Vacation rentals in Sasso Pisano

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Top-rated vacation rentals in Sasso Pisano

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Top guest favorite

Aerial view showcases the rustic property nestled among the lush vineyards. Sunlight casts a warm glow over the hills, while a sparkling pool is situated near the residences, surrounded by greenery. The tranquil landscape includes gently rolling hills and rows of grapevines.

Condo in Noce

5 out of 5 average rating, 251 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

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Loft in Massa Marittima

4.88 out of 5 average rating, 183 reviews

Authentic Cave House in the heart of the Village!

The house is in the heart of Massa Marittima, a medieval village which is setting on the top of a hill in the Maremma countryside. This authentic historical small town is short driving distance from many amazing beaches of the Mediterranean coast: Cala Violina, Torre Mozza, the Baratti Etruscan Riviera.. Ideal for a romantic escape but also for those who are looking for a local experience in a relaxed, suggestive, historical context far away from mass tourist routes. PLEASE READ ALL DESCRIPTION!

Top guest favorite

The image displays a tranquil outdoor setting featuring a stone swimming pool surrounded by lush greenery. In the background, a historic tower rises among tall trees, while olive trees are seen in the foreground, enhancing the natural beauty of the landscape.

Castle in Montecatini Val di Cecina

4.99 out of 5 average rating, 116 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.

Top guest favorite

A spacious lawn gently slopes up towards a beautifully restored two-level house, featuring warm yellow and red hues. Tall cypress trees line the property, complementing the lush greenery of the surrounding gardens. Soft clouds drift above, enhancing the serene countryside setting.

Home in Gambassi Terme

4.99 out of 5 average rating, 176 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favorite

A view of the entrance to a countryside property is presented, featuring a gravel driveway that meanders through lush greenery. Tall cypress trees line the pathway, while olive trees and rolling hills create a serene backdrop under a partly cloudy sky.

Condo in Asciano

4.96 out of 5 average rating, 352 reviews

Romantic Yellow apartment in Crete Senesi

Apartment consisting of a comfortable double bedroom (it is possible to make 2 single beds on request), an equipped kitchen, a living room, and a bathroom. TV, BBQ, (if needed, we have a washing machine available from 9 a.m. to 8 p.m., which is in our laundry room). A car is recommended as we are in the countryside, so you can be self-sufficient and visit the magnificent Tuscan countryside as well. Free parking and wifi. I look forward to showing you the real Tuscany!

Top guest favorite

A wooden table is set for dinner outdoors, featuring bowls of pasta, fresh salads, and a bottle of wine. Two glasses of white wine are placed on the table beside fork and knife settings. The cobblestone pathway is softly illuminated by warm ambient light, suggesting a serene evening atmosphere.

Apartment in Montemassi

4.97 out of 5 average rating, 103 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

Guest favorite

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

Apartment in Castelnuovo Berardenga

4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Guest favorite

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

4.93 out of 5 average rating, 118 reviews

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.

Guest favorite

A balcony is adorned with blooming flowers and greenery, offering a scenic view of the rolling hills and vineyards. Small outdoor furniture is positioned for relaxation, while the sky features scattered clouds, enhancing the tranquil atmosphere of the surrounding landscape.

Condo in Castelnuovo dell’Abate

4.91 out of 5 average rating, 288 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Guest favorite

A spacious green garden is visible, dotted with trees offering natural shade. A wooden dining table with chairs is positioned under the trees, providing an inviting setting for outdoor meals. The rustic brick building stands in the background, complementing the serene surroundings.

Farm stay in Simignano

4.89 out of 5 average rating, 197 reviews

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!

Top guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 398 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

Top guest favorite

Farm stay in Pisa

4.99 out of 5 average rating, 298 reviews

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.

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Other great vacation rentals in Sasso Pisano

Guest favorite

An indoor spa area features a private pool with bubbling water, surrounded by elegant stone walls. Soft blue lighting enhances the tranquil ambiance, while a large glass door offers a view of the outdoor space. A shower is positioned adjacent to the pool.

Home in Massa Marittima

5 out of 5 average rating, 14 reviews

Loft SPA

GretaRating, 5 stars4 days ago

Great place clean home unique stay calm and cozy

Top guest favorite

Home in Chiusdino

5 out of 5 average rating, 27 reviews

Il Camino: cosy & artfully inspired country house

MildredRating, 5 stars1 month ago

Thomas was so sweet and helpful. He was an absolute gentleman and wonderful host. The views were amazing. Very homey and decorated in the Tuscany style. Close to town but perfect for a quiet escape in the Tuscan countryside.

Guest favorite

An outdoor dining area is set up with a long table adorned with tableware, surrounded by wooden chairs. Tall cypress trees rise in the background, with soft twilight hues in the sky, hinting at a peaceful evening atmosphere.

Farm stay in Suvereto

4.92 out of 5 average rating, 25 reviews

operaviva - organic farmhouse in Maremma_Francesca

AxelRating, 5 stars1 day ago

Operativa is a small dream in beautiful Tuscany. By car in a maximum of half an hour you can reach various great beaches and visit small villages. The highlight of the accommodation is not even the landscape or the house, it is Marina! She was there to help us and booked tables at the restaurants, recommended places and locations and provided us with everything we needed. It was wonderful! I appreciate it. Thanks

Top guest favorite

A dedicated workspace is provided with a television mounted on the wall above a light wood desk. A green chair with a heart-shaped cutout is positioned at the desk, accompanied by various storage drawers and decorative items on shelves, creating a functional yet charming environment.

Private room in Massa Marittima

4.93 out of 5 average rating, 253 reviews

Room in Massa Marittima

filippoRating, 5 stars2 weeks ago

Highly recommended, cordial availability from the owners. Clean and tidy, quiet place.

A narrow pathway is lined with stone buildings and greenery, leading to an awe-inspiring view of rolling hills. Potted plants add color to the scene, while trees frame the walkway, hinting at the tranquil and picturesque surroundings.

Apartment in Castelnuovo di Val di Cecina

5 out of 5 average rating, 3 reviews

Il Nido di Ninne

KrzysztofRating, 5 stars1 month ago

I felt like in second home!

Top guest favorite

Apartment in San Gimignano

4.98 out of 5 average rating, 42 reviews

Herons Superior Apartment - Splendid view!

MicahRating, 5 stars2 weeks ago

Highly recommend anyone new to Italy to try San gimigano first. Staying here allowed us flexibility to explore other cities and had plenty of great spots in walking distance. Lorenzo provided fantastic recommendations and assisted with everything we asked for.

Top guest favorite

A stylish seating area features a round table accompanied by cylindrical stools, complemented by delicate vases showcasing dried flowers. Natural light enters through an open door, illuminating a small outdoor space with a bistro table and chairs, surrounded by a vibrant garden.

Casa particular in Florence

5 out of 5 average rating, 9 reviews

Apartment by a Renowned Designer

MaxRating, 5 stars1 week ago

I have nothing but incredible things to say about our stay at Eugenio’s place! It was so easy to find and it was great meeting Eugenio in person prior to check in and learning more about the area. The apartment was pristine and beautifully decorated, and the bed was so comfy which helped a ton with any potential jet lag. Quietly tucked away from the touristy areas of Florence but close enough to walk to all the action. Overall one of the best stays I’ve had using Airbnb!

Guest favorite

A hot air balloon drifts peacefully above a misty landscape, revealing layers of rolling hills and dense greenery. The soft hues of the morning sky blend seamlessly with the fog, creating a serene atmosphere. The silhouette of trees can be seen in the foreground.

Cottage in San Gimignano

4.94 out of 5 average rating, 272 reviews

Small renovated barn

TheoRating, 5 stars3 weeks ago

Absolutely recommend the accommodation and the location is fantastic, even if San Gimignano has many day tourists, the hustle and bustle goes by and yet you are only 3 minutes walk from the city gate. We enjoyed the stay very much and were able to leave the world behind us on this beautiful property. We enjoyed the city in the evening and did activities in the region during the day. We stayed at the place for 5 days and it was great. Conclusion: 100 percent recommended!

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Vacation rentals in Sasso Pisano

Top-rated vacation rentals in Sasso Pisano

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Other great vacation rentals in Sasso Pisano

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