Monteriggioni Villas - Best Villa Monteriggioni 2026

A cobblestone square with historic buildings, a fountain, and a church with a bell tower.

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Our top choices for Monteriggioni villas

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

1. Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

17 Nov - 18 Nov

A large estate with a swimming pool, tennis court, and multiple guest rooms.

2. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Colle Val D'Elsa

includes taxes & fees

29 Nov - 30 Nov

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

3. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

Siena

Ron M.

includes taxes & fees

4 Nov - 5 Nov

An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

4. Villa Mami: A Tuscan retreat full of elegance and charm

Toscana

includes taxes & fees

5 Nov - 6 Nov

A stone building with a swimming pool, wooden deck, and a tall tree.

5. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda in Chianti

"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...

JIm B.

includes taxes & fees

8 Nov - 9 Nov

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

6. Rooster House, Cooking Classes, and Opera

Tavarnelle Val di Pesa

includes taxes & fees

5 Nov - 6 Nov

A stone building with a tower, surrounded by trees and a garden.

7. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Vico dʼArbia

Marina O.

includes taxes & fees

4 Nov - 5 Nov

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

8. Villa Torre Among the Hills of Siena

Vico dʼArbia

includes taxes & fees

4 Nov - 5 Nov

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

9. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Gaiole in Chianti

Bernard K.

includes taxes & fees

15 Nov - 16 Nov

A covered balcony with a brick railing, a bench, and a view of lush greenery.

10. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Certaldo - Firenze

Kelly C.

includes taxes & fees

4 Nov - 5 Nov

A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

11. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

includes taxes & fees

4 Nov - 5 Nov

A villa with a swimming pool, surrounded by lush greenery and vineyards.

12. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Montespertoli

includes taxes & fees

4 Nov - 5 Nov

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

13. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

includes taxes & fees

4 Nov - 5 Nov

A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

14. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Montespertoli

Krista G.

includes taxes & fees

29 Nov - 30 Nov

A person in a swimming pool with a view of a vineyard and hills.

15. "A Casa di Franca Villa con piscina"

Gambassi Terme

"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...

Anonymous traveller

includes taxes & fees

4 Nov - 5 Nov

A building with a large entrance, potted plants, and a statue in the foreground.

16. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

Scott M.

includes taxes & fees

4 Nov - 5 Nov

A courtyard with a building, potted plants, and a grassy area.

17. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

Toscana

includes taxes & fees

4 Nov - 5 Nov

A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

18. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Rapolano Terme

Toon M.

includes taxes & fees

4 Nov - 5 Nov

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Top Monteriggioni Hotel Reviews

Palazzo Ravizza

10/10 Excellent

"Beautiful sunset views from The terrace garden. Wonderful Breaksfast! Would stay here again."

Castelfalfi

10/10 Excellent

"Get ready to be impressed if you stay here. Every staff member from our arrival to our departure genuinely greeted us and welcomed us and many remembered our name. They always asked if we needed anything or offered help or suggestions in a genuine “we want to help way”. The concierge before our stay was ultra responsive, during our stay they were always present. You want attention to detail, Castelfalfi has it covered. Drinks are carefully made and delivered. Turn down service straightened the room, put little clothes under anything we had on the bathroom sink or room table, a new bookmark was left next to my book on the nightstand, cords were always wrapped and made to look tidy, I could go on and on. The food in the various restaurants was amazing. The little meat and cheese shop made a tremendous& fresh sandwich sliced up right in front of us on fresh baked bread. The view of sunset from the back deck had many guests out watching for good reason. The spa pool was great and the gym was pretty big. The breakfast buffet had everything you could want. Want fresh honey? There was a station with a honeycomb taken from their property…it drips fresh honey into a tray that empties into a bowl for you. The wine tasting was fun and delicious and worth it. Everything is on site and you will not want to leave the property during your stay or at the end of your trip. Castelfalfi- I hope and pray I return some day, thank you!!"

Il Chiostro del Carmine

10/10 Excellent

"Everything about this place is excellent. We had a wonderful stay and beautiful views of the sunrise! One thing to note is that you do have to take a flight of stairs to your room as there is no elevator. If you have luggage you may want to take this into consideration. We did and it was manageable!"

Hotel Borgo San Luigi

10/10 Excellent

"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."

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Monteriggioni Villas information

Number of reviews	66
Accommodation	1548 Villas
Lowest Price	€127
Highest Price	€11,800

Frequently asked questions

How much do villas in Monteriggioni cost?

Villas in Monteriggioni cost between €127 and €11,800 per night. These stays give you the privacy of your own space at a price that's friendly to your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Monteriggioni?

Monteriggioni has 1548 villas to pick from. Find your next perfect stay quickly and easily by clicking the "Villa" checkbox under the "Property type" tab in our filter tool.

Why book your villa in Monteriggioni with Expedia?

We think holiday time should be a breeze, so if you're searching for villas at a nice price, Expedia is here to help. Keep the budget under control and choose an all-inclusive stay, or splurge on a 5-star villa to spoil the ones you love most. Take advantage of our search filters to find a place in Monteriggioni that matches your needs.

How can I find cheap villas in Monteriggioni?

A fantastic way to track down cheap villas in Monteriggioni is with Expedia's handy filter tool. Refine your search results by budget, star rating and amenities to grab unbeatable deals in only a couple of clicks.

What is there to do near my villa in Monteriggioni?

After you've settled into your villa, set out and discover the awesome things Monteriggioni has on offer. San Leonardo al Lago is a top attraction to add to your must-do list.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Monteriggioni villas

1. Villa Montecastello

2. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

3. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

4. Villa Mami: A Tuscan retreat full of elegance and charm

5. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

6. Rooster House, Cooking Classes, and Opera

7. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

8. Villa Torre Among the Hills of Siena

9. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

10. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

11. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

12. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

13. Villa Capanna: A Window onto Tuscany

14. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

15. "A Casa di Franca Villa con piscina"

16. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

17. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

18. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Find holiday rentals that suit your style

Top Monteriggioni Hotel Reviews

Palazzo Ravizza

La Certosa di Pontignano - Place of Charme

Castiglion del Bosco, A Rosewood Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Castelfalfi

Il Chiostro del Carmine

Hotel Borgo San Luigi

Salvadonica - Borgo del Chianti

Hotel Chiusarelli

Find out more about Monteriggioni

Monteriggioni Villas information

Frequently asked questions

Search Villas in Monteriggioni

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Monteriggioni villas

1. Villa Montecastello

2. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

3. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

4. Villa Mami: A Tuscan retreat full of elegance and charm

5. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

6. Rooster House, Cooking Classes, and Opera

7. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

8. Villa Torre Among the Hills of Siena

9. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

10. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

11. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

12. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

13. Villa Capanna: A Window onto Tuscany

14. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

15. "A Casa di Franca Villa con piscina"

16. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

17. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

18. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Find holiday rentals that suit your style

Top Monteriggioni Hotel Reviews

Palazzo Ravizza

Find out more about Monteriggioni

Monteriggioni Villas information

Frequently asked questions