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Holiday rentals near Castello del Trebbio

We found 5,852 holiday rentals — enter your dates for availability

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September 2025

October 2025

If you'd like to stay close to Castello del Trebbio, scroll through and discover holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Castello del Trebbio

Showing deals for:26 Dec - 2 Jan

Exceptional

(35 reviews)

Florence Loft - Near Duomo

Florence, Toscana

9% off

for 7 nights, 1 apartment

AU$724 per night

includes taxes & fees

Exceptional

(33 reviews)

Top floor with garden bordering the historic city walls in San Niccolo district

Florence, Città Metropolitana di Firenze

9% off

for 7 nights, 1 apartment

AU$1,185 per night

includes taxes & fees

Exceptional

(114 reviews)

Wonderful city apartment with breath taking views over Florence.

Florence, Toskana

10% off

for 7 nights, 1 apartment

AU$448 per night

includes taxes & fees

Exceptional

(201 reviews)

Amazing Views of Ponte Vecchio and Uffizi - Extremely silent - Modern - WiFi

Florence, Toscana

13% off

for 7 nights, 1 apartment

AU$433 per night

includes taxes & fees

Exceptional

(103 reviews)

Under the stars, Surrounded by greenery a stone's throw from the center of Florence.

Florence, Toscana

8% off

for 7 nights, 1 home

AU$236 per night

includes taxes & fees

Exceptional

(47 reviews)

LA LIMONAIA - CASA RABATTI 1823 - THE GARDEN IN THE HEART OF FLORENCE

Florence, Toscana

13% off

for 7 nights, 1 apartment

AU$311 per night

includes taxes & fees

The CANAPY bedroom with the canapy bed and the balcony on the garden area

Exceptional

(59 reviews)

Beautiful Apartment in the Historic City Centre of Florence

Florence, Toscana

8% off

for 7 nights, 1 apartment

AU$362 per night

includes taxes & fees

Apt. Brunelleschi in Villa Cafaggiolo and the wonderful swimming pool

Exceptional

(31 reviews)

VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.

Rignano sull'Arno, Toscana

9% off

for 7 nights, 1 villa

AU$647 per night

includes taxes & fees

Exceptional

(82 reviews)

DiladdArno Holiday Home, cozy and bright apartment in Florence.

Florence, Toscana

8% off

for 7 nights, 1 apartment

AU$310 per night

includes taxes & fees

The main house with the guest house on the right

Exceptional

(28 reviews)

Beautifully restored farmhouse in Greve, heart of Chianti

Greve in Chianti, Chianti

5% off

for 7 nights, 1 room

AU$1,022 per night

includes taxes & fees

Exceptional

(8 reviews)

Wonderful Villa in Tuscany Coutryside with hydromassage pool and private garden

San Godenzo, Toscana - Italia

9% off

for 7 nights, 1 home

AU$305 per night

includes taxes & fees

Exceptional

(28 reviews)

Historic Dante's Manor, 5 Bdr Villa, Pool, Garden, Jacuzzi, AC, 5 min Florence

Florence, Toscana

9% off

for 7 nights, 1 villa

AU$3,532 per night

includes taxes & fees

Exceptional

(142 reviews)

TWO BEDROOM LOFT NEAR PONTE VECCHIO/OLD BRIDGE WITH FREE BREAKFAST ITEMS OFFERED

Florence, Toscana

8% off

for 7 nights, 1 apartment

AU$619 per night

includes taxes & fees

Exceptional

(30 reviews)

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

Londa, Tuscany

12% off

for 7 nights, 1 home

AU$536 per night

includes taxes & fees

Exceptional

(10 reviews)

CountryHouse con Piscina Privata 5 min dal centro

Florence, Città Metropolitana di Firenze

9% off

for 7 nights, 1 villa

AU$591 per night

includes taxes & fees

Exceptional

(18 reviews)

Convert your vacation into a highly regenerating life experience.

Pontassieve, Tuscany

6% off

for 7 nights, 1 home

AU$165 per night

includes taxes & fees

Exceptional

(207 reviews)

"Renaissance Retreat" by WP Relais , Palazzo Uguccioni, in Piazza della Signoria

Florence, Toscana

9% off

for 7 nights, 1 apartment

AU$1,168 per night

includes taxes & fees

Exceptional

(15 reviews)

Villa Franchetti - Luxurious Florentine Villa with Swimming Pool

Bagno a Ripoli, Toscana

9% off

for 7 nights, 1 villa

AU$1,510 per night

includes taxes & fees

Villa MURGIANO's Infinity Edge Pool & spacious Lounging Area

Exceptional

(103 reviews)

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

Impruneta, Tuscany

7% off

for 7 nights, 1 villa

AU$1,636 per night

includes taxes & fees

Find spaces that suit your style

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Find properties near top attractions in Castello del Trebbio

Castello del Trebbio

Find the best place to stay - Castello del Trebbio

MAGNIFICENT 9BR VILLA WITH HEATED POOL & STUNNING VIEWS IN TOP CHIANTI LOCATION!

Sleeps 18 · 9 bedrooms · 7+ bathrooms

Elegante villa con piscina a soli 12 km da Firenze ideale per famiglie e gruppi

Sleeps 12 · 5 bedrooms · 5 bathrooms

In the Hills of Mugello Tuscany in a recently renovated 17th Century Monastery

Sleeps 7 · 2 bedrooms · 3 bathrooms

ONE MILE FROM HEART OF HISTORIC FLORENCE, STUNNING 5BD-5BA VILLA W/ HEATED POOL!

Sleeps 10 · 5 bedrooms · 5 bathrooms

Top rated rentals - Castello del Trebbio

Premier Host

Visit to Florence

The apartment overlooking the Duomo was perfect

Rebecca L.

Stayed May 2025

Villa "Torre in Chianti" your homeaway in Tuscany!!!

Premier Host

Beautiful Villa in a great central location

The Villa has everything you need for a more than comfortable stay. Centrally located for exploring many of the local Tuscany highlights with a quick tram to Florence.Worth staying in to enjoy the pool and surrounds when the weather is good. Great outdoor space! We were 15 adults.

Suzanne G.

Stayed May 2025

Premier Host

Fabulous apartment

Super close to everything, very well presented in every way, decor, cleanliness and amenities. Hosts Elisabetta and Claudio ever so welcoming pre, during and post stay. We loved our stay and would stay again if we return to Florence. Thank you Elisabetta and Claudio

Frank M.

Stayed Apr 2025

Gorgeous tuscan villa

Amazing villa, great check in process. Rooms gorgeous, living space's very comfortable. We stayed with 2 families over Christmas, very cosy. A car is very useful to see neighbouring towns.

Yolanda C.

Stayed Dec 2024

Premier Host

Amazing house like a dream.

Amassing cottage exactly as describe, super clean plenty of space for a family. Great location right in the heart of Tuscany with incredible views and it was super peaceful. Magdalena was so nice and knowledgeable very responsive and gave us numerous recommendations for the local area. The house is ease to find through google maps instead of GPS. Truly a dream house in the quiet, beautiful countryside. I can’t wait to return.

Elso C.

Stayed June 2024

Premier Host

A truely magical stay

What a wonderful experience. The location is extraordinary but to focus solely on the location is selling this apartment short. The presentation of the apartment in this 16th century building was everything we had hoped for. The host, Lorenzo, was so welcoming and generous, nothing was too much trouble. A bottle of wine on arrival, so beautifully presented, was the perfect start to our stay. A lift meant we didn’t have to lug our suitcases up multiple flights of stairs. And then there is the location! Beware though, being opposite Florence’s famous leather market might result in some damage to your wallet! Thank you Lorenzo for a truely memorable stay.

Stephen M.

Stayed Jan 2024

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