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Holiday rentals in Filare

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Top-rated holiday rentals in Filare

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Top guest favourite
Apartment 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.

Superhost
Flat in Scarlino
5 out of 5 average rating, 7 reviews

Lotus Flower

The Fior di Loto apartment is a romantic retreat immersed in the quiet on the slopes of the scrub, with stone walls and unique furnishing details. A cozy room, a kitchen, a bathroom, and a small terrace where you can enjoy outdoor meals. An intimate and relaxing atmosphere, perfect for those seeking peace and beauty, with everything you need to feel at home in a timeless place. ACCOMMODATION TAX NOT INCLUDED: from 05/01 to 08/31 €1.00 per person to be paid at check-in. National Identification Code (CIN): IT053024C24SSA7XXU

Guest favourite
An outdoor patio is showcased, featuring a shaded seating area with wooden furniture. The surrounding landscape displays lush greenery and distant hills under a clear blue sky. Stone paving leads to the entrance of the apartment, enhancing the serene setting.
Cottage in Scarlino
5 out of 5 average rating, 11 reviews

Source above

Fonte di Sopra is a spacious 86-square-meter apartment, built on the first floor. Equipped with 1 double bedroom and 1 twin bedroom. In addition to the living room with kitchen, it has a large porch area (18 square meters) and a garden. In these outdoor spaces there are tables and chairs for outdoor dining, and comfortable deckchairs to admire the magnificent starry sky of the Maremma. Fonte di Sopra is one of the apartments in the small ecological village of Poggio la Croce, 3 villas in the Bandite di Scarlino park.

Top guest favourite
Flat 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
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, 38 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 spacious terrace offers stunning views of the surrounding mountains and the charming town below. Potted plants line the edges, while a wooden dining table with matching chairs is positioned for outdoor dining. The soft sunlight enhances the inviting atmosphere of the space.
Flat in Ravi
4.92 out of 5 average rating, 24 reviews

Casa Vacanze Enos & Iside

In the heart of the charming historic center of Ravi is Casa Enos&Iside, perfect for families looking for relaxation and tranquility. This spacious home is ideal for those who want to immerse themselves in the authentic atmosphere of an ancient village, while enjoying all modern comforts. Located in a strategic position, the house allows you to easily discover the wonders of the surrounding area, from medieval villages to green hills, from food and wine routes to pristine beaches

Guest favourite
A narrow stone hallway is seen from a small balcony, showcasing the rustic architecture of the surrounding buildings. An archway is featured overhead, and decorative iron railings frame the view of the cobblestone street below, lined with planters and dappled in sunlight.
Apartment in Caldana
4.94 out of 5 average rating, 32 reviews

La Casina nella Contrada

If you are passionate about Tuscan villages, you will love this charming place. The 'Casina nella Contrada' is located in the heart of Caldana, which is an medieval town in the province of Grosseto. From here, you can enjoy the view of the historical centre. The house is suitable for 2 people, both for short and long stays. It only takes 20/30 minutes to reach beach destinations, such as Follonica, Castiglione della Pescaia, Punta Ala and the beautiful Cala Violina.

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.
Flat 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.

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 charming stone cottage is depicted, featuring a dark roof and a welcoming entrance. Vibrant purple flowers in the foreground provide a splash of color against the gravel pathway, while warm sunlight casts a gentle glow, highlighting the serene surroundings.
Flat in Castiglione della Pescaia
4.96 out of 5 average rating, 104 reviews

Casetta Venere Tuscan relaxation 3 km from the sea

Casetta Venere: Sea, nature and Pet-Friendly. Just 3 km from the crystal clear sea of Castiglione della Pescaia, Casetta Venere is a small Tuscan jewel among olive trees, perfect for couples, families, and travelers with pets. The house offers well-kept spaces, a beautiful private garden and an intimate and welcoming atmosphere. We look forward to welcoming you for a slow, authentic and beautiful stay in the midst of nature.

Top 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.
Flat 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 Filare holiday rentals

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