Castiglione della Pescaia

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Satellite / Cable TV

Entertainment

Hair Dryer

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Bathroom

Blender

Coffee Maker

Dishwasher

Espresso Machine

Freezer

Fridge

High Chair

Juicer

Kettle

Kitchen

Kitchen Utensils

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Oven

Stove

Toaster

Kitchen & Dining

Cot / Crib

Drying Rack

Iron

Ironing Board

Washing Machine

Bedroom & Laundry

Laptop Friendly Workspace

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Free Parking

Parking Available

Private Entrance

Self Check-in / Check-out

Parking & Access

Barbeque

Garden

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Patio / Terrace

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Mosquito Net

Nice to haves

Pets Allowed

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Child Friendly

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For a peaceful garden retreat close to the coast, look no further. Bright and welcoming, this colourful home has a beach-house vibe, which is fitting – the beach is mere moments away. You’ll also be just 2 kilometres from the little town of Castiglione della Pescaia, which you can reach on foot or by bike. When you’re not out exploring or splashing in the surf, you’ll likely spend most of your time in the garden. Doze on sun loungers before dining alfresco in the shade of the portico, or unwind inside. The villa is contemporary and cheerful, thanks to bold splashes of colour. 

Pine Shade

Smart TV

Bathtub

Rain Shower

Cooking Essentials

Outdoor Pool

Private Pool

Sauna

Swimming Pool

Wellness & Fitness

Sun Loungers / Beach Chairs

Nestled in the Maremma countryside and surrounded by olive groves, a mere four kilometres from the beach of Castiglione della Pescaia, this charming villa waits to welcome you home. It’s worth noting that the keeper lives on-site in a separate home near the entrance gate, and there’s an annexe on-site for the exclusive use of the owner, but don’t let that detract from everything this home offers. With a poolside gazebo that boasts a living area, dining area and kitchen, an outdoor gym, and a basement floor dedicated to wellness with a sauna, reaction tub, and another living space, there’s something for everyone here. 

Olive Delight

Private Parking

Fenced Property

Immerse yourself in the beauty of southern Tuscany with a stay in this home near the picturesque town of Castiglione della Pescaia. Surrounded by a dense pine forest, you'll be just a short walk from sandy beaches and an easy drive from shops, restaurants, and Grosseto. The terrace calls for alfresco breakfasts and evening sundowners, while the coastal-inspired interiors are the essence of calm. It has everything you need for a relaxing stay, including air conditioning, private parking, and a cot and high chair for little ones.

Wave & Pine

Netflix

Board Games

DVD Player

Sonos

Sound System

Streaming Services

Heated Towel Rail

Luxury Toiletries

Ice Machine

Rice Maker

Dryer

Extra Pillows and Blankets

Hangers

Vacuum Cleaner

Bicycles

Desk

Printer

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Gated Community

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Balcony

Beach / Pool Towels

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24-Hour Front Desk

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Safe

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Smoke Detector

It might not look it, but this home is just a short walk from a private beach in Roccamare. Nestled in a tranquil pine forest, the villa is made for beach days with family or friends – on the shoreline, you'll have access to a private cabana with a dining table and a separate cabin, perfect for storing beach equipment. Cool off in your private pool, shaded by the surrounding pine trees, or relax on a deck chair in the garden. The spacious outdoor sofa is the perfect spot to gather for drinks in the evening, while the sleeping arrangements are ideal for little ones – we particularly love the five-person bedroom and double bunk beds. While there's plenty to occupy your time with here, you're also just a short drive from Follonica.

Quiet & Serene

With a private pool, sunny garden, and access to Roccamare's long sandy beach, this villa has outdoor living written all over it. Even with its traditional appearance inside, it feels like a true getaway, especially since it's surrounded by a pine forest. The many terraces are perfect for catching rays (or enjoying a sundowner or two), and though the pool is only open from April to October, it's ideal for spending lazy days at home. When you fancy an adventure, you're just steps from the beach – plus, Castiglione Della Pescaia is about a 5-kilometre drive away.

Tuscan Pine

Balcony / Patio

This clifftop villa caught our eye for its views across the Tyrrhenian Sea. Located in the coastal town of Punta Ala, you’ll have direct access to the water, via steep private steps from the garden (the trek back up isn’t for the faint-hearted). There are two living rooms here (although the design may not be everyone's cup of tea), and all of the bedrooms are en-suite, so it’s a great option for a group. We love the outdoor spaces most of all – you’ll have a choice of spots to enjoy a morning espresso, alfresco lunch, or sundowner while admiring the panoramas. Location-wise, you'll find a beach, a golf course, and Punta Ala Marina all within a few minute's drive.

Two Seas

Ping Pong Table

Single-Level Home

This beautiful home is nestled amidst a lush pine forest, just a stone's throw from the Punta Ala Equestrian Centre, the Punta Ala Golf Club, and the beaches, so there’s plenty to keep you occupied during your stay. Comfortable for an extended family or large group of friends, this villa invites relaxation. We love the outdoor space, with covered dining areas and sofas, centuries-old holm oaks, cypresses, and strawberry trees, and of course, the centrepiece – the private pool. When you’re ready to explore, we recommend visiting the beaches of Cala Violina and Castiglione della Pescaia, or discovering inland villages like Tirli and Massa Marittima.

Maremma Muse

Library of Books

Mini Bar

Jacuzzi

Early / Late Check-Out Available

Helipad

Outdoor Bathtub

Sun Umbrellas

Breakfast Included

This unique home offers an unparalleled escape to a private island in Tuscany, where the sea sparkles and time slows. Once a lighthouse, it's been beautifully restored, blending historic character with effortless luxury. You’ll step into a bright living room with cosy seating, a library of lighthouse tales, and a spiral staircase leading to the terrace. Here, the en-suite bedrooms open onto a private space with parasols and loungers. The on-site chef curates every meal with fresh local produce, allowing you to truly kick back and relax. Days are made for basking in the sun, soaking in the hot spring tub, paddleboarding, snorkelling, or quiet reflection under the stars. To reach the island, you'll need to purchase a dinghy or helicopter taxi service, but it's absolutely worth it for the seclusion, beauty, and unforgettable experience.

Lighthouse Island

Hot Tub

Lift Access

Whitewashed and modern with unbroken views of rolling hills, this villa is the perfect gathering place for a family or group of friends looking to unwind in style. Inside, it’s all glass walls and minimalist spaces, while the outside area is a fanfare of colour with evergreen shrubs and blooming flowerbeds. 

Gather together for tasty Italian-inspired lunches on the covered terrace – grill local produce on the barbecue or whip up dishes in the fully-equipped kitchen. When the sun reaches its highest point, cool off with a swim in the secluded infinity pool or find a shady spot with an ice-cold drink. 

In the late afternoon, take the twenty-five-minute stroll down to Maga Alpa – or jump in the car, it’s only a three-minute drive. Explore the pine forest before stretching out on the golden sands and swimming in the glittering Mediterranean. Return home in the early evening to watch the sunset from your balcony followed by a serious pamper session in your private wellness room.

Bellissimo

Baby Bath

Cleaning Products

Desk / Workplace

Free Parking On Premises

Free Parking On Street

You’re 300 metres from the sea at this charming apartment in Marina di Grosseto. The neo-classic streets of this coastal town are filled with seafood restaurants, pizzerias and waterfront bars, all within walking distance from the apartment, as well as the lounger-lined soft sand of the beach. Just behind the apartment, there’s a pine forest for shaded walks. If you want to explore the local area, your host can arrange vineyard tours, horseback riding and canoeing on the Ombrone River.

The private terrace is the best spot for a cold drink in the evening, with its lounger chair and wooden dining table in the shade. Step through the French doors into the open-plan living area where painted floorboards and driftwood sculptures are a reminder of your seaside locale. We love the nautical design touches and palette of sand and forest green. The sleek, dine-in kitchen has all you need to whip up breakfast, lunch and dinner and boxes brimming with toys lets you know this place is family-friendly. There’s also a vast garden, shared with one other home, with a kids’ playpark and barbecue area. 

Seaside & Pine Forest

Pod Coffee Machine

Courtyard

If you love the artsy side of life, you'll thrive in this contemporary loft. Colourful art pieces stand out, with some splashes of colour added by the feature walls. Natural light pours in through the large kitchen windows – the perfect chance to watch the morning birds fly by. You even get a lovely view of the courtyard from the bedroom too. 

Spend the day at Constanti winery – this is where your host works, so she will be more than happy to give you a tour of the place. Beautiful vineyards surround the loft and a wide range of wineries to sample some of the tastiest glasses of red.

Return home to sit at the dining table while the scent of a home-cooked Italian meal fills the room from the nearby kitchen. After you've eaten, pick a book off of the shelf, and snuggle up on the sofa while the moonlight shines through the windows. Pop the TV on for background noise or simply enjoy the peace and quiet that Montalcino brings.

Artistic Grapes

Amazon Prime

Throws

This charming apartment is in the old town of Colle di Val d'Elsa, a typically medieval region of Tuscany famous for crystal glass production. It’s a ten-minute stroll into the centre where you’ll find restaurants, cafés and archaeological museums beyond the ancient town walls. Further afield, the city of Siena is a half-hour drive away, ideal for a day trip.

The apartment itself is housed in a striking 16th-century building just outside the bridge that leads to il Castello. Wood beams on display hark back to the building’s roots, but the decor is decidedly modern. Vibrant modern art is displayed above the plush, L-shaped sofa and the kitchen is a sleek space of white cabinets. The best bit is the view from French-style windows, which shows off golden fields and hills, even though you’re a short walk from the town centre.

Beyond the Bridge

Perched above Punta Ala's marina, this apartment offers stunning views. Our favourite spot to soak up the scenery is on the terrace. Though the furniture could use a refresh, the panoramas pair perfectly with a glass of wine. The design inside pays homage to the coastal setting, with shades of blue and wicker accents. It's a little dated but no less comfortable. When you're ready to venture out, the sea and beach are a short walk away.

Sunrise at Sea

Cafetiere

Security Cameras

​​Restored by an Italian architect with a gentle touch, this villa has been updated and split into more modern apartments, but without ever compromising on the original charm. By honouring the villa's history – and thereby retaining its character – the home feels traditionally Tuscan with its terracotta tiles and wooden beams. Walk barefoot across the floors to savour the coolness of those tiles on hot days, or light a fire in the wood-burning stove and stare up at the beams, imagining what life would’ve been like here. Nonnas rolling out pastry for tortellini, children helping churn gelato, wine flowing, and bowls of food changing hands in a celebration of ingredients, and life. You might even wish to recreate that – a holiday well spent.

Alternatively, spend lazy afternoons sitting under the vines outside as you watch the sunset on the horizon. Head out to authentic Italian pizzerias for pizza and gnocchi, or make a gelato run before exploring the surroundings. 


Bellissima Casa

Games Room

Outdoor Fireplace / Firepit

Umbrellas

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

Shared Pool

Just a sort drive from the beach at Follonica, this home is ideally located for a laidback coastal getaway. You’ll also have access to a communal swimming pool with beautiful views across the neighbouring 18-hole golf course. There are peaceful gardens and you’ll have a private terrace for alfresco dining and drinks. You will need a car to get around here, but it’s just a short drive to the hilltop town of Massa Marittima where you can stroll ancient streets and soak up the magic of Tuscany. 



Follow the Moment

This charming apartment is nestled in the picture-perfect village of Suvereto. Cute and cosy, it's ideal for couples looking for a romantic getaway, or a solo traveller who wants a tranquil base when exploring the wonders of Tuscany.

Step inside, and you'll find a gorgeous space that reflects its rustic location perfectly. There are plenty of traditional touches, from the exposed brick and wooden ceiling beams, to the distressed wood dining table. Pick up some local ingredients, and practice your Italian-style cooking in the kitchen – it's a homely space where you can whip up the perfect risotto. When you've finished eating and sipping some Pinot Grigio, you can get comfortable in the peaceful bedroom, for a restful night's sleep. 

Although petite, Suvereto is packed with cultural delights. Wander through the labyrinth of passageways dating back to the medieval era, and stop off in the family-run restaurants for delicious pasta and pizza. Don't miss the Aldobrandesca Fortress and the beautiful Romanesque church, both just a few minutes away from your front door. A twenty-minute drive will bring you to the Etruscan Coast, with its hidden coves and pinewood forests – so, whether you want to lie on a beach or take an invigorating hike through the woods, you'll be very happy here. 

Cracked Black Pepper

Tucked away in the Tuscan countryside, this villa is just the spot to switch off and relax. We love the seamless blend of traditional and modern and the opportunity to find space for socialising or solitude. The outdoor space is sure to be a firm favourite – with a private pool, sun-kissed terraces, ample opportunity for alfresco dining and far-reaching views, it’s not hard to see why this home caught our eye. When you’re ready to explore, the local village of San Sano has a restaurant and small grocery store, or you can hop in the car for a trip to Siena. 

Terracotta & Vine

Workplace

This marvellous Tuscan villa is perfect for groups eager to sample the unique delights of the Chianti region. Set back from civilisation in the region's rolling hills, up to eight guests can rest comfortably across four en-suite bedrooms, or wander the expansive grounds dotted with trees and surrounded by olive groves. Inside the villa's stone walls you'll also find an abundance of regional charm, including terracotta floors, exposed beam ceilings, a pizza oven, and elegant living areas. However, arguably the jewel in its crown lies outside, in the form of a dazzling hillside infinity pool. And with the town of Gaiole in Chianti close by and the city of Florence around an hour away, local delights go far beyond wine.

The Chianti Hills

Tee off in Tuscany at this home on a golf resort in Grosseto. Perched on the edge of an 18-hole course, you can also take advantage of the complex's shared swimming pool, clubhouse, and restaurant. The gardens are part communal, but a private patio is tucked behind hedges and makes for a sweet spot for alfresco dining. Inside, the interiors are contemporary and cosy – there's a sleek kitchen, a small office ideal for remote working, and a fuss-free living area. Fancy a change of pace? Wander the ancient streets in nearby Massa Marittima, drive twenty minutes to Follonica's beach, or set sail to the Tuscan isles from Piombino or Punta Ala.

Tee Time in Tuscany

In the heart of the Val d'Orcia, this villa offers sweeping views as far as the eye can see. Montepulciano, San Quirico d'Orcia, and Seina further afield are all within driving distance – and all make great options for days out and about in the countryside. But even better than the location is the garden waiting for you back home. There's an ivy-covered pergola ideal for alfresco dining, a private pool overlooking the vineyards, and swings to keep little ones entertained. Inside, modern comforts blend with traditional character. Every bedroom has an en-suite bathroom, making this ideal for families or friends.

Sunflower Sunset

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

Exercise Equipment

Built in local stone, this renovated home is packed with character features, such as chestnut wood beams and handcrafted terracotta floors, which blend with modern luxuries. There are two living rooms here and there’s an exercise room which is on the lower floor. Outside, there's a dining area, a pergola with an alfresco lounge and an infinity pool with panoramic views of the Tuscan hills. Location-wise, this home is a short drive from the thermal springs of Terme di Saturnia. The beaches of the Tyrrhenian coast, such as Giannella Beach, are also reachable in around half an hour by car.

Tuscan Valleys

Nestled in the Tuscan countryside, this villa is a place for a family or group of friends to spend quality time together in the sunshine. From the hanging chair to sun loungers, the outside space offers ample opportunities to enjoy the views. Plus, there’s a covered terrace for alfresco dining. The sleeping quarters are on the lower ground floor with direct access to the garden and pool (something to keep in mind if you’re staying with young children), and the main bedroom has an open-concept en-suite, which may not be to everyone’s taste. If you fancy a change of scenery, the town of Castel del Piano is a short drive away.

The Italian Rose

This villa is a rural oasis just south of Siena in the peaceful countryside, surrounded by woodlands and hills with panoramic views of Montalcino and Monte Amiata. You're just 24km from the charming city, while the Tuscan coast and Florence are also just over an hour's drive away, making it the ideal destination for those wanting to explore the area. The villa provides plenty of outdoor living space, including an alfresco dining area, a shaded lounge space and a poolside deck with a private pool. Inside, a bright and spacious living area with traditional features awaits you, as well as a country-style kitchen and five welcoming bedrooms, benefitting from wood beams and exposed brick. 

The Olive House

Offering views of the surrounding hills and the owner's vineyard, this eco-friendly villa is set within the Chianti countryside. While the interior is fairly subdued and the unpaved road leading here isn't the best drive, this home promises a paradisal outdoor living space. You'll find a poolside dining area and a hot tub in the garden, plus you can enjoy fresh produce from the chicken coop and vegetable patch. Exploring Tuscany? Gaiole is two kilometres away, and Radda is eight.

Tuscan Idyll 

Lounge by the lavender-edged 18-metre lap pool with its beautiful views of the forested hills and distant hilltop village of Castagnoli. You can’t see the pool from the house, as it's 70 metres down a track, past the owner's villa – but once there, it’s a sight to behold. Or relax on your terrace or balcony in the private garden. It’s the perfect spot for an Italian feast cooked on the barbecue or rustle up something in the kitchen on the first floor with its marble worktops. If you need to top up on ingredients, then Gaiole, 4 kilometres away, has a selection of shops, as well as restaurants, while the nearest village, Barbischio, 1 kilometre away, has a superb trattoria. 

The Vines of the Vineyard

Perched on the edge of Monte Argentario, this adults-only retreat sets the tone for blissful Italian getaway. Occupying the first floor, the apartment boasts stunning views which you can admire from the large terrace. Head inside and you’ll find the living room and bedroom come equally impressive views and all the essentials you could need to relax and unwind. And when it comes to explorations further afield, you can follow the steep steps down to the sea or the hidden beach. It’s also just a short drive along the coast to Porto Santo Stefano. 


The Sweet Heart

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind. You can enjoy access to the shared swimming pool and there are plenty of spots where you can sit back and admire the views. It also makes a great base for exploring this beautiful region. From here, its a short drive to the local villages of Lecchi and San Sano, while Siena and Florence are also within driving distance. 

Chianti Sunrise

You’ll find this restored Tuscan farmhouse nestled in the Livorno countryside, surrounded by hills and woodland – it’s a true escape back to nature. With interiors that seamlessly blend a contemporary style with the traditional bones of the house, it’s a welcoming retreat for large groups of family or friends. Outdoors, the private pool, shaded dining spots and sun-kissed terraces provide the perfect place to gather together and socialise. Locally, the small town of Gabbro, boasting a range of shops and restaurants, is just three kilometres away, or you can drive a little further to explore Castiglioncello, Livorno or Pisa. 

Sweet Skylark

Private Washing Machine

The quintessential Tuscan villa, this hillside four bedroom home looks out over the verdant Val d'Orcia. Ideal for families or friend groups seeking an authentic taste of Italian country life, the house sleeps eight and offers plenty of space for work, rest and play. More active guests can explore the sweeping grounds, play table tennis in the second living area, or cool off in the shared pool. Meanwhile, those seeking tranquillity can settle on a sun lounger, dine out on the terrace, or refine their cooking in the eye-catching wooden kitchen. The historic city of Siena lies 10km away, where the hectic Il Palio horse race turns the streets into a bustling festival twice a summer.

Siena Charm

DVD Library

Bathrobes

Black-Out Blinds

Stair Gates

Nestled among the lush greenery of an expansive 1,000-acre private estate, this beautifully restored stone villa is ideally located to allow you to enjoy the ultimate holiday with your family or a group of close friends. Picture yourself serenely floating in the infinity pool while taking in the view of the rolling Tuscan hills below. Imagine sipping a medium-bodied Chianti and tucking into fresh pasta on the sun-drenched terrace while waiting for the Instagram-worthy sunset. There are a couple of barbecues, so you can always indulge in plenty of Florentine steaks if you get weary of pizza and pasta (is that even possible?). When you've had your fill of sumptuous Italian fare, play your favourite tunes on the Bose sound system and chill out with some board games by the fireplace. If you feel like you might have over-indulged, fear not. You can keep up your workout regime by sweating it out in the fitness room or hiking through the surrounding countryside. The medieval village of San Gusmè is a mere five-minute drive away, while Siena is a 30-minute trip from your villa, in case you want to do some shopping or sightseeing. Your host provides a complimentary concierge service, too, so that all your holiday whims will be taken care of. Before long, you'll feel like a local.

Chianti Kisses

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