Apartment holiday rentals in Castiglione della Pescaia

A view of the historic Pitigliano skyline features ancient stone buildings nestled against a dramatic cliffside. The prominent clock tower stands tall amidst a tapestry of rooftops, while the circled monolocale indicates its location within this picturesque landscape.

4.95 out of 5 average rating, 180 reviews

La Sorpresa Studio Apartment

Studio apartment in the heart of Pitigliano, a short walk from the Synagogue and the Etruscan Vie Cave. The apartment offers a beautiful view of the Meleta valley. It is carefully furnished with antique and valuable furniture and objects. It offers a smart working station. The house is located in the center of Pitigliano, just a few meters from the Synagogue and the “Etruscan hollow streets”. It offers an amazing view of the Meleta Valley. The apartment is furnished with care and with fine antiques.

4.92 out of 5 average rating, 194 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.

A spacious open-plan living area is displayed, featuring a modern kitchen with sleek cabinetry and an island. The dining table is set for meals, and a comfortable sofa is positioned in the background. Natural light fills the room, highlighting the wooden beams overhead.

4.89 out of 5 average rating, 116 reviews

Bruna's House

LA CASA DI BRUNA A finely renovated apartment, furnished with love and attention to detail, is located inside a historic building The entrance opens onto a living room with a very comfortable sofa connected to a large and comfortable kitchen From the living room, we access the terrace overlooking the fortress where you can enjoy wonderful sunsets On the same floor, there is a bathroom and a bright double bedroom Upstairs is the second bathroom and another comfortable bedroom

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.

4.94 out of 5 average rating, 179 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.

An open kitchen and dining area feature a wooden table surrounded by four chairs. Natural light enters through a window, illuminating the space. A kitchenette with wooden cabinets is present, and a staircase leads to an upper level. Decorative artwork is displayed on the walls.

4.88 out of 5 average rating, 82 reviews

Apartment da Iris

Apartment on the doorstep of the centre and seaside resorts of Castiglione della Pescaia. A 15-minute walk from the first beach, a 5-minute bike ride! A few meters from the major supermarkets and the small shopping center with fishmonger, pharmacy, laundry and basic necessities. It also offers a green area (condominium) and views of the hills. Everything is easily accessible on foot, by bike ( FREE on request ) and by car, with free parking on site.

A tranquil landscape is captured at sunrise, with the sun rising above a misty valley. Soft golden light filters through layered clouds, illuminating the distant hills. The scene conveys a sense of peace and natural beauty, set against a backdrop of serene fog.

4.93 out of 5 average rating, 127 reviews

Apartment with panoramic garden in San Gimignano

Located close to the walls of San Gimignano, the apartment is surrounded by nature with every desirable comfort and an amazing panoramic view. The apartment consists of 1 kitchen, 1 double bedroom, 1 living-dining room, panoramic garden and reserved parking next to the house. - 2 minutes' walk from the city center, surrounded by nature - panoramic view - every desirable comfort -private parking - 1 kitchen, 1 bedroom, 1 bathroom, 2 living rooms

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.

4.95 out of 5 average rating, 132 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.

4.92 out of 5 average rating, 119 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.

An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.

4.94 out of 5 average rating, 280 reviews

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

A light-filled living area features a comfortable sofa adorned with decorative cushions. Adjacent, glass doors open to a terrace illuminated by natural light, where a small table and chairs invite outdoor dining. Wall art adds a subtle touch of design to the space.

4.96 out of 5 average rating, 26 reviews

Brand new apartment “Summer Wind”

Brand new apartment located in a cool and strategic area, where you can enjoy a relaxing vacation with every comfort. Looking out from the terrace you can admire the Diaccia Botrona Nature Reserve and the sea in the background. Beaches and downtown are easily reached on foot or by bike.

An outdoor terrace offers seating for four, featuring a table and chairs. The view captures the skyline illuminated against a twilight backdrop, showcasing notable landmarks such as the Torre del Mangia and the Duomo in the distance.

4.89 out of 5 average rating, 184 reviews

Terrace with a view of Siena

A fianco della Basilica di San Domenico, a pochissimi passi dal Duomo e da Piazza del Campo, in questo splendido ed elegante attico potrete godere della splendida vista e della comodità di raggiungere a piedi in pochi minuti tutti i maggiori punti di interesse della città.

4.76 out of 5 average rating, 78 reviews

Prile Apartment, sea view apartment

Prile Apartment is a white apartment with sea view that overlooks the old town of Castiglione della Pescaia and its port below. The 3-bedroom apartment is 50 meters from the sea, with free and organized beaches.

Popular amenities for Castiglione della Pescaia apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.94 out of 5 average rating, 67 reviews

The terrace of Rosi, houses in the villagge

A dining space is highlighted by a table adorned with a patterned tablecloth, offering a view of the sea and distant coastline through large glass doors. A retractable awning provides shade, while light filters softly into the interior.

4.91 out of 5 average rating, 23 reviews

Apartment with amazing views

An outdoor dining area is set on a terrace with a sea view, featuring a wooden table surrounded by metallic chairs. Soft lighting from candles and lanterns creates a warm ambiance. The horizon is illuminated by the fading light of dusk, while palm trees and moored boats are visible in the background.

4.95 out of 5 average rating, 20 reviews

La Torre-Luxury attic - BEACH FRONT - Tuscany

A well-lit kitchen area showcases modern cabinetry and appliances, including a stove and oven. A dining table with four chairs is positioned nearby, set with plates and drinks. A beige sofa with blue accent pillows adds comfort to the open living space.

4.83 out of 5 average rating, 99 reviews

Apartment on Corso di Castiglione 2

A modern kitchen is equipped with sleek cabinetry and contemporary appliances. A dining table is surrounded by six yellow chairs, complemented by a patterned rug beneath. Natural light is provided through large windows, enhancing the spacious feel of the room.

4.88 out of 5 average rating, 17 reviews

Casa Nina, a short walk from the sea.

5 out of 5 average rating, 5 reviews

Podere Lagoprile – Apartment "Montepescali"

4.79 out of 5 average rating, 29 reviews

Casa Azzura on the sea near the seabeach

An aerial view of a rustic stone farmhouse is presented, surrounded by lush greenery and rolling hills. The expansive grounds feature manicured gardens and olive trees, with paths leading to various outdoor seating areas. The horizon stretches to reveal distant hills and the coastline.

4.77 out of 5 average rating, 13 reviews

Santa Agata "Terrazza", 6-8 people 9 km to the sea

Private apartment rentals

The villa is surrounded by a lush green lawn, showcasing a two-story structure with a tiled roof. Large windows provide ample natural light, highlighting the spacious outdoor areas. A terrace extends outward, offering an inviting view of the tranquil countryside.

4.89 out of 5 average rating, 18 reviews

Just a Short Walk from the Sea - Villa San Michele

5 out of 5 average rating, 15 reviews

Aurora House - breathtaking sea view and parking

5 out of 5 average rating, 17 reviews

Vicolo Porte 21/23, Massa Marittima, Jacuzzi

A cozy living room features two reclined leather chairs and a wooden table, complemented by a decorative rug. A rustic fireplace is positioned against a wall, and framed artworks adorn the space. Natural light streams through two wooden windows, enhancing the warm ambiance.

5 out of 5 average rating, 126 reviews

Villa Mocarello "IL LECCIO"

The building features a two-story design with a textured brick facade and blue shutters. A small garden area is visible, adorned with potted plants and a decorative table and chairs, offering a welcoming outdoor space. Round windows are positioned above the balconies.

4.67 out of 5 average rating, 6 reviews

beautiful house with a garden in the center

A small terrace features a table with two purple cups, set against a backdrop of blooming flowers and lush greenery. The expansive view overlooks the countryside extending to the sea, with a clear sky enhancing the serene landscape.

4.77 out of 5 average rating, 26 reviews

Two-room apartment with a view in the historic center

A functional bathroom is presented, featuring a stone accent wall and tiled floors. A wooden vanity with a sink is complemented by a mirror above. A bidet and toilet are positioned adjacent, while a standing shower can be seen in the corner.

4.89 out of 5 average rating, 28 reviews

Tempomare

The kitchen area features a mix of wooden cabinetry and modern appliances, including a stove and refrigerator. A dining table with four chairs is centrally placed, complemented by a decorative tablecloth. Natural light enters through a large window dressed with patterned curtains.

5 out of 5 average rating, 4 reviews

Spacious and comfortable three-room apartment

Apartment rentals with a hot tub

An outdoor jacuzzi is situated within a landscaped garden, surrounded by lush greenery. Two lounge chairs are placed nearby on the well-maintained grass, offering a relaxing space to enjoy the countryside views. A large umbrella provides shade over the jacuzzi.

4.88 out of 5 average rating, 72 reviews

Three-room apartment with courtyard for 4 people 5 min. from the center Yes

A stone pathway leads to a rustic building adorned with vibrant yellow flowers, framed by wooden shutters. Surrounding greenery adds a lush atmosphere, while a small stone feature is visible to the side, enhancing the tranquil garden setting.

4.88 out of 5 average rating, 76 reviews

Romantic farmhouse, garden apartment with panorama

A spacious outdoor area features a framed view of rolling green hills in the distance. A swimming pool is visible, surrounded by grass, with a sunshade above a table and chairs. The peaceful landscape showcases the natural beauty of the Tuscan countryside.

5 out of 5 average rating, 43 reviews

Beautiful Sunset Apartment

A cozy wooden veranda features a hot tub surrounded by soft lighting. Two lounge chairs are present, along with a small table and decorative plants. Wooden steps lead to the hot tub, creating a serene space to relax and enjoy the peaceful surroundings.

4.9 out of 5 average rating, 50 reviews

Lucrezia's Secret ~ Le Fraine and Olives Glamping

The living area features a stylish design with a dark gray sofa and two deep red armchairs. A round glass table sits on a marble floor, enhanced by natural light from the two windows with light curtains. A decorative mirror and elegant light fixtures adorn the walls.

4.98 out of 5 average rating, 106 reviews

Domus Nannini - L'Arco di Matteotti Spa

The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.

4.98 out of 5 average rating, 108 reviews

Luxury frescoed apartment in the historical center

The kitchen area features rustic wooden ceiling beams and terracotta floor tiles. A dining table with chairs is set for meals, while modern appliances, including an oven and a refrigerator, are visible in the background. Natural light streams through the window, enhancing the inviting space.

5 out of 5 average rating, 19 reviews

Tuscan Farmhouse with Pool & Panoramic View

An outdoor dining area is set beneath a pergola adorned with grapevines, offering a scenic view of the surrounding hills and valleys. A table is arranged with dinnerware, surrounded by metal chairs, creating an inviting space for meals while enjoying the landscape.