Certaldo

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

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

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

Satellite / Cable TV

Bathtub

Cooking Essentials

Espresso Machine

High Chair

Microwave

Toaster

Cot / Crib

Drying Rack

Ironing Board

Washing Machine

Outdoor Pool

Private Pool

Swimming Pool

Wellness & Fitness

Self Check-in / Check-out

Patio / Terrace

Sun Loungers / Beach Chairs

Mosquito Net

Pets Allowed

Pets

Child Friendly

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

Hot Tub

Fireplace

Balcony

Barbeque

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

Baby Bath

Rain Shower

Juicer

Cleaning Products

Shared Pool

Temperature Control

Bike Shed

Multiple Sets of Keys

Single-Level Home

Fenced Pool

Outdoor Fireplace / Firepit

Umbrellas

Fire Extinguisher

First Aid Kit

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

Vacuum Cleaner

Desk

Balcony / Patio

Sun Umbrellas

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

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

Blender

Private Washing Machine

Private Dryer

Dryer

Private Parking

Free Parking

Gated Community

Wheelchair Access

Garden Games

Hammock

Outdoor Shower

Carbon Monoxide Detector

Smoke Detector

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

Piano

Ping Pong Table

Pod Coffee Machine

Tennis Court

Exercise Equipment

Ceiling Fans

Courtyard

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

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

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

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

This apartment shares its location with a family-run farm in pretty Montespertoli. The family produces wine and olive oil from a picturesque spot amid the gentle Chianti hills, surrounded by vineyards, olive groves and woods – it’s delightfully rustic. 

The apartment sits within these grounds, benefitting from the large garden and beautiful views. It has its own private garden too, just off the bedroom – the perfect romantic setting for a glass of wine and some stargazing. Traditional features like stone walls and a terracotta floor add to the romance of the apartment, as does the four-poster bed. 

When you’re not exploring the surrounding woodland and countryside on foot, you might like to venture further afield to take in more of wonderful Tuscany. The medieval town of San Gimignano is forty-one minutes away by car, and it takes forty-seven minutes to get to Siena. Wander through these historic towns with a gelato, taking in the architecture and shopping for keepsakes. When you return to the apartment, enjoy an alfresco dinner while admiring the view – it's the ideal way to round off your day. 


A Glass Of Chianti

Nestled on the ancient walls of the watch tower in a restored farmhouse, this home promises a tranquil escape in the Tuscan countryside. With a communal swimming pool and gardens, it’s easy to make the most of the Mediterranean climate – and this apartment boasts a private patio and courtyard, too. The traditional interiors showcase the home’s past, and while there’s no oven here, you can whip up light bites in the kitchen. Locally, it’s a short drive to San Gimignano – perfect for dining out, and a visit to its famous towers is a must. 

A Tuscan Soul

Located on a small family-run farm in Montespertoli, nestled in the gently rolling hills of Chianti, is this ‘Forno’ brick-style Italian home. Start your first evening here with the bottle of wine from your welcome basket which has been produced on the vineyard here, as you enjoy the incredible views from your private garden. Then, when you wake the next day, start your morning with a sugary sweet coffee – also provided in your welcome basket – before you relax in a deck chair with a good book. 

For those who love walking or cycling, this beautiful setting provides the perfect area for exploring, as the farm is surrounded by vineyards, olive groves and woodlands that you can wander freely. In the early evening, we would love to stop at the shaded terrace overlooking the large gardens to taste the farm’s wines, while admiring the view of the surrounding hills. 

Then for dinner, why not take advantage of the barbecue, and cook some delicious Spiedini skewers, to enjoy in Italian alfresco style with a glass of refreshing wine, accompanied by the fantastic vista on offer. When you retire inside, the home’s natural elements of stone walls, terracotta floors and wooden ceilings will keep the rooms pleasantly cool in the summer and warm in the winters, while the twentieth-century furnishings provide comfort for relaxing hours before bedtime. 

Chianti Cheers

Smart TV

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

Nestled in a restored farmhouse in the heart of the Tuscan countryside, this apartment is the perfect place to immerse yourself in nature. Tailor-made for two, the traditional interiors may not suit everyone, but the classic four-poster bed is sure to bring a smile to anyone’s face. With no oven here, the kitchen is best suited to light bites – but all the more reason to dine out locally on Italian cuisine. On days not spent lounging by the communal pool, a visit to nearby San Gimignano to see the iconic towers is a must.

Stone & Vine

Boasting floor-to-ceiling windows that make the most of the surrounding Tuscan countryside, this cosy villa is perfect for a small family or group of friends. Set on a complex alongside other villas and apartments, you can enjoy the communal swimming pool and gardens here – but, as a bonus, this home also has a private terrace. Its traditional style may not tick everyone’s boxes, and there’s no oven here, but with San Gimignano a short drive away, dining out is sure to be on the menu – as is a visit to the town’s famous towers.

Sunset in the Hills

Tucked away in the vineyards and olive groves of Chianti, stands this old brick farmhouse. This apartment is located on the ground floor, with private access to a hideaway garden. Just you and the Cypress trees. Ancient brick takes over the walls of this home, wooden beams line the slanted ceilings, and terracotta stone sweeps over the floors. This little haven is how Tuscan living should be – rustic, traditional, and stripped back, with gorgeous views, wine, and olives to keep you entertained no end.

Waking up here is a little slice of heaven. Enjoy a coffee on the large terrace which overlooks the rolling Chianti hills. Spend a lazy morning switching between here and your private garden, from sunbathing to daydreaming. You're encouraged to roam the grounds of this beautiful farmhouse, including its own vineyards and wine groves. Come the afternoon, explore the medieval village of Montespertoli – you're just a thirteen-minute drive from the centre. It's considered one of the wine capitals of Tuscany, perched on a hilltop, overlooking miles upon miles of vineyards. Speaking of which, you're not short of vineyards and wine tours. For something different, a cycling wine tour is a great way to see the area while tasting some fine wine along the way. Tuscany Wine and Bike offer exactly this – they're based in the heart of Montespertoli, so you can reach them easily. Round off the day with a hearty meal in the village centre, or head back to grill something delicious on the outdoor barbecue. Enjoy your new favourite local wine and watch the golden sun dip behind the hills.

Oliva Farmhouse

This beautiful home in Tuscany is rich in history. The apartment is part of an estate that dates back to the 11th century when it was a defense watchtower for the castle of Santa Maria Novella. It’s been lovingly restored so the apartment is packed full of charm, as well as being a comfortable and convenient place to stay. 

The apartment is set in a park of oak trees, with sweeping views of the rolling countryside all around. It’s at the heart of Chianti so there are many vineyards in the countryside surrounding the home – it would be almost rude not to sample some of the region’s most famous export. Azienda Agricola Montefioralle is a winery thirty-one minutes away by car. Take a tour of the vineyard, partake in a wine tasting, and maybe stay for lunch – it’s a lovely way to spend an afternoon. 

Despite the rural setting of this home, it’s still easy to get out and explore Tuscany. Florence is a thirty-seven-minute drive away, and it’s well worth the journey. Set out early and make a day of it – walk up to Piazzale Michelangelo for the views, admire the wonderful art of the Uffizi, and dine on some of the best food in Italy. 

Back at the villa, don your hiking boots and set out on foot to explore the countryside. If that’s a little too active for your tastes, take a seat on the terrace and breathe in the views from there. Sunset from this vantage point is particularly striking. 


Chianti Country

DVD Player

Sound System

Ice Machine

Beach / Pool Towels

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

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 

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

Combining African influence with old-world Tuscan charm, this countryside villa is a laidback retreat in the rolling hills. The architecture is very much traditional Italian, with arched French doors and sash windows that look out over golden fields lined with cypress trees. Interiors are inspired by Africa, as prints and musical instruments hang on walls. Spend days in the large gardens, which have a swing and paddling pool for little ones. Big kids can fire up the barbecue and relax on the large oak table. The home is also in an excellent position for exploring the region, with medieval towns and vineyards only a short drive away.

Mambo Beats

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

Tucked away in the countryside, surrounded by vineyards and olive trees, this apartment is the rural retreat you’ve been searching for. Sure, its traditional style may not suit everyone. In addition, the kitchen is basic – so don’t expect to be whipping up huge family feasts. That said, it’s all the more reason to indulge in delicious local cuisine – just head to San Gimignano. And, with a communal swimming pool and gardens, this home is the perfect place for basking under the Tuscan sun in pure peace. 

Marble & Olives

Laundry Supplies

Electricity Adaptors

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

Vineyards stretch as far as the eye can see at this Chianti villa. Settings rarely get more picturesque than this – we can already picture lazy afternoons by the private pool and alfresco drinks on the covered terrace, all while admiring the views. Inside, you'll find plenty of 17th-century charm, including a brick domed ceiling in the bathroom and an ornamental fireplace that housed the estate's former furnace. You'll have double the space here, too, since the home is two separate apartments. Location-wise, it's halfway between Florence and Siena, so the possibilities for day trips and adventures around Tuscany are endless.

Vine & Blossom

Ground yourself in the extraordinary landscapes of Chianti at this elegant apartment set on a farm estate and yet just a fourteen-minute drive from the charming medieval town of Montespertoli.
 
Belonging to a multi-generational family farm, this place brings all the Tuscan farmhouse charms you're chasing with cool terracotta floors, exposed stonework, and lofty wooden beams. An excellent choice for a couple or small family sharing, the elegant bedroom sleeps three with a sofa bed tucked away in a cosy corner that's perfect for a child.
 
But it's outside amidst the vast vineyards, olive groves, and woodlands where we think you'll be spending most of your time. While away the afternoon in the apartment's private garden – there's everything you need to rustle up a feast in the sleek, modern kitchen when thoughts turn to food. And if you fancy a glass of the local grape, you've come to the right place. Book a wine tasting session on the estate to savour the fruits of the harvest – the extra virgin olive oil and wine are exceptional.
 
When it's time to change up the pace, Florence and Siena are just a forty-minute drive for your cultural fix. Or pack up a beach bag and head for the sea – the Tyrrhenian coast is just a scenic one-hour drive away over the rolling hills.


Into the Groves

Fenced Property

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

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

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

Netflix

Blu Ray Player

Board Games

DVD Library

Home Cinema Setup

Streaming Services

Baby Changing Mat

Children's Dinnerware

Shared Dryer

Luxury Bedding

Printer

Buzzer / Wireless Intercom

Early / Late Check-Out Available

EV Charger

Video Intercom

Throws

Safety Gates

You might think that you have to pick between homes that respect tradition and those that embrace more contemporary design, but villas such as this one in the Florentine countryside show that you can have both if you choose wisely.

Step behind the front door and you'll spot some of the rustic features common in the region's homes, be that wooden ceiling beams, stone archways or the large fireplace in the lounge. However, the glisteningly modern kitchen packed full of appliances will be a treat for the culinarily gifted among guests, and the bathrooms are equally as easy on the eye.

Perhaps the most striking recent addition to the address lies beyond the four walls in the shared garden – it's remarkably easy to picture long afternoons spent gliding through the swimming pool before drying off on a lounger under the Tuscan sun. The picturesque outdoor space is completed with a ping pong table and a private terrace on which to enjoy alfresco feasts.

The location is certainly secluded, but there's a shop 400 metres from the front door and a restaurant another 200 metres beyond that. You're more than welcome to spend your time exploring the local Poggiosole region, but the city of Florence takes about half an hour in the car to reach and rewards those that make the journey with some of the most famous artworks in the world.

A Midsummer Daydream

Book a stay in one of the best homes in Certaldo

We selected the 3080 homes worth renting in this location

Who's coming along?

Home spotlights in Certaldo

We selected the top 3% holiday homes in Certaldo

Most popular homes in Certaldo

Check upcoming rates & availability for Certaldo

Frequently asked questions