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Holiday houses in Valpiana

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Top-rated holiday rentals in Valpiana

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Top Guest favourite
Condo in Valpiana
5 out of 5 average rating, 45 reviews

Infinity pool overlooking the woods, sea just minutes away

Experience authentic Tuscany between the sea and the countryside! 10 km from Follonica and Massa Marittima, our Casetta Valmora agritourism offers apartments with private patio, Wi-Fi, air conditioning and breakfast on request, surrounded by olive groves and woods, ideal for couples and families. From May 2026, the new panoramic infinity pool overlooking the forest will be available for moments of pure relaxation. In the surrounding area, discover medieval villages, Cala Violina, bike routes, golf (two courses 15 km away), and local products.

Top Guest favourite
Apartment in Caminino
4.91 out of 5 average rating, 184 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.

Guest favourite
A bright living area is seen, featuring a cozy sofa and a media unit with woven baskets. Steps lead to a charming stone wall, enhancing the space's historic character. Soft lighting creates a subtle ambiance, contributing to the warm atmosphere of the loft.
Loft in Massa Marittima
4.87 out of 5 average rating, 201 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!

Guest favourite
Home in Massa Marittima
5 out of 5 average rating, 16 reviews

Like your Home, Low cost for Independent Travelers

Questo alloggio minimal è la soluzione per chi vuole godersi la Maremma toscana a un prezzo Low-cost. Per poter mantenere tariffe super basse, non includiamo il servizio di biancheria e pulizie: “gli ospiti sono invitati a portare le proprie lenzuola e a lasciare l’alloggio pulito nel rispetto di chi arriverà dopo.” Un modo carino per offrire a tutti la possibilità di visitare la Maremma. Ideale per viaggiatori indipendenti, amanti della natura meravigliosa che la Maremma offre. Grazie🙏

Guest favourite
The living and dining area features exposed stone walls and wooden beams, enhancing the rustic charm. A spacious sofa sits adjacent to a wooden dining table, surrounded by four chairs. Natural light filters in through a window, illuminating the tiled flooring.
Holiday home in Massa Marittima
4.93 out of 5 average rating, 107 reviews

Design apartment in Massa Marittima, "slow city"

A great 65 m2 - 2 bedroom Apartment, entirely renovated in freestone and exposed beams, with design touch. In the upper, medieval part of Massa Marittima, Siena in miniature, with a superb Romanesque cathedral. Central but quiet area. Many restaurants and oeno-gastronomic specialties. Magnificent freshwater lake, Lago dell'Accesa, 10 minutes by car. Sea at 20 minutes. Siena at 1:15 a.m. Massa, "Citta slow", offers many other activities: museums, wine cellars, horse riding, Bike Park, MTB

Guest favourite
An inviting interior space showcases a large arched window allowing natural light to flood in. Rustic brick walls complement the wooden beams overhead. A dining table is paired with clear chairs, while a cozy seating area is designated by a small table. Decorative items are placed on the table.
Barn in Gavorrano
5 out of 5 average rating, 11 reviews

Charming former agritourism barn in Maremma, Tuscany

You will sleep in a former barn in the heart of the Maremma, you will wake up to the chirping of birds, you will open the windows of the veranda and you will be able to admire the olive grove, the real protagonist of the property. A private road for the exclusive use of guests of this accommodation allows access. Relaxation, silence, a historic and medieval area, villages with an ancient flavor, the beaches of Follonica "Blue Flag" also in 2024, the spas of Petriolo and Sassetta nearby.

Top Guest favourite
Home in Massa Marittima
5 out of 5 average rating, 41 reviews

Design loft with private SPA in Tuscany

Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

Top Guest favourite
A modern kitchen area features grey cabinetry, a built-in oven, and ample counter space. A white dining table is accompanied by four chairs with striped patterns. A large arched window allows natural light to illuminate the space, while potted plants add a touch of greenery.
Condo in Massa Marittima
4.99 out of 5 average rating, 176 reviews

Casa Vecchio Forno

The apartment is on the ground floor, in the historic center of Massa Marittima, just 100 meters from the Cathedral square. It is easily accessible from all the parking lots in the historic center and within walking distance you can find: cafes, restaurants, banks, grocery stores, a pastry shop and a pharmacy. The recently renovated 68m house has a separate entrance and consists of: a kitchen with kitchenette, a double bedroom, a living room with sofa bed and a bathroom.

Top Guest favourite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Apartment in Montemassi
4.97 out of 5 average rating, 116 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.

Top Guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 447 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Guest favourite
A wooden deck offers a serene view of rolling green hills extending into the distance. Two sun loungers are placed on the deck, inviting relaxation amid the natural surroundings. Trees frame the scene, creating a peaceful atmosphere, ideal for enjoying the landscape.
Cottage in Vetulonia
4.96 out of 5 average rating, 126 reviews

La Dolce Vita Romantic Sea-view Cottage. Tuscany

Welcome to Il Baciarino, a rustic agriturismo in the green hills of Maremma, Tuscany’s wild and less-traveled coastal region. Our property offers unique, handcrafted cottages with sea views, privacy, and direct contact with nature. Set within 19 acres of hillside wilderness in the charming Etruscan town of Vetulonia, Il Baciarino is the perfect place to escape the city, slow down, and enjoy unspoiled landscapes, fresh seafood, and good wine.

Guest favourite
A ceramic vase filled with vibrant yellow flowers is prominently displayed on a table. Soft light from a lamp illuminates the rustic stone wall in the background, enhancing the warm ambiance of the space. Two mugs sit beside the vase, adding a touch of comfort.
Apartment in Scarlino
4.92 out of 5 average rating, 112 reviews

Leo's porch

Stay in this unique place and spend unforgettable evenings gazing at the horizon. Breathe clean air and enjoy the relaxation offered by the village of Scarlino. Ideal for couples or small families who want functional and comfortable accommodation. FROM MAY 1 TO AUGUST 31, a tourist tax of €1.00 per night/person is applied for each day of stay. Bed linen and towels are NOT INCLUDED in the final price of the accommodation.

Popular amenities for Valpiana holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Grosseto
  5. Valpiana