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Vacation home rentals in Siena

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Popular amenities for Siena vacation home rentals

Family-friendly vacation home rentals

Top guest favorite
The exterior of a stone country house showcases a charming garden filled with vibrant flowers, including red tulips and purple irises. A grassy area leads up to the entrance, which features a large arched doorway and a small balcony above.
Vacation home in Montecatini Val di Cecina
4.88 out of 5 average rating, 8 reviews

I Castagnini - Orange

MaryRating, 5 stars8 months ago
My partner and I spent four days in Marco's apartment, they were four days of relaxation, we felt welcomed as family. Antonietta and Francesco, Marco's father and mother (two people like there aren't many, kind, generous, two people with whom it is pleasant to get lost in their stories) who live upstairs from the apartment, pampered us and made us feel at home. We'll definitely be back next time, the three of us.
Superhost
Vacation home in Città della Pieve
4.6 out of 5 average rating, 5 reviews

Foresteria 4 Relax on hill: Jacuzzi, Boules, Pool

RaushanaRating, 5 stars12 months ago
Maria’s place was such a treat for a long weekend. There are many things to do outdoors and for us it was perfect to relax with the sound of nature 24/7. There are many kids activities in the house (toys, games, puzzles$ and the nature surrounding the house is fun to explore! Mini playground is also great just across the street. We enjoyed her hospitality and kindness. Maria was always responsive, helpful, and gave great restaurant and activities recommendations.
Guest favorite
The stone farmhouse is set amongst vibrant greenery and blooming flowers, showcasing a blossoming tree in front. The entrance is framed by the surrounding landscape, with a subtle path leading to the door, inviting guests to explore the rustic charm of the property.
Vacation home in Casole d'Elsa (SI)
4.9 out of 5 average rating, 222 reviews

Studio in Tuscan farmhouse with pool & views

MarleneRating, 5 starstoday
Beautiful accommodation in Tuscany with fantastic views. Simply great, we are thrilled and definitely want to come back. Fabio is super nice and the place offers everything you need. Highly recommended !
Top guest favorite
An aerial view captures the layout of the Podere La Castellina, surrounded by lush greenery. The stone buildings and pathways are visible, alongside a serene swimming pool. Shared outdoor spaces, including seating areas, are interspersed among the natural landscape, promoting relaxation and connection to nature.
Vacation home in Sovicille
4.97 out of 5 average rating, 141 reviews

Podere La Castellina - No. 1 COTTAGE

CatherineRating, 5 stars6 months ago
Daniele and Simone’s place in Tuscany is beautiful. It is such a peaceful and pretty setting with amazing views particularly from the lovely terrace. Our cottage was perfect for our family of four. Comfortable beds and everything we needed. We explored some of the villages nearby as well as wineries and restaurants recommended by Simona which were excellent. We would love to have stayed another night.
Top guest favorite
A charming red house is visible, framed by lush greenery and a neatly trimmed hedge. The entrance features a wooden door surrounded by white shutters. A small porch with a few steps leads to the front door, enhancing the inviting appearance of the home.
Vacation home in Montespertoli
4.95 out of 5 average rating, 135 reviews

Tuscan Orchard

FabiolaRating, 5 stars3 weeks ago
I loved the house! It was so beautiful, cozy and clean. I will definitely book it next time I am in Montespertoli. Fiammetta and Leonardo were very sweet!
Guest favorite
The rustic farmhouse is framed by a stone wall, featuring a pathway leading to a stairway entrance. Lush greenery and flowering plants are visible along the edges, complementing the natural setting. The warm tones of the stone structure contrast with the clear blue sky.
Vacation home in Castelnuovo Berardenga
4.88 out of 5 average rating, 69 reviews

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

ThereseRating, 5 stars7 months ago
Arnaldo's home was wonderful!!! It was perfect for three couples. With private entrances to each apartment, we could all have our privacy but also gather together in the larger downstairs apartment or around the pool. Lorenza was very responsive, even though she was in Portugal when we arrived. She made sure her father and mother were there to show us around and even opened the gate remotely for our friends who arrived a day later than us so we could begin exploring the area and didn't have to be there when they arrived. The villa is beautiful and was exactly as described. We LOVED our time there--a perfect place to celebrate our 50th wedding anniversary!
Guest favorite
Vacation home in Guardistallo
4.89 out of 5 average rating, 53 reviews

Apartment with swimming pool and garden

NikolajRating, 5 stars6 months ago
Very beautiful views and Serena as a hostess is the best you can get. Very attentive, understanding and forthcoming.
Superhost
A stone statue is positioned near a private pool, surrounded by greenery and flowering plants. The pool reflects the blue sky, while tall trees frame the view of the lush landscape beyond. The scene offers a serene atmosphere in a secluded outdoor space.
Vacation home in Arezzo
4.71 out of 5 average rating, 49 reviews

Ancient stone farmhouse with park and pool

JessicaRating, 5 stars1 month ago
We had a wonderful stay at Stella’s farmhouse. The grounds and surroundings were excellent for walking and exploring in the mornings and late afternoons. The accommodations very comfortable for our multigenerational family. Stella was an excellent host! Very kind, helpful with all our questions, and provided us some nice recommendations for the region. We would love to return!

Vacation home rentals with a patio

Top guest favorite
Vacation home in Castiglione della Pescaia
4.97 out of 5 average rating, 32 reviews

Country house short distance from the sea ​​

LucasRating, 5 stars5 days ago
We had a very nice week at Silvia's place! We immediately felt comfortable and lacked nothing! We will be happy to come back!
Superhost
Bright red flowers are seen in terracotta pots alongside a stone wall. Sun loungers with blue fabric are arranged nearby, offering a view of the lush greenery surrounding the area. Natural light filters through the scene, enhancing the vibrant colors of the plants.
Vacation home in Piegaro
4.67 out of 5 average rating, 3 reviews

il Forno - 2-bedroom poolside

MortenRating, 5 stars10 months ago
we had an amazing time in piagaro,and Thomas gave so mutch information about the Village and a guide around when we arrived. that was really good. he was also a really interesting and reflected man. We had some really good conversations and I would love to come back to his place. I used the cafe every morning for the morning coffee just to take in the atmosphere in the village with the most lovely staff there . LOVELY 😃. truly a special stay for us. we wish them the very best 🥰 Morten with family
Guest favorite
A large swimming pool is surrounded by lush greenery and olive trees. Rolling hills and vibrant vegetation are visible in the background, creating a serene outdoor space for relaxation. Sun loungers are positioned around the pool, inviting guests to enjoy the scenic views.
Vacation home in Campagnatico
4.85 out of 5 average rating, 13 reviews

Cozy Cottage with a beautiful view - Casa Luciano

ThomasRating, 5 stars1 month ago
We had a very nice time at Casa Luciano! Unfortunately, we could not use the great pool in March (although ice bathing is becoming more and more popular ;-)). The area is very nice and quiet. We were able to hike, explore Campagnatico and other places. Once we were able to enjoy the good food in Vecchia Oliviera. (Attention: Pizza is only available from about May) We also supported the village shop properly. It has a decent selection for its size. Thanks Mel for the always timely support with questions and problems! We will recommend the accommodation and maybe we will also manage to vacation here during the pool season.
Top guest favorite
A spacious bedroom features a king-size bed with an intricately designed headboard. Soft lighting from two bedside lamps creates a warm glow. Natural light enters through a window with sheer curtains, offering a view of the greenery outside. A built-in wardrobe is visible in the corner.
Vacation home in Petrignano del Lago
4.97 out of 5 average rating, 65 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

JessicaRating, 5 stars1 day ago
Michelangelo's Airbnb was the perfect place for a relaxing break. Everything was as in the pictures - very modern, clean and with a lot of love for detail. Nothing was missing. Michelangelo was a great host, always quick to reach and gave us helpful tips.
Superhost
An aerial view captures a restored farmhouse nestled in the green landscape of Tuscany. Surrounding hills are visible, with patches of trees and a glimpse of the swimming pool. The winding road leads to the property, enhancing the tranquility of the rural setting.
Vacation home in Montaione
4.8 out of 5 average rating, 25 reviews

Podere Sant'Anna | Fiordaliso House

OmarRating, 5 stars3 weeks ago
The place of the house is very beautiful and calm and also the hostess Romanella was very helpful. We enjoyed this very residence in a special place. You can go to Florence and Pisa by one hour
Guest favorite
The farmhouse is showcased with its rustic stone exterior, featuring multiple windows and a tiled roof. Surrounding greenery and flower beds enhance the tranquil setting. Two chimneys are visible, and a dirt road leads up to the entrance, inviting guests into the countryside atmosphere.
Vacation home in I Castagni
4.88 out of 5 average rating, 24 reviews

Gorgeous tranquil farmhouse 5 min from Castiglione

LarissaRating, 5 stars3 weeks ago
We loved our stay at this farmhouse near the Lake! very roomy and clean and well stocked for our group of 7. Easy to coordinate travels around Umbria and Tuscany, and we loved exploring the Lake towns, especially the Castiglione del Lago center! Easy to follow instructions for house operations, access and directions! We loved the decor, and local ceramics, and the great reading selections- fun library of history, art, cookbooks, and local travel ideas. We loved having downtime and the tranquil area amid pastured and horses; my kids took advantage of sunny weather in early April and did watercolor painting and naps in the sun amid the olive trees in the back yard. It was a little too remote for walking to town (the ruts in access roads were hard on our car, and road construction nearby made for minor inconveniences,) but all in all, a perfect place for our holiday!
Guest favorite
The sleeping area features a spacious bed adorned with a patterned blanket and decorative pillows. Natural light filters through curtained windows, illuminating the room. A wardrobe and shelves provide storage, and the wooden flooring adds warmth to the space.
Vacation home in Figline Valdarno
4.86 out of 5 average rating, 90 reviews

Vacation home Il piccolo rifugio

ClaireRating, 5 stars1 week ago
We had a lovely stay at Annalisa's. She had nice touches for us and we thank her. She is also very responsive.
Guest favorite
A living area features a light blue couch adorned with decorative pillows. A glass coffee table sits in front of the couch, complemented by a vase of fresh flowers. A vintage wooden dresser adds elegance to the space, with natural light entering through a wooden-framed window.
Vacation home in Panicale
4.92 out of 5 average rating, 12 reviews

Il Pollaio guests house

ScottRating, 5 stars2 weeks ago
We enjoyed 3 nights in this beautiful home. Everything in the home was lovely and we wish we could have stayed longer. We met with Elisa and she shared some local recommendations for us which we greatly appreciated. She also left us a lovely bottle of wine which was very thoughtful. Although Panicale is small, we felt right at home immediately. We loved that you could walk to two little cafes and several amazing restaurants. We enjoyed two wonderful meals in Panicale and our morning coffee and pastry at one of the small cafes. We loved this location and explored several other small Italian villages which were close by. We enjoyed talking to some of the locals and learning more about this charming town. Our stay at Elisa's was very nice and we had everything we needed. We hope to come back.

Vacation home rentals with a washer and dryer

Superhost
A private pool is set within a landscaped garden, featuring vibrant greenery and decorative pots. A diving board extends over the clear blue water, while a shaded seating area is visible nearby. Sunlight reflects off the pool's surface, creating a refreshing ambiance.
Vacation home in Capannori
5 out of 5 average rating, 6 reviews

Beautiful rustic shabby, swimming pool on request

ElisaRating, 5 stars30 months ago
Carla's house is beautiful,finished. The owner was very kind and accommodated our requests. He welcomed us with a great aperitif. We were all pleasantly amazed and satisfied. We couldn't have expected better. We will definitely be back! Thank you Carla!
Top guest favorite
Vacation home in Figline e Incisa Valdarno
5 out of 5 average rating, 41 reviews

Farmhouse in the countryside with swimming pool Solatìo

ZachRating, 5 stars1 week ago
We highly recommend Marco's Airbnb! The apartment itself is stylish and spotlessly clean, with exceptionally comfortable beds ensuring a restful night's sleep. What truly stood out was Marco's outstanding hospitality. His local recommendations were spot on, and when we had a slight navigation mishap, he went above and beyond by personally guiding us to the property. Marco's responsiveness and care made our stay truly memorable. Thank you!
Top guest favorite
The image captures a lush landscape framed by a rustic stone window. Rolling green hills and scattered trees extend into the horizon, under a clear blue sky. The view conveys the serene beauty of the surrounding Tuscan countryside.
Vacation home in Monteroni d'Arbia
4.9 out of 5 average rating, 68 reviews

White lily with a view of Siena

CarolineRating, 5 stars1 week ago
This was the second time we stayed in one of Marta‘s apartments! I think that says it all already. We are just in love with the location and the apartments always make you feel at home right away! Thank you again Marta for hosting us (and the delicious vino 🍷😄). We will be back 100%!
Superhost
Vacation home in Scandicci
4.79 out of 5 average rating, 33 reviews

"VERDE" apartment 2/5 people, swimming pool, garden

MassimoRating, 5 stars3 months ago
My partner and our two dogs only stayed two days from December 31 to January 2 in the "Green Apartment"; The apartment was very clean and well-stocked from every point of view ( kitchen, bathroom and bedroom) the spaces are quietly there for a long vacation. We are from the Florence area, and finding ourselves in the middle of all that greenery very close to the center and all the services did not seem true. The entire farm is very well cared for and you can enjoy the stay in relaxation, being very quiet. Unfortunately, staying in winter we could not enjoy the very large outdoor pool, but you can see that it is well maintained. We'll definitely be back to get away from the routine towards the hottest season. Highly recommended for those who want to visit Florence and its surroundings and spend a long vacation.
Guest favorite
A gracefully designed staircase features intricate wrought iron railings. A large arched window allows natural light to illuminate the space, offering a view of greenery outside. The walls display elegant molding, contributing to the historical character of the building.
Vacation home in Centro Storico
4.91 out of 5 average rating, 267 reviews

Melarancio Residence

JenniferRating, 5 stars2 weeks ago
Fabulous location, and looks just like the photos. Loved the ease of check in at the nearby hotel and ability to store luggage there. Having a washer and dryer combo (especially a dryer - this seems like it may be a more rare amenity here) was so helpful for packing light! Very comfortable beds and quiet for sleeping considering how close the apartment is to all the action. Loved that there was an elevator but it was also just a couple flights up the stairs so you had two good options. Loved our stay!
Guest favorite
A charming villa is surrounded by lush greenery and features a sloped, tiled roof. Two white umbrellas provide shade over outdoor seating areas, while a gravel pathway leads through the inviting garden towards the scenic hillside in the background.
Vacation home in Siena
4.9 out of 5 average rating, 40 reviews

Apartment in historic Villa in Siena_"IL MANGIA"

YuRating, 5 stars1 month ago
This was such a wonderful experience, enjoyed the beautiful courtyard for 4 days, clean rooms, quaint and textured furnishings and set up, it does have a warm home feel.Many times I want to be lazy in the room, enjoy the sunshine of the courtyard, and enjoy all the amenities provided in the room.I highly recommend this homestay, take a bus at the door for a few minutes to the ancient city of Siena, we go up each time to the ancient city on foot, you can enjoy the pastoral scenery of Tuscany all the way, thank you Cristina and her brother for their warm and thoughtful service, and the opportunity to come back here later.
Superhost
A view of a charming medieval square surrounded by historic stone buildings, featuring a canopied area with potted plants. Clothes hang drying from a window, while the sky is filled with clouds and streaks of blue, enhancing the inviting atmosphere of the village.
Vacation home in Colle di Val d'Elsa
4.74 out of 5 average rating, 31 reviews

Tower House of the 1000

GabrieleRating, 5 stars1 week ago
Wonderful, very nice apartment in an original house. Great view! The hostess is very friendly and straightforward, really recommended!
Guest favorite
An ornate wrought iron gate opens into a private courtyard adorned with greenery. A stone fountain is visible in the background, surrounded by potted plants. Soft natural light permeates the scene, enhancing the tranquil atmosphere of the entrance.
Vacation home in Centro Storico
4.84 out of 5 average rating, 340 reviews

The Cricket's Cage <Anna Maria> (A-04)

CarlingRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay. This was such a perfect location. It was very central, but so quiet and extremely peaceful! The space was beautiful and everything was as described. The staff was very helpful, friendly and accommodating! We would love to stay again when we visit Florence!

Destinations to explore

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  4. Province of Siena
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