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Holiday homes Tuscany

Personally selected by specialists

Holiday homes and authentic agriturismo in Tuscany

Do you dream of a holiday home in Tuscany, nestled among rolling hills, cypress trees, and vineyards? At Triptoscana, you will find a carefully curated selection of holiday homes, agriturismos, and villas in Tuscany – all personally visited and reviewed.

We are not a mass platform, but a Tuscany specialist. That means: no thousands of houses, but only the places we fully endorse. From charming agriturismos to luxury villas with private pools – always with personal service and honest advice.

Why a holiday home in Tuscany?

Tuscany is one of the most beautiful regions of Italy and perfect for a relaxing holiday. Here you will find:
  • Picturesque villages such as San Gimignano and Montepulciano
  • Extensive vineyards in the Chianti region
  • Peace, space, and nature
  • Fantastic food and local wines
A holiday home in Tuscany gives you the freedom to discover the region at your own pace – away from the hustle and bustle and right in the heart of Italian life.

Which region in Tuscany suits you?

Each region in Tuscany has its own character. We are happy to help you choose:

Chianti region
Perfect if you love wine, a central location, and rolling landscapes.

Val d’Orcia
Perhaps the most beautiful part of Tuscany, with iconic views and tranquility.

Tuscan Coast
Ideal if you want to combine nature with the beach.

Florence & Siena surroundings
Suitable for those who want to combine culture and cities with a stay in nature.

Undecided? We will advise you personally based on your wishes.

Holiday home in Tuscany with swimming pool

For many people, a holiday home with a swimming pool is the ideal way to experience Tuscany. Especially during the warm summer months, a private or shared pool is certainly not an unnecessary luxury.

We offer:
  • Holiday homes with a private pool
  • Small-scale agriturismos with a pool
  • Child-friendly accommodations

Vakantiehuizen voor gezinnen en koppels

Whether you are traveling with children, as a couple, or with friends – we have suitable options:
  • Families: safe environment, swimming pool, space to play
  • Couples: peace, romance, and intimacy
  • Groups: spacious villas with multiple bedrooms

Why book via Triptoscana?

Wat ons anders maakt dan grote aanbieders:
  •  Alle accommodaties persoonlijk bezocht
  •  Direct contact met de eigenaar
  •  Eerlijk en persoonlijk advies
  •  Specialist in Toscane (geen massatoerisme)
Wij helpen je niet alleen een vakantiehuis te vinden, maar zorgen dat jouw vakantie écht klopt.

Personal advice for your holiday in Tuscany

The selection is vast, and choosing can be difficult. That is why we are happy to help you personally.

Tell us:
  • how many people you are traveling with
  • when you want to go
  • what is important to you
We will send you a selection that suits you perfectly.

I would like a proposal

Villa Mazzanta

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  • Swimming pool: yes
  • Restaurant: no
  • 2-6 persons
  • From € 570 per week

Pacina

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  • Swimming pool: yes
  • Restaurant: no
  • 2-8 persons
  • From € 840 per week

Agriturismo Sanguineto

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  • Swimming pool: yes
  • Restaurant: yes
  • 2-6 persons
  • From € 590 per week

Borgo Lucignanello

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  • Swimming pool: yes
  • Restaurant: no
  • 2-7 persons
  • From € 950 per week

Agriturismo Cosona

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  • Swimming pool: yes
  • Restaurant: no
  • 2-11 persons
  • From € 665 per week

Agriturismo San Giacomo

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  • Swimming pool: yes
  • Restaurant: yes
  • 2-6 persons
  • From € 500 per week

Fattoria La Loggia

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  • Swimming pool: yes
  • Restaurant: no
  • 2-6 persons
  • From € 780 per week

Tenuta Bichi Borghesi

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  • Swimming pool: yes
  • Restaurant: no
  • 2-8 persons
  • From € 610 per week

Santa Maria a Poneta

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  • Swimming pool: yes
  • Restaurant: no
  • 2-4 persons
  • From € 630 per week

Castello Ginori di Querceto

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  • Swimming pool: yes
  • Restaurant: yes
  • 2-8 persons
  • From € 470 per week

L'Antica Fornace

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  • Swimming pool: yes
  • Restaurant: no
  • 2-6 persons
  • From € 900 per week

Antico Borgo di Tignano

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  • Swimming pool: yes
  • Restaurant: yes
  • 2-6 persons
  • From € 700 per week

Podere San Lorenzo

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  • Swimming pool: yes
  • Restaurant: yes
  • 2-4 persons
  • From € 665 per week

Castelvecchio

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  • Swimming pool: no
  • Restaurant: no
  • 2-6 persons
  • From € 380 per week

Agriturismo Piettorri

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  • Swimming pool: yes
  • Restaurant: no
  • 2-5 persons
  • From € 460 per week

Il Frutteto

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  • Swimming pool: yes
  • Restaurant: yes
  • 2-6 persons
  • From € 510 per week

Borgo al Cerro

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  • Swimming pool: yes
  • Restaurant: no
  • 2-6 persons
  • From € 589 per week

Villa Montecastello

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  • Swimming pool: yes
  • Restaurant: no
  • 2-10 persons
  • From € 1450 per week

Agriturismo Canale

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  • Swimming pool: yes
  • Restaurant: no
  • 2-6 persons
  • From € 588 per week

Il Castagno

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  • Swimming pool: yes
  • Restaurant: no
  • 2-8 persons
  • From € 650 per week

Tenuta San Vito

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  • Swimming pool: yes
  • Restaurant: yes
  • 2-14 persons
  • From € 650 per week

Borgo La Casaccia

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  • Swimming pool: yes
  • Restaurant: no
  • 2-8 persons
  • From € 490 per week

Borgo Bottaia

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  • Swimming pool: yes
  • Restaurant: no
  • 2-7 persons
  • From € 580 per week

I Moricci

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  • Swimming pool: yes
  • Restaurant: no
  • 2-6 persons
  • From € 973 per week

Glamping at Lucia

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  • Swimming pool: yes
  • Restaurant: no
  • 2-7 persons
  • From € 1190 per week

Il Cerreto

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  • Swimming pool: yes
  • Restaurant: yes
  • 2-8 persons
  • From € 600 per week

Poggio La Croce

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  • Swimming pool: yes
  • Restaurant: no
  • 2-6 persons
  • From € 900 per week
This overview is a selection of our accommodations for inspiration. Please contact us for a free proposal.
For more holiday homes contact us
This offer is not covered by the STO Garant guarantee. You can find the conditions for this
guarantee scheme on STO Garant’s website (www.sto-garant.nl/de/downloads).

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Luxury villas

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Plant trees for a green and healthy world
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© 2026 Triptoscana
  • Home
  • Accommodaties
    • Vakantiehuizen
    • B&B
    • Luxe Villa's
  • Arrangementen
    • Kookreizen >
      • Koken in Toscane
      • Kookreis op maat
    • Antiekmarkt Arezzo
    • Luxe arrangement in Villa Petriolo
    • Pakketreizen voor- en najaar >
      • Pakketreis Wine & Food
      • Pakketreis Kunst & Cultuur
      • Pakketreis Strand & SPA
    • 5-daagse Bike Tour van Florence naar Siena
    • 7-daagse Bike Tour door Toscane
    • Olijfpluk arrangement
    • Thermen & spa
    • Schildervakantie Toscane
  • Experience
  • Auto huren
  • Treinen naar Florence
  • Blog
  • Contact
    • Onze service
    • Over ons
    • Recensies
    • Nieuwsbrief
  • Home
  • Stay
    • Holiday Homes
    • B&B
    • Luxury Villas
  • Package deals
    • Cooking Tours >
      • Cooking in Tuscany
      • Tailor-made cooking tour
    • Antique market Arezzo
    • Luxury package at Villa Petriolo
    • Spring and Autumn Holidays >
      • Wine & Food Holiday
      • Art & Culture Holiday
      • Beach & SPA Holiday
    • 5-Day Bike Tour from Florence to Siena
    • 7-Day Bike Tour through Tuscany
    • Picking olives package
    • Thermae & spa
    • Painting Holiday in Tuscany
  • Experience
  • Rent a car
  • Contact
    • Our services
    • About us
    • Reviews
    • Newsletter
  • Startseite
  • Ihr Aufenthalt
    • Ferienhäuser
    • B&B
    • Luxusvillen
  • Pauschalangebote
    • Kochreisen >
      • Kochen in der Toskana
      • Individuelle Kochtour
    • Antiquitätenmarkt von Arezzo
    • Luxuspaket in der Villa Petriolo
    • Frühling und Herbst in der Toskana >
      • Wein & Speisen Urlaub
      • Kunst & Kultur Urlaub
      • Strand- und Wellnessurlaub
    • 5-tägige Radtour von Florenz nach Siena
    • 7-tägige Radtour durch die Toskana
    • Olivenernte-Paket
    • Therme und Spa
    • Malkurs in der Toskana
  • Erlebnisse
  • Autovermietung
  • Kontakt
    • Unsere Dienstleistungen
    • Über uns
    • Bewertungen
    • Newsletter