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Search results; Over 1,000 homes in Cortona

Top guest favorite
Bed and breakfast
Wake to valley views and friendly donkeys at this B&B in an olive grove near Cortona
1 bedroom, 1 bed, 1 private bath
Aug 17 – 22
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4.98 out of 5 average rating, 204 reviews
Top guest favorite
From this historic Cortona house’s terrace, you’ll take in valley and lake views
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
Top guest favorite
Look out over the Valdichiana from 2 terraces at this country chic Cortona apartment
4.99 out of 5 average rating, 184 reviews, 3 bedrooms, 3 beds, 1 bath
Sep 26 – Oct 1
Top guest favorite
Wake to Val di Pierle views at this Cortona farmstay with a pool and fireplace
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
Top guest favorite
A secret garden and jetted tub await you at this Cortona townhouse
5.0 out of 5 average rating, 75 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 24 – 29
Superhost
This Cortona house gives you Tuscan countryside views and alfresco dining
5.0 out of 5 average rating, 4 reviews, 6 bedrooms, 6 beds, 5 baths
Oct 2 – 7
Top guest favorite
Gaze over Lake Trasimeno from the infinity pool at this hilltop Cortona villa
5.0 out of 5 average rating, 95 reviews, 5 bedrooms, 8 beds, 4 baths
Sep 20 – 25
Soak in panoramic views from your private hot tub at this stone Cortona house
2 bedrooms, 2 beds, 1 bath
Sep 8 – 13
Top guest favorite
Look out over Valdichiana and Lake Trasimeno from this top-floor Cortona apartment
4.97 out of 5 average rating, 179 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 15 – 20
Guest favorite
Stone walls and valley views greet you at this renovated Cortona farmstay with a pool
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 5 beds, 2 baths
Sep 13 – 18
Top guest favorite
This newly renovated Cortona apartment gives you a private terrace with a barbecue
5.0 out of 5 average rating, 39 reviews, 1 bedroom, 2 beds, 1 bath
Aug 29 – Sep 3
Top guest favorite
Look out over Lake Trasimeno from this renovated Cortona apartment
4.97 out of 5 average rating, 186 reviews, 1 bedroom, 1 bed, 1 bath
Aug 21 – 26
Guest favorite
This renovated Cortona condo gives you a city view from the historic center
4.96 out of 5 average rating, 139 reviews, 1 bedroom, 1 bed, 1 bath
Oct 26 – 31
Guest favorite
This Cortona farmhouse gives you a private pool and alfresco dining in the hills
5.0 out of 5 average rating, 10 reviews, 5 bedrooms, 6 beds, 5.5 baths
Sep 14 – 19
Top guest favorite
Perched on Etruscan walls, this 3-floor Cortona house gives you valley views and a fireplace
4.95 out of 5 average rating, 201 reviews, 2 bedrooms, 2 baths
Sep 1 – 6
Top guest favorite
Tuscan terracotta and whitewashed beams greet you at this shabby chic Cortona apartment
4.96 out of 5 average rating, 416 reviews, 1 bedroom, 2 beds, 1 bath
Oct 27 – Nov 1
Top guest favorite
Exposed beams and antique furniture greet you at this restored Cortona home
4.88 out of 5 average rating, 275 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 12 – 17
Top guest favorite
Look out over Piazza Signorelli from this frescoed Cortona vacation home
4.89 out of 5 average rating, 106 reviews, 1 bedroom, 3 beds, 1 bath
Aug 20 – 25
Guest favorite
Look out over the Valdichiana from this Cortona apartment’s outdoor dining area
4.98 out of 5 average rating, 53 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 14 – 19