Holiday rentals near Hannibal's Journey

We found 3,765 holiday rentals — enter your dates for availability

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July 2025

August 2025

If you'd like to stay close to Hannibal's Journey, take a look at private holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Hannibal's Journey

Showing deals for:24 Oct - 31 Oct

Exceptional

(7 reviews)

Beautiful Tuscan farmhouse in the countryside with swimming pool

Cortona, Tuscany

5% off

AU$1,020 per night

includes taxes & fees

Exceptional

(7 reviews)

10 bedroom cottage for groups, wine/oil tasting, cooking lessons, private pool

Piegaro, Umbria

9% off

AU$1,601 per night

includes taxes & fees

Exceptional

(19 reviews)

FABULOUS 6BR HOME WITH WONDERFUL SWIMMING POOL & GARDEN IN THE HEART OF TUSCANY!

Lucignano, Tuscany

9% off

AU$1,210 per night

includes taxes & fees

Big salted water pool 12x6 mt. with relaxing spaces plus lounges to relax

Exceptional

(100 reviews)

Exclusive hideaway nestled in woods with stunning lakeview Tuscany/Umbria border

Passignano sul Trasimeno, Provincia di Perugia

20% off

AU$337 per night

includes taxes & fees

Exceptional

(6 reviews)

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

Cortona, Tuscany

18% off

AU$755 per night

includes taxes & fees

Exceptional

(39 reviews)

Beautifully restored 16th C farmhouse w/ exclusive pool, woodlands, olive groves

Cortona, Toscana

5% off

AU$372 per night

includes taxes & fees

Wonderful

(22 reviews)

Attractive Renovated Stone Mill House, Lovely Private Pool, Sleeps Max 5 People.

Cortona, Tuscany

9% off

AU$280 per night

includes taxes & fees

Exceptional

(16 reviews)

An unforgettable holiday between nature and art. Ideal family friendly location.

Umbertide, Umbria

8% off

AU$789 per night

includes taxes & fees

Exceptional

(16 reviews)

Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

Montepulciano

9% off

AU$960 per night

includes taxes & fees

Exceptional

(26 reviews)

Villa Costa Piccola with private pool "amazing holiday in green heart of Italy"

Umbertide, Perugia

9% off

AU$921 per night

includes taxes & fees

Exceptional

(24 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena, Tuscany

9% off

AU$485 per night

includes taxes & fees

Exceptional

(11 reviews)

Country house, heated pool, 4 en-suite bedrooms, stunning views sleeps 8 wi-fi

Monte Santa Maria Tiberina, Umbria

5% off

AU$805 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Hannibal's Journey

Showing deals for: 20 Oct - 23 Oct

House with garden and panoramic view over Lake Trasimeno

Sleeps 9 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 villa

AU$507 per night

includes taxes & fees

Apartment in Sant 'Angelo di Cortona, immersed in the Tuscan hills

Sleeps 5 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$216 per night

includes taxes & fees

Case Ginezzo: The Farm and the Refuge. Cortona

Sleeps 20 · 8 bedrooms · 6 bathrooms

for 3 nights, 1 home

AU$1,139 per night

includes taxes & fees

Rustic Farmhouse for 8+2 person with Private Swimming Pool

Sleeps 10 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 villa

AU$631 per night

includes taxes & fees

An organic writer and producer, she creates food for the body and mind

Sleeps 4 · 3 bedrooms · 1 bathroom

for 3 nights, 1 room

AU$115 per night

includes taxes & fees

HouseAle Villa with garden in the heart of Tuscany 10

Sleeps 10 · 4 bedrooms · 1 bathroom

for 3 nights, 1 villa

AU$124 per night

includes taxes & fees

Top rated rentals - Hannibal's Journey

Premier Host

Loved Our Stay In Montepulciano

Our first time in Italy, we loved our three night stay in Montepulciano and the apartment made it so much more special, the home had everything you need and is located in a perfect spot with amazing views and an easy walk to everywhere in the village. Host was great and spent some time with us at check in, showing us the best restaurants to eat in and other villages to visit that were close by. We will definitely stay again if we go back to Italy. Highly recommend!

glen b.

Stayed Mar 2025

Premier Host

Tuscan birthday

We had a luxurious time with friends and family for my wife's birthday. Local restaurants were great even in winter . Parking in Chiusi can be interesting. A memorable stay for all the right reasons

Stuart S.

Stayed Feb 2025

Premier Host

A pleasant stay near beautiful town of Montepulciano.

Thank you, Franco for your friendliness and for helping us with transport.

Anna H.

Stayed Dec 2024

Premier Host

Beautiful stay

We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful.

Murray H.

Stayed Oct 2024

Premier Host

Love villa in Tuscany

We loved our stay at this villa in Cetona. We got some great use of the pool and spa. Our only wish was some AC for the nights it can get a bit hot some evenings. Great place to explore lots of nearby towns and vineyards. Valerio had some great recommendations and made some bookings for us which was greatly appreciated!

Stephanie H.

Stayed June 2023

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