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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

Guest favourite
Villa in Bucine
4.96 out of 5 average rating, 23 reviews

Charming property, wi-fi, weddings ,cooking class

ColetteRating, 5 stars10 months ago
Our wedding at Villa Cini was truly magical. The venue’s blend of natural beauty and elegance provided the perfect backdrop for our stay during the week and our special day. The gardens and stunning views created a fairy tale atmosphere and allowed to us have both an Indian wedding and an Italian Civil one. The arches ballroom, offered a romantic and inviting ambiance. We are incredibly grateful to have a chosen a place which has passed down for generations and has such a heartfelt attention to detail. If you're looking for a dream wedding venue and a beautiful place to stay then look no further than Villa Cini.
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 Fornaci
5 out of 5 average rating, 15 reviews

Villa with pool,tennis court,village walk distance

EmelineRating, 5 stars8 months ago
Superb spacious and well-located villa with a great view! Awesome pool and tennis class Big tables for eating out There are enough sunbeds for everyone We had a lovely time at this beautiful villa It is just missing a large oven (there is a mini oven that troubleshoot well) and be careful the washing machine is in a residence next door and for a fee (€4 laundry detergent)
Guest favourite
Villa in Pergine Valdarno
4.82 out of 5 average rating, 17 reviews

Exclusive Villa with Private Pool and Air Cond.

KaraRating, 5 stars10 months ago
Our stay at Villa Chiara was nothing short of delightful. Nestled in the hills it offered a picturesque view of the Tuscan countryside. The villa itself was spacious and well maintained. It felt like home away from home. The pool and back patio are surrounded by lovely flowers, herbs and olive trees. Offering a spectacular view of the evening sunsets. The location was perfect to take short day trips to Siena, Florence and Montepulciano. Highly recommend for a serene, peaceful and relaxing getaway.
Superhost
Villa in Capoliveri
5 out of 5 average rating, 3 reviews

EXCLUSIVE ENTIRE VILLA A STONE'S THROW FROM THE SEA

manuelaRating, 5 stars31 months ago
Our stay at Villa Tina was memorable. Paolo and Laura are very good hosts and we didn't miss anything. Perfect for 2 families. Private beach access. Wonderful sea view. Highly recommend Paolo's place.
Superhost
Villa in Montecarlo
4.85 out of 5 average rating, 13 reviews

Villa Flora, a Luxury 3 bedrooms Farmhouse with Po

ShemaiahRating, 5 stars1 month ago
Inside: This home looks exactly like the pictures and was beautifully decorated. Each bedroom had its own spacious bathroom and each bedrooms window showed an amazing view of the backyard. The hot tub was a wonderful way to end our March days since the pool was not open yet. The Host: Silvana greeted us at check in and showed us around the home. She was available by phone for any of our needs and was very responsive throughout our stay. The owners are across the street but we did not see them during our stay. Location: This home is about 20 minutes from Lucca- a beautiful, beautiful small city. It is about 35 minutes from Pisa and about an hour from Florence city center. We rented a car from Florence airport and traveled with ease from the house to the major cities. It was so nice to turn down the isolated road to the home at the end of our day. And enjoy the quiet. The area is very suburban, with groceries very close by. We can’t wait to come back in the summer and use the pool!
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 stars9 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.

Luxury villa rentals

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!
Superhost
Villa in Montepulciano
5 out of 5 average rating, 4 reviews

Villa Rosa - Private Jacuzzi

CarolRating, 5 stars10 months ago
Truly wonderful stay at Terra Antica for a group of five. The villa we stayed in, Villa Nobile, was modern and newly furnished with all of the amenities that guests could ask for. Each room was very comfortable. The overall property at Terra Antica was also great with a gym, pool and large areas to walk through. Highly recommend.
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 Bolsena
5 out of 5 average rating, 47 reviews

Villa Blue Melon - private beach

LorenzoRating, 5 stars1 week ago
We had a memorable stay, Andrea's house is tastefully furnished, every detail is taken care of. Honorable mention especially in the garden, full of wonderful flowers and plants, with barbecue, hammock and deck chairs where you can relax.
Top guest favourite
Villa in Paciano
5 out of 5 average rating, 5 reviews

Villa Lidia, la Dolce Vita at its Best!

IsaRating, 5 stars7 months ago
From the beginning, Marlene was an excellent host and Stijn, a most excellent property mgr. The house is even more beautiful in person. This is a magical place for tranquility and relaxation. The house is pristine and has all the amenities , we immediately felt right at home. We asked and they recommended farm to table cooking classes, and nearby towns to visit. All excellent experiences. Wonderful memories were made cooking and grilling, picking herbs from the garden. We enjoyed this truly spectacular home. The views from the hilltop where the house is located are breathtaking. There is a beautiful infinity pool and a great barbecue area. Watching sunsets and star gazing . We had just celebrated our daughter’s wedding and traveled from Rome and the serenity and Zen of the house and surroundings were just what we needed. Stijn took great care of us. We will return to this slice of heaven on earth. Thank you Marlene for sharing your beautiful home with us. It exceeded our expectation
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.
Superhost
Villa in Florence
4.8 out of 5 average rating, 41 reviews

Villa with great view over Florence, pool, Wi-Fi

JeffRating, 5 stars3 weeks ago
Great place, responsive host. Will be back.

Villa rentals with a pool

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

Villa La Gemma

DeryaRating, 5 stars8 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 Campagnatico
4.8 out of 5 average rating, 5 reviews

Charming villa on two levels - Casa Lola

SofiaRating, 5 stars10 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, 41 reviews

Villa Angiolina

MichelleRating, 5 stars3 days ago
We traveled with a family of 8 and this rental was more than we could have dreamed of. There was plenty of space with bedrooms and bathrooms for everyone. The grounds were luxurious, and we ordered the grocery service, so the kitchen accommodations were wonderful for breakfast and coffee. We enjoyed the welcome cocktail and evening pizza service as well. The host was extremely responsive to every request and helped us significantly with taxi service as well. We all had a wonderful, relaxing time! Thank you so much.
Top guest favourite
Villa in Rosignano Marittimo
4.92 out of 5 average rating, 25 reviews

Villa Castiglioncello - access to the private sea

JürgRating, 5 stars7 months ago
House, location: right by the sea, fantastic views, spectacular sunsets, large house with special architecture offers plenty of space and privacy, ideal for a large family. Various garden terrace areas. Everything very well maintained and well equipped. Camilla is a very warm and competent host. We will be happy to come back!
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 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.
Top guest favourite
Villa in La Poggerina
4.97 out of 5 average rating, 37 reviews

Villa La Poggerina, private pool and amazing view

BryanRating, 5 stars8 months ago
A rare circumstance where both property and hosts exceeded our expectations. The house is spacious with lovely views and a patio and pool for exclusive use by guests. It is well stocked and appointed, including a pool table and multi-game arcade machine. Much appears recently renovated. For those wanting to cook traditional wood-fired pizzas, there are two outdoor ovens, plenty of wood, and a host at the ready to provide assistance as needed. Emanuele and his wife are excellent hosts - gracious and welcoming yet non-intrusive. They had a fantastic charcuterie board and wine ready on our arrival and helped us with guidance and reservations multiple times throughout the week. They live in the house next door, but you wouldn't know it. All in all, one of our best AirBnB experiences in nearly a decade of stays - very highly recommended!

Quick stats about villa rentals in Monticiano

  • Total rentals

    10 properties

  • Nightly prices starting at

    $237 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