Apartment holiday rentals in Castiglione della Pescaia

An aerial view captures the agriturismo surrounded by lush green fields and a neatly arranged row of tall cypress trees. The inviting pool reflects the serene landscape, and the winding dirt road leads towards the property, nestled amid the picturesque Crete Senesi.

4.97 out of 5 average rating, 162 reviews

Loggia 1 in farmhouse with shared pool

Apartment for 2 people in the Santa Lucia farmhouse (farmhouse DIVIDED IN 7 APARTMENTS) in the Crete Senesi, 10 km from Siena. Located on the second floor with a private table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room FOR A FEE according to consumption.

4.91 out of 5 average rating, 183 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 doorway opens to a warm, inviting space featuring a cozy bedroom with a spacious bed dressed in light linens. The room includes wooden ceiling beams and a small table with chairs in the background, complemented by natural light filtering through the window.

4.94 out of 5 average rating, 196 reviews

Casa Fusari - Apartment next to the Duomo

! Please check the house rules before booking ! Completely renovated apartment with fine finishes located in a building of 1746, one minute walk from Piazza del Duomo and two minutes from Piazza del Campo. Strategic position in the heart of the historic center, very convenient raised ground floor from which you can see part of the Duomo, next to the apartment you will find two great restaurants. A few steps away you will also find the escalator to the parking lot Santa Caterina.

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.

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.

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.

4.93 out of 5 average rating, 167 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.

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.

4.93 out of 5 average rating, 107 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.

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.

4.96 out of 5 average rating, 100 reviews

Casetta Venere relaxing Tuscan 3 km from the sea

Venus cottage: 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 animals. The house offers curated spaces, a beautiful private garden, and an intimate and welcoming atmosphere. We are waiting for you for a slow, authentic and beautiful stay in the middle of nature.

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.

4.95 out of 5 average rating, 268 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 scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.

4.89 out of 5 average rating, 381 reviews

Panoramic Country Suite Montalcino

Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored surrounded by beautiful garden-park, 2 km from Montalcino with amazing views on Tuscan hills. We offer a beautifully furnished apartment with independent entrance and all facilities.

A panoramic view of a coastal area showcases sandy beaches, clear blue waters, and a marina filled with boats. The town features historic buildings with red rooftops nestled against green hills in the background, extending toward a mountainous landscape.

4.78 out of 5 average rating, 171 reviews

Apartment in Castiglione della Pescaia

First floor apartment located along the main street, thirty meters from the beach and a short walk from the historic center. It consists of a kitchen living room with sofa bed, another bedroom with bunk bed, bathroom.

The expansive view of rolling hills is captured under a dynamic sky filled with scattered clouds. The lush greenery contrasts with the golden fields, creating a serene landscape. In the foreground, the garden area is surrounded by rustic pathways and trees, enhancing the natural setting.

4.89 out of 5 average rating, 340 reviews

Le Splandole Farm – Crete Senesi

Facing the beautiful XIX Century Farm of Splandole, farm of historic importance and symbol of the Crete Senesi area, we have comfortable and graciously appointed apartment with a view of the valley below.

A well-lit space features a spacious bed with a tufted headboard, complemented by soft bedding. An elegant sitting area includes a wooden side table and a modern lamp, with natural light streaming in through a large window adorned with sheer curtains.

4.99 out of 5 average rating, 405 reviews

Diacceto19 Siena Apartments Int.1

One of the two class apartment ( Int.1-Int.2 ) in the heart of Siena, furnished with great care, and equipped with every comfort, with one of the most beautiful and photographed view of the city.

Popular amenities for Castiglione della Pescaia apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

The spacious living area features a modern, angled sofa in dark grey, accompanied by a dining table with black chairs. Natural light enters through large windows, covered by sheer curtains. A kitchen is visible, equipped with white cabinetry and appliances, and a wall-mounted TV is present.

4.94 out of 5 average rating, 17 reviews

Large three-room apartment in the center of Castiglione della Pescaia

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.

4.85 out of 5 average rating, 13 reviews

Just a Short Walk from the Sea - Villa San Michele

A shaded gazebo is featured under a wooden roof, surrounded by an assortment of terracotta pots filled with vibrant greenery and citrus fruits. A table with chairs is visible, creating a peaceful outdoor dining space, all set against a clear blue sky.

4.86 out of 5 average rating, 43 reviews

house in a quiet farmhouse 3 km from the sea

An expansive terrace offers a dining table surrounded by chairs, under a large awning. Decorative elements, including potted plants, are visible. A panoramic view of the sea and coastline is presented in the background, enhancing the outdoor experience.

4.95 out of 5 average rating, 77 reviews

Sea view penthouse with 130 sqm terrace

A bright sitting area is showcased, featuring a comfortable sofa and a wooden table set for two. Natural light filters through a window adorned with sheer curtains, enhancing the room's warmth. Decorative wall plates add a rustic touch to the inviting space.

5 out of 5 average rating, 20 reviews

Apartment in a wine estate

A warm evening scene captures a heated whirlpool with soft purple lighting. Olive trees frame the area, and a rustic villa is visible in the background, surrounded by tall cypress trees against a gently fading sky.

4.96 out of 5 average rating, 70 reviews

San Giovanni in Poggio, Crepuscolo app. 60 sqm

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.

4.82 out of 5 average rating, 97 reviews

Apartment on Corso di Castiglione 2

A landscaped garden features a dining table with a checkered tablecloth, surrounded by chairs. Sun loungers provide a comfortable spot for relaxation, with the sea visible in the background. An umbrella offers shade over the dining area, enhancing outdoor enjoyment.

4.77 out of 5 average rating, 48 reviews

BELLAVISTA Charming view on the island of Elba

Private apartment rentals

A sleeping area is presented with a spacious bed adorned with neutral linens and a yellow plaid throw. Natural light flows in through double doors leading to a small balcony. A mirror above the bed reflects the room's soft tones, while a wooden bedside lamp adds a cozy touch.

4.75 out of 5 average rating, 20 reviews

Angeli Studio Apartment

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.

4.95 out of 5 average rating, 21 reviews

Brand new apartment “Summer Wind”

A light-filled living space features a modular entertainment unit with a television. Shelves above display decorative items. A dining area is visible in the background, with a table and chairs. An arched entrance leads to an adjoining room, enhancing the open layout.

4.96 out of 5 average rating, 25 reviews

Casa Lorena

A panoramic view features ancient castle ruins nestled on a hillside, overlooking the serene blue sea. Distant mountains rise above the horizon, with rugged cliffs contrasting against the vibrant waters. A marina with boats is visible along the shoreline, surrounded by lush greenery.

4.74 out of 5 average rating, 35 reviews

Apartment near the sea air-conditioned 6+1 p.l.

A bright living area features a gray sofa and a round dining table surrounded by chairs. Double doors open to outdoor space, with natural light illuminating the room. A potted plant adds a touch of greenery, complementing the neutral interior elements.

5 out of 5 average rating, 37 reviews

Villetta Serendipity - The Nido Apartment : 40mq

The illuminated swimming pool features a serene blue glow as evening falls, creating a calming ambiance against the backdrop of a sunset with soft hues. The surrounding landscape remains partially visible, silhouetted by the fading light.

4.82 out of 5 average rating, 17 reviews

Maremma Tuscany in Scarlino - Elegant apartment

A spacious terrace is shown, featuring comfortable seating arrangements, including lounge chairs and a small dining table. The area is partially shaded by awnings, with a view of the surrounding landscape. A table is set with fresh strawberries and beverages, inviting relaxation.

5 out of 5 average rating, 50 reviews

Terrace on the walls of Siena

A dining table is set with vibrant green and blue glassware, along with neatly arranged plates. A cork placemat with the phrase 'Served with love' is centered. A large vase filled with colorful flowers adds a decorative touch. A view of historical buildings is visible through the window.

5 out of 5 average rating, 28 reviews

The Historical View

Apartment rentals with a hot tub

A tranquil pool area is surrounded by lush greenery and large rock formations. The building, featuring warm yellow tones, is partially visible behind a tall palm tree. The clear blue water reflects the sky, creating a calm and inviting scene.

5 out of 5 average rating, 5 reviews

Three-room apartment + swimming pool MaremmaToscana

An inviting entrance features wooden doors framed by rustic stone walls. A small wooden table with two chairs is positioned beside it, adorned with potted flowers. A traditional ceramic jar adds character, enhancing the welcoming atmosphere.

4.94 out of 5 average rating, 36 reviews

SerenaHouse

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, 73 reviews

Romantic farmhouse, garden apartment with panorama

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

4.94 out of 5 average rating, 125 reviews

Domus Nannini - L'Angolo di Paradiso Spa (Spa)

The spacious living area features a dining table set for four, surrounded by wooden chairs. A cozy seating arrangement of two light-colored couches is visible, with decorative pillows. The elegant archway above connects the living space to the mezzanine, enhancing the open layout.

4.91 out of 5 average rating, 138 reviews

Penthouse in Siena near Piazza del Campo and Palio

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, 102 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.