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Holiday rentals in San Gemini

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Top-rated holiday rentals in San Gemini

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia
4.92 out of 5 average rating, 596 reviews

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

Top guest favourite
A stone building is viewed from the cobblestone square, featuring a staircase leading to an upper floor. A lantern is mounted on the wall, casting a gentle light. The valley beyond offers a scenic backdrop with rolling hills and a partly cloudy sky.
Holiday home in Orvieto
4.96 out of 5 average rating, 284 reviews

The Loggia of San Giovenale

The house is in the oldest square in Orvieto, San Giovenale, with the beautiful 11th-century Romanesque church. A small loggia with a breathtaking view of the Paglia valley, from where you can see Amiata, Monte Cetona, and Monte Peglia. Furnished with custom-made furniture crafted by master carpenters from Orvieto, the wooden ceilings on the first floor and the handmade terracotta floor tiles make it a charming accommodation where you can enjoy a wonderful stay in Orvieto. Tax Code IT055023C202019060

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

Chef’s Retreat

Beautiful hillside home, the perfect space for relaxation and fun. Enjoy the spectacular sunset across the pool overlooking the ancient Tiber valley. Umbria rich history and culture surround you and its centuries of culinary and artisanal tradition are at your doorstep. The Etruscan towns of Orvieto, Todi, Amelia are easily reached by car, or take the local train to Rome or Florence. A 3-minute drive away is Guardea with a supermarket, butchers, cafés, shops and an outdoor market on Sundays.

Top guest favourite
A shaded pergola stands by a large swimming pool, draped with light curtains. Comfortable outdoor seating surrounds a circular table. Lush greenery and flowering plants create a serene backdrop, enhancing the tranquil atmosphere of the estate.
Villa in Guardea
4.99 out of 5 average rating, 100 reviews

Exclusive 10 Acre Estate w/ Pool & Olive Grove!

Enchanting, exclusive 10acres estate on a hill, memorable sunsets; large pool framed by lavender&rosemary, open year-round. New air conditioning, Starlink internet. Very private&peaceful 2 floors, 4bedrooms, 4baths, jacuzzibathtub, 55inch smartTV, well-equipped kitchen, porch & pergola for alfresco dining, Weber barbecue, pizza oven, olive grove, fireplace; 20 min. to Orvieto,Todi,Amelia; 10 minutes drive to train station to Rome/Florence, 5min drive to shops in town. Grounds/pool caretaker

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house in Macciano
4.97 out of 5 average rating, 227 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Guest favourite
A panoramic view of the rooftops of San Gemini is presented, framed by lush greenery and distant hills. The clear blue sky features a few birds in flight, enhancing the serene landscape. Architectural details of historic buildings are visible, showcasing the area's charm.
Apartment in San Gemini
5 out of 5 average rating, 18 reviews

The house in the Medieval Village

Arroccato nel centro storico di San Gemini l'alloggio nasce da un concetto di vivibilità che unisce tradizione ed innovazione. "Rifugio al Borgo" è un bilocale accogliente e silenzioso dove il tempo è scandito dal rintocco delle campane. Un luogo family friendly, il borgo in estate offre una splendida piscina con attività per bambini e un ricco programma di eventi open air. Siamo in posizione strategica per visitare Perugia, Todi. Spoleto, Assisi e Orvieto, a pochi km dalla E45 Orte Cesena

Guest favourite
Flat in San Gemini
4.83 out of 5 average rating, 6 reviews

San Gemini Fiori - InBorgo

Welcome to your charming retreat in the stunning historic center of San Gemini (TR), Italy! Stay in a cozy and elegantly restored apartment, perfect for those who want to experience the authentic Italian atmosphere in one of Umbria’s most enchanting medieval villages. Accommodations: ✔ 3 comfortable bedrooms ✔ 1 full bathroom + 1 half bath ✔ Spacious and cozy living room ✔ Fully equipped kitchen Experience the magic in the Heart of San Gemini with all the comforts of an Italian home!

Top guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.93 out of 5 average rating, 311 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top guest favourite
Home in Ampognano
5 out of 5 average rating, 44 reviews

Nature, Comfort & Privacy: Villa in Valnerina

In the heart of the Valnerina, a new and bright villa welcomes you among olive trees and mountains, with an idyllic view and absolute silence. The interiors combine a living room and kitchen in a single elegant and super-equipped open space; a double bedroom, full bathroom and sofa bed make the space perfect for couples, families or a group of friends. Outside, an area with a small table and three seats awaits you for a sunset aperitif. 100% electric house with seasonal air conditioning.

Guest favourite
Home in Todi
5 out of 5 average rating, 6 reviews

The Lost Stone paradise with pool, views and AC

The Old Stone is a 2025 fully refurbished 200 yrs old stone house in the hills of Todi, Umbria. It features a magnificent new pool, AC, high speed Wi-Fi and it is immersed in beautiful nature. It has a large garden, 3 patios, two kitchens, 3 bedrooms, 2.5 bath and a spectacular living room. Designed for comfort and entertaining, every detail has been thoughtfully curated to blend rustic charm (wood beams, cotto floors and stone walls) with moder luxury in a peaceful, panoramic setting.

Top guest favourite
A spacious bedroom features a large, inviting bed adorned with a light blanket. Natural light floods through sheer curtains draped over a large window, revealing views of the lush valley outside. The rustic walls, made of tufo, add a unique character to the room.
Flat in Civita
4.94 out of 5 average rating, 281 reviews

The Cellar (Palazzo Pallotti)

The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

Top guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment in Pienza
5 out of 5 average rating, 149 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Popular amenities for San Gemini holiday rentals

  1. Airbnb
  2. Italy
  3. Umbria
  4. Terni
  5. San Gemini