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Search results; Over 1,000 homes in Cortona

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Guest favourite
Holiday home in Cortona
Arianna's winery
3 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
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4.9 out of 5 average rating, 21 reviews
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Top guest favourite
Flat in Cortona
Cortona’s Rooftop Nest
3 bedrooms, 3 beds, 1 bathroom
6–11 Nov
4.99 out of 5 average rating, 187 reviews
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Superhost
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
5 bedrooms, 8 beds, 4 bathrooms
6–11 Oct
5.0 out of 5 average rating, 96 reviews
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Top guest favourite
Flat in Cortona
Cortona Shabby Chic House - independent & balcony-
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 419 reviews
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Top guest favourite
Apartment in Cortona
Chicca: Cortona's historic center
1 bedroom, 2 beds, 2 bathrooms
26–31 Oct
4.99 out of 5 average rating, 221 reviews
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Top guest favourite
Home in Castiglion Fiorentino
Hidden gem in Tuscany
3 bedrooms, 3 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 53 reviews
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Top guest favourite
Flat in Cortona
Casa AlMa: air conditioning and private terrace
1 bedroom, 2 beds, 1 bathroom
28 Oct – 2 Nov
5.0 out of 5 average rating, 44 reviews
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Home in Cortona
Relais Tosca Slow and Rural Life
2 bedrooms, 2 double beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Cortona
Casa del Passerino
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 224 reviews
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Guest favourite
Flat in Cortona
La Corte Apartment
3 bedrooms, 3 beds, 3 bathrooms
14–19 Sept
4.79 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Cortona
Breathtaking views: Historic House w/Terrace & BBQ
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 25 reviews
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Top guest favourite
Flat in Cortona
SIGNORELLI HOUSE
3 bedrooms, 3 double beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 12 reviews
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Superhost
Farm stay in Cortona
Relaxing-unspoiled country place Il Monte...
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Guest house in Macciano
Tuscan cottage with an heavenly view
1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
4.97 out of 5 average rating, 245 reviews
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Superhost
Flat in Montepulciano
Under the sunset, Montepulciano
2 bedrooms, 3 beds, 2.5 bathrooms
16–21 Nov
4.98 out of 5 average rating, 163 reviews
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Superhost
Farm stay in Cortona
Relaxing-unspoiled country place La Loggia...
1 bedroom, 1 king bed, 1 bathroom
6–11 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Flat in Cortona
I Terrazzini apt.1
2 bedrooms, 3 beds, 1 bathroom
30 Oct – 4 Nov
4.97 out of 5 average rating, 181 reviews
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Guest favourite
Farm stay in Cortona
Rural Tuscany | Farmstay with pool & garden
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.86 out of 5 average rating, 37 reviews
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Superhost
Flat in Cortona
Terrazza Silena, historic center with Cortona view!
1 bedroom, 1 double bed, 1 bathroom
5–10 Oct
4.98 out of 5 average rating, 88 reviews