Vacation rentals in Monteoliveto

4.99 out of 5 average rating, 190 reviews

Home in San Gimignano

Garden House

"Casa del giardino" ...... a blooming oasis within the medieval walls.. The owners Mario and Donella would like to offer you a unique vacation in San Gimignano. You can enjoy the wonderful garden, an extraordinary oasis of peace and silence, in the city center, for the exclusive use of those who rent the apartment. Thus, reading a book, relaxing in the sun, sipping an excellent glass of Chianti or having breakfast surrounded by greenery and among the flowers of this garden will be a memorable experience!

4.97 out of 5 average rating, 220 reviews

Casa Irene

Casa Irene is a delightful Tuscan-style apartment, located on the second and top floor of a building just a 5-minute walk from the center, 50 meters to Porta San Matteo and another 50 meters to Via Francigena. Given the secluded location, it is easily reached by car to park in the immediate free parking. The apartment equipped with WiFi and air conditioning is divided into an open space living room/kitchen, bedroom and bathroom with shower and a large terrace overlooking the walls of San Gimignano

Farm stay in San Gimignano

The historic towers of San Gimignano are illuminated against a dark sky, highlighting their distinctive architecture. The surrounding buildings are softly lit, creating a serene nighttime atmosphere that emphasizes the town's medieval character.

4.89 out of 5 average rating, 208 reviews

Oleandro double room with pool in San Gimignano

Double room in the peaceful countryside of San Gimignano, just 5 min from town by car. Located in Montegonfoli Farm, an ancient estate like a hidden hamlet, surrounded by olive trees, vineyards, and a private forest with a stream. Guests can enjoy the pool during the warm season. The room has a 160x190cm queen bed, large bathroom, fridge, microwave, and a terrace with dining table (no kitchen/fires). A perfect place for couples or solo travelers seeking tranquility, charm, and a touch of Tuscany

4.98 out of 5 average rating, 128 reviews

Apartment at ground floor with garden

A refined and very central setting, between Piazza della Cisterna and Piazza del Duomo. The house has the rare value of combining a comfortable ground floor, with independent entrance, to a stunning view of the famous Devil's tower.The exclusive garden, equipped to dine outdoors, read or stay between flowers and towers, is an extraordinary oasis of peace and silence, just around the corner of the two lively main squares.Possibility of parking in a private box for a fee at a cost of €8.00 x day.

4.96 out of 5 average rating, 282 reviews

The image captures the historic skyline of San Gimignano, featuring its characteristic medieval towers and stone buildings set against a vibrant blue sky with scattered clouds. Lush green hills and trees surround the town, providing a picturesque backdrop.

Condo in San Gimignano

Cozy apt overlooking the Duomo, San Gimignano

Super central apartment located right in the main Piazza of San Gimignano, overlooking the Duomo. Great location in the vibrant heart of the town with all services at your doorstep: chemist, cafés, restaurants, groceries, museums, tourist information office.. Walking out through Porta San Giovanni you'll find the Coop supermarket and the bus stop to Poggibonsi railway station (12km away). Car parks are also located outside the city walls just a few minutes' walk away.

4.93 out of 5 average rating, 118 reviews

A scenic view of rolling hills and lush greenery is visible from a window. Terracotta roofs and a winding path can be seen below, enhancing the historic charm of the medieval surroundings.

Condo in San Gimignano

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

4.98 out of 5 average rating, 42 reviews

Herons Superior Apartment - Splendid view!

Goditi una vacanza all'insegna dello stile in questo spazio nel centro di San Gimignano. Finemente arredato e con una vista spettacolare sulle colline toscane, Herons Superior Apartment è pronto a ospitarti insieme alle persone che ami. ___________________________________________________ Tassa di soggiorno da pagare sul posto secondo il seguente calcolo: 2,5€ X numero di ospiti sopra gli 11 anni X numero di notti (si pagano al massimo 5 notti).

4.98 out of 5 average rating, 40 reviews

A private pool is surrounded by lush green grass and flowering plants. Bright turquoise water glimmers in the sunlight, with the pool's tiled border providing a distinct outline. The setting is tranquil, ideal for relaxation amidst the natural landscape.

Home in San Gimignano

Tuscany:Stone house, private pool and garden

The house is composed by 2 independent apartments, with private pool and garden. It's perfect for a bigger family and friends: everyone has its privacy, but at the same time you can enjoy your holidays together. It's right for you if you want to visit the main Tuscany cities (Florence, Siena, Lucca , Pisa etc) or just relax in the pool, have a barbecue enjoying the garden and the swings for children. Wine tasting, oil tasting nearby.

Condo in Castelnuovo dell’Abate

A balcony is adorned with blooming flowers and greenery, offering a scenic view of the rolling hills and vineyards. Small outdoor furniture is positioned for relaxation, while the sky features scattered clouds, enhancing the tranquil atmosphere of the surrounding landscape.

4.91 out of 5 average rating, 288 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.

An ancient stone tower stands prominently against a clear blue sky. The structure features a narrow rectangular window and a bell opening at the top, while the textured stone walls reflect the rich history of the surrounding area.

4.88 out of 5 average rating, 219 reviews

D!Mora - New, Modern, Central and WiFi 100mbs free

Apartment WITHOUT KITCHEN (it is possible to request it extra at a cost of € 10 per day) recently renovated in a modern style in the heart of the town. Rooms equipped with all comforts, very large, bright and quiet to enjoy a relaxing holiday in the most beautiful town in Tuscany! There is no parking. For details see the section "Location" - "Getting around" It is not possible to bring bicycles inside the apartment.

4.96 out of 5 average rating, 249 reviews

A serene salt-water pool is surrounded by lush greenery and colorful flowers. Sun loungers are positioned around the pool, offering seating for relaxation. Rolling hills and cypress trees create a picturesque backdrop, showcasing the tranquil beauty of the Tuscan countryside.

Condo in Panzano

Apt. Panzanello-Panzano in Chianti

The apartment offers all the comforts and tranquility of the Tuscan countryside. Enjoy the wonderful view that you can admire from your private terrace, a perfect place to spend peaceful and serene moments accompanied by a good glass of Panzanello wine. Access to the apartment is private and free parking is available. The kitchen is equipped with everything you need to prepare delicious meals.

4.91 out of 5 average rating, 215 reviews

Farm stay in Simignano

Casa al Gianni - Fico

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

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Popular amenities for Monteoliveto vacation rentals

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Other great vacation rentals in Monteoliveto

Tiny home in San Gimignano

A rustic stone house is shown surrounded by lush greenery and olive trees. The entrance features a wooden door and large windows, adding warmth to the facade. A shaded seating area with outdoor furniture is visible beside the house, inviting relaxation in the natural landscape.

5 out of 5 average rating, 7 reviews

La Capanna, tuscan tiny house

JodieRating, 5 stars1 week ago

This was such a peaceful and private location and we loved our time in the tiny house. If you want something close to San Gimignano (5 min drive) but peaceful and private then this is perfect. It’s also only 50 mins to Siena and 45 mins to the Chianti region. We loved our stay here, the place was quaint and had everything you need. We also loved having access to the pool up at the main house (7 min walk) on the hotter days, which was clean and well cared for. You definitely need a car to stay here as it’s too far to walk with luggage from local towns. Our host was responsive and gave us great local recommendations and lots of options for in house eating also. Would definitely stay again!

A window view reveals a distant landscape of San Gimignano's towers against a blue sky. Lush greenery surrounds the base, while a cluster of vibrant pink flowers sits on the windowsill, adding a touch of color to the serene scene.

4.79 out of 5 average rating, 313 reviews

The nest under the towers

ToddRating, 5 stars3 weeks ago

This was a beautiful house that met our needs very well. What beautiful views of San Gimignano! It was like we were in the movie "Room with a View."

Farm stay in San Gimignano

A serene swimming pool is surrounded by lush greenery and features clear, inviting water. Sun loungers are positioned along the perimeter, and backdrop buildings blend harmoniously with the natural setting under a bright blue sky.

4.76 out of 5 average rating, 131 reviews

Fugnano Winery Farm

NickRating, 5 stars1 month ago

Laura and all staff at Fattoria di Fugnano were the best! Amin, Lorenzo, Andrea, and Lydia are excellent hosts and even better people! We have already recommended Fattoria di Fugnano to friends and family and can’t wait to return!

Condo in San Gimignano

5 out of 5 average rating, 4 reviews

Lo Scrigno Dei Sogni San Gimignano Apartment

EvaRating, 5 stars2 months ago

Fantastic hospitality, Romina is splendid and her apartment reflects her personality. Ideal location.

A lush outdoor area is revealed, featuring a grassy space with vibrant flowers and two umbrellas providing shade. Tables and chairs are positioned for relaxing while enjoying the expansive views of the rolling hills and vineyards that stretch into the distance.

4.88 out of 5 average rating, 52 reviews

Podere Le Macine - Saffron 2

RubyRating, 5 stars2 weeks ago

Beautiful views and easy to get into the town centre :)

A garden area features a large, well-maintained lawn with several sunloungers positioned for comfort. Flowering plants are arranged in terracotta pots, and olive trees adorn the backdrop. A view of the surrounding countryside and medieval town towers is visible in the distance.

Cottage in San Gimignano

4.88 out of 5 average rating, 105 reviews

Countryside Cottage With View - Le Papere apt

RamseyRating, 5 stars2 weeks ago

Amazing place, big garden and amazing view. Will be back for sure

The exterior of a stone building showcases a rustic architectural style, with a tiled roof and tall windows. A well-maintained garden area features green grass and planted shrubs, while decorative elements such as a wooden barrel and flowers add character to the entrance.

5 out of 5 average rating, 6 reviews

Orcio Suite

StuartRating, 5 stars8 months ago

This is an incredible property to stay at in the Tuscany region of Italy. The room was large and with a very comfortable bed. The bathroom was spacious and clean. The property itself is gorgeous with a great swimming pool and views of the surrounding area. The breakfast was ‘okay’. Small selection and on mornings where all the other guests eat at the same time they ran out of items quickly and were slow to restock. Communication is also ‘okay’. Holidu is the Airbnb host but there are on site staff as well so there isn’t really a direct line of contact to the actual ‘host’. But when we asked the on site staff for help they were very friendly and helped as quick as they could. If you are planning to walk into San Gimignano be prepared for a healthy walk. It’s very doable (we are 31years old) but if you can’t comfortably walk ~20min (up hill going into town) you’ll want to drive and parking can be a nightmare. All in all, fantastic Airbnb and would recommend.

A serene bedroom features exposed brick walls and wooden beams, creating a rustic ambiance. A spacious bed is positioned in the foreground, while a small desk and chair are visible against the opposite wall. Natural light filters through the window, enhancing the calm atmosphere.