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House vacation rentals in Monteriggioni

Find and book unique houses on Airbnb

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Popular amenities for Monteriggioni house rentals

House rentals with a pool

Guest favorite
A spacious outdoor pool is surrounded by lush greenery, featuring olive trees and vibrant plants. The pool's crystal-clear water reflects the sky, while a sun terrace with lounge chairs is available for relaxation. The serene landscape enhances the tranquil atmosphere of the setting.
Home in Montaione
4.94 out of 5 average rating, 103 reviews

Cercis - La Palmierina

DennisRating, 5 stars1 week ago
Miruna hat uns herzlich empfangen und direkt vor Ort alles gezeigt. Die Anlage ist sehr gepflegt und schön angelegt. Das absolute Highlight ist der traumhafte Blick von der schönen Terrasse. Der Pool ist schön groß, toll angelegt, dort lässt es sich gut aushalten. Die Unterkunft ist sehr sauber und gepflegt, urig, zum wohlfühlen. Besonders war, dass wirklich alle Dinge des täglichen Bedarfs, wie Kaffee, Süßigkeiten, Nudeln, Wein, Öl, Duschbad, Pflaster etc. vorhanden waren. Die Lage ist für Tagesausflüge ebenfalls sehr gut. Wir hatten eine tolle Zeit, danke dafür.
Guest favorite
A shaded outdoor dining area features a large table surrounded by several chairs, nestled under a pergola with lush greenery. The shared swimming pool glistens in the background, framed by terracotta tiles and scenic views of the Tuscan landscape.
Home in San Miniato
4.92 out of 5 average rating, 133 reviews

Private villa/swimming pool in Tuscany

MārcisRating, 5 stars6 days ago
Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!
Guest favorite
A private pool is set within a well-kept garden, surrounded by lush greenery and gently sloping grass. The octagonal pool is framed by stone pathways and features a small tree at its center. The tranquil outdoor space invites relaxation and enjoyment.
Home in Gaiole in Chianti
4.86 out of 5 average rating, 262 reviews

Charming estate with views

StefanRating, 5 stars3 days ago
Wir hatten wunderschöne Urlaubstage mitten in den Weinbergen der Toskana. Bernadino ist ein sehr angenehmer, unaufdringlicher und aufmerksamer Gastgeber.
Top guest favorite
A rustic dining area is highlighted by a long wooden table surrounded by several chairs. A vase of sunflowers sits at the center. The stone wall adds warmth to the space, while a clock and decorative items provide an inviting touch.
Home in Bagno A Ripoli
4.95 out of 5 average rating, 138 reviews

Casetta Melograno - Cozy farmhouse in Chianti

JennaRating, 5 stars2 days ago
Sonia was extremely helpful from start to beginning. Gave us great recommendations which ended up being some of our favourite nights! The most stunning location and beautifully kept place, with everything you could possibly need to live in. 30 mins from Florence, 1 hour from Siena and miles of beautiful scenery and wineries as far as the eye can see As a british couple in our 20’s we loved our stay here ❤️
Superhost
A charming stone farmhouse is set against a backdrop of green hills. The exterior showcases rustic features, including wooden shutters and a tiled roof. A pathway leads to the entrance, bordered by lush greenery and flowering plants, creating a serene environment.
Home in Figline Valdarno
4.96 out of 5 average rating, 107 reviews

The Owl: view, pool and garden

StephenRating, 5 stars1 month ago
We stayed 5 amazing days at Il Gufo and loved every minute. Jacopo is an amazing host and went out of his way throughout to make our stay great. Even meeting us locally and showing us the way to the house. We highly recommend staying at The Owl. The location, high in a valley provides spectacular views and is perfect to relax and unwind. We do not know what was better. The location, accommodations or the fact that we met Jacopo and became immediate friends. That combination made for the greatest memories. Also Luba, their beautiful dog, immediately loved us and greeted us ever time we returned. A little secret, he is an amazing chef and if you get a chance to go to his restaurant do it. Also his dinner recommendations were great. We had dinner at Corte Dei Frati 2 times. Thank you Jacopo for making our 30th Anniversary trip so amazing. We feel privileged to have met you and we will return on our next trip to Italy. You are an amazing person and host. Love Steve & Vicki
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
Home in Lecchi in Chianti
4.96 out of 5 average rating, 136 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars7 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Top guest favorite
The outdoor pool features clear turquoise water, surrounded by a stone patio. Lush green hills and tall cypress trees create a scenic backdrop, while a few lounge chairs are positioned nearby for relaxation.
Home in Subbiano
4.99 out of 5 average rating, 82 reviews

Romantic cosy flat - Toscana Italy

JoeRating, 5 stars3 days ago
Norma was an absolute treasure, and her home and family were lovely. The property sits overlooking a lovely castle and a beautiful church with great views on the other side. The property has a great pool with plenty of privacy or interaction with the family, I only wish I spoke more Italian to be able to sit and chat with her lovely in-laws! Norma offered great recommendations for day trips, and overall the local area was great to explore. My only advice would be the usual: rent a smaller car to make life easier! Sitting on the patio overlooking the castle, with a glass of wine, is a memory we will never forget, and is highly recommended. Whether during the day or after the sun has gone down and the fireflies comes out (weather permitting) it's a Tuscan treat you won't want to miss. We truly felt like a part of the family and would love to return to her home the next time we come back. Truly a wonderful experience!
Guest favorite
An open natural swimming pool is surrounded by lush greenery, featuring wooden lounge chairs positioned along the poolside. The tranquil water reflects the surrounding landscape, while a gentle waterfall can be seen emerging from one end, enhancing the serene environment.
Home in Certaldo
4.91 out of 5 average rating, 129 reviews

Paluffo Stillo House

LisaRating, 5 stars1 month ago
Il Paluffo was a beautiful place in the Tuscan hills. Stilla, our accommodation, was relaxing and provided most everything we needed. The views were amazing and the staff friendly. The highlight of our stay was the cooking class with Monica. She was a burst of energy and patient as she guided us through a 4-course meal. It was absolutely delicious and plentiful. I would stay a Il Paluffo again and recommend to anyone.

Weekly house rentals

Guest favorite
The image captures a tranquil outdoor area featuring a swimming pool surrounded by well-maintained grass and foliage. A shaded structure offers seating beside the pool, with steps leading into the water visible. Rolling hills and clear blue skies are seen in the background.
Home in Sovicille
4.95 out of 5 average rating, 74 reviews

Cozy country house Podere Scorno with pool

ErikaRating, 5 stars1 week ago
Un posto davvero magico! L’appartamento è bellissimo, curato nei dettagli e perfettamente inserito in un contesto tipico e affascinante. Lo spazio esterno è meraviglioso, perfetto per rilassarsi, e la zona piscina è un vero gioiello. Un’oasi di pace e bellezza. Virginia è stata super gentile e accogliente, sempre disponibile e attenta. Ci siamo sentiti davvero a casa. Consigliatissimo!
Guest favorite
The stone exterior of the house features a wooden front door and multiple windows with dark shutters. A small potted plant is positioned by the entrance, adding a touch of greenery to the rustic facade. The surrounding area includes a paved path and a quiet street.
Home in Castelnuovo Berardenga
4.97 out of 5 average rating, 90 reviews

Casa in campagna vicino a Siena

JasonRating, 5 stars4 days ago
Place was as described. The house was in pristine condition when we check in. Nested in a quite and peaceful countryside, it was exactly what we wanted. Parking was just a few meters from the main door. Host Patrizia was very friendly and responded to my questions promptly. Her check in instructions were clear and we found the place easily. A short drive from local attractions and wineries, it is a good launch point to tour the region.
Top guest favorite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home in San Quirico d'Orcia
4.99 out of 5 average rating, 208 reviews

Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni

HildeRating, 5 stars1 week ago
If you are looking for a little piece of heaven look no further. Vignoni Alto is peaceful and incredibly beautiful. Stefano met us and showed us everything about the apartment and the historic hamlet. His instructions and recommendations were very helpful. The apartment is not far from the restaurants in Bagno Vignoni. Stefano really is a perfect host—responsive, friendly and proactive. Our only regret was that after a week we had to leave.
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 71 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars6 days ago
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!
Top guest favorite
A bright living area showcases large glass doors leading to an outdoor terrace with scenic views. A colorful area rug lies on the wooden floor, complemented by a modern sofa and decorative artwork on the wall. Natural light fills the space, enhancing its openness.
Home in Vaiano
5 out of 5 average rating, 241 reviews

The MOONLIT & SUNNY COTTAGE near Florence

Jan-JaapRating, 5 stars3 days ago
We really enjoyed our stay at Alessandro’s place 🇮🇹✨ The house was clean, nicely decorated and had everything we needed 🏡 The area was peaceful, yet well located to explore the region 🚗 Alessandro was responsive, thoughtful and easy to communicate with 🙌🏼 BEST AIRBNB 5/5 ⭐️⭐️⭐️⭐️⭐️
Top guest favorite
Home in San Gimignano
4.95 out of 5 average rating, 223 reviews

Tuscan house: green, relax: amazing view!

DanishaRating, 5 stars3 weeks ago
This is my favorite Air BnB host of all time. This is a lovely Tuscan home which is exactly what we wanted. The home had all the old farmhouse touches. Beatrice went out of her way to be helpful and provide lots of great information about the area. We did everything she suggested and had a great time in the area. Will definitely be back. thank you B.
Top guest favorite
Home in Siena
4.99 out of 5 average rating, 177 reviews

Podere Piazza casa con vista panoramica

DianneRating, 5 stars4 weeks ago
Sofias house is beautifully renovated, with a fabulous downstairs area with open fireplace. The views from the backyard are stunning, and very peaceful. Location was great, with a 10 min drive, or 20 minute walk to Siena. Sofia was extremely friendly and helpful with local tips. We will definately go back!
Top guest favorite
The image showcases the exterior of an ancient stone building within the historical walls of San Gimignano. Sunlight illuminates the textured facade, highlighting the charming architectural details, including windows and balconies. A quiet pathway leads to the entrance, surrounded by greenery.
Home in San Gimignano
4.97 out of 5 average rating, 78 reviews

Casa Maurino

CharlesRating, 5 stars1 week ago
Casa Maurino is the ideal accommodation for anyone visiting San Gimignano and surrounding areas - very close to all attractions within the town; right on the edge of the countryside for great walks and magical vistas; quiet serenity when you need to withdraw from the torist hordes. All of the previous glowing reviews are correct 100%. Very highly recommended.

Private house rentals

Guest favorite
The villa is positioned on a hillside, offering panoramic views of the rolling Tuscan countryside at sunset. Olive trees are scattered throughout the landscaped garden, with a covered terrace visible, inviting outdoor relaxation and dining. Warm light bathes the scene, enhancing the natural beauty.
Home in Castelmuzio
4.98 out of 5 average rating, 40 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars1 week ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Guest favorite
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home in Asciano
4.97 out of 5 average rating, 33 reviews

Family Forest - Piscina nelle Crete Senesi

SylviaRating, 5 stars2 days ago
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!
Top guest favorite
A charming countryside building is surrounded by lush greenery and rolling hills. A circular pool is situated in the garden, accompanied by several lounge chairs. A shaded seating area offers a relaxing spot, with trees and olive groves enhancing the serene landscape.
Home in Siena
5 out of 5 average rating, 8 reviews

la casina del castagno

CarolaRating, 5 stars1 week ago
Casa di Laura è un sogno. Ho condiviso la location a tutti i miei amici perché venire qui è proprio un regalo meraviglioso da farsi. Siamo andati via a malincuore, come quando si lascia una casa vacanza a cui ci si è affezionati. I dintorni sono stupendi, così come la casa, un giardino tranquillo e curato in ogni minimo dettaglio con la piscina che cambia tutta la vacanza. Un tuffo prima di scendere a Siena a visitare (che è a 15 minuti di macchina, neanche) è uno tornando a casa prima di scendere per cena. Ideale per rinfrescarsi dal caldo estivo. È stato veramente stupendo, e torneremo! Grazie mille Laura per aver condiviso con noi ristornati per pranzo, cena e aperitivo e per essere stata così flessibile con l’orario. Non ci siamo neanche incontrate ma dopo essere stata a casa tua è come se ti conoscessi. Grazie!
Top guest favorite
A charming stone structure is framed by well-maintained greenery and steps leading to a welcoming entrance. Two wooden doors are set within the brick façade, complemented by a small garden area filled with plants, creating a serene outdoor setting under a clear blue sky.
Home in Siena
4.96 out of 5 average rating, 80 reviews

Oliveta Verde con giardino vicino al centro

NickRating, 5 stars2 months ago
Amazing property - stunning views, and outside space. Warm and cosy with beautiful decore. Spotlessly clean. So close to Siena , a very easy walk! Elena was extremely responsive and could not be more helpful
Guest favorite
A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.
Home in Castellina in Chianti
4.98 out of 5 average rating, 98 reviews

Explore Chianti from a Charming Stone House

ThierryRating, 5 stars1 week ago
La récompense est au bout de quelques centaines de mètres de chemin empierré mais praticable: l'environnement de la maison est superbe et la vue sur la campagne du Chianti est magnifique. La maison n'est pas très grande mais convient pour 4 personnes. Elle est très bien entretenue et équipée. Les produits que Monica laisse gentiment à disposition dans les salles de bains sont raffinés. La piscine (commune aux différents logements du hameau) est suffisamment grande pour pouvoir se détendre en nageant, avec une vue imprenable sur la campagne toscane. A partir de Castellina, il est facile de rayonner pour découvrir Sienne (à moins d'une demi-heure de route) et toute la région du sud du Chianti. Florence est un peu plus loin (compter une bonne heure de route). Séjour magique. Et Monica est très réactive pour aider ses hôtes.
Top guest favorite
Home in Pontassieve
4.96 out of 5 average rating, 81 reviews

La casina ridente in Toscana con vista mozzafiato

JetRating, 5 stars1 week ago
What a magical, unforgettable place to stay! The home is the perfect size for two, and we felt right at home. It’s very clean with plenty of towels, blankets, pillows, and cooking appliances. We really enjoyed waking up to the sound of birds singing and having breakfast on the patio before making excursions to Siena, Florence, Poppi, or nearby Rufina. The neighbor’s cats also greeted us home when we returned (very lovingly!). Would absolutely love to stay again!
Top guest favorite
A charming stone villa is framed by lush greenery and tall trees. Natural stone pathways lead to the entrance, where wooden shutters are seen beside arched windows. Shadows from the surrounding foliage create a tranquil ambiance, reflecting the serene countryside setting.
Home in Radda in Chianti
5 out of 5 average rating, 20 reviews

Villa le Scope 5*

ColeRating, 5 stars1 week ago
Beautiful home. Extremely clean. Riccardo was extremely responsive and made our check in process very easy. Definitely would stay again!
Guest favorite
A bright kitchen features a large wooden window overlooking a leafy garden. Fresh flowers are arranged in a vase on the countertop, accompanied by a bowl of eggs. Natural light enhances the space, highlighting the white cabinetry and sink area.
Home in Colle di Val d'Elsa
4.94 out of 5 average rating, 63 reviews

Countryhometuscany - House with Garden -

MarcinRating, 5 stars1 month ago
We had a wonderful stay in this beautiful accommodation in Tuscany. The views are stunning, and the property includes a small, fenced garden, which was perfect for our dog. There's also a large pool available to all guests, which was a huge plus. Having a car is a must. The location is ideal for visiting local spots like Siena, San Gimignano, and Val d’Orcia. The host provides a fantastic guidebook with recommendations, and we were never disappointed by any of the places he suggested. The fully equipped kitchen made it easy to prepare meals, and we enjoyed relaxing dinners in the garden under the lights. Overall, it's a cozy and comfortable place, perfect for a Tuscan vacation

Destinations to explore

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