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Villa vacation rentals in Monticiano

Find and book unique villas on Airbnb

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Popular amenities for Monticiano villa rentals

Private villa rentals

Superhost
Villa in Chiusi
4.67 out of 5 average rating, 3 reviews

Tuscany 2 Villas sleeps 12 private heated pool

PiotrRating, 5 stars46 months ago
In reality villas present themselves a lot prettier than in photos on website. The area and surroundings are beautiful, calm and quite. Place is perfect as exit basis for exploring and sightseeing Tuscany. Rooms and beds are adequately big and clean. Kitchen and utensils are in sufficient quantity. Pool is clean, water warm. There’s no need for a battle for lawn chairs. Jacopo is very helpfull, communicative, serves his help everyday. The place is worthy of recommendation. We spent our holiday time comfortably in quaint area. All the best!
Superhost
Villa in Florence
4.88 out of 5 average rating, 16 reviews

Villa La Cingallegra

MiltonRating, 5 stars7 months ago
Fantastic all around experience. Thank you Elio and team 🙏🙏
Guest favourite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars7 months ago
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Superhost
Villa in Montepulciano
5 out of 5 average rating, 3 reviews

Terra Antica Suites & Villas - Villa Vino - Private Jacuzzi

HeatherRating, 5 stars5 months ago
Our stay at Terra Antica was a dream. The location is perfect and the property and villa are exceptional. We were close enough to town to get to restaurants and shopping and then come back for some quiet relaxing time. There are numerous wineries to visit in the area. Day trips to other local towns are easy to do as well. The private jacuzzi was an extra bonus & we used it several times during our stay. We will be back again!
Guest favourite
Villa in Sarteano
5 out of 5 average rating, 14 reviews

Villa "La Civetta" with swimming pool, sauna and jacuzzi

JariRating, 5 stars4 months ago
We stayed here for the last days of the year. We were greeted by the host, who was immediately friendly and helpful. The house is beautiful, organized on three floors (the last one reachable with a slightly narrow spiral staircase), very spacious and welcoming. Equipped with 4 bathrooms, one with a hot tub and a small sauna, a living room, a laundry area, a study with a piano and a large kitchen overlooking the beautiful garden with pool. It was the ideal space to spend a few days in peace with friends and visit the nearby Tuscan villages. It definitely exceeded our expectations!
Superhost
Villa in Provincia di Arezzo
4.91 out of 5 average rating, 43 reviews

Villa near Florence: Pool, AC, Vast natural garden

JackRating, 5 stars8 months ago
Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.
Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 9 reviews

Casa Faraona, villa with private pool

VaughanRating, 5 stars7 months ago
A beautiful property in a stunning location with great views. The property was easy to find using Waze. Once inside everything was clean and all rooms were luxurious and clean.
Guest favourite
Villa in Vicopisano
4.88 out of 5 average rating, 8 reviews

Elegant luxury villa with private pool

BjörnRating, 5 stars6 months ago
An amazing, spaceous and beautiful located estate. Highly recommended.

Luxury villa rentals

Guest favourite
Villa in Palaia
5 out of 5 average rating, 9 reviews

Villa La Gemma

DeryaRating, 5 stars7 months ago
The stay was wonderful! The villa was amazing, the views, the furniture, the rooms and the pool. We were so happy to be there. The rooms were new and clean. Every detail was taken care of. Christina was incredibly helpful and always available. Without her, we'd be lost. Unfortunately, we often had private problems and every time she helped us and brought us solutions. For me and my friends, this stay was unforgettable!
Superhost
Villa in Poppi
4.8 out of 5 average rating, 5 reviews

Villa for 22 people w/private pool

Marie-ClaireRating, 5 stars7 months ago
This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.
Guest favourite
Villa in Sodo
4.95 out of 5 average rating, 22 reviews

The House of the Sole del Sodo

ClaireRating, 5 stars7 months ago
We chose Il Sole del Sodo because it had 6 en-suite rooms, a pool, was close to a town and a train station and had a well- regarded host who could provide extras like breakfast, dinners, cooking classes and olive oil tastings e.g. Claudia! While rustic, the villa’s charm and peaceful spaces draw you right in and Claudia’s hospitality is unsurpassed. The villa fronts to the road to Cortona and backs to a field of sunflowers. Our family and friends dined on the private patio and found a back way to walk up to Cortona for exercise. A unique and wonderful experience!
Guest favourite
Villa in Orvieto
4.9 out of 5 average rating, 31 reviews

Spectacular villa with a view and infinity pool

RayRating, 5 stars8 months ago
Superb villa for 12 guests. 10 mns drive to a fabulous town or stay at home in comfort including an excellent pool surrounded by Impressionist views. Teresa is a gem. Pia recommended Eugenio and Pasquale of Italian Show Cooking and they produced a magnificent eight course banquet for my wife's 70th birthday party. This villa holds a very special place in our hearts and the hearts of our guests. Cman you give more than five stars?
Top guest favourite
Villa in Rignano sull'Arno
5 out of 5 average rating, 12 reviews

villa "La Fonticina"

StefanRating, 5 stars6 days ago
If you are looking for authenric Tuscany experience this is it from the beautiful villa and the view to furnitue and other little details. It is secluded, paeceful and ful of character. You will love your stay here and Cesare is a great host.
Guest favourite
Villa in Colle di Val d'Elsa
4.95 out of 5 average rating, 22 reviews

Villa l'elsa beautiful country home with view - vi

KelseyRating, 5 stars4 days ago
A great place for a large group! Loved the outdoor space and view. A truly beautiful home. An overall great stay. Tentative manager. Pros: - Spacious house - Many rooms - Outdoor space - Games/kids supplies - Charging Adapters - Washer & Dryer - Many bathrooms Cons: - Not a self check-in. It was stressful coordinating with the manager while trying to travel and coordinate with our large group. - Hot tub wasn’t clear on how to heat and we would have loved to have it full and warm for arrival after a long travel day for us and the kids. - Downstairs bed was very firm. - We didn’t have enough dishwasher pods, toilet paper or paper towels for our group so we had to buy some. I feel that should be included.
Superhost
Villa in Torrita di Siena
5 out of 5 average rating, 4 reviews

Villa Scianellone

NickRating, 5 stars36 months ago
We had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.
Top guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 47 reviews

Sestuccia

RebeccaRating, 5 stars6 months ago
We had a marvelous stay at Villa Sestuccia. The house is spacious, as are the grounds. Both are well maintained. There is ample room with different areas to relax indoors and outside. We communicated with Briggita who was quick to respond, always friendly and always helpful. We particularly liked the location which has easy access to many spots of interest and restaurants. We enjoyed collecting eggs in the morning for our breakfast - such a fun touch. We highly recommend Villa Sestuccia and would not hesitate to stay here again.

Villa rentals with a pool

Superhost
Villa in Campagnatico
4.8 out of 5 average rating, 5 reviews

Charming villa on two levels - Casa Lola

SofiaRating, 5 stars9 months ago
Mel is a fantastic host and the place is exactly like in your most vivid Tuscany dreams.:) It's not our first time here and we absolutely loved everything about the place. We booked all three homes available at Mel's place and had an unforgettable week with the entire family - highly highly recommended! Thank you, Mel for being absolutely fabulous!✨
Top guest favourite
Villa in Montecucco
4.9 out of 5 average rating, 40 reviews

Villa Angiolina

ErinRating, 5 stars6 months ago
Villa Angiolina is truly beautiful!!! The view is incredible and everything was spotless and beautifully decorated. Our host was lovely and gracious and responded very quickly to all communications. She even arranged for an amazing pizza party with a private chef that was just one or the memorable moments from our time at the Villa. If this Villa is available…just book it!!! You will be glad that you did!!!!
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 122 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars3 weeks ago
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!
Superhost
Villa in San Casciano In Val di Pesa
4.83 out of 5 average rating, 30 reviews

Poggio degli Ulivi, charming Chianti with pool

MicaelaRating, 5 stars9 months ago
The stay was beautiful. The view is fantastic, the pool very clean, surrounded by a beautiful, huge garden. Breakfast on the terrace is fantastic as the kitchen goes right to the terrace. The house is beautifully decorated and very clean. the air conditioning works perfectly, the nearest supermarket can be reached by car in less than 15 minutes, as well as there are various restaurants that can be reached in less than 20 minutes by car. Like that of The Sor Paolo or the Barrachina.
Superhost
Villa in Terranuova Bracciolini
4.8 out of 5 average rating, 5 reviews

Casa 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!
Superhost
Villa in San Gimignano
4.79 out of 5 average rating, 24 reviews

Elisa Villa

DominiqueRating, 5 stars6 months ago
Beautiful house in the vines surrounded by sumptuous hillsides in an incredible postcard setting. Perfect for gatherings for families or with friends. The location is ideal to radiate between Siena, Florence and Chianti or resting while enjoying the pool. Elisa, always attentive, is very responsive and will respond almost without delay.
Guest favourite
Villa in Volterra
4.98 out of 5 average rating, 51 reviews

Villa Casa al Povero

AnthonyRating, 5 stars3 weeks ago
I don’t even know where to begin describing this place. It was the most amazing place I have ever stayed. If you are looking for a peaceful and private villa with incredible views, then stop looking. This is it !! All of the reviews we read before we arrived talked about how amazing the views are and that you must take up the offer if Paola and Alessandro offer to cook a meal for you. Both recommendations are spot on. The sliced beef was one of the best meals I have ever had, and I often found myself wandering around outside the villa looking at the 360 degree views in all directions. We all felt so sad to leave this magic place. Paola and Alessandro were perfect hosts. Always friendly and with a smile on their faces. It’s a long way from Australia but I really hope we get an opportunity one day to return to this majestic place.
Top guest favourite
Villa in Montaione
4.96 out of 5 average rating, 23 reviews

Private Villa with semi-Olympic pool and Tennis

KaitlynRating, 5 stars5 months ago
We had a truly excellent holiday cooking, playing tennis, and exploring nearby towns. Our hosts were very attentive via text and in person, and helped us plan all of the additional activities we wished. Our group would unanimously return, given the chance. Highly recommend!

Quick stats about villa rentals in Monticiano

  • Total rentals

    10 properties

  • Nightly prices starting at

    $235 CAD before taxes and fees

  • Total number of reviews

    50 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Monticiano
  6. Villa rentals