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Vacation rentals in Serre di Rapolano

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Top-rated vacation rentals in Serre di Rapolano

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Asciano
4.96 out of 5 average rating, 117 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Guest favorite
Vacation home in Petrignano del Lago
4.98 out of 5 average rating, 123 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

Situata nelle colline a cavallo tra Montepulciano,Castiglione del Lago e Cortona, Fontarcella si presenta come una villetta indipendente immersa nel verde, che offre jacuzzi e parcheggio privati; Scoprirete un luogo senza tempo, per condividere momenti preziosi. La struttura, arredata in stile mediterraneo, dispone di climatizzazione e wi-fi gratuita. Il giardino, interamente recintato, offre vari comfort. A pochi minuti dalle autostrade, Fontarcella è facilmente raggiungibile dai viaggiatori.

Top guest favorite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 207 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favorite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower in San Quirico d'Orcia
5 out of 5 average rating, 103 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Guest favorite
The landscape features rolling green hills under a clear sky, with a rustic building nestled among the greenery. A gravel road winds through the scene, leading towards the structure, which is surrounded by trees and distant hills.
Condo in Asciano
5 out of 5 average rating, 9 reviews

Casa Biancospino Crete Senesi | Podere Fossaccio

Casa Biancospino is an apartment with a private courtyard inside the Podere Fossaccio. Suitable for short and medium/long stays and is located in the heart of the Crete Senesi. The location is strategic for visiting the most interesting places in Tuscany. The green areas and a magnificent infinity pool overlooking the surrounding hills will be available to you and the other guests of the Podere. A warm and welcoming atmosphere where you can breathe the authentic Tuscan atmosphere.

Top guest favorite
Two individuals are seated in comfortable chairs on a wooden deck, enjoying a serene moment as the sun sets. A bottle of wine and two glasses are placed on a small table nearby, surrounded by lush greenery and vibrant flowers.
Home in Greve in Chianti
4.99 out of 5 average rating, 70 reviews

Relaxation and comfort in the hills of Florence

Apartment in a typical Tuscan stone farmhouse: measuring 160 square meters, it is finished with typical Tuscan materials, pietra serena and terracotta. It consists of a large living room at the entrance, dining room, kitchen, 2 bathrooms, storage room, 3 bedrooms, and a study area. Arranged in an east-west position thanks to a large terrace, a patio and a large private garden, it allows you to enjoy the sunrise for your breakfast and the sunset for a pleasant aperitif.

Top guest favorite
An outdoor dining area features a wooden table accompanied by black chairs, situated beneath a pergola. Lush greenery surrounds the space, offering views of rolling hills and a clear sky, creating a serene setting for meals and relaxation.
Home in Serre di Rapolano
5 out of 5 average rating, 18 reviews

Casina La Fonte - Patio with panoramic view -

Casina La Fonte was my home that, later, I decided to make a private place to let the beauty of our territory known to all those who love to travel and discover other cultures and relax in the nature It is the ideal base for trips to the different sites of the Crete Senesi, Siena, Val d'Orcia and Val di Chiana; Chiana, all within 30 km. Likewise it is a perfect place to relax on the spot, enjoy the rural surroundings, the hiils, the views and the spa at 3 km away

Top guest favorite
The countryside property is nestled among lush greenery, featuring rustic architecture and terracotta roofs. Surrounded by rolling hills and trees, the natural landscape creates a peaceful setting. A gravel path leads to the house, enhancing the connection to the serene outdoor environment.
Farm stay in Sovicille
4.93 out of 5 average rating, 163 reviews

House at Gianni - Olmo

Hi, we're Cristina & Carmelo! We invite you to discover the rustic charm and authenticity of "Casa al Gianni," our farmhouse in the heart of the Tuscan countryside, 20 minutes from Siena. After a recent renovation, our accommodations are ready to welcome you with all modern comforts without losing the essence of tradition. In the Olmo Apartment, brand new beds await you, a promise of peaceful and regenerating sleep, a new kitchen and a new bathroom.

Superhost
A fenced pool area is surrounded by lush greenery, featuring a clear blue water pool. Several lounge chairs are set up around the pool, complemented by colorful umbrellas providing shade. A wooden structure offers additional seating options near the poolside.
Farm stay in Serre di Rapolano
4.78 out of 5 average rating, 9 reviews

Il Pino Apartment

The holiday apartment "Agriturismo Ischieto - Il Pino" is located in Serre di Rapolano and offers a wonderful setting for a relaxing getaway. The 50 m² property consists of a living room with a sofa bed for 2 people, a well-equipped kitchen, 1 bedroom, and 2 bathrooms, accommodating up to 2 people. Amenities include high-speed Wi-Fi (also suitable for video calls), TV, and air conditioning. The property also offers a ping pong table.

Guest favorite
A covered dining area features a table set for breakfast, with plates, cups, and food arranged neatly. In the background, olive trees are visible on a gently sloping landscape, providing a serene rural view, while sunlight casts warm tones on the setting.
Home in Scrofiano
4.97 out of 5 average rating, 65 reviews

The House of Olives

Your private oasis in Tuscany: Wake up to the sound of birdsong and the view of the hills from your cottage nestled among olive trees. This elegant accommodation, furnished with Tuscan taste, offers you everything you need: a fully equipped kitchen, a comfortable double bed, a spacious bathroom and free Wi-Fi. Relax in your private garden, perfect for outdoor dining, or explore the wonders of the extraordinary surrounding area!

Superhost
Farm stay in Asciano
5 out of 5 average rating, 5 reviews

AGRITURISMO PODERE SCURCOLI TOWER

It consists, on the ground floor, of a kitchen-living room equipped with a sofa bed and a bathroom. A covered veranda allows you to eat and spend time outside enjoying the wide panorama and beautiful sunsets. On the first floor there is a double bedroom with a small balcony and a bathroom with shower. The house is served by an air conditioning system. Independent entrance. Square meters: 45. Sleeps: 3.

Superhost
Apartment in Pogi
5 out of 5 average rating, 4 reviews

Borgo Iesolana Country Retreat Family Suite Sup.

Charming Family Suite inside the Borgo Iesolana Estate, set in an enchanting, silent and unspoiled landscape and close to the cities of Siena, Arezzo and Florence. Situated on first floor with 2 bedrooms, 2 bathrooms, Living room, pool, parking, Airco, WiFi and TV. Tasty Restaurant in the property for breakfast, light lunch, aperitif and dinner. Breakfast included.

Popular amenities for Serre di Rapolano vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Serre di Rapolano