Holiday rentals near Casa di Santa Caterina

We found 3,755 holiday rentals — enter your dates for availability

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January 2026

February 2026

If you'd like to stay close to Casa di Santa Caterina, take a look at holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a hot tub. At the end of the day, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Casa di Santa Caterina

Showing deals for:24 Apr - 1 May

Exceptional

(27 reviews)

BEAUTIFUL VILLA with private Pool in the heart of Chianti

castelnuovo berardenga

7% off

for 7 nights, 1 villa

AU$2,245 per night

includes taxes & fees

Exceptional

(75 reviews)

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Pievasciata

9% off

for 7 nights, 1 villa

AU$1,084 per night

includes taxes & fees

Wonderful

(7 reviews)

Beautiful 1-bedroom cottage with garden and views over olive groves, pool

Castellina in Chianti, Toscana

10% off

for 7 nights, 1 cottage

AU$307 per night

includes taxes & fees

Exceptional

(52 reviews)

Farmhouse in the greenery of the Tuscany countryside with private pool and view

Murlo

9% off

for 7 nights, 1 home

AU$492 per night

includes taxes & fees

Wonderful

(6 reviews)

Wonderful apartment in a Tuscan farmhouse with swimming pool and panoramic terrace

Casole d'Elsa Siena

8% off

for 7 nights, 1 apartment

AU$231 per night

includes taxes & fees

Exceptional

(18 reviews)

Sangiovese Country House, apartment with pool in a small village in the hills of Chianti

Tavarnelle Val Di Pesa

6% off

for 7 nights, 1 apartment

AU$292 per night

includes taxes & fees

Exceptional

(20 reviews)

Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views

Castellina in Chianti

10% off

for 7 nights, 1 villa

AU$983 per night

includes taxes & fees

Exceptional

(11 reviews)

Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

Radda in Chianti

9% off

for 7 nights, 1 villa

AU$2,461 per night

includes taxes & fees

Exceptional

(44 reviews)

Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

Quercegrossa

9% off

for 7 nights, 1 villa

AU$453 per night

includes taxes & fees

Montegonfoli and San Gimignano. Part of our 1000 olive trees and of our vineyard

Exceptional

(13 reviews)

Montegonfoli 3 Stunning San Gimignano Apartment with pool, Patio & Scenic Views

san gimignano

8% off

for 7 nights, 1 apartment

AU$227 per night

includes taxes & fees

Exceptional

(39 reviews)

Il Boschetto an oasis of peace and nature in Siena

Siena

9% off

for 7 nights, 1 villa

AU$909 per night

includes taxes & fees

Exceptional

(9 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Villa A Sesta

7% off

for 7 nights, 1 home

AU$244 per night

includes taxes & fees

Exceptional

(94 reviews)

Hilltop house in the heart of Tuscany with private pool

Montisi

9% off

for 7 nights, 1 villa

AU$413 per night

includes taxes & fees

Exceptional

(40 reviews)

An enchanting small villa, perfect for two, with an unparalleled view.

Gaiole in Chianti

9% off

for 7 nights, 1 villa

AU$474 per night

includes taxes & fees

Exceptional

(40 reviews)

Bufati - A House in Chianti - Yellow Apartment

Barberino Tavarnelle

8% off

for 7 nights, 1 home

AU$243 per night

includes taxes & fees

Wonderful

(28 reviews)

Wonderful Tuscan farmhouse in the Tuscan countryside

Colle di val d'Elsa

6% off

for 7 nights, 1 home

AU$251 per night

includes taxes & fees

Exceptional

(66 reviews)

La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

Siena

10% off

for 7 nights, 1 apartment

AU$308 per night

includes taxes & fees

Exceptional

(25 reviews)

Typical Tuscan residence in an ancient village on the outskirts of Siena

Monticiano

8% off

for 7 nights, 1 apartment

AU$203 per night

includes taxes & fees

Exceptional

(17 reviews)

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Siena

14% off

for 7 nights, 1 villa

AU$564 per night

includes taxes & fees

Exceptional

(65 reviews)

Private villa with swimming pool and spectacular views of Siena

Casetta

8% off

for 7 nights, 1 home

AU$566 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Casa di Santa Caterina

Castellare Degli Ugurgieri Central Apt in Siena

Sleeps 6 · 2 bedrooms · 1 bathroom

Top rated rentals - Casa di Santa Caterina

Premier Host

Apartment in Siena

Stunning and very large apartment. Very close to all major attractions. Federica was very helpful. Check in was very easy. Highly recommend this apartment.

John M.

Stayed May 2025

Image of Modern comfort and historic charm in the heart of Siena

Premier Host

Rebecca

Was an excellent place to stay and the hosts very very helpful. Would throughly recommend a stay here.

Rebecca B.

Stayed Dec 2024

Image of Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

Premier Host

Very Central and Very Authentic

Our group of friends (Australian) very much enjoyed our 4 nights in the Apartment. It is very centrally located alongside the Piazza Salimbeni. Our hosts Gianluca and Alex were easy to communicate with via WhatsApp, and helped us with valet parking for our mini van, prior to entering the city centre. We lucked upon the celebration for the recent Palio and enjoyed the fanfare. There’s heaps of restaurants nearby and all the sights are within easy walking distance. There was a bit of noise on the Saturday night, in particular, but we were happy to put up with it. We all agreed we’d stay again.

Angus D.

Stayed Oct 2023

Image of HOUSE WOW panoramic terrace *.*

Sensational

Beautiful apartment with breathtaking views. Central location with everything you need within walking distance. Very welcoming host. Thank you for a very memorable stay x

Jen N.

Stayed June 2023

Great apartment and fantastic welcome

A fantastic second floor apartment in central old Siena with a short walk to the Campo. Very clean with everything you need for a great stay. A great welcome from the owners that made you feel very relaxed. Super bathroom and comfortable bed. Good selection of restaurants and places for a glass of wine within easy walking distance.

Gary D.

Stayed Oct 2017

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