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Villa holiday rentals in Monteriggioni

Find and book unique villas on Airbnb

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Popular amenities for villa rentals in Monteriggioni

Private villa rentals

Guest favourite
Villa in Palaia
4.92 out of 5 average rating, 12 reviews

Villa La Gemma

JoshRating, 5 stars2 weeks ago
I was genuinely impressed by this place. So beautiful! The pool is incredible, they had prosecco and limoncello for us and provided several supplies for a successful stay. I would 100000% come back here!
Guest favourite
Villa in Buonconvento
4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

MartinRating, 5 stars8 months ago
We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!
Top guest favourite
Villa in Pistoia
5 out of 5 average rating, 62 reviews

Church of the Vaioni

KarlRating, 5 stars1 week ago
The renovated church was incredibly interesting and I was fascinated by its long history. The church is nestled within a tranquil olive grove which made it easy to relax and disconnect from the stressors of the big city. Roberto was absolutely incredible and I cannot give higher praise—he is truly the standard when it comes to hosts. He was attentive, responsive to any issues, and helpful to solve any difficulties that we had with travel arrangements. It’s easy to see why this property is in such high demand. It was my first time staying in Tuscany and Roberto’s church is already calling me back for another stay! Most highly recommended.
Guest favourite
Villa in Siena
4.97 out of 5 average rating, 39 reviews

Capanna Di Elfo

MichaelRating, 5 stars1 month ago
The property was comfortable, spacious and spotlessly clean. The owners of the property , Claudio and Angelica, are helpful and delightful. However, the “host” BoMVillas , who acts as a middleman, was rude and disrespectful when we had a miscommunication. I would not make another booking that was offered by BoMVillas.
Top guest favourite
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 28 reviews

Sestuccina

RubyRating, 5 stars4 days ago
Beautiful place to stay! • Super nice location (lots of nature and very quiet) • Communication always runs smoothly • Great restaurants and delicious ice cream within 5 minutes' drive • Equipment exactly as specified I would recommend it again and again! Luciano and Brigitta are great hosts 😊
Top guest favourite
Villa in Rignano sull'Arno
5 out of 5 average rating, 16 reviews

villa "La Fonticina"

ClaraRating, 5 stars1 day ago
The villa is beautiful and the host Cesare is incredible. And I mean incredible. We have had excellent hosts before but he is beyond belief. He even helped us when there was a train strike by picking us up in Florence. He is warm, responsive, friendly, funny. He answered every text in a minute. Family with kids went and the place is beautiful, spacious and the pool is large and fabulous. It was the best week of our vacation. We also had a wonderful cooking class at the villa that Cesare recommended. Gabriella was so much fun. Florence is 30 minute car or a train ride but we always took train. We hope we can return.
Superhost
Villa in Capannori
4.96 out of 5 average rating, 26 reviews

Luxury Tuscany Villa on the hill with private pool

SandraRating, 5 stars4 days ago
We were very satisfied with our vacation home from Stefania. Great, spacious, secluded garden with many olive trees. Pergola with seating area invites you to linger. The cleanliness of the place was also extremely good. The beds or mattresses were very comfortable and the bedrooms nicely furnished. Stefania provided us with many tips and recommendations. She also booked a table for us twice at the nearby Osteria di Valgiano. Great food at a reasonable price with a great view of Lucca. Stefania responded quickly and kindly to questions. We would have liked to stay longer and will definitely come back!
Top guest favourite
Villa in Sinalunga
5 out of 5 average rating, 45 reviews

The twigs

JeffreyRating, 5 stars2 weeks ago
Pictures don’t do it justice, prettier in person. Very relaxing get away after spending a few days in Florence.

Luxury villa rentals

Top guest favourite
Villa in Cortona
5 out of 5 average rating, 76 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

ChelseaRating, 5 stars1 week ago
This was our second time visiting Mogens and Suzie's beautiful home in Cortona. One reason for coming back was the sheer beauty of the property and the proximity to fantastic medieval towns with incredible history that endures even now. For wine enthusiasts, there are tons of wine tasting opportunities with lunch, dinner or just great wine. Another reason for our return visit was an opportunity to spend time again with Mogens and Suzie, by far the best AIRBNB hosts we have ever encountered. They do everything imaginable to make your time as enjoyable as possible and to say that they go the extra mile would be a gross understatement. We can't wait to come back a third time.
Top guest favourite
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Top guest favourite
Villa in Sarteano
4.97 out of 5 average rating, 125 reviews

Stone farmhouse in Val D'Orcia

Theng JuhRating, 5 stars2 weeks ago
Stefania was super nice to wait for us despite we were later for 3 hours. Her house was very beautiful and lots of space for 10 of us. Everyone can have their own space on the balcony or terrace. Can have BBQ too. House was very well equipped with everything that we expected. Had a wonderful time. Thank you.
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 126 reviews

Villa in Montepulciano with a Pool

SantiagoRating, 5 stars1 week ago
We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!
Top guest favourite
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 52 reviews

The Lazy Oak

KathleenRating, 5 stars1 day ago
We (2 couples) had a wonderful time at the Lazy Oak Villa. The booklet in the house had great recommendations for dinner in Loro Ciuffenna. We did wine tastings at 2 family vineyards located very close to the villa- Morandi Organic Winery with Denis and Società Agricola Caspriano with Simona. Highly recommend both. One of our couples was celebrating an anniversary and Mario arranged for a chef to come to the villa and prepare a traditional Tuscan meal. It was beyond words! The pool was pristine and such a great bonus with the summer heat.
Top guest favourite
Villa in Monsummano Terme
4.98 out of 5 average rating, 128 reviews

Le Maggioline Your Tuscany country house

LisaRating, 5 stars1 week ago
Olga's villa is absolutely stunning. Our family of 9 had the most wonderful visit. We enjoyed cooking in the beautiful and well appointed kitchen, eating outside on the terrace, swimming in the pool, and relaxing outside on the terrace, enjoying the peaceful beauty and breathtaking views of Tuscany. Olga's place is truly special. Olga was very communicative, helpful and kind. We highly recommend her villa to others.
Top guest favourite
Villa in Montepulciano
5 out of 5 average rating, 48 reviews

Terra Antica Suite & Ville - Montepulciano

JohnRating, 5 stars1 month ago
Beautiful property. Staff were amazing, responsive and friendly. Location ideal for visiting other cities by car. Exactly as pictured. Breakfast which was added on a day to day basis was spectacular. Very relaxing sitting on patio and by the pool.
Superhost
Villa in Volterra
4.95 out of 5 average rating, 22 reviews

Podere La Casetta - 2 People - Private Pool

ShemaiahRating, 5 stars10 months ago
My husband and I stayed here to celebrate our anniversary. This was our first experience in Tuscany and it did not disappoint. The house is very private, there is only 1 house behind it however from most viewpoints you cannot see it and we never saw anyone. Volterra is a beautiful medieval place that will make you feel like you are in a movie. An hour from Pisa, drivable to many many wineries in the surrounding regions, this air bnb is a perfect place to stay and we hope to return again.

Villa rentals with a pool

Guest favourite
Villa in Pozzuolo
4.91 out of 5 average rating, 43 reviews

Fabulous Farmhouse with Pool & 360 Panoramic View

Kaidy FendyRating, 5 stars3 weeks ago
Caroline's villa was absolutely stunning. We visited as a family of 8 adults and it was even more beautiful in person. It's completely private with amazing views all around. It's also in a great location to visit other picturesque villages nearby with a car. The pool was a great addition to combat the Tuscan heat. As this is in the countryside, be aware that there will be insects and wildlife. We came across a snake and a scorpion, but that's not an issue with the house, but rather the natural environment. The property manager Bianca greeted us upon arrival. She was super friendly and helpful with tips. And Caroline left us super detailed recommendations for restaurants, itineraries, and wineries. She was always available and friendly. We had an amazing time and would definitely visit again!
Guest favourite
Villa in Gambassi Terme
4.96 out of 5 average rating, 54 reviews

Villa Via Francigena

BettyRating, 5 stars1 week ago
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.
Guest favourite
Villa in Casole d'Elsa
4.85 out of 5 average rating, 13 reviews

La Casa di Bohaz - Cantona Estate

Alper AviRating, 5 stars2 weeks ago
Antonio’s place was everything we were looking for during our getaway in Tuscany! The villa, the pool, and the views were absolutely stunning. We were pleasantly surprised by how modern and well-renovated the amenities were. Antonio also provided Nespresso pods daily, and the unit was stocked with thoughtful essentials like olive oil and pasta. The only small caveat was the limited wardrobe space in the rooms, aside from a small rack, there wasn’t much room to put clothes away. Overall, we would highly recommend this accommodation!
Guest favourite
Villa in San Gimignano
4.88 out of 5 average rating, 72 reviews

Lilium,delux farmhouse in the chianti hills

CharlotteRating, 5 stars3 weeks ago
We had a fantastic stay at Concetta's beautiful home! The house itself is gorgeous and traditionally Tuscan. It is also in the most incredible scenery and sitting outside and taking in the view was an absolute joy. However, by far the best thing about our stay was Concetta and her husband Paolo. They could not have done more to make us feel more at home and it honestly felt like we were part of the family while we were there (including making us the most incredible meal, which I would strongly recommend you do if you stay!) Their hospitality, helpfulness and warmth made it feel like a true escape and I could not recommend it more.
Top guest favourite
Villa in Volterra
5 out of 5 average rating, 24 reviews

Romantic Villa with private pool - "Il Pollaio"

ErinRating, 5 stars4 weeks ago
A beautiful home to base ourselves in while exploring Tuscany. Lovely country surrounds. House has everything you need, spacious. Gorgeous terraces and pool. Enjoyed Volterra, San Gimignano and Siena but always great to come back to our Tuscan home! Silvia gave fantastic recommendations - pasta making at Ristorante de Beppino and in house chef Beppe highlights. Also loved Monterosola winery tasting. Very highly recommend. One of the best!
Top guest favourite
Villa in Asciano
4.95 out of 5 average rating, 79 reviews

Podere on the Crete Senesi

NahkitaRating, 5 stars3 weeks ago
We could not have asked for a more beautiful setting to celebrate my partner’s 40th birthday. Our week was perfectly balanced between visiting nearby Montalcino wineries & surrounding villages, a day trip to Siena, and lazing about the pool & villa. Monica was kind, generous & helpful from the time of booking. She accommodated all requests and even left a gift for my partner to celebrate his birthday! Will be back! Would rate this 6 stars if we could.
Top guest favourite
Villa in Montenero d'Orcia
5 out of 5 average rating, 22 reviews

Tuscany Villa With Pool & Magnificent Garden

GreyRating, 5 stars8 months ago
Barbara’s place was above and beyond our expectations in every way! If you are looking for a place to stay in this general area, don’t hesitate! Barbara was a wonderful host and all the instructions were very clear. The kitchen is very well stocked and we cooked all of our dinners there as we were traveling with a baby. We spent a lot of time hanging out as a family and there was more than enough room for us and both sets of grandparents. The home is very well situated and we loved exploring. There are so many great restaurants in the area. I can’t over state the beauty of the area and the house itself…my family is already dreaming about coming back!
Top guest favourite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa at Mulino del Cerchiaio

MathildeRating, 5 stars8 months ago
Thank you!! We enjoyed our vacation with 9 friends! A little humid because of the weather, but the place is ideal in summer and comforting by the fire when the good weather is not present!

Destinations to explore

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