Vacation rentals in San Martino A Maiano

Farm stay in San Gimignano

Lush green hills are interspersed with orderly rows of olive trees, leading to a charming rustic building. In the distance, the silhouette of San Gimignano's historic towers is visible against a clear blue sky, creating a scenic view of the Tuscan landscape.

4.89 out of 5 average rating, 209 reviews

Oleandro double room with pool in San Gimignano

Double room in the peaceful countryside of San Gimignano, just 5 min from town by car. Located in Montegonfoli Farm, an ancient estate like a hidden hamlet, surrounded by olive trees, vineyards, and a private forest with a stream. Guests can enjoy the pool during the warm season. The room has a 160x190cm queen bed, large bathroom, fridge, microwave, and a terrace with dining table (no kitchen/fires). A perfect place for couples or solo travelers seeking tranquility, charm, and a touch of Tuscany

Farm stay in Montespertoli

An expansive outdoor space is highlighted by a covered terrace featuring a barbecue area. The surrounding landscape includes rolling hills, olives, and various garden sculptures. The open area provides ample seating for gatherings, with natural beauty evident in every direction.

4.91 out of 5 average rating, 101 reviews

Piccionaia apartment with garden for 2 people

In Montespertoli, among the rolling hills of Chianti, there is Podere Paglieri, a small family-run farm where wine and oil have been produced for generations. We are located halfway between Florence and Siena, in a perfect position to discover San Giminiano, Volterra, Siena, Lucca, and the Tyrrhenian coast, which are just a few kilometers away. The farm is surrounded by vineyards, olive groves and woods where you can walk freely, has a large and well-kept garden and a beautiful shaded terrace.

Castle in Montecatini Val di Cecina

4.99 out of 5 average rating, 118 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here with our sons and our mission is to give the best to our guests, to fully enjoy this marvelous place.

4.99 out of 5 average rating, 276 reviews

Apartment in Poggibonsi

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment, halfway between Florence and Siena, is conveniently located for quick access to Florence, Siena, San Gimignano , Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

4.93 out of 5 average rating, 119 reviews

A scenic view of rolling hills and lush greenery is visible from a window. Terracotta roofs and a winding path can be seen below, enhancing the historic charm of the medieval surroundings.

Condo in San Gimignano

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

4.93 out of 5 average rating, 106 reviews

Aerial view of a rustic countryside house surrounded by lush olive groves and tall trees. A historic castle is visible on a distant hill, framed by a clear blue sky and soft clouds, highlighting the serene rural landscape.

Home in Montespertoli

Costalmandorlo, a rustic home in the heart of Tuscany

Costalmandorlo is your corner of peace in the center of Tuscany. A charming country cottage restored and furnished with care and a style that reconciles ancient and modern. Here you can slow down and relax surrounded by the sounds of nature, admiring beautiful sunsets and having long breakfasts in the garden. A short distance between Florence, Siena and Pisa, it is an excellent base for the Tuscan tour.

Home in Barberino Tavarnelle

A scenic view of rolling hills and vineyards stretches across the landscape, illuminated by soft natural light under a partly cloudy sky. Lush greenery and trees frame the foreground, creating a serene and inviting backdrop typical of the Tuscan countryside.

4.91 out of 5 average rating, 145 reviews

La Casa di Nada - Suite

Every window of my house opens onto wonderful views of the Tuscan hills, an enchantment that will accompany every moment of your stay. My kitchen is fully equipped and the rooms are comfortable and bright, with a private bathroom for each room. In the living room, I have a beautiful fireplace all for you. A practical, complete laundry room in this refuge in the Heart of Chianti

4.89 out of 5 average rating, 198 reviews

A stone patio is seen outside a rustic building, featuring a table set for two. Lush greenery surrounds the area, including tall trees and shrubs. A tranquil countryside view is visible in the background, contributing to the serene outdoor setting.

Farm stay in Simignano

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

4.97 out of 5 average rating, 112 reviews

A charming balcony is featured, adorned with colorful flowers and greenery along the wall. A small wooden table and two foldable chairs are positioned against the wall, while a planter brimming with pink flowers sits nearby, creating a pleasant outdoor space.

Apartment in Certaldo

House in a medieval tower with a view in Certaldo

Vacation home located in the heart of the medieval village of Certaldo. Second floor apartment without elevator consisting of kitchen with dining room, bedroom with plasma TV and terrace, bathroom with shower, bedroom with sofa bed, relaxation area and panoramic view. Large garden with barbecue! Sleeps 4. Free Wi-Fi!!!

Condo in Barberino Tavarnelle

A rustic stone building is surrounded by lush greenery, featuring wooden shutters on the windows. A gently sloped path leads to a fenced yard with a wooden gate, inviting guests into a serene outdoor space.

4.93 out of 5 average rating, 110 reviews

Apartment with panoramic view in Chianti

Large newly renovated apartment nestled in the Chianti hills, overlooking the property's olive grove and the surrounding hills. Located halfway between Florence, Siena and S. Gimignano, it is an ideal solution for couples, families and groups of friends who want to spend a relaxing stay in an authentic Tuscan home.

4.99 out of 5 average rating, 298 reviews

Farm stay in Pisa

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

4.98 out of 5 average rating, 169 reviews

A spacious living area features elegant brick arches overhead, creating a unique architectural element. Large glass doors open to a scenic view of the surrounding greenery. A cozy seating arrangement and a wooden dining table provide ample space for relaxation and dining.

Farm stay in Palaia

Countryside Dream farm in Tuscany

Great place in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

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Other great vacation rentals in San Martino A Maiano

Home in Barberino Tavarnelle

4.77 out of 5 average rating, 56 reviews

7 min Cantina Antinori | Pool | Casa Sala & Pepe

NinaRating, 5 stars5 days ago

We spent a week in Silvio and Margherita's house with our two young children (5 and 6 years old). The hosts were always easily and quickly accessible and very helpful and friendly. The house is surrounded by vineyards and you have a fantastic view. There are some very good restaurants around that can be reached quickly by car. The garden is sweetly designed, but you share it with two other neighbors. However, you have your own garden section and pool to yourself. The house was clean, but very noisy (which did not bother us). A few pieces of furniture could be renewed (but did not restrict us and looks a bit authentic ;-) We would definitely come back.

4.96 out of 5 average rating, 25 reviews

Two glasses of red wine are clinked together, emphasizing a celebratory moment. A neutral table setting with a linen tablecloth is visible, featuring a dark plate of green grapes and minimalist tableware, creating an inviting dining atmosphere.

Condo in Certaldo

Poggio ai Grilli Apartment

PeterRating, 5 stars2 weeks ago

Veronica was a great host full of information, place was lovely and clean and the neighbours was so friendly made us not Italian speaking very comfortable , loved our stay such a beautiful area and great train system . Everyone we meet was friendly and it made our stay so special

4.83 out of 5 average rating, 120 reviews

Home in Montespertoli

I Limoni Apartment in Tuscany

WiktoriaRating, 5 stars1 month ago

Incredible home, with stunning views! I hosted a group of friends here before my wedding, and we all agreed it was the most beautiful Airbnb we have ever stayed in. The hosts (Francesco and his wife Illaria) were extremely responsive and kind. They recommended a local chef to us, which turned into one of the best nights of our trip. 100% recommend and will be re-booking next time I travel to Tuscany.

5 out of 5 average rating, 6 reviews

The restored barn house is surrounded by tall trees and lush greenery, featuring a spacious pool area with a rectangular pool. Sun loungers are placed nearby, and a shaded seating area is visible, creating a serene outdoor setting for relaxation.

Home in Lucardo

Between dream and reality, villa with private pool

LisaRating, 5 stars1 week ago

We had a wonderful stay at Massimo's house. Five stars are not enough! Massimo is a perfect host. We will definitely come back again. The view is amazing and the house is perfectly equipped and very clean. One of the best Airbnbs we ever stayed.

Condo in Castelfiorentino

A well-maintained exterior features a stone patio with potted plants, including one large, rounded green pot. The entrance is marked by an arched door framed by green shutters, allowing natural light to enter. Shadows from nearby trees create a serene atmosphere.

5 out of 5 average rating, 7 reviews

Casa al Profeti

AdeleRating, 5 stars1 week ago

We had a great stay at Maurizio’s place! The apartment was clean, nicely furnished, and the kitchen was very well equipped. Maurizio gave us great tips for local trips and activities, which really made our stay special. The only downside was that the street outside could be a bit noisy at times, but overall it didn’t bother us much. This Airbnb is a great base for visiting Florence, Siena, and Pisa — either by car or by train. The historic towns of San Gimignano and Certaldo are also nearby, making it perfect for exploring Tuscany. Thanks again, Maurizio — we’d be happy to come back!

The image captures a serene view of rolling hills, shrouded in a gentle morning mist. The landscape is dotted with vineyards and trees, stretching towards distant mountains, creating a tranquil atmosphere. The scene is framed by the edge of a stone building and lush greenery.

Cottage in San Gimignano

4.84 out of 5 average rating, 209 reviews

Countryside Cottage With View - Le Rondini apt

EwelinaRating, 5 stars2 weeks ago

The place is just perfect, peaceful and beautiful, yet very close to San Gimignano ( 6 minutes drive), Sienna, Pienza, Florence, Montepulciano, Lucca, Volterra. The house is pretty, the view breathtaking. a large garden was loved by our dog. We would love to come back one day. Owners were very helpful and friendly. Thank you!

A spacious bathroom features a modern shower with glass doors and a vanity sink on a wooden countertop. Adjacent, a bright bedroom includes a queen-sized bed covered with a neutral-toned blanket. Natural light filters through two windows, complemented by soft drapery.

Apartment in Certaldo

4.82 out of 5 average rating, 212 reviews

Medieval Village Apt btwn Florence Siena

MartinRating, 5 stars2 weeks ago

Great place. Right in the medival town. Easy to find, comfortable, good communication. Stayed in hot weather yet the place was very cool. Nice cafes nearby. Would recommend! Thanks so much Silvia