Castiglione della Pescaia

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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

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

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

Set among olive groves and cypress trees, this villa overlooks the rolling Tuscan countryside all the way to the medieval towers of San Gimignano. The style is contemporary country chic – think exposed beams, brick archways and warm, earthy colours. The living room is on the smaller side, but if it's relaxation you're after, there's a spa with a wood sauna, hammam, and jacuzzi, plus an outdoor infinity pool. Dining is best enjoyed on the terrace, soaking up those panoramic views. Fancy a change of scenery? There are villages to explore, local vineyards to visit and hiking trails winding through the surrounding hills.

Tuscan Dreamcatcher

Sitting discreetly on the Argentario peninsula, this home welcomes you to an idyllic stay with stunning views. Outside, the grounds offer peace, privacy and a swimming pool for refreshing dips. There’s also a tennis court for family fun and a wonderful terrace with a barbecue for magical evening meals. All of the bedrooms come with en-suite bathrooms for optimum privacy and there’s an office room for remote workers. And when it comes to explorations, you can follow the path down to the rocky shore, hire a boat in nearby Porto Ercole or adventure to Porto San Stefano and Orbetello.

Horizon of Wonder

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

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

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

In the heart of the Tuscan countryside, this farmhouse promises a tranquil retreat surrounded by rolling hills and lush greenery. Seamlessly blending traditional charm with contemporary comfort, the living area is sure to be a hit with all, with a mezzanine area and large corner window that invites natural light in. Alternatively, you can unwind in the garden, complete with a swimming pool, sun loungers, and a shaded dining area. Ready to get out and about? It’s easy to explore the nearby towns, beaches, and cities like Pisa and Livorno, all easily accessible from this idyllic location.

Pines & Vines

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

​​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

A blend of rustic charm and modern comfort, this apartment offers an authentic Tuscan experience. You can relax on the private terrace here or wander through the communal gardens to the pool with its views of the Tuscan countryside. Inside the apartment, we love the character features such as the beams and natural lime walls. This place is the perfect base for exploring the nearby villages, such as Sassetta with its Medieval castle and Suvereto, which overlooks the Tyrrhenian Sea.

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Types

Book a stay in one of the best homes in Castiglione della Pescaia.

We selected the 1182 homes worth renting in this location

Who's coming along?

Home spotlights in Castiglione della Pescaia

LIGHTHOUSE
ISLAND

MAREMMA
MUSE

VERDANT
VALLEY

We've selected the top 3% homes in Castiglione della Pescaia.

Most popular homes in Castiglione della Pescaia.

Tuscan
Dreamcatcher

Horizon of
Wonder

A Tuscan
Rhapsody

Beyond the
Bridge

Two
Seas

Pines &
Vines

Tee Time
in Tuscany

Bellissima
Casa

Tuscan
Dreamcatcher

Horizon of
Wonder

A Tuscan
Rhapsody

Beyond the
Bridge

Two
Seas

Pines &
Vines

Tee Time
in Tuscany

Bellissima
Casa

Step Back
Through Time

Check rates and availability for Castiglione della Pescaia.

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Frequently Asked Questions

Book a stay in one of the best homes in Castiglione della Pescaia.

We selected the 1182 homes worth renting in this location

Home spotlights in Castiglione della Pescaia

LIGHTHOUSEISLAND

MAREMMAMUSE

VERDANTVALLEY

We've selected the top 3% homes in Castiglione della Pescaia.

Most popular homes in Castiglione della Pescaia.

TuscanDreamcatcher

Horizon ofWonder

A TuscanRhapsody

Beyond theBridge

TwoSeas

Pines &Vines

Tee Timein Tuscany

BellissimaCasa

TuscanDreamcatcher

Horizon ofWonder

A TuscanRhapsody

Beyond theBridge

TwoSeas

Pines &Vines

Tee Timein Tuscany

BellissimaCasa

Step BackThrough Time

Check rates and availability for Castiglione della Pescaia.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Castiglione della Pescaia?

LIGHTHOUSE
ISLAND

MAREMMA
MUSE

VERDANT
VALLEY

Tuscan
Dreamcatcher

Horizon of
Wonder

A Tuscan
Rhapsody

Beyond the
Bridge

Two
Seas

Pines &
Vines

Tee Time
in Tuscany

Bellissima
Casa

Tuscan
Dreamcatcher

Horizon of
Wonder

A Tuscan
Rhapsody

Beyond the
Bridge

Two
Seas

Pines &
Vines

Tee Time
in Tuscany

Bellissima
Casa

Step Back
Through Time