
Vacation rentals in Simignano
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Top-rated vacation rentals in Simignano
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Guest favorite

Apartment in Pogi
4.94 out of 5 average rating, 89 reviewsBorgo Iesolana Suite Superior
RobertRating, 5 stars2 weeks ago
5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!
Guest favorite

Home in Sovicille
4.94 out of 5 average rating, 47 reviewsAcacia
TessaRating, 5 stars3 weeks ago
A beautiful accomodation in a quiet town, with a lovely host who was able to provide recommendations and solutions for our travel!! Thanks Sylvia!
Guest favorite

Villa in Montepulciano
4.95 out of 5 average rating, 217 reviewsAmazing Tuscany Villa, FREE parking
StephenRating, 5 stars1 week ago
A super cute place to stay, while it was just outside of the main town of Montepulciano, it was very peaceful and lovely home with plenty of character. Pier Luigi was a gracious host and even gave us welcome and departing gifts. We loved our stay here, Thank you Pier for your hospitality.
Top guest favorite

Castle in Montecatini Val di Cecina
4.99 out of 5 average rating, 116 reviewsBelforti Tower
CharlieRating, 5 stars4 days ago
This was an incredible and relaxing getaway—we honestly wish we had stayed longer. The tower is just as magical as the photos, and the views, olive grove, and pool were even better than expected. The surrounding town is darling and quiet, with just a couple of small restaurants and markets, which made it feel like a true escape. Luca was kind and responsive throughout our stay. Just a few things to note: there are a lot of stairs, and you’ll want a smaller car to navigate the narrow roads leading up to the tower. It’s a real castle, so it’s older and rustic—but full of charm and clearly loved. The only downside was that the hot tub on the roof no longer works, which was a bit of a letdown. Still, we absolutely loved our time here and would highly recommend it.
Top guest favorite

Home in Rio Marina
5 out of 5 average rating, 79 reviewsCaptain's House | Monte Grosso, Elba
CaterinaRating, 5 stars3 weeks ago
The Captain's House is a place that reconciles you with the world. Beauty is experienced for the eyes, spirit, and mind. The views are breathtaking, the view from every window is a painting, and peace and tranquility are guaranteed. The hosts have created a masterpiece by renovating the house: they have respected the original structure by adding every possible comfort. Andrea and Michael are very kind, they anticipated all our possible needs, they provided us with fresh flowers and fragrant herbs in every room, fresh fruit and everything necessary to "start" the kitchen (oil, salt, spices, etc.). Due to a technical issue, we were unable to use the Jacuzzi for one day and they offered us a dinner to apologize. We've never found hosts of this level. We hope to be able to go back and take back those pieces of our hearts that we left at the Captain's House.
Top guest favorite

Apartment in San Gimignano
4.98 out of 5 average rating, 41 reviewsHerons Superior Apartment - Splendid view!
JanineRating, 5 stars1 month ago
Words can’t describe how beautiful the view is from the apartment! We had a lovely week in San Gimignano with our six month old. So peaceful and everything within walking distance. Communication was great and use of the parking garage was much appreciated. Would definitely recommend!
Top guest favorite

Cottage in Monteriggioni
4.96 out of 5 average rating, 236 reviewsMonteriggioni Castello, holiday house in Tuscany
LucyRating, 5 stars1 month ago
Matteo was very friendly and helpful. The castle is a Tuscan jewel and there is plenty to see and do in the surrounding area. Parking was easy to use but if you have a soft top car bring something to cover it as there are lots of cats. (Matteo’s sister kindly provided us with a blanket). The little courtyard was just perfect to eat outside and the kitchen well equipped. Thank you Matteo.
Top guest favorite

Home in Monteroni d'Arbia
5 out of 5 average rating, 11 reviewsGolden View - Dream farmhouse in Tuscany
OliwiaRating, 5 stars1 week ago
The stay was like a fairytale – I highly recommend this place. We can’t wait to come back!
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Piazza del Duomo (Pisa)
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Mugello Circuit
- Fortezza da Basso
- Cala Violina
- Parco delle Cascine
- Uffizi Gallery
- Piazzale Michelangelo
- Piazza della Repubblica
- Kite Beach Fiumara
- Marina di Grosseto beach
- Mercato Centrale
- Pitti Palace
- Giardino Bardini
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Teatro Verdi
- The Boboli Gardens