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Vacation rentals in Trequanda

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Top-rated vacation rentals in Trequanda

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Top guest favorite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.97 out of 5 average rating, 132 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Top guest favorite
A wooden table is set with two cream-colored cups and a small vase filled with dried wheat and decorative grasses. The white brick wall creates a warm backdrop, enhancing the inviting atmosphere of the dining area.
Apartment in Montepulciano
4.99 out of 5 average rating, 280 reviews

Montepulciano Historic Center

Nice 60-square-meter apartment located on the main street of the town. It is located on the second and top floor of a historic building. The entrance is located on the main street of the town while the windows face the outside of the walls offering a breathtaking view. The apartment consists of: an entrance, a living room with a double sofa bed, a bedroom, a kitchen, and a bathroom with a roof window. It is equipped with a microwave, large oven, dishwasher, washing machine and wifi.

Guest favorite
An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.
Condo in Asciano
4.96 out of 5 average rating, 325 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, fully equipped kitchen, large living room, and bathroom. TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room to those who request it). We recommend a car as we live in the countryside, both to be independent and to visit the magnificent Tuscany. You will like the outdoor environment because it is magical by day and at night Free parking and WiFi Convenient location to visit both Tuscany and Umbria.

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, 154 reviews

"Dimora Valinda" Montepulciano Piazza Grande + A/C

Welcome to Montepulciano, a historical gem! Our apartment, located in the heart of the historic center, offers the perfect location to experience the authenticity of this unique place: just a few steps from Piazza Grande, excellent restaurants, shops, and all the main attractions. Whether you come to explore the wineries, for a romantic getaway, or to learn about the history and culture of Montepulciano, here you will find the perfect place for an unforgettable experience.

Guest favorite
Townhouse in Trequanda
5 out of 5 average rating, 17 reviews

Romantic Tuscan Holiday House

Recently renovated Casa Etruria features a chic modern home inside its ancient stone walls, with every modern convenience,lots of original charm and the most beautiful sunset view from the bedroom and balcony . Casa Etruria is a 13th century gate house over the Western entrance to Trequanda - Porta al Leccio. Trequanda is medieval borgo located in Val d'Orcia , south of Siena. Val d'Orcia was recognised by UNESCO in 2004 as a World Heritage Site for its outstanding beauty.

Top guest favorite
Farm stay in San Giovanni d'Asso
4.94 out of 5 average rating, 134 reviews

Flat, Agriturismo "Biofattoria l'Upupa"

The flat is on the first floor of a classic Tuscan farmhouse called ‘Biofattoria l'Upupa’. Magnificent hillside location between the Val d'Orcia and the Crete Senesi. Suitable for families with children. Consisting of kitchen, large living room, bathroom with shower, 1 double bedroom and 1 bedroom with bunk beds. There is a double sofa bed in the living room. The flat is equipped with wifi. Free parking on private property. Complete breakfast kit including homemade cakes.

Top guest favorite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5 out of 5 average rating, 103 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Top guest favorite
A compact room features a spacious bed with a rich red coverlet, accompanied by neatly stacked white towels. A small kitchenette is visible with a microwave and seating area. A television is mounted on the wall, enhancing the modern design.
Apartment in Sinalunga
4.97 out of 5 average rating, 147 reviews

Resort Panoramic - 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 . Tourist tax 1€ .

Top guest favorite
The exterior view captures a rustic stone house bordered by tall trees. A pathway leading to the dwelling is visible, accompanied by lounge chairs set on a grassy area. The tranquil setting reflects the peaceful ambiance of the countryside.
Home in Scrofiano
4.97 out of 5 average rating, 163 reviews

Jenny's Barn

The ancient barn, now finely restored, is located in the heart of the Valdichiana a few steps from the characteristic medieval village of Scrofiano. From the house you can enjoy a breathtaking view of the green Sienese hills where centuries-old olive trees and vineyards alternate from which the prestigious Chianti is obtained. Ideal for 2 people looking for a relaxing stay away from the chaos of the city. On request it is possible to add a baby bed and a cot.

Top guest favorite
A rustic stone farmhouse is embraced by mature olive trees and lush greenery. The building features traditional window shutters and is set against a clear blue sky, with a gravel pathway leading up to the entrance, enhancing the tranquil countryside ambiance.
Farm stay in San Quirico d'Orcia
4.99 out of 5 average rating, 101 reviews

Podere Pereti Nuovi – Modern Tuscan Villa

Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

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, 136 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?

Top guest favorite
Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.
Apartment in Monticchiello
4.97 out of 5 average rating, 173 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.

Popular amenities for Trequanda vacation rentals

When is the best time to visit Trequanda?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$54,575 GYDG$63,566 GYDG$54,784 GYDG$58,966 GYDG$55,621 GYDG$57,712 GYDG$61,894 GYDG$63,566 GYDG$62,730 GYDG$52,484 GYDG$54,157 GYDG$59,803 GYD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Trequanda?

    Four-legged friends are welcome in Trequanda. Choose from more than 190 vacation rentals for guests traveling with pets.

  • Are there Trequanda vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 240 vacation homes with pools in Trequanda, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in bed and breakfast rentals in Trequanda?

    Experience the best of Trequanda with our bed and breakfast rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do farmstay rentals in Trequanda have a kitchen?

    Absolutely! We offer over 10 farmstay rentals with a kitchen in Trequanda. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Villa Rentals in Trequanda?

    Enhance your stay in our Villa Rentals with the most popular amenities: over 30 homes with a kitchen, over 40 homes with wifi, over 30 homes with air conditioning, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do condo rentals in Trequanda have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Trequanda. Enjoy a tailored experience with all the comforts you desire.

  • Do serviced apartment rentals in Trequanda have free parking?

    Absolutely! We offer over 10 serviced apartment rentals with free parking in Trequanda. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Trequanda?

    Trequanda has more than 190 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there vacation rentals with a dedicated workspace in Trequanda?

    Yes! Work meets play with ease at over 100 vacation rentals in Trequanda featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do farmstay rentals in Trequanda have air conditioning?

    Absolutely! We offer over 20 farmstay rentals with air conditioning in Trequanda. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Trequanda

  • Total vacation rentals

    Explore 310 vacation rentals in Trequanda

  • Nightly prices starting at

    Trequanda vacation rentals start at G$12,546 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,880 verified reviews to help you choose

  • Family-friendly vacation rentals

    180 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 190 rentals that welcome pets

  • Vacation rentals with a pool

    230 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    300 of Trequanda vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Trequanda rentals

  • 4.8 Average rating

    Trequanda stays are highly rated by guests—averaging 4.8 out of 5!

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