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Villa vacation rentals in Gaiole in Chianti

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Popular amenities for Gaiole in Chianti villa rentals

Private villa rentals

Superhost
A scenic pathway leads through a lush green landscape, bordered by flowering lavender and vibrant red blooms. The pathway is flanked by neatly trimmed trees, creating a serene and inviting atmosphere that connects the property to the natural surroundings.
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.
Superhost
The spacious living room features a decorative ceiling with ornate detailing. Various art pieces adorn the walls, while elegant furnishings are arranged throughout. Natural light streams in through several windows, creating a bright and welcoming environment accented by carefully curated decor.
Villa in Florence
4.88 out of 5 average rating, 16 reviews

Villa La Cingallegra

MiltonRating, 5 stars6 months ago
Fantastic all around experience. Thank you Elio and team 🙏🙏
Superhost
A spacious sitting room is presented, featuring ornate wallpaper and a chandelier above. Elegant seating arrangements include two armchairs and a couch, with a coffee table placed centrally. Large windows allow natural light to illuminate the room, while a fireplace adds a classic touch.
Villa in Chiusi
4.88 out of 5 average rating, 8 reviews

Villa Febea - Villa Febea 16

YonitRating, 5 stars21 months ago
Nestled in a stunning landscape, the villa is a marvelous retreat that captivates with its beauty and generous space. Meticulously maintained to uphold high standards, the villa's kitchen is thoughtfully equipped with all the essentials for a comfortable stay. Furthermore, each room is fitted with its own shower and toilet, ensuring privacy and convenience for all guests. The pool adds an extra touch of wonder to the experience. As for the hosts, Alice and Jacopo, they are simply delightful, providing warm hospitality throughout your stay. I wholeheartedly recommend this exceptional villa for an unforgettable getaway
Guest favorite
An outdoor seating area features dark wicker chairs arranged around a small table, situated on a gravel terrace. Planters with greenery line the railing, while a canopy provides shade. The spacious vista includes rolling hills under a bright, partly cloudy sky.
Villa in Cortona
5 out of 5 average rating, 6 reviews

Villa Pietrenta

RandallRating, 5 stars8 months ago
This is a very comfortable house with beautiful views and a terrific pool. The house really consists of two apartments which works great when traveling with family. The living spaces are not large but work well- we spent most of our time outside anyway. About a 35-40 minute walk into the center of town. Parking in Cortona is tricky, so it’s nice to have the option to walk. Overall, a very good value, comfortable, well-maintained, and easy to use as a hub getting around the small villages of Tuscany and Umbria.
Guest favorite
A well-kept garden area is visible, featuring a stone table surrounded by lush greenery. The structure is framed by mature trees, providing shade and a sense of tranquility. Arched windows of the villa can be seen in the background, offering glimpses of the interior.
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
A two-story villa is surrounded by a lush green lawn and tall trees. Two lounge chairs are positioned on the grass, inviting relaxation. The building is made of stone and wood, featuring balconies that overlook the landscape of vineyards and Tuscan hills.
Villa in Montepulciano
5 out of 5 average rating, 3 reviews

Terra Antica Suites & Villas - Villa Vino - Private Jacuzzi

HeatherRating, 5 stars4 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!
Superhost
A charming stone farmhouse is set against a clear blue sky, framed by lush greenery. In the foreground, a private saltwater pool reflects the vibrant flowers in planters on the wooden deck, creating a serene outdoor scene ideal for relaxation.
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 favorite
A stone villa is illustrated with large windows and an expansive terrace. A well-manicured lawn stretches to a sparkling pool, complemented by sun loungers. Lush greenery surrounds the area, enhancing the serene outdoor space.
Villa in Gaiole in Chianti
5 out of 5 average rating, 9 reviews

Casa Faraona, villa with private pool

VaughanRating, 5 stars6 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.

Luxury villa rentals

Guest favorite
An aerial view showcases a modern villa surrounded by lush greenery, featuring a private infinity pool. Lounge chairs are positioned beside the pool, and the outdoor dining area is elegantly set on a spacious terrace, enhancing the outdoor living experience.
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!
Guest favorite
A spacious dining area is featured, complete with rustic wooden beams and a large wooden table. Surrounding chairs and a cozy seating area with plush couches create an inviting atmosphere. Natural light filters through multiple windows adorned with greenery, enhancing the room's warmth.
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 favorite
Villa in Casale
4.96 out of 5 average rating, 24 reviews

Villa with pool in chianti Rufina area 13 sleeps

AnnaRating, 5 stars5 days ago
The house was amazing, perfect fit for our group of 10 people. The main house as well as the additional apartment were very clean, well equipped with everything you need and the highlight was the pool and jacuzzi. Great place to calm down and have private space with some friends or a big family. The check-in was easy and the lady was very friendly, had some suggestions for our stay and is professional. The property was clean, cute tuscany decorations of the rooms and all in all it felt like home.
Top guest favorite
A welcoming living area is characterized by elegant furniture, including a pair of intricately designed chairs and a spacious couch. A decorative coffee table sits in the center, surrounded by soft natural light from the windows, and a vintage chandelier hangs above.
Villa in Rignano sull'Arno
5 out of 5 average rating, 9 reviews

villa "La Fonticina"

Maria ElenaRating, 5 stars1 week ago
This house is a jewel and I feel so lucky Cesare shared it with us. Highly recommend to anyone looking for a comfortable and beautiful place!
Top guest favorite
Villa in San Miniato
4.88 out of 5 average rating, 40 reviews

Historic home with exclusive pool

AylaRating, 5 stars9 months ago
We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. Parking has enough. Only the potholes and the access to the villa are a bit challenging - but doable!
Superhost
A spacious living area features a classic design with elegant seating arrangements, a round coffee table, and a decorative rug. Large windows allow natural light to illuminate the room, while offering views of the terrace and garden beyond.
Villa in Fiesole
4.86 out of 5 average rating, 22 reviews

Villa Lualdi

SallyRating, 5 stars7 months ago
Had a lovely week at the villa. Amazing place and beautiful views! Florence a short drive away, but we also enjoyed walking about 35 minutes to Fiesole for restaurants and views.
Superhost
An outdoor terrace is visible, featuring stylish seating arrangements with comfortable cushions. A panoramic view of the rolling hills and expansive sky fills the background, offering a serene setting for relaxation. Natural light brightens the space, enhancing the tranquil atmosphere.
Villa in Paciano
5 out of 5 average rating, 4 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
Guest favorite
The outdoor area showcases a uniquely shaped swimming pool surrounded by verdant grass and olive trees. Sun loungers are positioned for relaxation, while natural stone elements add a rustic charm. A gentle slope leading to the villa is visible in the background under a clear blue sky.
Villa in Colle di Val d'Elsa
4.95 out of 5 average rating, 21 reviews

Villa L 'elsa

MarcelaRating, 5 stars6 days ago
The house is amazing and the exterior is beautiful

Villa rentals with a pool

Guest favorite
A large private swimming pool features clear turquoise water, surrounded by sun loungers and umbrellas. Olive trees are visible nearby, and a traditional farmhouse stands in the background against a clear blue sky, providing an inviting outdoor space for relaxation.
Villa in Baco
4.86 out of 5 average rating, 83 reviews

Tuscan Villa

DeeRating, 5 stars7 months ago
Five friends made to feel very welcome to this beautiful spacious villa with a lovely pool set amongst olive groves. The scenery that surrounded us was beautiful. Invited to Mark's villa who shared his knowledge and history of the olive groves which was very interesting and the hospitality received was first class (vino and yummy bruschetta's). This was the perfect place to stay and would highly recommend.
Top guest favorite
An aerial view captures the villa’s expansive layout, featuring a private pool surrounded by lounge chairs. Lush greenery and cypress trees border the property, while terracotta roofs and open balconies contribute to the charming Tuscan landscape.
Villa in Montecucco
4.9 out of 5 average rating, 39 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 favorite
The exterior of the villa showcases a brick façade supported by wooden columns. A well-maintained lawn extends alongside the building, bordered by a rustic wooden fence. The serene landscape in the background highlights trees and open fields under a clear blue sky.
Villa in Montepulciano
4.91 out of 5 average rating, 122 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars1 week 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 stars8 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.
Guest favorite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa at Mulino del Cerchiaio

MathildeRating, 5 stars6 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!
Top guest favorite
An outdoor space features a rectangular swimming pool surrounded by a stone patio. Sun loungers and a dining table with chairs are positioned under a large umbrella. Lush greenery and flowering plants enhance the scenic view of the hillside in the background.
Villa in Ortignano Raggiolo
4.94 out of 5 average rating, 69 reviews

Private Villa with swimming pool in Tuscany

TomášRating, 5 stars6 months ago
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!
Superhost
The image showcases an ancient stone villa surrounded by a spacious lawn, with a private swimming pool in the foreground. The pool is characterized by a rounded shape, complemented by white lounge chairs positioned nearby. Lush greenery and rolling hills are visible in the background under a partly cloudy sky.
Villa in San Gimignano
4.79 out of 5 average rating, 24 reviews

Elisa Villa

DominiqueRating, 5 stars5 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 favorite
Villa in Volterra
4.98 out of 5 average rating, 51 reviews

Villa Casa al Povero

AnthonyRating, 5 stars2 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.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Gaiole in Chianti
  6. Villa rentals