Trequanda

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

Satellite / Cable TV

Library of Books

Pool / Snooker Table

Sound System

Entertainment

Bathtub

Hair Dryer

Bathroom

Coffee Maker

Cooking Essentials

Dishwasher

Espresso Machine

Fridge

High Chair

Kettle

Kitchen

Kitchen Utensils

Microwave

Oven

Pod Coffee Machine

Stove

Toaster

Blender

Kitchen & Dining

Cot / Crib

Drying Rack

Hangers

Iron

Ironing Board

Washing Machine

Bedroom & Laundry

Outdoor Pool

Private Pool

Swimming Pool

Wellness & Fitness

Laptop Friendly Workspace

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Fireplace

Heating & Cooling

Free Parking On Premises

Parking Available

Private Entrance

Parking & Access

Balcony

Barbeque

Courtyard

Garden

Outdoor Seating

Patio / Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

Outdoor

Pets Allowed

Pets

A true rural oasis, this flower-framed Tuscan farmhouse beautifully blends traditional charm with modern comforts to create the perfect quiet retreat. Hills teeming with olive trees, cypresses and holm oaks surround it on all sides, best enjoyed from the home's panoramic terraces. Inside, meanwhile, brick-clad archways, stone flooring and exposed beam ceilings blend with elegant furnishings in the living room to create a feeling of countryside grandeur. Wander around the garden brimming with lemon trees, jasmine and oleander plants and down the path to the secluded swimming pool where sun loungers invite luxurious afternoon relaxation. An outdoor dining table beckons at mealtimes for barbecue feasts, while the indoor pool table and the bedroom reading platform are perfect for whiling away quiet hours when the sun gets too hot. With the medieval village of Trequanda just a few minutes walk away and Siena reachable by car in just forty-five minutes, there’s plenty of exploring to enjoy in and around your private haven. 

Oleander Oasis

Board Games

DVD Library

DVD Player

Games Room

Rain Shower

Toiletries

Freezer

Wine Cellar

Wine Cooler

Private Washing Machine

Private Dryer

Dryer

Black-Out Blinds

Cleaning Products

Extra Pillows and Blankets

Sauna

Exercise Equipment

Desk / Workplace

Ceiling Fans

Self Check-in / Check-out

Single-Level Home

Hammock

Outdoor Shower

Mosquito Net

Nice to haves

Safe

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Smoke Detector

Other

Bookended by the olive groves, cypress trees and rolling green hills of Southern Tuscany is this 1960s-style architectural feat designed and curated by a sculptor and architect duo. Perfect for two couples or a small group of friends looking to explore the region, this cleverly converted warehouse is airy and open-plan with large crittall-style windows looking out over the vineyard and rambling countryside beyond. We particularly liked the stone fireplace and curated pieces of art dotted around that make for a real visual statement. Through to the bedrooms, where you'll find minimalist interiors, crisp white bed linens and antique objects that combines traditional touches with modern influence. Spend mornings idly relaxing underneath the warm Tuscan sun by the stunning 20-metre lap pool or recharging in the sauna, before cycling to the nearby village of Montisi. Take a half-hour drive to the famous vineyards of Montepulciano and bring a few bottles of vino back with you – to be chilled in the home's wine cellar and enjoyed out on the terrace, as you look out across the medieval ruins of Montelifrè Castle. Be it wine, history, interior design, or art, this home delivers in spades. 

Architectural Narrative

Heated Towel Rail

Jacuzzi

Hot Tub

Fenced Garden

Fenced Property

Located in the Tuscan countryside, this impressive estate is an excellent choice for a couple of large families looking for an easygoing stay. Set across a main building and two guest houses, the residence, dating back to the 1600s, has been carefully restored and boasts fantastic views of Val d’Orcia. Although the traditional interiors may not be to everyone’s taste, the space is functional and perfectly suited to group dining and relaxing. Need a hand planning activities? Your host provides a wide range of experiences from truffle hunting to wine tasting – all on your doorstep.

Titiro Toscano

Cafetiere

Child Friendly

This incredible Tuscan villa dates back to the 1600s and has been lovingly transformed into an organic and eco-sustainable farm. The landscape surrounding this home is impressive too – especially from the panoramic pool – as it's situated in Val d'Orcia, a UNESCO World Heritage Site. Spread over two floors, the space includes a fully-equipped kitchen and plenty of outdoor dining space, as well as BBQ facilities and a wood-burning oven for alfresco cooking. If any guests have mobility issues, three of the en-suite bedrooms on the ground floor are easily accessible from outside. We recommend a car to explore the area with ease – the Medieval village of Trequanda is just 5km away.

The Masterpiece

Desk

Beach / Pool Towels

This stunning villa is surrounded by 32 hectares of woods, olive groves, and vineyards. It benefits from a fantastic location close to Tuscany, Umbria and Lazio, making it perfect for families and friends wanting to explore more of Italy. You can reach Siena in forty-five minutes and Rome in ninety – you’ll have your pick when it comes to exciting day-trips. There’s plenty to keep you occupied at the villa, too, with a private pool, barbecue, and billiards. Two guests will be sleeping in an adjacent cottage, which is ideal for a couple seeking more privacy. 

A Tuscan Legacy

Free Parking On Street

Balcony / Patio

Resort Access

Set on a farm, parts of which are more than 200 years old, you’ll find this apartment, which is light and bright thanks to the large arched windows. Outside, as you’d hope for – there are gorgeous vistas over the Tuscan countryside and instead of a farm pond, there’s now a beautiful shared pool, which is a short walk through the communal gardens. When you fancy exploring the area – go for a hike in the Val di Chiana, discover the medieval hilltop town of Montepulciano, or spend the day at one of the beaches at Lake Trasimeno.

The Tuscan Vineyard

Located in the Tuscan countryside, this home in Torrita di Siena offers endless peace, quiet and picturesque scenery. With views stretching to Lake Trasimeno, it's a spot for those keen to reconnect with nature while discovering the attractions of Tuscany. There's a shared swimming pool on-site, and you'll have your own private garden space here. The alfresco dining area is perfect for sitting with a glass of local wine and an Italian aperitivo. Meanwhile, the open-plan living area makes for a sociable living space to kick back after a long day of exploring.

Casa di Siena

Security Cameras

This home is a handsome retreat in the heart of Val di Chiana. Outside, you can enjoy stunning views across olive trees and vineyards while lounging by the private pool. There are plenty of shaded areas for lazy afternoon reading sessions, while the terrace lends itself perfectly to evening drinks. The rooms are set across three independent cottages – all of which feature a kitchen and living room. It’s worth noting you will need a car to get around here, but it’s just a short drive to the village of Sinalunga where you’ll find restaurants and shops. It’s also the ideal base for exploring nearby Siena, Arezzo and Montepulciano.

The Vittoria 

Shared Pool

This home is part of a resort set between the gorgeous valleys of Val d'Orcia and the Val di Chiana. The decor isn't the most exciting, but you can't beat this picturesque location. An easy drive from quaint villages and the city of Siena, it's the perfect starting point for exploring Tuscany. Spread over two floors, the first floor is dedicated to the large master suite, and we're big fans of the private terrace – perfect for enjoying a glass of wine at sunset. There's a communal swimming pool and solarium for relaxing during summer, and a wine bar and restaurant for trying some of the region's best wines. Your host can also help arrange a plethora of exciting activities, including truffle hunting, wine tastings and cooking classes.


The Tuscan Farmhouse

Gated Community

Nestled in a Tuscan country estate, this pet-friendly home offers the best of both worlds – a private terrace for alfresco dining and the option to share breakfast with your neighbours at the buffet. After snoozing by the communal pool, why not join a truffle hunt? Or rent a bike and cycle through the area. Maybe sipping local sundowners in the on-site bar will inspire a next-day trip to medieval Montepulciano, so you can see where that regional wine comes from.

Tuscan Getaway

Situated on a private resort, this villa drops you in the heart of the Tuscan countryside to indulge in pure rest and relaxation. Set over two floors, there’s plenty of space for guests to spread out, plus an inviting private terrace to soak up the rural vistas. Cool off from the Italian heat in the seasonal communal pool, while a visit to the on-site wine bar is a must to taste some local delights. For an additional fee, you can also enjoy a delicious breakfast buffet, an Italian cooking class or a truffle hunting experience. 

Tuscan White

EV Charger

Looking for the wow factor? This home fits the bill. Each room effortlessly blends Tuscan tradition with contemporary aesthetics – none more so than the living area, with its brick archways, stone walls and beamed ceilings. There's also an annexe offering even more space for groups, containing an additional kitchen and living room, as well as the fifth and sixth bedrooms (one of which is wheelchair-accessible). Outside, the swoon-worthy views from the infinity pool and Jacuzzi are hard to resist. Meanwhile, the shaded pergola is perfect for Aperol Spritzes at sundown. And did we mention daily maid service is included? If you can tear yourself away from this stunning home, Montefollonico is a thirty-minute walk, while Siena is an hour's drive.

The White Vine

This converted Tuscan home provides a great base to explore one of Italy’s most iconic areas from. Though the interior perhaps lacks a bit of cosiness, it is well-kept and provides you with all you need for a comfortable stay, including a fully-equipped kitchen and a nice open-plan dining area which leads onto a private terrace. Guests can also make use of the resort’s facilities, such as the shared outdoor pool and rooftop. Make the most of the area by sampling some of its famous wines and visiting the picturesque towns. 

The Alighieri

Netflix

Streaming Services

Buzzer / Wireless Intercom

Pool House

Welcome Hamper

While away spectacular sunny days lost in the pages of a good book by the pool, drink fantastic local wines as you relax in the bubbling Jacuzzi, and tuck into Tuscan classics cooked on the brick barbecue at this beautiful countryside chic apartment located within a spectacular villa close to the charming hilltop village of Rigomagno.

The interior is a typically Tuscan affair, with terracotta tiled floors underfoot, a large brick fireplace to gather around, and earth tones that soothe the soul, all sitting beneath an exposed beam ceiling. In the bedroom, elegantly draped material adds a touch of Renaissance drama, while the spacious marble bathroom is perfect for post-pool pampering sessions.

Step into the shared outdoor space, and you'll find yourself surrounded by eighteen acres of pristine protected forest, with breathtakingly beautiful walks departing right from the front door. In addition to the stunning gardens (complete with table football, table tennis and a playground), you can up your relaxation game at the thermal baths in Rapolano Terme, a fifteen-minute drive away.

If you'd like to explore further afield, the lovely medieval city of Siena and the hilltop Renaissance town of Montepulciano are well within day-trip distance, with both approximately half an hour's drive away.

Rigomagno Rustico

This apartment near Torrita di Siena has lovely views over this little slice of Tuscany from the terrace – perfect for alfresco meals. Or have a stroll through the communal gardens to the shared swimming pool. When you feel like exploring, visit Torrita di Siena with its pretty streets lined with stone-built houses or go for a hike around Mount Amiata. Alternatively, spend the day in one of the many parks in the area, such as Giardini Pubblici and Parco Via Ruffilli.

Tuscan Sweet

Juicer

Private Parking

You can take your pick from Tuscany's best bits with a stay at this modern apartment. The historic towns of Val d'Orcia and the famous cities of Florence, Perugia, Siena, Arezzo, and Orvieto are all within easy reach. Set within the grounds of a 200-year-old farm estate, while little of the historic charm remains inside the home, the fuss-free interiors are well-suited to a family holiday. Outside, the private veranda with an alfresco dining set-up is tailor-made for evening meals. While over on the grounds, there's a communal swimming pool which you'll share with the thirteen other lodgings and an on-site bar to grab breakfast and obligatory sundowners.

Tuscany's Holy Grail

Ping Pong Table

Free Parking

This Tuscan farmhouse dates back to the 16th century. It’s been restored to maintain its historic charm, with a Leopoldine tower and the original stone and terracotta. The villa and annex – you won’t all be sleeping under the same roof here – sit within 2.6 hectares of parkland in the Tuscan countryside. Admire views of the town of Sinalunga from beside the swimming pool and in the oak-, olive-, and vine-filled garden. There’s an alfresco dining area in the shade of a pergola, with a barbecue and wood-fired stove to cook on. You can easily visit Montepulciano, Siena, and Florence from this rural Tuscan base. 

Embers & Sunlight

Playground

From traditional interiors to the typical Tuscan landscape, there's a lot to love about this villa. It dates back to the 18th century and was once home to an aristocratic family – and boy, does it show. Frescoed ceilings, antique furniture, and other original features add a sense of grandeur. Several bedrooms provide plenty of space for large groups. Outside, the extensive garden is home to tucked-away seating areas and a large swimming pool ideal for a summertime dip. Take a scenic stroll through the surrounding private park, or when you fancy an adventure, visit Arezzo or Siena – they're both less than an hour away by car.

Traditions of Toscana

Set in the heart of Tuscany, this home, featuring traditional Tuscan colours and exposed beams, has a lovely location on a 200-year-old former farm. There's a shared outdoor swimming pool and wine bar to enjoy at this resort. At the apartment, large arched doors open out to a private terrace with stunning views of the Tuscan countryside, while inside, whitewashed walls and beams keep the stylish interiors light and fresh. When you feel like exploring the area, the historic towns and villages of Val d'Orcia are within easy reach.

Tuscan Vineyard

Peaceful Tuscan retreats don’t get much better than this. This stunning home – spread between the main villa and an annex – is a special base in Italy, tucked amid the Tuscan Hills yet within easy reach of the art and culture of nearby Montepulciano and Pienza. This is a refined, stylish home designed to blend the antique and the modern. You can look forward to the villa’s original beamed ceilings and stone walls as well as a steel kitchen and contemporary features. We love the alfresco dining setup and the private infinity pool – it’s a breathtaking spot for admiring sunsets over Val D’Orcia. 

A Tuscan Rhapsody

Discover the Val di Chiana with a stay in this cosy homestead. Just 3 kilometres from the centre of Lucignano, you'll be well-connected to explore Arezzo, Montepulciano, and Siena. With a private, above-ground swimming pool, you'll also have plenty to enjoy back home, too. The lounge chairs in the garden are perfect for a snooze in the sunshine, while the terraces make excellent spots for alfresco meals. The design inside is contemporary with a touch of traditional Tuscan character. We think it works well for families and friends.

Chiana Charm

Surrounded by Tuscan countryside, this apartment is a comfortable base from which to explore the region. Spread over two floors, the kitchen’s fully-equipped and there’s a fireplace in the living room, which is ideal if you're visiting during the winter. Guests staying here have access to a communal pool and a wine bar. Plus, on-site reception staff are happy to assist with questions or queries. The rural location means you’ll need a car if you intend on exploring – Torrita di Siena is within easy driving distance. 

Tuscany Retreat

Smart TV

This home, composed of three suites and two cottages, sits on an exclusive estate just 1 kilometre from the historic centre of Montepulciano. It’s in a breathtaking spot overlooking a vineyard-filled valley, with the marvellous views visible from inside and out – the living room boasts floor-to-ceiling arched windows. The outside space is stunning, with a private pool and gardens filled with fragrant roses, fruit trees, and even a vegetable patch. We love the rustic touches that sit alongside modern amenities – you get the best of both worlds here. 

Sunflower Hill

Amazon Prime

Sonos

Bathrobes

Luxury Toiletries

Shared Washing Machine

Shared Dryer

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Electricity Adaptors

Printer

Workplace

Temperature Control

Accessible Parking

Umbrellas

This gorgeous house is nestled within the medieval hilltop village of Castelmuzio. The vibrant garden features cypress, fig, pomegranate and local flowers, with its own plunge pool and spaces for sunbathing and alfresco dining. There are three main suites, plus a single bedroom that shares an entrance and en-suite with one of the double rooms, making it ideal for families. It's a twenty-minute drive to the autostrada A1, and we do recommend hiring a car here if you're hoping to take a trip to the cities of Siena or Florence.

A Magic Touch

Parking On Premises

Basking in the Tuscan countryside, this home promises an escape from the daily routine. Sure, some of the bedrooms are a little bit of a squeeze, and the kitchen isn’t the biggest, but the home offers everything needed for a restful stay. Besides, with rolling countryside vistas and a private pool to cool off in, much of your time will be spent outdoors. Perfectly placed to explore the local areas by car, we’d recommend a trip to Pienza, just fifteen minutes away, to sample their famous Pecorino cheese. 

Beyond the Vines

Step-Free Access

Located on the border between the Val d'Orcia and the Val di Chiana in Tuscany, this 200-year-old farm has been transformed into a small resort village with fourteen homes. There’s a beautiful shared outdoor swimming pool to enjoy during the hot Tuscan summers and a wine bar for when you fancy a tipple (breakfast is also served here if you wish). Out and about, explore famous cities such as Florence, Perugia, Siena, Arezzo and Orvieto which can be easily accessed by car.

Transparent Skies

This beautiful home is perfect for celebrations and special occasions. The hilltop villa boasts panoramic views from Monte Amiata to Siena in the lap of Val d’Orcia, a UNESCO World Heritage Site. The restored stone property is a winery licensed for events, and with its terracotta floors, vaulted ceilings, and antiques, it’s bound to impress. There are multiple living areas and a professional kitchen, as well as a garden with stunning vistas and a gorgeous alfresco dining space. Whether you’re staying here for an event or just want an elegant home-from-home in Italy, this villa is sure to make for a memorable stay. 

Winery Way

Perched on a Chianti hillside, this expansive estate comprises the main villa and two beautifully restored barns – an ideal setting for large groups, retreats or unforgettable celebrations. From the terraces, you’ll enjoy views that stretch from Monte Amiata to Siena, with vineyards unfolding in every direction. Traditional Tuscan through and through, the interiors might not suit modernists, but for those drawn to character and heritage, it’s a dream. Outside, you’ll find a pool, alfresco dining areas and plenty of quiet corners for aperitivos. Your host can arrange everything from private chefs to wine tastings, too. Plus, with medieval hamlets, castles and thermal spas just a short drive away, there’s no shortage of ways to explore the region.

Chianti & Vines 

This hilltop villa offers panoramas from Monte Amiata to Siena and boasts sweeping vineyard views – what more would you wish from a stay in the Chianti region? Licensed for weddings, it's a magical setting for special occasions – just ask your host for details. The interiors lean traditional, perfect for those who appreciate classic Tuscan charm. That said, you’ll likely want to spend most of your time outdoors – taking dips in the pool, sipping wine on one of the terraces and gathering for alfresco meals – your host can arrange private chefs, too. And with castles, medieval villages, vineyards and thermal spa towns within easy driving distance, you’ll be spoilt for choice here. 

Classico Chianti

One of two three-bedroom apartments set within a traditional Tuscan farmhouse, it offers a welcome respite from the hustle and bustle of everyday life, overlooking the hilltop town of Montepulciano.

Despite its recent renovation, your hosts have done their utmost to maintain the period features that made this villa so special in the first place, so the original archways, exposed beams and wooden windows remain. However, stylish contemporary furnishings and a sleek kitchen bring it firmly up to date. All en-suite bedrooms complete the interior offering, each with views over the medieval town of Montepulciano, while guests staying in the main suite benefit from direct access to the balcony.

Vista a Montepulciano

Located in the heart of Tuscany, this resort apartment is well-placed for excursions across Italy's most famous region. While the home's interior is simple and certainly not the most luxurious in our collection, the creamy colours and windows mean it's awash in sunlight. The communal pool, open during warmer months, is the real highlight here, offering plenty of spots to enjoy the sun and views of rolling Tuscan hills. Resort living also means you can arrange a cooked breakfast and organise trips through the reception. Nearby, you can find the charming villages of Val d'Orcia.

The Rosemary Pit

Set within the grounds of a 200-year-old farm estate, surrounded by rolling Tuscan hills, the setting is picture-perfect. One of thirteen homes set apart across the complex, within the vast communal grounds, you'll find a swimming pool and on-site bar for sundowners. While the interiors of this home may not be as characterful as the farmhouse's exteriors, you'll love the sense of space. The home is spread across two floors, and there's a private terrace for barbecues. Location-wise, you're perfectly placed to explore Tuscany. The historic towns of Val d'Orcia and the famous cities of Florence, Perugia, Siena and Arezzo are all within easy reach.

Tuscan Lavender

Situated in the beautiful Val d'Orcia in Tuscany, this 200-year-old farm is the setting for fourteen lovely homes. There's a communal outdoor swimming pool to enjoy during the hot summer days and a wine bar where breakfast is served. The apartment itself has oodles of Tuscan charm and a private terrace area for watching the sunset with an aperitif. If you can tear yourself away, explore the gorgeous cities of Florence, Perugia, Siena, Arezzo and Orvieto, which can be reached by car.

Pops of Flowers

Book a stay in one of the best homes in Trequanda

We selected the 3106 homes worth renting in this location

Who's coming along?

Home spotlights in Trequanda

We selected the top 3% holiday homes in Trequanda

Most popular homes in Trequanda

Check upcoming rates & availability for Trequanda

Frequently asked questions