Vacation rentals in Contignano

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Top-rated vacation rentals in Contignano

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Guest favorite

Villa in Chianciano Terme

4.92 out of 5 average rating, 104 reviews

Cottage in Val d'Orcia, Jacuzzi & HotTub with view

Welcome at Luxury Cottage in Tuscan Villa, with private patio for al fresco dining overlooking the garden! We're in Val d'Orcia, Unesco Site, nearby Montepulciano, Pienza, Cortona, Siena! Enjoy natural hot pools and falls! Fully equipped kitchen, magnificent bathroom with double Jacuzzi, and large bedroom with new Memory foam mattress. Thanks to old and thick walls, it's very cool in summer! We arrange Winery tours & tasting ! Free wifi, comfy sitting and sofas and Hot Tub in the garden!

Top guest favorite

Guesthouse in Macciano

4.96 out of 5 average rating, 163 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 favorite

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

4.95 out of 5 average rating, 218 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

Guest favorite

A private terrace is visible, adorned with vibrant flowers and a small table set for two. A bottle of wine and two glasses are elegantly placed, inviting relaxation with a view of the terracotta rooftops and the distant landscape under a pastel sky.

Condo in Montepulciano

4.92 out of 5 average rating, 125 reviews

"Dimora Valinda" Montepulciano Piazza Grande +A/C

🏠 Ideal location: within walking distance of stores, restaurants and attractions in the historic center. ❄️ Air conditioning for maximum comfort during hot days. 🛁 Washing machine for extended stays or simply for traveling light. 🌅 Private terrace for relaxing moments outdoors. 🍴 Full kitchen with dishwasher, perfect for those who love to cook even on vacation. 🌐 Ultra-fast 150 Mb/s Wi-Fi, ideal for smart working ☕ Well-stocked coffee station for a perfect start to the day.

Top guest favorite

A historic architectural scene showcases a church featuring a bell tower and intricate stone façades, framed by weathered columns. An inviting plaza lies in the foreground, with a solitary figure strolling, surrounded by buildings that display a blend of classic designs and rustic charm.

Condo in Asciano

4.96 out of 5 average rating, 352 reviews

Romantic Yellow apartment in Crete Senesi

Apartment consisting of a comfortable double bedroom (it is possible to make 2 single beds on request), an equipped kitchen, a living room, and a bathroom. TV, BBQ, (if needed, we have a washing machine available from 9 a.m. to 8 p.m., which is in our laundry room). A car is recommended as we are in the countryside, so you can be self-sufficient and visit the magnificent Tuscan countryside as well. Free parking and wifi. I look forward to showing you the real Tuscany!

Guest favorite

A wooden balcony table is set for tea, featuring delicate china cups accompanied by cookies. A simple vase holds fresh flowers. The stunning countryside view stretches across rolling hills under a clear sky, enhancing the serene atmosphere of the outdoor space.

Apartment in Montepulciano

4.94 out of 5 average rating, 191 reviews

I Tramonti di Eramo, Montepulciano city center.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historical center offers a breathtaking view of the surrounding countryside, giving an authentic and unforgettable experience. You can leave the house and taste the historic atmosphere of Montepulciano. Within walking distance you will have the extraordinary Piazza Grande, high quality restaurants and services of all kinds. Tuscany awaits you to experience unique emotions.

Top guest favorite

An outdoor terrace is visible, furnished with several tables and chairs, providing ample seating. Flower pots with colorful blooms adorn the railing, while a panoramic view of the surrounding hills and greenery stretches into the distance under a clear sky.

Apartment in Sinalunga

4.99 out of 5 average rating, 270 reviews

Resort Panoramic view - Free parking

Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Sala da tea ad uso gratuito . Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

Guest favorite

A charming two-story villa is set amidst a spacious green lawn, surrounded by trees and shrubs. The building features red shutters and a welcoming porch that invites relaxation. Scenic countryside views extend beyond the property, enhancing the tranquil setting.

Apartment in Monticchiello

4.97 out of 5 average rating, 152 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

Top guest favorite

An arched stone entrance frames a quaint Tuscan street. Vibrant flowers adorn a balcony above cobblestone pathways, while rustic buildings with green shutters and brick facades contribute to the historic charm of Monticchiello. Softly glowing street lamps add to the inviting atmosphere.

Vacation home in Monticchiello

4.97 out of 5 average rating, 104 reviews

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Guest favorite

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.

Condo in Castelnuovo dell’Abate

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.

Guest favorite

A charming stone building is surrounded by greenery and colorful flowers. An outdoor seating area with two chairs is visible, creating a peaceful space for relaxation. Sunlight brightens the surroundings, enhancing the natural beauty of this historic setting.

Apartment in Bagnoregio

4.98 out of 5 average rating, 443 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".

Guest favorite

Farm stay in Simignano

4.89 out of 5 average rating, 196 reviews

Casa al Gianni - Capanna

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 Contignano vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Contignano

Top guest favorite

A stone pathway leads to an entrance framed by a rustic archway. The doorway features a wooden door with a glass panel, flanked by potted flowers in vibrant hues. Natural stone walls and greenery create a charming setting.

Apartment in Monticchiello

5 out of 5 average rating, 45 reviews

Casa Tórta - comfort room

CharlotteRating, 5 stars3 days ago

Genuinely a secret little heaven, I cant recommend staying here more! Monticchiello is so beautiful and peaceful and their place is just perfect! I can’t wait to hopefully return one day!!

Top guest favorite

Villa in Cetona

5 out of 5 average rating, 12 reviews

Country Charm & Jacuzzi

GaryRating, 5 stars1 week ago

An Unforgettable Stay with the Best Host Ever! Flaminia is truly the best host we’ve ever had the pleasure of meeting. From the moment we arrived, she made us feel completely at home. She’s incredibly helpful—always available and willing to assist with anything we needed, no questions asked. Her warm, down-to-earth personality made our stay not only comfortable but genuinely special. What made the experience even more memorable was her recommendation to try her father’s amazing Roman cuisine, perfectly paired with local wines. It was an unforgettable meal and a true highlight of our trip. The farmhouse itself is beautifully located in the heart of Tuscany. It’s the perfect base for exploring nearby cities and the stunning countryside. Thanks to the central location, we were able to easily travel around and soak in all the beauty Tuscany has to offer. Flaminia went above and beyond in every way

Top guest favorite

Apartment in Contignano

5 out of 5 average rating, 12 reviews

Tre Fontini

SebastianRating, 5 stars1 month ago

Alessandro and his wife were very helpful and accommodating! Messages were always answered very quickly! Alessandro had kindly shopped for us, everything perfect! The place was very spacious, clean and with beautiful views! Clear recommendation!

Top guest favorite

A private terrace is displayed, featuring a small table and two wrought iron chairs. A potted flower brightens the space, and expansive views of the surrounding greenery and historical architecture are visible in the background under a partly cloudy sky.

Apartment in Monticchiello

4.98 out of 5 average rating, 47 reviews

PoliFlora Panorama

OmarRating, 5 stars2 months ago

Kindest host! Beautiful view of the tuscan landscape

Home in Contignano

4.95 out of 5 average rating, 43 reviews

Sweet home Tuscany with swimming pool

JulienRating, 5 stars9 months ago

Excellent apartment in a fully privatized neighborhood. The pool is a big plus, and check-in went smoothly. Please note that it is necessary to contact an on-site "concierge", not through Airbnb. In any case, for 3 nights, it's great: cool water when you arrive, a few restaurants nearby very affordable, we are in the middle of Tuscany (20 minutes from magnificent viewpoints). We recommend it!

Top guest favorite

Natural thermal springs are depicted, showcasing layered rock formations with a distinctive pale blue water color. Gentle waterfalls cascade over rocky ledges, surrounded by lush greenery and sparse trees. The scene conveys a serene and tranquil environment, inviting exploration of the natural beauty.

Home in Bagni San Filippo

5 out of 5 average rating, 8 reviews

Boutique House San Filippo

AnnaRating, 5 stars1 week ago

Very nice property, tastefully furnished. All new, very comfortable bed, perfect cleanliness, the owner is very kind and welcoming. Perfect location for both the spa and the restaurant. All within walking distance. Highly recommended property.

Guest favorite

A vibrant garden features blooming yellow and red roses, alongside lush greenery. The rustic stone structure is framed by the flowers, and a palm tree adds to the serene atmosphere. A pathway leads to a spacious entrance, welcoming guests into the agriturismo.

Farm stay in Località Spedaletto, Pienza

4.97 out of 5 average rating, 144 reviews

Spedaletto Castle, Val d'Orcia, Pienza

LukasRating, 5 stars5 days ago

Laura's place is located in a very nice neighborhood. You have a wide view into the scenery. The accommodation itself looks even more beautiful in real life than in the photos. Laura and her team were totally friendly, the room was clean, nicely decorated and equipped with air conditioning (important in Tuscany). The breakfast was excellent! There is also a large pool with enough loungers for all guests. We highly recommend a stay!

Top guest favorite