Holiday Homes in Sinalunga

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Our top choices for Sinalunga holiday homes

1. Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
7.0 out of 10, Good, (2 reviews)
"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...
United States
Harald B.
The price is NZ$388
includes taxes & fees
13 Nov - 14 Nov
Romantic farm in the Sienese hills

2. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is NZ$162
includes taxes & fees
9 Nov - 10 Nov
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

3. Double room with private bathroom in the countryside, 5 minutes from Montepulciano

Double room with private bathroom in the countryside, 5 minutes from Montepulciano
Toscana
The price is NZ$308
includes taxes & fees
9 Nov - 10 Nov
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

4. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
Monte San Savino
6.0 out of 10, (2 reviews)
"My husband and I booked this place and were unable to stay due to lack of communication regarding check-in procedure. The listing states the host will make contact 3 days before which didn’t happen. We sent several messages the day of check-in and didn’t hear from the host until well after the check-in time (4pm). Given the remote location and time of day, we were worried we wouldn’t have anywhere to stay for the night so we booked a hotel in Arezzo which we were lucky to get on a holiday...
Canada
Anonymous traveller
The price is NZ$407
includes taxes & fees
9 Nov - 10 Nov
Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

5. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (12 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is NZ$231
includes taxes & fees
9 Nov - 10 Nov
"Il Focolare" Superior Apartment in Monticchiello

6. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
The price is NZ$149
includes taxes & fees
9 Nov - 10 Nov
Vacation home with a panoramic terrace, ideal for families and couples

7. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is NZ$181
includes taxes & fees
12 Nov - 13 Nov
Montecchio di Cortona

8. Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi
Trequanda
The price is NZ$947
includes taxes & fees
9 Nov - 10 Nov
Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

9. Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
foiano
The price is NZ$2,206
includes taxes & fees
9 Nov - 10 Nov
Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

10. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is NZ$551
includes taxes & fees
14 Nov - 15 Nov
Arc two-bedroom apartment

11. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
The price is NZ$240
includes taxes & fees
9 Nov - 10 Nov
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

12. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveller
The price is NZ$575
includes taxes & fees
9 Nov - 10 Nov
Holiday Home in Villa Pandolfina near Montepulciano

13. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is NZ$196
includes taxes & fees
9 Nov - 10 Nov
Dolce Casa 2 by Tiny Away

14. Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi

Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi
Monte San Savino
The price is NZ$652
includes taxes & fees
9 Nov - 10 Nov
Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi

15. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is NZ$679
includes taxes & fees
10 Nov - 11 Nov
Charming Siena Countryside Stay

16. Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley

Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
Torrita di Siena
The price is NZ$1,283
includes taxes & fees
11 Nov - 12 Nov
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley

17. Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: The spaciousness of the modern house was perfect. We felt right at home. The big pool was highly appreciated. Cons: -"
United States
Anonymous traveller
The price is NZ$1,076
includes taxes & fees
9 Nov - 10 Nov
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

18. Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is NZ$517
includes taxes & fees
9 Nov - 10 Nov
Eagle House

19. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is NZ$291
includes taxes & fees
11 Nov - 12 Nov
Holiday Home 'La Casina All'angolo'

20. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is NZ$197
includes taxes & fees
9 Nov - 10 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Sinalunga

This medieval hilltop town offers authentic Tuscan charm with its historic piazza and Renaissance-era Collegiate Church of San Martino. Enjoy local wines at family-run vineyards, then explore nearby Val d'Orcia's rolling landscapes or visit the thermal baths in Chianciano Terme.

A historic town with a prominent church tower on a hill, surrounded by lush greenery and traditional buildings.