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Villa vacation rentals in Siena

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Popular amenities for Siena villa rentals

Private villa rentals

Superhost
An aerial view reveals a spacious villa surrounded by a large green park. A private swimming pool is situated adjacent to the villa, with comfortable sun loungers placed around it. Nearby, a private tennis court is visible, complementing the outdoor amenities.
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)
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
Superhost
The villa features a classic architectural design with a decorative roofline. A wrought iron balcony extends across the front, complemented by several large windows. The entrance is framed by greenery, with a gravel pathway leading up to the building.
Villa in Marlia
4.87 out of 5 average rating, 23 reviews

Charming Villa -private swimming pool -16 people.

LauraRating, 5 stars8 months ago
Beautiful house in a stunning location. Pool was great. Perfect for a large family. Owners were very helpful and available when needed. Rooms were hot overnight but this is expected in peak summer in Italy.
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!
Guest favorite
The villa is surrounded by a lush garden, featuring well-maintained greenery and colorful flower beds. Two large umbrellas provide shade over the outdoor seating area, and a swing hangs from a sturdy tree, inviting relaxation in the peaceful setting.
Villa in Sarteano
5 out of 5 average rating, 13 reviews

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

BrynRating, 5 stars6 months ago
Lovely modern home in a beautiful, quiet town in southern Tuscany. We had a wonderful 8 days there with our 6 year old son.
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.
Superhost
Villa in Florence
4.8 out of 5 average rating, 41 reviews

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

JeffRating, 5 stars4 days ago
Great place, responsive host. Will be back.
Guest favorite
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 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!
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.
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!
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 stars5 days 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 friends) enjoyed staying at the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She sent us a lot of tips about the area (including the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed something, an answer came very quickly. The villa is well equipped and the surroundings are beautiful. There is plenty of parking space. Only the potholes and the access to the villa are a bit challenging - but doable!
Guest favorite
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.
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 stars3 days ago
The house is amazing and the exterior is beautiful
Superhost
The expansive garden features well-maintained grass and elegant trees casting shadows on the ground. In the background, the villa's rustic brick facade complements the natural surroundings, while additional greenery and an open sky create a serene atmosphere.
Villa in Torrita di Siena
5 out of 5 average rating, 4 reviews

Villa Scianellone

NickRating, 5 stars35 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.

Villa rentals with a pool

Superhost
A large pool with clear blue water is framed by lounging chairs and shaded areas. Lush greenery and cypress trees surround the landscape, while a picturesque house sits atop the hill, under a bright blue sky dotted with clouds.
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!✨
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
Villa in Casale
4.96 out of 5 average rating, 23 reviews

Villa with pool in chianti Rufina area 13 sleeps

NilsRating, 5 stars7 months ago
Great stay in a lovely remote area. The pizza oven was a major highlight
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, 121 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 Petrognano
4.86 out of 5 average rating, 7 reviews

Villa Iris with Swimming Pool

KateRating, 5 stars7 months ago
I have so much positive to say about this place! Despite what some reviews mention about the drive, it's absolutely worth it. There's a small restaurant just 2-3 minutes away, easy access to the city, and you're only about an hour from Pisa and some beaches. The house was perfect—everything well thought out and worth every penny. The pool was amazing, and the host was very responsive. If you're visiting in autumn or spring, bring warm clothes for the chilly evenings. We were sad to leave, and I can't wait to come back to this dreamy property!
Superhost
Villa in Capannori
4.96 out of 5 average rating, 23 reviews

Luxury Tuscany Villa on the hill with private pool

JanetRating, 5 stars1 week ago
This villa was something out of a dream. Stefania was so lovely and wonderful with recommendations and booking us a rez at a fantastic local gem of a restaurant. The views were incredible and the atmosphere was so relaxing. The villa itself was cozy and inviting. The outside seating area was well used by us for nightcaps, dinner and conversations about falling in love with Tuscany and all it's amazing nooks and crannies. We wanted a picturesque and home-like central base for our 10 day adventure in Italy and we're delighted with the accommodations that really was like something out of a movie. Lucca was only a short drive away and offered the best grocery store-Esselunga! Thank you Stefania for your warm generosity, kindness and suggestions. This was a birthday trip that we will never forget and cemented our longing to return soon!
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.

Quick stats about villa rentals in Siena

  • Total rentals

    30 properties

  • Nightly prices starting at

    $60 before taxes and fees

  • Total number of reviews

    1.2K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 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. Siena
  6. Villa rentals