really authentic finishes. Sara is the best host I’ve ever seen (and I’ve been traveling a bit). She goes above and beyond to make your stay perfect. She even prepared us the evening bath with natural essential oils which were fantastic after a day of exploring Tuscany. On top of that, she recommended us all kinds of places to visit and restaurants which were really good and gave us insights as a local. Is someone wants to go in this area, should really try Tuttomio. It’s therapy for the soul.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 45 reviews
Price from
US$267.71
1 night, 2 adults

Casa dei Girasoli

Castiglion Fiorentino

Boasting air-conditioned accommodation with a pool with a view, garden view and a patio, Casa dei Girasoli is set in Castiglion Fiorentino.

R
Ramesh
From
United Kingdom
Amazing host, Luigi was so helpful with our arrival and during our time in Castiglion. He was such a warm man who made us feel at home. The pool area and the space was also fantastic
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 9 reviews
Price from
US$346.28
1 night, 2 adults

San Michele al Borgo

Castiglion Fiorentino

Comfortable Accommodations San Michele al Borgo in Castiglion Fiorentino offers family rooms with one bedroom and one bathroom.

M
Monica
From
Australia
We didn't stay here, we stayed at sister property, as we were upgraded, San Michele al Castello which is BEAUTIFUL. Staff are lovely, views and garden divine and breakfast cakes oh my goodness. I'm still dreaming about Marcella's crostata. Beautiful owners. I can't recommend San Michele al CASTELLO enough.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 91 reviews
Price from
US$124.54
1 night, 2 adults

Camera e Appartamento Toscana - B&B Palazzo Robicci

Castiglion Fiorentino

Housed in a historic building, Camera e Appartamento Toscana - B&B Palazzo Robicci offers accommodation with a garden and free WiFi in Castiglion Fiorentino, 20 km from Piazza Grande.

D
Dirk
From
Netherlands
The location in center of a medeaval town. The excellent host, and support .
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 5 reviews
Price from
US$115.23
1 night, 2 adults
All holiday rentals in Castiglion Fiorentino

Most booked holiday rentals in Castiglion Fiorentino and surroundings in the past month

See all

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 50 reviews

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 14 reviews

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 91 reviews

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 120 reviews

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 84 reviews

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 128 reviews

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 101 reviews

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 104 reviews

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 232 reviews

Popular with guests booking holiday rentals in Castiglion Fiorentino

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 452 reviews

These holiday rentals in Castiglion Fiorentino and nearby have options with free cancellation

La Cascina nel Roseto

Rigutino
Free cancellation options available
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 2 reviews

Set in Rigutino, 15 km from Piazza Grande and 44 km from Terme di Montepulciano, La Cascina nel Roseto offers an open-air bath and air conditioning.

Margherita Holiday Home

Cortona
Free cancellation options available
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 55 reviews

Boasting pool with a view and views of pool, Margherita Holiday Home is a farm stay set in a historic building in Cortona, 28 km from Piazza Grande.

From US$178.67 per night

B&B Il Mandorlo

Cortona
Free cancellation options available
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 42 reviews

Offering a garden and garden view, B&B Il Mandorlo is situated in Cortona, 28 km from Piazza Grande and 38 km from Terme di Montepulciano.

From US$83.80 per night

MAGNOLIA

Cortona
Free cancellation options available
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 58 reviews

Featuring garden views, MAGNOLIA provides accommodation with a garden and a patio, around 38 km from Terme di Montepulciano.

From US$161.79 per night

SIGNORELLI HOUSE

Cortona
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 9 reviews

SIGNORELLI HOUSE is situated in the Cortona Old Town district of Cortona, 48 km from Perugia Train Station, 50 km from Corso Vannucci and 35 km from Magione Motorspeedway.

From US$872.96 per night

Noi Due a Cortona

Cortona
Free cancellation options available
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 60 reviews

Set in Cortona, 30 km from Piazza Grande and 37 km from Terme di Montepulciano, Noi Due a Cortona offers air conditioning.

From US$128.03 per night

La Corte Di Ambra

Cortona
Free cancellation options available
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 86 reviews

La Corte Di Ambra is located in Cortona's historical centre. Free Wi-Fi access is available in all areas.

From US$384.10 per night

Dolce Maria

Cortona
Free cancellation options available
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 419 reviews

Just 100 metres from Piazza della Repubblica, the Dolce Maria is located in the mediaeval hill town of Cortona.

From US$133.85 per night

Highly rated holiday rentals in Castiglion Fiorentino and nearby

Agrisalotto

Cortona
8.0+ review score
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 144 reviews

Boasting an infinity pool and views of pool, Agrisalotto is a farm stay set in a historic building in Cortona, 30 km from Piazza Grande.

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 46 reviews

Situated in Cortona, 31 km from Piazza Grande and 37 km from Terme di Montepulciano, Cortona's Rooftop Nest features accommodation with free WiFi in a historic building.

La Casa di Iole

Cortona
8.0+ review score
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 35 reviews

Set in Cortona, 30 km from Piazza Grande and 37 km from Terme di Montepulciano, La Casa di Iole offers accommodation with free WiFi in a historic building.

Casa Dreosti

Cortona
8.0+ review score
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 191 reviews

Set within 32 km of Piazza Grande and 38 km of Terme di Montepulciano, Casa Dreosti offers rooms with air conditioning and a private bathroom in Cortona.

From US$144.21 per night
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 68 reviews

Offering city views, La finestra sulla Toscana is an accommodation located in Cortona, 38 km from Terme di Montepulciano and 47 km from Perugia Train Station.

From US$201.36 per night
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 6 reviews

Set in Cortona, 31 km from Piazza Grande and 50 km from Perugia Cathedral, Agriturismo Il Torrino offers air conditioning.

From US$267.71 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 101 reviews

Situated in Castiglion Fiorentino, Tuscany region, Suite La Gioconda is located 44 km from Terme di Montepulciano. The property features city and quiet street views, and is 20 km from Piazza Grande.

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 5 reviews

Housed in a historic building, Camera e Appartamento Toscana - B&B Palazzo Robicci offers accommodation with a garden and free WiFi in Castiglion Fiorentino, 20 km from Piazza Grande.

Holiday Rentals with swimming pools in Castiglion Fiorentino and nearby

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 3 reviews

Boasting quiet street views, Dolci Colline Resort Capannina is located in Castiglion Fiorentino, around 46 km from Magione Motorspeedway.

From US$141.40 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Featuring an outdoor pool, a sauna and a hot tub, Borgo Dolci Colline Resort Limonaia is located in Castiglion Fiorentino, 22 km from Piazza Grande and 47 km from Terme di Montepulciano.

From US$154.25 per night
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 3 reviews

Boasting an outdoor pool, a sauna and a hot tub, Borgo Dolci Colline Resort Querce is situated in Castiglion Fiorentino, 22 km from Piazza Grande and 46 km from Terme di Montepulciano.

From US$179.96 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Situated in Castiglion Fiorentino, 22 km from Piazza Grande and 47 km from Terme di Montepulciano, Borgo Dolci Colline Resort Loggia offers barbecue facilities and air conditioning.

From US$192.81 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Borgo Dolci Colline Resort Granaio offers a hot tub and free private parking, and is within 22 km of Piazza Grande and 46 km of Terme di Montepulciano.

From US$488.44 per night

L'Orangerie

Cortona
Swimming pool

Featuring a garden, private pool and mountain views, L'Orangerie is located in Cortona. There is an on-site restaurant, plus free private parking and free WiFi are available.

From US$296.81 per night
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 45 reviews

Featuring a spa bath, Tuttomio Suite con idromassaggio is located in Castiglion Fiorentino.

From US$270.04 per night
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 14 reviews

Offering city views, Pozzonovo is an accommodation set in Castiglion Fiorentino, 21 km from Piazza Grande and 42 km from Terme di Montepulciano.

Enjoy breakfast in Castiglion Fiorentino and nearby

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 20 reviews

Situated in Castiglion Fiorentino, 20 km from Piazza Grande and 44 km from Terme di Montepulciano, Casa Letizia features accommodation with free WiFi in a historic building.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 36 reviews

Featuring garden views, Suite Romantica con Giardino in Dimora Storica - Camera e Appartamento - B&B Palazzo Robicci offers accommodation with a garden and a balcony, around 20 km from Piazza Grande.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 35 reviews

Featuring city views, Camera Romantica con Giardino in Dimora Storica - B&B Palazzo Robicci offers accommodation with a patio, around 20 km from Piazza Grande.

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 33 reviews

Situated 20 km from Piazza Grande and 44 km from Terme di Montepulciano, Casa il Cassero features accommodation in Castiglion Fiorentino. The apartment has family rooms.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 48 reviews

Boasting garden views, Casa La Girandola offers accommodation with a garden and a terrace, around 44 km from Terme di Montepulciano. With city views, this accommodation provides a balcony.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 104 reviews

Set in Castiglion Fiorentino, 20 km from Piazza Grande and 44 km from Terme di Montepulciano, San Lazzo Luxury Room - ROOM & PERSONAL SPA offers air conditioning. A hot tub is available for guests.

From US$249.09 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 17 reviews

Offering a garden and city view, Casa FONTESECCA is set in Castiglion Fiorentino, 20 km from Piazza Grande and 46 km from Terme di Montepulciano.

From US$197.87 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 9 reviews

Boasting air-conditioned accommodation with a pool with a view, garden view and a patio, Casa dei Girasoli is set in Castiglion Fiorentino.

FAQ about holiday rentals in Castiglion Fiorentino

Holiday rentals that guests love in Castiglion Fiorentino

See all
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 6 reviews
Perfect location, lovely owners who supplied us with a small gift of their garden products. Very good location, clean and lovely house, air conditioning working perfectly. We wholeheartedly recommend this place to anyone considering a vacation rental in Tuscany.
Guest review by
chomik
Solo traveller
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 4 reviews
The host Manuela was super nice, easy to communicate with, always helping solve our requests or questions. The villa is amazing, nice pool big house.. just perfect!
Guest review by
Petr
Family with young children
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 14 reviews
Beautiful house with amazing view. We have been to Tuscany a few times and this was by far the best location we had. The house was fully equipped with everything imaginable. With a fully gated, large garden, it is also a petfriendly location. A 15-20 minute drive to the old village with great restaurants, while the house is quiet, private and surrounded by nature. Leo and Elena were great hosts, and we would be very happy to come again.
Guest review by
Silke Pinkhof
People with friends
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 3 reviews
This place felt more personal than a lot of other villa's we have stayed in.
Guest review by
Kelly
Solo traveller
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
Everything was amazing. The villa, the pool, the property. We enjoyed our stay so much.
Guest review by
Mikhail
Family with young children
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
Beautiful villa nestled in a gorgeous medieval town.
Guest review by
Daniel
People with friends
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 36 reviews
Authentic and romantic palace or villa at the medieval wall in Castiglion Fiorentina. Tosca is a very pleasant and professional host to accommodate an unforgettable stay.
Guest review by
Anonymous
Young couple
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review
Beautiful villa, very peaceful, very well equipped with everything you need. Only a 20 minute walk to town/station. Panacotta made for us one evening by the host
Guest review by
Alison
Family with young children