Apartment holiday rentals in Massa Marittima

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, 167 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.

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, 185 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 modern living area features a dining table set for two, adjacent to a well-equipped kitchen. Floor-to-ceiling windows provide a view of the surrounding hills, while light filters through sheer curtains. A cozy sofa invites relaxation, completing the inviting ambiance.

4.95 out of 5 average rating, 150 reviews

Wi-Fi Fiber Large Apartment in Montepulciano

Strong fiber wi fi/Smart working too.This spacious and modern 140 sq-mt apartment offers a fresh and shining permanence with super fast fiber wi fi. It has 2 large bedrooms, 2 full equipped toilette, 2 balconies-terraces with view, 2 living rooms with tables/desks, 1 fully equipped kitchen, 1 sofabed. Perfect to avoid high density cities and enjoy the beautiful history and countryside of Montepulciano, Tuscany. WI FI Smart Monitor. Free-safe car parking at50-100mt. Super clean and disinfected.

The spacious living area features large windows offering panoramic views of the countryside. A designer sofa and two armchairs provide comfortable seating around a round table. Shelving holds dishes and books, while rustic beams grace the ceiling, enhancing the room's warmth.

4.96 out of 5 average rating, 300 reviews

A view from the gate, Montepulciano.

The house(castoldi apartments site), renovated in 2019, close to the main street and the Square has AC, 2 double rooms (1 or 2 master), 2 bathrooms ensuite with shower and a large kitchen-living room with 4 windows and a small terrace, overlooking the hills The apartment offers a spectacular view somet available in season a nice garden 50 mt away where to have a wine tasting for all the guests of our 4 apartments or grilled meat always with paired wines. Private parking in our garden.

The spacious living area features rustic wooden beams and terracotta tile flooring. A wooden dining table is accompanied by several chairs, while a cozy seating area with a sofa is positioned nearby. A stone fireplace adds a traditional touch, and large windows allow natural light to fill the space.

4.9 out of 5 average rating, 125 reviews

"L'Ovile" Apartment with a view of Val d'Orcia

In the countryside, along the panoramic road that leads from Pienza to Monticchiello, 2 km from Pienza, large studio divided into sleeping area, with double and single bed, living-dining area, kitchenette, bathroom. Veranda for outdoor dining and relaxation. Panoramic view of Val d'Orcia and its villages. A few kilometers from Montepulciano and Montalcino, and the Bagno Vignoni hot springs. From June to September PRIVATE SWIMMING POOL There is NO breakfast service

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, 171 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 independent building is surrounded by lush greenery, featuring blue shutters and a terracotta patio area. Small tables are set for outdoor seating. The expansive garden includes mature trees and various plants, creating a serene outdoor environment.

4.96 out of 5 average rating, 124 reviews

Podere Le Murella "Sunset"

A cozy retreat for two, set among the green Tuscan hills. Enjoy a private patio for outdoor dining, large garden, free Wi-Fi, fully equipped kitchen, coffee machine, washing machine, dryer, barbecue area, and linens included. Private parking. Ideal for a romantic escape or relaxing stay near Pisa, Florence, Volterra, and charming villages. A perfect base to explore nature, art, and local life—all year round.

A welcoming entryway features a mural depicting a serene landscape framed by arches. Built-in shelves display decorative items and books. Natural light illuminates the wood flooring, while a small globe and a vase with dried plants add subtle warmth to the space.

4.98 out of 5 average rating, 110 reviews

Casa Guardiavigna in Chianti, Italy

The Casa Guardiavigna apartment offers the opportunity to enjoy a unique and extraordinary experience, full of emotions and happiness. Located a stone's throw from the small medieval village of San Gusme' and surrounded by beautiful vineyards, woods and flowery meadows. Free indoor parking with an automatic gate.

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.

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.

4.88 out of 5 average rating, 162 reviews

Penthouse with a view of Siena

Next to the Basilica of San Domenico, a few steps from the Duomo and Piazza del Campo, in this splendid and elegant penthouse you can enjoy the splendid view and the convenience of walking to all the major points of interest in the city in just a few minutes.

A serene outdoor scene features a stone building partially obscured by greenery. The sunlight casts a warm glow over the gravel pathway, enhancing the inviting atmosphere. A vibrant flower bush adds a touch of color as the sun sets in the background, illuminating the landscape.

4.99 out of 5 average rating, 145 reviews

Stunning Tuscan apartment in 14 Century Palazzo 2

L'appartamento si trova al secondo piano di un edificio risalente al 1400, il borgo di Castiglioncello del Trinoro risale al 1100, si affaccia sulla val d'orcia con vista a 360 gradi.

Popular amenities for Massa Marittima apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A rustic stone building is set against a clear blue sky, featuring arched windows and a slate roof. The surrounding landscape includes a gravel pathway and green trees, contributing to a serene ambiance.

4.95 out of 5 average rating, 40 reviews

Apartment in Old Farmhouse

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, 71 reviews

San Giovanni in Poggio, Crepuscolo apartment 60 sqm

A spacious bedroom features warm wooden beams above and a large window allowing natural light to fill the space. A comfortable double bed is adorned with neutral-colored linens. An elegant armchair sits beside a small side table, complemented by a decorative rug on the polished wooden floor.

4.91 out of 5 average rating, 23 reviews

Zafferano Rooftop Terrace Tower House

4.81 out of 5 average rating, 16 reviews

A cozy living area features a sofa with decorative cushions and a soft armchair. Exposed star-vaulted ceilings draw attention upward. Natural light enters through a window beside the fireplace, and decorative wall art complements the neutral color palette.

Flat in Volterra

Charming Apartment Near Piazza

A large swimming pool is visible, featuring clear blue water and surrounded by lounge chairs under sun umbrellas. Lush green hills stretch in the background, complementing the serene outdoor space, ideal for relaxation and enjoyment.

4.95 out of 5 average rating, 19 reviews

Tuscany between Florence and Siena with tennis.-

4.92 out of 5 average rating, 51 reviews

Two sunbeds are positioned on a terrace, overlooking the expansive Tuscan countryside. Lush greenery and vibrant yellow flowers are surrounding the area, while a small tree offers partial shade. The landscape features rolling hills and distant farmhouses under a partly cloudy sky.

Flat in Gambassi Terme

Traditional Tuscan apartment with amazing views

4.77 out of 5 average rating, 73 reviews

Prile Apartment, sea view apartment

A light-filled living area features a wooden dining table surrounded by white chairs. Natural textures are introduced with exposed wooden beams overhead and soft-toned, simple furnishings. A balcony door opens to a lush view, with framed artwork displayed on the walls.

4.94 out of 5 average rating, 72 reviews

Panoramic View & Balcony · Charming Apartment ·A/C

Private apartment rentals

4.82 out of 5 average rating, 45 reviews

Casa Bruna – Cipresseta del Chianti

An inviting kitchen area is showcased, featuring exposed brick walls and wooden beams. A dining table is set with blue dishware, accompanied by wooden chairs. A cozy sofa sits nearby, creating a comfortable and functional space for relaxation and dining.

4.86 out of 5 average rating, 14 reviews

Nest in the alley: sea & old town

A well-lit kitchen and living area features high wooden ceilings with exposed beams. Modern appliances, including an oven and dishwasher, are incorporated into sleek cabinetry. The space is defined by a cozy seating arrangement that invites relaxation, complemented by large glass doors leading to an outdoor balcony.

5 out of 5 average rating, 13 reviews

Relax in the countryside (Tuscany)

A spacious living area features exposed wooden beams and stone walls. A comfortable seating arrangement includes two sofas and a wooden dining table set with plates and pastries. A television is mounted above a central fireplace, while soft lighting enhances the warm ambiance.

5 out of 5 average rating, 7 reviews

Four-room villa (3 bedrooms and kitchen)

A spacious living area features a light blue accent wall and a large, comfortable sectional sofa adorned with decorative pillows. A glass coffee table sits in front of the sofa, complemented by a wooden surfboard artwork mounted above. Natural light fills the room through adjacent windows.

4.89 out of 5 average rating, 108 reviews

“Among the waves of Follonica” apartment

A serene outdoor space features a weathered wooden bench and a round table with a plate, surrounded by lush greenery. Large arched windows provide a view into the brightly lit interior, complemented by colorful flower pots, enhancing the garden-like setting.

4.93 out of 5 average rating, 86 reviews

Chianti Patio Apartment

An outdoor dining area features a decorative tiled table surrounded by wrought iron chairs. Lush greenery and colorful flowers create a serene backdrop. The rustic stone walls and pathways enhance the inviting atmosphere, making it an ideal spot for al fresco meals.

4.85 out of 5 average rating, 34 reviews

La Limonaia Delightful Apartment in Montepulciano

An open-concept living area is presented, featuring a hanging chair and stylish black furnishings. Arched doorways lead to the dining space, which is brightened by natural light. Potted plants add greenery to the environment, alongside a cozy rug on the tiled floor.

4.99 out of 5 average rating, 70 reviews

Herons Superior Apartment - Splendid view!

Apartment rentals with a hot tub

A serene sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light enters through an open window, showcasing views of the surrounding landscape. Two bedside tables hold lamps, and textured wall decor adds a touch of charm.

4.98 out of 5 average rating, 217 reviews

"Sunflower" apartment with view of Siena

A spacious living area features a white leather sofa, a large ottoman, and a decorative chandelier. Exposed stone walls and wooden floors create a warm ambiance. Natural light filters in through two open windows, complemented by a large flat-screen television and decorative shelves.

4.85 out of 5 average rating, 142 reviews

Executive Apartment City Center

The luxurious bedroom features a stunning ceiling adorned with a captivating fresco. A spacious bed is placed in the center, accompanied by a state-of-the-art TV nearby. A hydromassage tub situated at the foot of the bed complements the elegant decor, with soft lighting and decorative elements enhancing the ambiance.

4.91 out of 5 average rating, 592 reviews

House of Delights - The Medici private leisure house

An open living area is shown, featuring a spacious wooden dining table surrounded by light-colored chairs. The modern kitchen, equipped with sleek appliances, is visible in the background. The space is enhanced by wooden beams on the ceiling and a large window allowing natural light.

4.79 out of 5 average rating, 761 reviews

.2 La Casa sui Tetti dell'Oltrarno

4.95 out of 5 average rating, 128 reviews

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

The modern studio features a spacious bed with soft linens, flanked by bedside shelves. A minimalist kitchenette is visible in the background, complemented by light-colored cabinetry. Natural light filters in through the window, highlighting the tasteful green accent wall.

4.87 out of 5 average rating, 132 reviews

Japan Apartment Port Area with Balcony and Jacuzzi

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, 103 reviews

Luxury frescoed apartment in the historical center

A rectangular swimming pool with a shallow and deep end is surrounded by a stone patio and lush greenery. A villa sits on a hillside in the background, featuring a terrace with windows and shutters. Poolside lights are placed around the pool for evening ambiance.