Certaldo

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Library of Books

Entertainment

Hair Dryer

Toiletries

Bathroom

Dishwasher

Freezer

Cafetiere

Kitchen

Oven

Stove

Kitchen Utensils

Fridge

Coffee Maker

Kettle

Kitchen & Dining

Hangers

Black-Out Blinds

Iron

Extra Pillows and Blankets

Bedroom & Laundry

Wi-fi

Desk / Workplace

Laptop Friendly Workspace

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Parking Available

Free Parking On Premises

Free Parking On Street

Private Entrance

Parking & Access

Garden

Outdoor Seating

Outdoor

Welcome Hamper

Nice to haves

Safe

Other

In a sleepy town in Tuscany, this breathtaking apartment is a unique find. Set in a former palazzo, it boasts classical Tuscan features like high ceilings, traditional archways, and a grand red brick exterior. Neutral colours inside contrast with the spectacular frescoed walls. We love the Rococo-style cherub fresco above the bed, lending the room a celestial aura. There is plenty of space to relax in the large open plan living area, and the fully stocked kitchen is perfect for practising your Italian home cooking. 

Certaldo Alto is a charming walled Medieval town, home to winding cobbled streets, picturesque churches, family run restaurants, and sprawling views of the verdant Tuscan countryside. It is 35km from Florence, making a day trip to the city easy. While you are there, be sure to sample some of the excellent wines from the region. After a day of exploring, kick back on the sofa in your opulent living room, before retreating to the serene calm of the bedroom for a perfect night’s sleep. With its romantic setting and unbeatable location, this would be the perfect getaway for couples. 

Fairytale in Fresco

Baby Bath

Cooking Essentials

High Chair

Microwave

Toaster

Private Washing Machine

Cleaning Products

Cot / Crib

Drying Rack

Ironing Board

Laundry Supplies

Vacuum Cleaner

Washing Machine

Swimming Pool

Wellness & Fitness

Desk

Electricity Adaptors

Fireplace

Multiple Sets of Keys

Balcony / Patio

Barbeque

Patio / Terrace

Sun Umbrellas

Pets Allowed

Pets

This Tuscan farmhouse is in a peaceful spot, nestled among olive groves and vineyards. The home consists of two apartments, each with its own entrance, garden, and patio, so is a great choice for a group – you can holiday together and still enjoy your own space. Carefully restored, the farmhouse retains many original features and is filled with antiques. Also, who could fail to be impressed by those countryside views? We think they're best enjoyed from the two private pools. When it comes to exploring, you’ve got Colle Val d'Elsa and San Gimignano within easy driving distance, and if you want to get off the tourist trail, your host is happy to suggest some hidden gems.

Groves & Vines

Outdoor Pool

Private Pool

Private Parking

Beach / Pool Towels

Sun Loungers / Beach Chairs

Mosquito Net

Child Friendly

Tucked into the vine-covered Tuscan hills, this home promises an idyllic escape from day-to-day life. Sure, the traditional interiors may not be everyone’s cup of tea, but you’ll find everything needed for a comfortable stay here and plenty of room to spread out and relax. The outdoor space is sure to become a favourite for the whole group, with sun beds, alfresco dining spots, and a private pool to enjoy. Ready to explore the local area? We recommend a trip to Certaldo. Here, you can take the funicular up to the old walled settlement or dine out on authentic Italian cuisine to your heart’s content. 

Olive & Grace

Temperature Control

Stair Gates

Set in the rolling Tuscan hillsides, with the towers of nearby San Gimignano in full view, the setting of this hilltop farmhouse is one-of-a-kind. Inside, the quietly elegant interiors allow the window's vistas to sing, and the mezzanine desk space will be handy for anyone planning to work. The other thing we love is the pool, and those established gardens and shady loggia for alfresco mealtimes are another perk. Location-wise, the medieval village of Certaldo Alto is a four-kilometre drive for evening meals and to pick up essentials. And when you're ready to hit the Tuscan city hotspots, jump on the train at Certaldo – you'll be there in no time.  

Gateway to Tuscany

Single-Level Home

If you’re seeking peace and quiet in the Tuscan countryside, this farmhouse surrounded by olive groves and vineyards is just the ticket. While the traditional interiors won’t be everyone’s cup of tea, we think they’re part of the charm. Outside, there’s a private garden overlooking the landscape, a shaded terrace for dining, and a small private pool. Although the rural location means having a car is essential here, you’re within easy driving distance of Certaldo and Emploi should you fancy embarking on a day trip.


Tuscan Mirage

Pod Coffee Machine

Ceiling Fans

Balcony

An extremely spacious Tuscan-style villa surrounded by acres of olive trees and vineyards, this place is ideal for exploring the countryside – and with its fairytale Italian charm, makes a very dreamy retreat too. 

Graze on a slice of local delicacy Torta Pistocchi beneath one of the many light gazebos scattered around and take in the idyllic views, before strolling across terracotta floors towards the pool. Nearby, you’ll find a brick barbecue just perfect for grilling up a delicious Tuscan steak and more than enough places inside and out to dine in style too. You’ll be spoilt for choice for verdant terraces to roam around, as well as cosy viewing stations dotted across the grounds.

If you’re keen to explore the surrounding area, there’s a range of wineries and vineyards within a ten-minute drive away, plus some stunning historical sights, such as the church Pieve di Santa Maria a Chianni, and the curious Medieval village of Certaldo.


Venus & Adonis

Piano

Ping Pong Table

Pool / Snooker Table

Bathtub

Espresso Machine

Exercise Equipment

Tennis Court

Courtyard

Hammock

Herb Garden

Pool House

Nestled away in the countryside outside the idyllic hilltown of San Gimignano, this extraordinary villa combines exquisite interior design and a sprawling collection of amenities to make for an address that is sure to win over even the most discerning of guests.

As you walk about the house for the first time, you might find it difficult to single out a favourite room. There's a timeless elegance to the dining room surrounded by floor-to-ceiling windows and centred around a grand piano, while the neighbouring kitchen is surprisingly modern in style and is sure to excite those with a culinary calling. 

And that's before we've even got around to the impressive grounds. On summer days, the swimming pool surrounded by leafy vegetation is sure to beckon, but there's also a wealth of peaceful spots out on the various terraces. As if that wasn't enough, guests are also blessed with a tennis court, which can be found about 500m from the home.

With this much to occupy you at the address, you just might never feel the need to leave, but San Gimignano – about 3km away – is well worth a visit. Don't just take our word, though –The historic centre is a UNESCO World Heritage Site. Both the cities of Siena and Florence are close enough to warrant a day trip, too.

One of the Greats

Dryer

Free Parking

Outdoor Shower

Carbon Monoxide Detector

Fire Extinguisher

Smoke Detector

In the hills overlooking the charming Tuscan village of Montaione, this two-bedroom villa is ready to welcome guests to an authentically Italian summer escape. With its modern interiors and comforting decor, guests will be charmed by the living and sleeping arrangements here – but the real highlight lies in the exterior. A large pool with sun loungers and umbrellas, multiple outdoor sofas and an idyllic alfresco dining table combine to make outdoor living a delightful experience here. When you’re ready to explore, Montaione is minutes away – from here you can plan excursions to San Gimignano, Volterra and San Vivaldo.

 The Hills of Montaione

Fenced Property

Situated in the heart of Tuscany, this home offers a peaceful retreat for families and friends. Set within beautiful gardens, there’s a private pool, shaded alfresco dining area and wonderful views over the countryside, as well as a slide and trampoline for the kids. Inside this home, there’s a traditional charm, with wooden beams and terracotta tiles. When you want to explore, this place is just a short drive from the town of Castelfiorentino – this home promises an unforgettable Tuscan experience.

Tuscan Olive Grove

Satellite / Cable TV

DVD Player

Sound System

Ice Machine

Nestled in the heart of the Chianti district and surrounded by vineyards, olive groves and cypress trees, this farmhouse couldn’t be more authentically Italian if it tried. Inside, the traditional style may not be to everyone’s taste, but its sympathetic renovation keeps the home's history alive – just watch your head on some of those low ceilings. Set on a 69-acre farm, you can even buy some of its specially-produced extra virgin olive oil, best sampled as part of an alfresco meal with loved ones. After all, with a private pool, sun-kissed terraces and countryside vistas, outdoors is the place to be. 

Lavender & Sunshine

Blender

Juicer

Private Dryer

Gated Community

Wheelchair Access

Garden Games

Umbrellas

First Aid Kit

The sprawling grounds of this Tuscan villa are home to woodland walks where you can spot birds, a big private pool for cooling dips and lots of different places to dine and unwind out in nature. Inside, the traditional decor won’t be for everyone – the kitchen feels a little dated, but it’s got everything you need for big group meals, and the ramshackle collection of sofas and armchairs is homely. There’s a ground-floor bedroom and bathroom adapted for accessibility, but the rest of the bedrooms are up a twisting stone staircase. Location-wise, it’s in the Chianti hills, surrounded by vineyards, and Florence is just a few kilometres away. 

The Hillside Escape

Hot Tub

This apartment, overlooking the beautiful vineyards of Tuscany, is situated in a historic palace that dates back to the 14th century. The place is packed with character, from the arched brick ceilings and terracotta tiles, to the chandeliers and antique furnishings.  Outside, the neat terrace is the perfect place to come together for lunch. Pick your spot at the table as tasty dishes are passed around and glasses are topped up with Chianti. Slip into the hot tub on cool evenings, with your favourite beverage in hand as a purple dusk falls across the landscape. And when it’s time to wind down, bedrooms strike a balance between elegance and comfort, so you’re guaranteed a restful night’s sleep. You’ll find this home in the small village of Marcialla, where family-run restaurants offering the very best of Tuscan cuisine are minutes from your doorstep. If you’d like to explore further afield, take to forty-minute drive into Florence for its world-famous sights – the iconic Galleria dell'Accademia, Duomo and Uffizi gallery await. 

Glass of Chianti

Shared Pool

Fusing Tuscan charm with contemporary design, this apartment nestled in a resort makes a fantastic base in the countryside. It's minimal, modern, and, most importantly, flooded with natural light. Pad out to the private terrace for drinks in the sunshine or stroll through the communal gardens to reach the shared swimming pool. Further afield, the towns of San Gimignano and Volterra provide plenty of opportunities for sightseeing, while the beaches of the Etruscan Coast are easily reachable within an hour's drive.

Stone & Linen

Smart TV

Self Check-in / Check-out

In the countryside just outside of the spa town of Gambassi Terme, this delightful villa looks out over the Volterra Hills. It’s peaceful and pretty, surrounded by typical Tuscan vegetation including cypresses, chestnuts, and olive trees. The well-kept garden – full of vibrant flowers and aromatic herbs – boasts a beautiful swimming pool, a lawn, and a gazebo for alfresco dining. The terrace is a splendid spot for sunset. Perfect for a couple of families travelling together, this home is spread between the farmhouse and the converted barn, so everyone can enjoy their own space.

Chestnut & Stone

Board Games

Games Room

Bicycles

Outdoor Fireplace / Firepit

This elegant home in Tuscany is in a dreamy spot in a valley, in a countryside setting that leads to absolute relaxation. The villa is full of character, with antique furniture and wooden beams, in addition to mesmerising views. 

The outside space is lush and pretty. Roses and lavender have been planted alongside a wealth of trees, making the garden feel like an oasis. In the morning, sip coffee at the table under the gazebo, admiring the views and planning your day. If you’re anything like us, you won’t be able to resist a dip in the hedge-lined swimming pool for long. Dry off on a sun lounger with a good book, or start a table tennis tournament with your friends. 

In the evening, set up outside at the long dining table. You might like to arrange for a local chef to come and cook for you – that way you can enjoy a cocktail hour on the terrace before dining as the sun sets beyond the valley. 

The villa is only a short walk along the river to the centre of peaceful Poggibonsi, so you can easily dine out in the local restaurants or grab a gelato. Montemorli vineyard is just a twenty-minute walk up the hill, while the medieval beauty of San Gimignano is a mere twenty-one-minute drive away. Slightly further afield, you can be in Siena in thirty minutes, and Florence in an hour.  


Verdant Valley

Foosball / Table Football

Nestled among the vineyards and olive groves of Chianti, this canary-hued 13th-century villa offers sweeping views as far as San Gimignano. Once a noble hunting lodge, it’s been lovingly restored with vaulted ceilings, terracotta floors and gilded paintings – plus modern comforts like air conditioning and daily maid service. One bedroom is named after Julia Roberts, a former guest, but the standout is the tower room with its own rooftop terrace. Outside, lush gardens surround a private pool and shaded terraces perfect for summer lunches. You’re on a working estate with wine, olive oil and honey for sale. And with Florence, Siena and hilltop villages all within easy reach, this is your gateway to the best of Tuscany.

Lady Julia

Just a short drive from historic San Gimignano and its iconic towers, this apartment is a delightful base for six. It’s on a complex in a stunning position close to vineyards and olive groves, and the views of the surrounding hills are breathtaking. You’ll have access to the shared pool, which is perfect for cooling off when the temperature climbs. The apartment is typically Tuscan in style, so you can expect exposed wooden beams and tiled floors. It’s rustic and full of charm. 

Ancient Hills

Once an old stone barn, this villa has been brought back to life and promises a serene stay in the heart of Tuscany. Sure, the traditional interiors may not be everyone’s cup of tea, but you’ll find all the key ingredients for a comfortable stay here. We love the outdoor space, with sun-kissed terraces, a private pool, and far-reaching views across the hills – what more could you want? Location-wise, San Gimignano is a mere stone’s throw away. A visit to this historic town, with its iconic towers, is a must. 

Love in Tuscany

Rain Shower

Conveniently located in San Filippo a Ponzano, a rural village on a hill in Chianti, from here you'll be within easy reach of Florence (a forty-five-minute drive away) and Siena (a thirty-minute drive away). Prepare to be blown away by the never-ending landscapes amidst fields of oak woods, vineyards, and olive groves upon arrival. 

Breathe in the fresh Mediterranean air as you spend your days making the most of the lavender fragranced garden. From the sun loungers by the swimming pool or over at the alfresco patio dining area shaded by the trees – you'll find plenty of places to enjoy a spot of relaxation surrounded by this heavenly setting. 

Inside the villa, the sparkling interiors unveil a charming space that invites guests to immerse themselves in an authentic Italian experience. Think antique furniture jewels, parquet flooring alongside terracotta floor tiles – each room is polished and accessorised to perfection. We particularly love the traditional yet homely feel presented in the bedrooms – many of which open out onto the second-floor balcony via huge French windows. The classic style bedrooms are complemented by the modern en-suite bathrooms, which ensure both comfort and practicality. 

A home that has preserved the very best of its traditional Italian roots, the admirable renovation work contrasts its traditional beauty with contemporary home comforts – required to ensure the space is in keeping with the current modern lifestyle and needs of its guests. 



Into the Olive Grove

Breakfast Included

This stunning Tuscan villa is perfect for groups of family or friends looking to unwind in style. The villa is tucked away in the beautiful Tuscan countryside, surrounded by trees and greenery so it feels a million miles from the hustle and bustle. Yet when you want to dine out or embark on a tour, you need only drive 8 kilometres to reach historic San Gimignano. There’s plenty to keep you entertained at the villa, too, with a private pool and a pergola that’s ideal for alfresco dining. Your host can even organise a private chef for you, so all you have to do is sit back, relax, and enjoy.

The Noble Hour

Surrounded by vineyards and olive trees in the Tuscan countryside, this apartment ensures a restful stay for a family or a group of friends. We loved the traditional features, particularly the exposed stone walls and the timber beams. Outside, there’s a dining table and chairs for alfresco lunches and a communal swimming pool for keeping cool in the summer. You’ll need to hire a car for stress-free exploring – the medieval city of Siena is less than an hour’s drive away.


A Touch of Tuscany 

Flooded with light, courtesy of the arched windows, this home is perfect for a couple’s getaway. Traditional in style, the main thing missing here is an oven – but isn’t that the perfect excuse to dine out on fine Italian cuisine instead? Outdoors, you’ll find generous gardens and a swimming pool, shared with the other residents, just perfect for soaking up the Tuscan sun. Ready to venture out? We recommend a trip to San Gimignano. Its famous towers are a must-see in the area, while the local restaurants will cater to your dinner needs. 

Heart of Tuscany

Sonos

Enjoy a scenic stay at this ivy-covered villa nestled between Florence and Siena. Rustic wooden beams, terracotta floors, and antique furniture inside evoke Tuscan tradition, while outdoors, lush gardens and a private pool offer sweeping views of the iconic Castle of Santa Maria Novella and the towers of San Gimignano. It's set on an estate, where a friendly caretaker lives on-site to help with any requests – though don't worry, you'll have plenty of privacy. Factor in the option to arrange cooking classes, breakfasts, wine tastings, and other exciting experiences, and it's no wonder it caught our eye. 

Wrapped in Ivy

Bike Shed

Fenced Pool

This beautiful home is one of a kind. It allows guests to experience Tuscan life in an authentic way, with everything you might need at your fingertips.

The apartment has been converted from the old barn of the farm, lovingly transformed into a traditional Tuscan home. You can look forward to wooden beams and shutters, antique furniture, and stunning views of the Tuscan countryside – it’s the perfect rustic escape. A fifteen-minute stroll will take you into the small country village of Vico d’Elsa, where you’ll find a fabulous pizzeria and a restaurant, as well as somewhere to stock up on groceries – ideal if you’re planning to cook on the barbecue. 

San Gimignano and its iconic towers are a twenty-two-minute drive. It’s a wonderful day trip – spend your time meandering around the narrow cobbled streets, stopping to enjoy coffee and gelato in a piazza, and soaking up the atmosphere of this historic town. 

Whether you spend your visit traversing the towns of Tuscany or prefer to stay close to home, you’ll be happy to have chosen this lovely spot. Sip lemonade by the pool as you recline in the sunshine and take in the view. Dine on the covered terrace, and admire the brightly coloured flowers dotted around the property. You’ll never want to leave. 


Tuscan Trees

Heated Pool

Nestled in the heart of Tuscany, this villa offers breathtaking views of the Val d'Elsa. A former barn dating back to 1620, expect to find plenty of character touches inside – we're talking 5-metre high ceilings, wooden beams, and even fossil shells contained in the external walls. Outside, the panoramic terrace is perfect for alfresco wining and dining. There's also a heated pool, where you can float the afternoon away and admire the scenery. Explore nearby medieval towns like San Gimignano, indulge in local delicacies with private chefs and cooking classes – your host can arrange them for a fee – and create unforgettable memories in this Tuscan paradise.

Elsa's Outlook

Heated Towel Rail

Fenced Garden

Situated in a small complex amid the Tuscan countryside, this pet-friendly home centres around a 13th-century tower. With a grand fireplace and stone arches awaiting inside, there's no better base for a fairytale holiday. While it's three to a bedroom upstairs and better suited to tight-knit families, the outdoor space gives everyone room to spread out. During the summer, your downtime will be spent enjoying poolside barbecues and lazing on the lawn. Maybe the historic setting will inspire a trip to the medieval town of San Gimignano.

Medieval Lullabies

Alarm System

Amid the olive trees of a private Tuscan estate, this home delivers an abundance of Italian charm. Dating back to the 1400s, you’ll be welcomed by a wonderful sense of character along with a range of comforts – including a private pool, hot tub and elegant rooms. Other highlights include the estate wine and olive oil, the nearby tennis courts and the open-air theatre held through the summer months (in the nearby woodland). It’s worth noting the grounds are shared with two neighbouring homes, but it still feels refreshingly private. You’ll also find this is a great base from which to explore the region – from here it’s just a forty-minute drive to Florence. 

Nature's Abundance 

The shared swimming pool takes centre stage at this Italian home. Surrounded by vineyards and olive trees, you’ll be treated to views of the Tuscan hills from the poolside. You’ll also have your own private garden area with a table and chairs – the perfect spot to enjoy an alfresco espresso in the morning or a sundowner in the evening. The traditional decor inside won’t be to everyone’s tastes, but we love the beamed ceilings and imposing fireplace here. The home is surrounded by 300 hectares of unspoiled nature, so there are plenty of opportunities for hiking on your doorstep, and if you want a slice of history, the medieval town of San Gimignano is within easy driving distance.

Tuscan Days

Jacuzzi

Early / Late Check-Out Available

Standing in the historic centre of medieval Poggibonsi, this home puts the centre of Tuscany at your fingertips. A short distance from Florence and Siena, you can venture out into the region's world-famous rolling hills for wine tasting from here, making it an ideal base for lovers of good food and drink. At home, the authentic Tuscan style, complete with frescoes, wooden beams and handcrafted furniture, make for a scenic backdrop as you relax in the evenings. And while the bathtub being in a bedroom might be inconvenient, it's still a perfect spot for unwinding.

A Dream of Tuscany

The small Tuscan village of Gambassi was once a famous spa destination, where the highest of Florentine nobility came for their rest and recuperation. You may not share a last name with 13th-century popes, but we think you’ll find blissful peace here all the same. This home, just outside the main village, is a platonic ideal of a rural idyll, with stone walls and arched doorways welcoming you into a traditional little farmhouse that’s renovated to include all the modern comforts. There is, of course, alfresco dining so you can appreciate the view of the hills over long family dinners, and the private pool is the perfect place to do a few laps or float beneath the high noon sun. 

Envelope For A Love Letter

Part of a sprawling villa in the Chianti region, surrounded by olive groves and vineyards, this home is the perfect place to relax. Having a car is a must here, especially if you want to visit Florence (36 kilometres) and Tavarnelle Val di Pesa (7 kilometres). Guests will occupy the right wing of the house, which is spread over four levels. While each bedroom is comfortable, the double room on the highest floor provides the best views of the countryside. Plus, there’s a fitness room, swimming pool and hot tub, and areas to dine or relax in the sunshine. 


Love in the Sun

Set in the Italian countryside and surrounded by vineyards, things feel like they haven't changed much in 200 years. Life is simpler here. Cool off in the private pool, before grabbing a space on the wrought-iron furniture near an old cart for glasses of Tuscany's finest or take in the panoramic vistas over the vineyards from the viewing platform.

Hearty meals can be cooked on the double stone barbecue or roasted in the cast iron oven. Gather everyone in to eat together around the long wooden table for a long, convivial dinner.
 
The living space is equally as charming, from the oak-beamed ceilings and polished wooden floors to the array of farming equipment which hangs on the walls. The bedrooms are simply done, with original stone arches and heavy shuttered windows that open out onto the expansive gardens. 

When you’re ready to explore, head to charming Colle di Val d'Elsa, a thirty-minute drive away or San Gimignano, fifteen minutes in the car.



Chardonnay Celebrations

EV Charger

Surrounded by olive and cypress trees, this home is the perfect setting to slow down and savour the magic of Italian living. Spend blissful days relaxing by the pool, sipping drinks on the terrace and dining under the stars. There’s plenty of space across the rooms to stretch out and socialise with two living rooms, an office and five cosy bedrooms. Your host is also on hand to help organise a range of extra services – including private chefs and guided tours. You will need a car to get around here, but it’s possible to drive to Florence for a day trip, while the nearest amenities are all within easy reach. 


The Sun Kingdom 

Playground

Projector

Bathrobes

With a spacious interior, plenty of period features and an inviting outdoor area – there's a lot to love about this recently renovated apartment, which is set within a traditional Tuscan farmhouse and purposely tucked out of the way in the gently rolling hills.

Thick stone walls, cool tiled floors, and exposed wooden ceilings lend this ground-floor residence a traditional vibe, while the gorgeous pool entices you to spend most of your days outside under the summer sun. In addition to the gorgeous shared spaces, the home also benefits from a private outdoor area where you're free to grill up gourmet offerings. Every meal here (except for breakfast... probably) will benefit from being accompanied by beautiful extra virgin olive oil and a mouthwatering medium-bodied chianti – all made by your host, Nicola.

Away from home, Montespertoli – one of Tuscany's renowned wine capitals – is just a five-minute drive, while the stunning Renaissance city of Florence is 35km away. No trip to Tuscany would be complete without at least one day spent exploring this bucket-list-topping destination. 

Wine in Your Water Glass

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