Vacation rentals in Roccatederighi

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Top-rated vacation rentals in Roccatederighi

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Top guest favorite

The image captures a stone building with a terracotta roof, featuring a tall cypress tree set against a vast landscape. Rolling hills and olive groves extend into the distance under a clear sky, with soft afternoon light illuminating the scene.

Home in Montemassi

4.96 out of 5 average rating, 49 reviews

Capezzuolo 33

At the foot of the castle of Montemassi, nestled in the medieval walls of the village, a 30 sqm studio apartment, carefully renovated, maintaining the materials of the past. The stone walls, terracotta floor, and fireplace create a cozy and romantic atmosphere. In the outdoor pergola, you can organize relaxing breakfasts and suggestive candlelit dinners. The village is located in the enviable position from which to start for historical and naturalistic itineraries and to reach the beaches of the Maremma

Guest favorite

Apartment in Caminino

4.91 out of 5 average rating, 168 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top guest favorite

A serene swimming pool is surrounded by lush greenery and tall cypress trees. Several lounge chairs are placed along the poolside, offering ample space for relaxation. The water's clear blue hue reflects the bright sky, creating a tranquil outdoor setting.

Guesthouse in Macciano

4.96 out of 5 average rating, 164 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

Home in Roccatederighi

5 out of 5 average rating, 17 reviews

Private Villas Privacy and Pool

San Giusto is located in the heart of the Tuscan Maremma. It is an old farmhouse dating back to 1928, completely renovated maintaining the characteristics of the old stone structures. The villa consists of two flats, each about 75 m in size, completely autonomous. San Giusto also offers a large garden equipped with tables, a Jacuzzi and a barbecue with a wood-burning oven. San Giusto offers a large 5m x 10m swimming pool, sunbeds, gazebo and parasols for moments of sunbathing and relaxation.

Top guest favorite

Loft in Roccastrada

5 out of 5 average rating, 35 reviews

"Casa Chiassarello" with pool

Casa Chiassarello is located in a quiet and panoramic position, a short walk from the center of Roccastrada. The house, entirely in stone, is built from an old oil mill. The accommodation is an open space of about 80 square meters where there is a very spacious kitchen, a bathroom, a sleeping area with TV and fireplace. The accommodation overlooks a spacious veranda that can be used as a dining and relaxation area. Available to guests is a garden with a swimming pool for exclusive use.

Top guest favorite

The villa is presented with a stone facade surrounded by well-maintained gardens. Tall cypress trees are located throughout the striking landscape. The building features a red-tiled roof and multiple windows, showcasing the serene countryside under a partly cloudy sky.

Home in Roccastrada

5 out of 5 average rating, 5 reviews

Apartment in the countryside

Welcome to our 18th century villa in Sticciano, nestled between Florence and Rome, in the Tuscan Maremma! The beautiful villa has been trasformed into a wine estate hostelry, offering ten apartments for an unforgettable stay. Expect to see rolling hills, vineyards, and expansive green landscapes. A traditional Tuscan dinner is served twice a week, and our delicious breakfast is available every morning on request. Enjoy the pool or a wine experience visiting our vineyards and cellars!

Top guest favorite

Villa in Roccatederighi

4.97 out of 5 average rating, 34 reviews

Villa Il Diaccio with view of the Tuscan Maremma

Villa in pietra con particolari rifiniture architettoniche immersa in un bosco di castagni. Un grande giardino, in parte pavimentato a pietra, correda la proprietà dal quale si può ammirare un panorama meraviglioso della maremma toscana. Immersi nella natura si nota da una parte il mare con il golfo di Follonica, l'isola d'Elba e la Corsica, dall'altra l'isola del Giglio. E' possibile fare lunghe passeggiate nella natura o raggiungere località balneari o città d'arte.

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.

Superhost

A two-story stone farmhouse is set against a clear blue sky, showcasing a rustic charm. The exterior features a mix of natural stone and terracotta elements, with a small terrace and garden area surrounded by greenery. A pathway leads up to the entrance.

Apartment in Roccatederighi

4.96 out of 5 average rating, 28 reviews

Apartment with pool - max 4 people

Pagiano del Ruggeri is a 4-star bio-agriturismo, located on the green hills of the Maremma. The agriturismo consists of only two apartments, totally independent from the main house. This apartment has been recently innovated and built from the old farm barn, equipped with two bedrooms, terrace, garden and exclusive use of the pool. The apartment overlooks the fantastic hilly panorama of the Maremma and offers a breathtaking view to the sea.

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.

Superhost

A rustic stone house is set against a clear sky, featuring a tiled roof and multiple windows. Lush green grass surrounds the structure, with a stone pathway leading to the entrance. Flowering plants add natural beauty to the foreground.

Home in Gavorrano

5 out of 5 average rating, 3 reviews

Casa Maremma with Jacuzzi

It is the old barn, renovated with taste and style with a pleasant combination of ancient and innovation, to accommodate families and friends up to 6 people. The beautiful covered panoramic terrace, directly in front of the house, is equipped with a large dining table and chairs. An outdoor shower, loungers, and a private hot tub are available for your relaxation. Swimming pool shared with all guests.

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!

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Popular amenities for Roccatederighi vacation rentals

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Pool

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Other great vacation rentals in Roccatederighi

Superhost

Private room in Buonconvento

4.84 out of 5 average rating, 145 reviews

"Cipresso Room" Quarantallina Farmhouse

DenisRating, 5 stars5 days ago

We instantly felt like home at Serena’s place. You have everything you need to relax at the house. The views of the surroundings are breathtaking. Definitely recommend! Thank you for having us!

Guest favorite

A medieval castle ruins are situated on a hilltop, overlooking the surrounding landscape. The sky above transitions from soft purples to light blues at dusk, while distant mountains create a serene backdrop. The natural beauty of the area is complemented by the presence of cypress trees.

Home in Montemassi

4.94 out of 5 average rating, 35 reviews

Magical place, medieval and nature!

MatthewRating, 5 stars8 months ago

This was probably one of the most unique and beautiful Airbnb stays I have ever had. Gabriella has an extremely unique place here, and I suggest you book it if it’s available!

A rocky shoreline is framed by lush green hills, with gentle waves lapping at the stones. A dog stands on the rocks, gazing towards the clear blue water. In the distance, a sandy beach and a few figures are visible enjoying the scenic view.

Apartment in Tatti

5 out of 5 average rating, 4 reviews

Apartment in the Maremma hills Pacha Mama House

AnneRating, 5 stars5 months ago

As we had a good time and at home in Manu and Vlady's apartment, helpful and very kind people. The house is a jewel, not too big, but just right for two people. The stove was very greedy for wood, but you could still warm up the house. The highlight was the illuminated staircase for us: so evocative! Upstairs, a good bed was waiting for us with a great view. What more could you want? We did some nice, long walks around. There are paths to it. The village is very nice and very lively. Everyone greet each other and in a week we met several Tatterini, all smiling and friendly. We can't wait to come back. Thank you very much Manu and Vlady for your warm hospitality.

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

Guest favorite

Home in Montemassi

4.83 out of 5 average rating, 6 reviews

Amazing Tuscany Window

EdoardoRating, 5 stars11 months ago

Really nice house, very well equipped! The village is small and lovely, with two good restaurants. The house is very spacious, beautiful and well-kept outside space, with the possibility to eat and relax (there is also a nice barbecue, with everything you need to light it) Spectacular view from the balcony! Fully stocked kitchen, plenty of sheets and towels. A special mention to the kindness and availability of the host, on our arrival he made us find a bottle of fresh Maremma white wine and snacks for the dog, really a kind gesture. Highly recommended for those who love the Maremma countryside!

Guest favorite

A stone farmhouse is set against a clear blue sky, surrounded by green olive trees and lush gardens. A wooden door is featured at the entrance, complemented by terracotta roof tiles that reflect natural tones. Scenic hills are visible in the distance.

Farm stay in Montalcino

4.95 out of 5 average rating, 58 reviews

Ginepro Apartment Podere Giardino

SophieRating, 5 stars1 week ago

It is a really beautiful and peaceful location and we loved staying in the countryside rather than in town. Our host Daniela was lovely. It is a very spacious house and the outdoor area was great for sitting around at mealtimes and relaxing. Thank you!

A rustic house exterior is depicted, featuring a spacious covered terrace with wooden pillars. Outdoor furniture, including a dining table and loungers, is positioned on the lawn. Surrounding greenery and a clear blue sky create a serene atmosphere.

Home in Sassofortino

5 out of 5 average rating, 3 reviews

Dimora del Re by Interhome

Katharina Und KaiRating, 5 stars9 months ago

Lovingly furnished house, wonderful terrace and nice cats. Great garden and the view all the way to the sea just lovely! We were very happy to be able to use this house! Thanks a lot!

Guest favorite