Rocca San Casciano Holiday Rentals

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Check prices for these dates

Tonight
14 Nov - 15 Nov
Tomorrow
15 Nov - 16 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in Rocca San Casciano

Apartment, 1 Bedroom, City View | Property grounds
House Of The Architect - Sweet Apartment

House Of The Architect - Sweet Apartment

Centro Urbano
The price is NZ$383
includes taxes & fees
16 Nov - 17 Nov
House Of The Architect - Sweet Apartment
Pool
Romantic detached cottage with pool, in a farm between Arezzo and Florence

Romantic detached cottage with pool, in a farm between Arezzo and Florence

PRATOVECCHIO
9.4 out of 10, Exceptional, (9)
"Very quiet place off the beaten track. You need a car to get to town. Owner was very nice and helpful. Apartment is small but has everything that is needed. To get to the bath room at night is a little challenging but we managed. We would rent it again if we come to the area."
United States
Frank A.
Romantic detached cottage with pool, in a farm between Arezzo and Florence
Outdoor pool
The Farmhouse of Caiano between nature, culture and swimming pool

The Farmhouse of Caiano between nature, culture and swimming pool

Londa
9.8 out of 10, Exceptional, (28)
"We were warmly welcomed, although our arrival was very delayed due to traffic. Guido was a great host and gave us lots of great recommendations for trips and restaurants. It really is a magical place and we enjoyed every second. Thank you for the wonderful time!"
Germany
Pia K.
The Farmhouse of Caiano between nature, culture and swimming pool
Outdoor pool
Villa Casalino your Tuscany wedding, 13 bedrooms and ensuites up 32 guests,

Villa Casalino your Tuscany wedding, 13 bedrooms and ensuites up 32 guests,

Pratovecchio
9.2 out of 10, Wonderful, (28)
"Alles wunderbar. Sehr liebe Gastgeberin, die sich ganz toll um uns gekümmert hat. Kommunikation lief auch gut mit ihr. Wir waren mit einer großen Gruppe mit Kindern vor Ort."
Germany
Veronika S.
Villa Casalino your Tuscany wedding, 13 bedrooms and ensuites up 32 guests,
Outdoor pool
An 800 villa in the Tuscan countryside - a quiet place - pool - culture

An 800 villa in the Tuscan countryside - a quiet place - pool - culture

Londa
9.4 out of 10, Exceptional, (30)
"We had 10 wonderful days at a peaceful and calm location with a very kind host, who gave interesting proposals and possibilities to explore in the area. Looking forward to come back in the future."
Germany
Alexander P.
An 800 villa in the Tuscan countryside - a quiet place - pool - culture
Apartment, Multiple Bedrooms, City View | Exterior
Les Trois Merveilles Green Fernando

Les Trois Merveilles Green Fernando

Centro Urbano
The price is NZ$273
includes taxes & fees
16 Nov - 17 Nov
Les Trois Merveilles Green Fernando
Outdoor pool
Large Watermill Villa near Florence - Mountain views

Large Watermill Villa near Florence - Mountain views

Londa
8.0 out of 10, Very good, (7)
"We had a fabulous stay at Villa Bucigna (end July 2025). We were a large group of 17. 14 adult's and 3 young children. There was ample space for all of us across the 2 villas and wellness centre. Communication with Peter and his family during our stay was excellent and some minor issues were dealt with promptly. The location is stunning with fantastic views and the sunsets over the mountains are fabulous. Its restful and peaceful location (although the cicadas can be quite vocal during the...
United Kingdom
Julie E.
Large Watermill Villa near Florence - Mountain views
Outdoor dining
Amazing countryside villa with private pool in Tuscany between Arezzo & Florence

Amazing countryside villa with private pool in Tuscany between Arezzo & Florence

Stia
9.8 out of 10, Exceptional, (46)
"Our Stia stay was exactly what we were looking for as a family of 2 grandparents, 4 adult children and 2 grandchildren, age 2 and infant, plus 3 other adults at times. We enjoyed a walkable town and excursions throughout Tuscany. Lucia was top notch and made our two weeks extraordinary - she booked a private chef, a pizza night at the home pizza oven, suggested wineries and helped with some transportation needs. She was attentive to all our requests! It's a beautiful property with a lovely pool...
United States
Sue M.
Amazing countryside villa with private pool in Tuscany between Arezzo & Florence
Outdoor pool
FANTASTIC RURAL HOUSE IN FULL RELAXATION IN THE HILLS WITH SWIMMING POOL

FANTASTIC RURAL HOUSE IN FULL RELAXATION IN THE HILLS WITH SWIMMING POOL

CIVITELLA DI ROMAGNA
9.8 out of 10, Exceptional, (37)
"Wunderschönes altes Bauernhaus in ländlicher Umgebung, und eine halbe Stunde nördlich von der kleinen Stadt Forli. Das Haus ist vollständig ausgestattet für einen Ferienaufenthalt und bietet genug Platz für vier Personen. Alles war sehr sauber und alles hat funktioniert, auch wenn es zum Teil recht rustikal war. aber gerade das macht den Charme dieser Ferienimmobilie aus. Der Besitzer Andrea spricht hervorragendes Englisch und hat uns sehr freundlich empfangen. Er war immer erreichbar und hat...
Germany
Arndt P.
FANTASTIC RURAL HOUSE IN FULL RELAXATION IN THE HILLS WITH SWIMMING POOL
Property grounds
Country House 2 <br>

Country House 2 <br>

Villafranca-San Martino
9.4 out of 10, Exceptional, (3)
"Check in mit Nadia lief problemlos. Sehr freundlich und herzlich. Die Küche ist klein aber alles da was man braucht. "
Germany
Moraya S.
The price is NZ$204
includes taxes & fees
19 Nov - 20 Nov
Country House 2 <br>
Outdoor pool
Poppiena Farmhouse "ABETE"

Poppiena Farmhouse "ABETE"

PRATOVECCHIO
10.0 out of 10, Exceptional, (9)
"Hele fijne vakantie gehad. Mooie plek, fijn huis en zwembad, leuk dorp. Zeer gastvrije host Maria. "
Netherlands
Elsbeth C.
Poppiena Farmhouse "ABETE"
Pool
Nespoli: House / Villa -Hillside house in the middle of nature

Nespoli: House / Villa -Hillside house in the middle of nature

Nespoli
9.6 out of 10, Exceptional, (76)
"We had a lovely time in Andreas house, which is ideally situated for exploring both the mountains (national park) and the seaside. Andrea has given us plenty of advice on where to go and what to do - including his favourite pizza place, a beautiful waterfall in the mountains and a quite natural part of the beach without a Lido, all of which we wouldn't have discovered without his help. We really recommend staying at his place!"
Germany
Ines D.
Nespoli: House / Villa -Hillside house in the middle of nature
Pool
WEDDINGS VILLA 4 SEASONS 13 bedrooms, private exclusiv pool per 16/30 guests

WEDDINGS VILLA 4 SEASONS 13 bedrooms, private exclusiv pool per 16/30 guests

Pratovecchio
9.8 out of 10, Exceptional, (11)
"Everything perfect."
Italy
Anonymous traveller
WEDDINGS VILLA 4 SEASONS 13 bedrooms, private exclusiv pool per 16/30 guests
Outdoor pool
Wonderful Villa with Private Pool near Arezzo and Florence, Wifi Free

Wonderful Villa with Private Pool near Arezzo and Florence, Wifi Free

Pratovecchio
9.8 out of 10, Exceptional, (36)
"Very nice and helpfull people and a very clean and authentic Toscana villa. We really enjoyed it."
Denmark
Emilie B.
Wonderful Villa with Private Pool near Arezzo and Florence, Wifi Free
Property grounds
La Casetta, romantic cottage with swimming pool (Bologna, Ravenna, Florence)

La Casetta, romantic cottage with swimming pool (Bologna, Ravenna, Florence)

Casola Valsenio
10.0 out of 10, Exceptional, (21)
"This property is exactly how I envisioned the italian countryside! Cornelius's sculptures only helped to enhance my experience. They are truly great hosts!!!"
United States
Christine D.
La Casetta, romantic cottage with swimming pool (Bologna, Ravenna, Florence)
Outdoor pool
VILLA CASE D'ARNO

VILLA CASE D'ARNO

Poppi
9.8 out of 10, Exceptional, (21)
"Host did not tell us final payment had to be in cash until the end of the stay. Had to go get 1100 euros! We were unaware we had to pay for all utilities including using lights, cooktop, hot water. WiFi was extra too. Winter heat was not turned on yet and it was cold and we had no way to turn it on. House as clean, the estate was very lovely, lots of privacy, would be nicer in good weather. Poppi is a very nice town just out of the way for day trips. "
United States
Hank P.
VILLA CASE D'ARNO
Outdoor dining
Villa + pool near Florence. La Casaccia . Sleeps 6+ 1 baby. Peace and views

Villa + pool near Florence. La Casaccia . Sleeps 6+ 1 baby. Peace and views

Londa (Florence)
9.2 out of 10, Wonderful, (48)
"Beautiful vacation."
United States
kitty k.
Villa + pool near Florence. La Casaccia . Sleeps 6+ 1 baby. Peace and views
Outdoor pool, a heated pool
In the heart of the Casentinesi Forest Park

In the heart of the Casentinesi Forest Park

Avena
9.6 out of 10, Exceptional, (30)
"We had a lovely stay! The house has everything you want but most of the time we where outside. The pool was clean and big enough to swim & play around. And the terras was beautiful and relaxing for your meals or to play a game (including some light when it went dark.The hosts where very friendly & helpfull.Overal a 10/10!"
Netherlands
Ruby d.
In the heart of the Casentinesi Forest Park
TV, fireplace, books
medieval watch tower and pool, near Florence, suitable for remote working

medieval watch tower and pool, near Florence, suitable for remote working

Londa ,Florence
9.8 out of 10, Exceptional, (59)
"Our stay at Adriana's gorgeous home exceeded our expectations. She is a kind, energetic, responsive host exuding Italian dolce vita not only in our interactions but also in the way she has created this magical property. There are happy flowers all over--inside and out--and the Tuscan landscape is gorgeous both near (right outside the doors and windows) and far on the surrounding hillsides. The home was perfectly neat, elegant, tastefully and traditionally decorated, well-stocked. We enjoyed...
United States
Chandler C.
medieval watch tower and pool, near Florence, suitable for remote working
Fridge, microwave, oven, stovetop
Perfect villa for 20 people!

Perfect villa for 20 people!

Tredozio
Perfect villa for 20 people!
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 Rocca San Casciano Hotel Reviews

Romantic detached cottage with pool, in a farm between Arezzo and Florence

Romantic detached cottage with pool, in a farm between Arezzo and Florence

10/10 Excellent
"Clean, comfortable, laundry available. "
Kira M. 3-night trip
Posted 12 days ago
Romantic detached cottage with pool, in a farm between Arezzo and Florence

Find out more about Rocca San Casciano

Everything you need to know about Rocca San Casciano holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rocca San Casciano holiday rental for you. At Expedia, you can take your pick from private holiday 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 Rocca San Casciano holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Rocca San Casciano holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rocca San Casciano. 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 Rocca San Casciano holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rocca San Casciano holiday rentals we have selected for you start as low as NZ$204 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Rocca San Casciano rentals

At Expedia, we put the best Rocca San Casciano holiday 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 Rocca San Casciano 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 Rocca San Casciano holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rocca San Casciano. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Frequently asked questions

Can I find a holiday rental in Rocca San Casciano?

Yes, there are holiday rentals close to the most popular sights in Rocca San Casciano, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Rocca San Casciano has to offer?

The Farmhouse of Caiano between nature, culture and swimming pool: This holiday home rental outside of Rocca San Casciano is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Rocca San Casciano?

Explore the area and family-friendly sights such as Indiana Park Terme della Fratta, or get out into nature at a spot like Civorio Waterfall. In the wider area, you’ll find Birthplace of Benito Mussolini and Caserma dei Carabinieri.

What’s a holiday rental in Rocca San Casciano like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rocca San Casciano. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for family trips or small group gatherings.