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Vacation rentals in San Gimignanello

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Top-rated vacation rentals in San Gimignanello

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

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Top guest favorite
Condo in Asciano
4.99 out of 5 average rating, 223 reviews

Pink like the sunset sky

The apartment is located on the 2nd floor, consisting of 2 bedrooms (possibility of making double or single beds depending on the needs of the customer), a bathroom, large living room and kitchen equipped for cooking. TV, (for those who request it, a washing machine is available from 9 a.m. to 8 p.m. in our laundry room). To come to us, a car is recommended, to be independent, and to visit the Tuscan countryside. Convenient location for visiting Tuscany I look forward to showing you the real Tuscany!

Top guest favorite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 497 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Guest favorite
Home in Asciano
4.96 out of 5 average rating, 130 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favorite
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.
Apartment in Montepulciano
4.96 out of 5 average rating, 313 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 king ), 2 bathrooms ensuite with shower and a large kitchen-living room with 4 windows and a small terrace, overlooking the hills, wine cellar The apartment offers a spectacular view 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.

Top guest favorite
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.
Guesthouse in Macciano
4.97 out of 5 average rating, 221 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.

Top guest favorite
An outdoor spa area is featured beneath a wooden pergola, surrounded by lush greenery. A hot tub sits on a wooden deck, accompanied by two small tables and a lantern. Comfortable lounge chairs can be seen in the background, inviting relaxation.
Villa in Montepulciano
4.92 out of 5 average rating, 302 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 favorite
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.
Condo in Pienza
5 out of 5 average rating, 146 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?

Superhost
A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.
Apartment in Montepulciano
4.91 out of 5 average rating, 278 reviews

I Tramonti di Eramo, downtown Montepulciano.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

Superhost
A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.
Condo in Castelnuovo dell’Abate
4.9 out of 5 average rating, 314 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Top guest favorite
A small stone alcove features a wooden table with a potted flower and two red folding chairs. The background reveals a serene view of lush hills, creating a quiet space for relaxation.
Apartment in Bagnoregio
4.98 out of 5 average rating, 489 reviews

The Enchantment of Civita (The Terrace)

L'Incanto di Civita is located inside the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot, you will need to walk along the bridge, the only way to access our "tufo pearl". L'Incanto di Civita is located in the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".

Top guest favorite
An exterior view of a charming Tuscan house featuring warm stone walls. The surrounding garden includes manicured grass and potted plants. A spacious patio with a table for outdoor dining is visible, alongside a stone pathway leading to the entrance.
Guesthouse in Montefollonico
4.98 out of 5 average rating, 125 reviews

Casale Santa Barbara - Exclusive Apartment

Your private Tuscan retreat between Pienza and Montepulciano. A spacious 100 m² apartment for two, with exclusive access, a large private garden and breathtaking views over the Val d’Orcia hills. Elegance, calm and authenticity — just you… and Tuscany.

Top guest favorite
The aerial view captures the historic structure nestled among rolling green hills, framed by tall trees. The stone walls reflect medieval architecture, while a terrace offers an inviting space below. The surrounding landscape showcases farms and cypress trees against a clear blue sky.
Home in Monticchiello
4.98 out of 5 average rating, 212 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Popular amenities for San Gimignanello vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. San Gimignanello