
Vacation rentals in Cortona
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Top-rated vacation rentals in Cortona
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Cortona vacation rentals
Boutique hotels in Cortona
Guest favorite

Hotel room in Siena
4.95 out of 5 average rating, 21 reviewsPandolfo Petrucci Suite
EmmaRating, 5 stars7 months ago
We highly recommend staying with Rita if you are ever in Siena. The suite is stunning, bigger and cosier than the photos! The location of the suite is very central to Sienna and close to everything you need. Not to mention a beautiful view of the Baptistery of Siena from your window… We were made to feel very welcome by all of the staff, and the team were incredibly helpful and responsive. We went for the valet parking option that they offered, which is well worth the money and stress free parking (if driving). Thank you again for hosting us!
Guest favorite

Hotel room in Siena
4.97 out of 5 average rating, 126 reviewsSleeping on Siena roof
JoshRating, 5 stars1 week ago
We had a lovely one night stay during our Tuscany trip. The room was clean, cozy, and the view is very special. Francesca gave clear instructions that made our visit seamless. In our room we found a list of her personal local recommendations for where to eat, walk, and shop. We enjoyed these very much.

Hotel room in Siena
4.84 out of 5 average rating, 56 reviewsDouble Classic room Duomo
benoitRating, 5 stars1 month ago
Very good stay with Dominico. Great place to visit Siena.
Guest favorite

Hotel room in Campagnatico
4.95 out of 5 average rating, 19 reviewsIndependent Deluxe Room with Panoramic View
SilviaRating, 5 stars5 months ago
On a weekend on a motorcycle, passing through the area we stayed in Servilio's wonderful guest house. The village of Campagnatico is a small gem worth visiting, getting lost in the streets to discover the cistern, the spring, the sundial and the steps of Dante Alighieri. Servilio's room, his home and hospitality are worth the trip alone. The renovated and tastefully furnished room has a beautiful view of the surrounding countryside and part of the town, and has everything you need to relax: a very comfortable king size bed, air conditioning, fridge, TV, kettle. The bathroom is huge, with a beautiful window with a view and a large walk-in shower. The host also allowed us to put the bike indoors and safely in his garage, making my partner so happy😉. He gave us tips on places to visit and recommended dining at the village restaurant and it was really worth it. Highly recommended! Silvia and Giovanni
Superhost

Hotel room in Siena
4.8 out of 5 average rating, 114 reviewsCharming Room at the Duomo 2
NadineRating, 5 stars2 weeks ago
perfect place to stay in the old town of Siena! Great room service and location:)
Superhost

Hotel room in Passignano sul Trasimeno
5 out of 5 average rating, 8 reviewsBoutique Room - Minor - From Hill to Hill
KatieRating, 5 stars22 months ago
We enjoyed 3 nights at this beautiful place, the surroundings are amazing and so relaxing. Giulio and the team working here are very attentive and all super friendly. We loved our stay!
Guest favorite

Hotel room in Piancastagnaio
5 out of 5 average rating, 19 reviewsAntica Foresteria Room 2
ChristophRating, 5 stars6 months ago
A Memorable Stay ! I had the pleasure of spending a few days at this beautiful hotel. The location is stunning, offering breathtaking views. Whether you’re enjoying the view from the Pool, the room, or the garden, the scenery is simply spectacular. A highlight was the guided tour of the property, which gave us a deeper appreciation for its history. You can feel the passion and care that have gone into maintaining this place. The breakfast was another highlight of our stay – absolutely delicious, with many homemade items that made it extra special. Overall, this hotel exceeded all expectations, offering so much more than meets the eye. It’s the perfect place to relax, and take in the beauty of the surroundings. I can highly recommend it!
Guest favorite

Hotel room in Bettolle
4.94 out of 5 average rating, 205 reviewsNice double room in a charming B&B
JINYIRating, 5 stars2 weeks ago
This place is simply a dream! Every window in the house looks like a painting—nature is framed so beautifully that it takes your breath away. The room itself was stunning, full of warmth and style. The host was incredibly kind and respectful. We truly appreciated the upgrade to a better room and all the thoughtful help we received. From showing us how to buy train tickets, to calling a taxi and even helping with our luggage—it felt like staying with a dear friend who truly cared. And yet, they were never intrusive—just wonderfully supportive when needed. And the food—wow! Every meal was delicious and generous. The breakfast croissants and fresh milk are unforgettable, and the cleanliness and cozy environment made everything feel perfect. We genuinely didn’t want to leave. “Home away from home” doesn’t even begin to describe it. It was beyond amazing. We wholeheartedly recommend this place to everyone—it’s an experience you don’t want to miss!❤️❤️❤️☺️
Other great vacation rentals in Cortona
Top guest favorite

Apartment in Mercatale Valdarno
4.98 out of 5 average rating, 80 reviewsPanoramic view from stone Apartment- Pool and A/C
ClaireRating, 5 stars6 months ago
While looking for a place to stay it’s often difficult to choose. If we had known how fabulous this place was it would have been a no brainer! We all agreed that this is the best Airbnb we have ever stayed in on all of our travels. Massimiliano was a delight and so personable. He made excellent suggestions one being having a cooking lesson. If you have a chance ask for Francesca! The BEST! One last thing…we left with amazing recommendations for the next part of our trip. Thank you so much for a wonderful stay! Good luck with the harvest!
Top guest favorite

Farm stay in Camucia
5 out of 5 average rating, 7 reviewsThe Garden of Olives | Casa Ippocastano
ViktorijaRating, 5 stars7 months ago
Everything was perfect! Nice place to rest with a wonderful chill lounge and a pool. Federica and Enrica were responsive and helpful hosts. Thanks for the time and all the recomendations.
Guest favorite

Villa in Asciano
4.95 out of 5 average rating, 75 reviewsPodere on the Crete Senesi
ChulaRating, 5 stars6 months ago
We spent a glorious and relaxing week at Sarchianello and could not recommend it more. The location was perfect for day trips to local places like Siena and Montalcino, and it was the ideal place to return to for an evening of eating and drinking. We loved our stay and were sorry to leave! It truly felt like a home away from home.
Superhost

Villa in Terranuova Bracciolini
4.8 out of 5 average rating, 5 reviewsCasa al Fiume - Villa with exclusive pool
MarcRating, 5 stars104 months ago
We thoroughly enjoyed our stay and highly recommend. Barbara was gracious and great to work with. The house was charming and just as great as it looks on the listing. The property and grounds are amazing. The town nearby was fun to visit with everything you need and lots to see. You are also in easy driving range of the other main Tuscany towns. Overall an excellent experience. Thank you Barbara!
Top guest favorite

Home in Campagnatico
5 out of 5 average rating, 7 reviewsBeautiful bright villa with view - Casa Luca
RafiRating, 5 stars1 month ago
We stayed at Mel's Casa Luca in March 2025 for over a week. Tucked away yet near medieval Campagnatico, it’s 5 minutes from the E78 to Grosseto/Siena, 15-20 minutes to Grosseto, and 30 minutes to the sea. Casa Luca, one of three stone farmhouses on what is essentially an olive farm, offers resort-like amenities which are shared with the guests of the other 2 houses: a trampoline, large pool, and ample walking space. Casa Luca is a single-storey house with two bedrooms with plenty of storage, comfy beds, an open-plan kitchen/dining/living area with Netflix, a big bathroom, and a well-equipped kitchen. Outside, there’s a private garden, terrace, BBQ. There is also a shared bakehouse with a pizza oven and huge dining table. We loved it and highly recommend it!
Superhost

Apartment in Greve in Chianti
4.67 out of 5 average rating, 3 reviewsOrlando House with terrasse
KatharineRating, 5 stars82 months ago
Authentic Italian home situated on a family winery in the stunning Tuscan countryside. Everyone provided us with a welcoming and memorable experience. The wine tasting is a must
Superhost

Apartment in Arezzo
4.5 out of 5 average rating, 4 reviewsPozzale Apartment 2+2 | 50m
KatrienRating, 5 stars9 months ago
We loved this place. The grandmother welcomed us and she was such a nice lady! There is a lot of space for the kids to play and the view from the swimming pool with the sunsets is amazing! It’s an ideal place to visit some villages in the neighborhood during the day and to relax at the end of the day at the pool. We would love to come back a bit longer!
Guest favorite

Home in Poggi del Sasso
4.92 out of 5 average rating, 114 reviewsLECCIONE RESIDENCE
IsabelleRating, 5 stars1 month ago
Beatiful house with everything you need. The house was really clean, and it has all the amenities you need. The contact with Andrea was good. In the surroundings there is not much to do, but if you are looking for peace and quite, and you don't mind driving a bit for activities, this is the perfect place.
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- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Piazzale Michelangelo
- Stadio Artemio Franchi
- The Boboli Gardens
- Teatro Verdi
- Basilica di Santa Croce
- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Teatro Tuscanyhall
- Casa Barthel
- Basilica of St Francis
- Podere La Marronaia, Sosta alle Colonne
- Tenuta Le Velette
- Nelson Mandela Forum
- Cantina Colle Ciocco
- Cantina de' Ricci
- Giardino Bardini
- Madonna del Latte
- Mount Subasio
- Castiglion del Bosco Winery
- Podere Il Cocco
- Cantina Contucci
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
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