Apartment • 13 People • 5

• 6

•

From

€

7,924 /night

Min Stay 1 night

Messina, Italy

€ 7,924 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Blissful Daze

Positioned atop the hilly landscape of Lipari island, with unbroken views across the Tyrrhenian, this sprawling homely villa is footsteps from the sea. Days will be spent toing and froing to the sea rocks, watching steam escape from fumaroles on the distant Vulcano Island and lounging by your shimmering pool. The expansive terraces bring with them the scents and sounds of a Mediterranean summer: the catch of the day grilling on the barbecue, a clattering of plates, the heady aroma of herbs drifting from the gardens and a salt-tinged ocean breeze. Inside, modern furnishings expertly contrast with original timber beams and stone walls to create a space that’s a pleasure to unwind in. To take the relaxation up a notch, call upon bar staff and a private chef to ensure dinner parties go without a hitch. When you’re ready to explore, your host can organise an exclusive boat tour or helicopter ride – there’s a helipad on the premises, n...More Details

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Messina, House for rent

House • 12 People • 6

• 7

•

From

€

6,101 /night

Min Stay 1 night

Messina, Italy

€ 6,101 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Bay of Bliss

With direct access to the beach and a private infinity pool, this home hits all the right notes when it comes to a rejuvenating retreat. You’ll also be serenaded by stunning views as well as a range of a luxurious home comforts – including a concierge service offering sweet extras like a private chef and catering. It’s worth noting one of the bedrooms is located in the independent garden annexe, but this is a great option for those seeking a little extra privacy. There’s also a gym, a home office for remote workers and plenty to explore in the surroundings. *Please note one of the bedrooms is located in an independent annexe, while two of the bedrooms are located in the rooms beneath the pool. *There are multiple levels here with stairs. *Housekeeping is included in your stay. *If you’re travelling with little ones, your host can provide a cot for free on request. *Private parking is available here. Air Conditioning Bathtub Centr...More Details

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Messina, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

5,029 /night

Min Stay 1 night

Messina, Italy

€ 5,029 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Painted Blue

The panoramic views across the Ionian and Taormina Bay, are what really caught our eye at this Letojanni villa. This home is all about maximising Sicilian living – multiple outdoor terraces for dining and lounging, a pristine pool and sun-bathing area, and minimalist bedrooms that open out onto the sea views. These vistas don't come so easy here – access to the villa is via a steep road – but it's worth the effort. The nearest beach is 2km away in Letojanni, while the cities of Taormina, Catania and Syracuse are great options for a day trip. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There's parking here. *While there's a ground-floor bedroom and bathroom here, this villa is spread across three levels and accessed via a steep road – it may not suit those with limited mobility. *Your host provides daily cleaning, a midweek change of towels and a weekly change of linens. *If you're trave...More Details

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Messina, Apartment for rent

Apartment • 14 People • 7

• 8

•

From

€

4,884 /night

Min Stay 1 night

Messina, Italy

€ 4,884 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Eruptions Of Colour

This is one of those villas that takes your breath away the moment you enter. Lined with palm trees, layered with viewing spots of the Mediterranean Sea and formed by deluxe fittings, it's a home drenched in luxury. Whichever part of the home you visit, you'll be able to see the rugged coastline blend into the deep blue water of the ocean. It's a view you never tire of, especially if you're seeing it from the comfort of the sun beds on the terrace. That terrace is where you'll spend most of your time, whether it's catching some sun on the beds or going for a swim in the pool. Furthering the vibe of paradise, a cute outdoor table faces the shoreline, perfect for sharing a deep Burgundy wine with an incredible view. We appreciate that for most of you, the views aren't enough – you want to explore Italy for yourself. Hop in the car and you're spoilt for choice on day trip options – Taormina, Syracuse and Catania offer an insight into ...More Details

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Syracuse, House for rent

House • 22 People • 11

• 11

•

From

€

3,630 /night

Min Stay 1 night

Syracuse, Italy

€ 3,630 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Blue Rose

They say good things come in threes, and these villas won't disappoint. Great for multiple families or large friend groups, this trio of homes are right by the Ionian Sea. You'll have your pick of rooftop terraces to watch the sunset and private pools to splash about in (though it's worth noting that not all the pools are open throughout the year). We recommend hiring a car here if you're hoping to pay a visit to Noto or Marzamemi or spots like Mount Etna or the Vendicari nature reserve. *Not all bedrooms or bathrooms are photographed, but we expect consistent style and quality throughout the home. *This home is made up of three neighbouring villas – two sleep eight guests and one sleeps six, with two guests on a sofa bed. *There's free private parking on the estate. *Your host can provide a free cot and high chair if you're travelling with little ones. *One of the three swimming pools is only open from 1st March to 30th November...More Details

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Giardini Naxos, Apartment for rent

Apartment • 20 People • 10

• 11

•

From

€

3,479 /night

Min Stay 1 night

Giardini Naxos, Italy

€ 3,479 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

No Sweeter Sight

It's hard to put a finger on what it is exactly that makes this address so extraordinary. Sure, the hillside location above the Sicilian coastline more than delivers when it comes to dramatically beautiful landscape to gaze out upon, but we've got a feeling that the villa would still wow in even the most uninspiring of settings. A lot of that is down to the effortlessly chic design that can be found throughout the four floors, with stylish furnishings, large light-filled communal areas and flooring so shiny that you can probably see your own face staring back in it. It does no harm that there are also a fair few balconies that offer a splendid vantage point from which to admire the scenery. As well as being easy on the eye, there's an enviable list of amenities at guests' disposal. Many of these lie outside, including the heated saltwater swimming pool and Jacuzzi surrounded by loungers, plus the covered outdoor kitchen with a barbecu...More Details

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Messina, Apartment for rent

Apartment • 12 People • 6

• 5

•

From

€

3,173 /night

Min Stay 1 night

Messina, Italy

€ 3,173 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Etna Sunrise

Everything about this stone and wood villa exudes Sicilian luxury – from the vast garden to the rustic interiors, bursting with vintage details. Start the day by greeting the sunrise over the Mediterranean with a few leisurely laps in the pool, then enjoy sipping your coffee on the sun-drenched terrace overlooking Mount Etna. You have all day long to stroll the beach, explore the harbour and the local museums, or take a drive along the coastline and pick up some seafood from the fishing villages. In the evening, grill freshly caught octopus and prawns on the wood-fired barbecue, and gather the whole party for dinner under the stars on the breezy veranda. Later you can retreat inside and cosy up by the fireplace or play a few tunes on the piano. If you're lucky enough to snag the master bedroom then you can soak in your own hot tub with a nightcap – trust us, with so much to do, your fellow guests won’t mind if you retreat to your own li...More Details

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Catania, Apartment for rent

Apartment • 8 People • 4

• 4

•

From

€

3,092 /night

Min Stay 1 night

Catania, Italy

€ 3,092 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Sultry Serenity

Situated between Catania and Taormina, this villa is ideally suited for those looking to discover the delights of Sicily. You'll be within a short drive of Etna Park and many of the area's charming towns. Featuring a private infinity swimming pool and jacuzzi, the villa's large garden setting also promises relaxing days spent at home. Another highlight is the outdoor dining terrace, providing a barbecue, plenty of seating for the entire group, and unspoilt views of the surrounding landscape. Inside, you'll notice the stylish designs that create a calming ambience throughout. All six bedrooms come with en-suite bathrooms and have been thoughtfully curated to a high standard. *Due to the location, we suggest hiring a car to get the most out of your stay. There's private parking here. \n *The villa is spread over multiple levels with an internal staircase, however, there's a ground-floor bedroom for those with limited mobility. \n *Whil...More Details

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Messina, Apartment for rent

Apartment • 16 People • 7

• 6

•

From

€

2,835 /night

Min Stay 1 night

Messina, Italy

€ 2,835 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Stirring Spectacle

This villa on the south coastline of Sicily sits as close to the Ionian Sea as it's possible to get without the water lapping against your bed every morning. It's a wonderfully picturesque spot, but what's perhaps most impressive is the villa's long list of amenities that will prise your attention away from this peaceful vista. Given the island's fruitful climate, it won't come as a surprise to learn that many of these can be found outside. There's something for every mood out here, whether you want to play in the swimming pool, relax in the Jacuzzi or feast yourselves silly on the pergola's alfresco dining table – all with the unmistakable sound and scent of the sea to keep you company. When you finally have to head inside, we're sure that you'll like what you see. The interior design mixes rustic features, such as patches of exposed stonework and the villa's old wine press, with more contemporary flashes – the minimalist kitchen and...More Details

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Messina, Apartment for rent

Apartment • 7 People • 4

• 4

•

From

€

2,819 /night

Min Stay 1 night

Messina, Italy

€ 2,819 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Oasis of Blue

With its dramatic, cliffside setting and expansive sea views, this home transports you to an instant state of relaxation. And while it feels like entering an idyllic retreat, you’ll find it’s also just a short walk from Taormina’s historic centre – providing the perfect opportunity to connect with the magic of Mediterranean living. Spread across multiple levels, there’s a self-contained apartment on the lower floor, while the second floor features a fully equipped kitchen, dining room and terrace – ensuring there's an abundance of space to relax and share quality time together. From quiet morning swims in the pool, delicious Italian lunches on the balcony and lazy afternoons on a sun lounger, every moment promises to be enriched by the mesmerising views across the Sicilian coast. Exercise enthusiasts will also appreciate the home gym, while the surrounding hills provide a wonderful opportunity for invigorating walks. You’ll find st...More Details

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Messina, Apartment for rent

Apartment • 12 People • 6

• 7

•

From

€

2,540 /night

Min Stay 1 night

Messina, Italy

€ 2,540 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Paradise Mirage

Located close to Taormina on the east coast of Sicily, this home is a luxury villa with a private swimming pool. The villa is situated in the beautiful countryside, surrounded by lush greenery and breathtaking views. A perfect retreat for those seeking peace and tranquility. Paradise Mirage exudes charm and elegance, with its tastefully decorated interiors and comfortable living spaces. With five spacious bedrooms, each with its own ensuite bathroom, the villa provides ample space for relaxation and privacy. The highlight of the property is its stunning garden, complete with furnished terraces and a private swimming pool. Guests can unwind in the sun loungers by the pool or enjoy al fresco dining in the shaded veranda. Whether you want to explore the historic town of Taormina or simply relax by the pool, an unforgettable holiday experience is promised. Air Conditioning Barbeque Carbon Monoxide Detector Central Heating Coffee Maker ...More Details

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Catania, Apartment for rent

Apartment • 16 People • 8

• 9

•

From

€

2,474 /night

Min Stay 1 night

Catania, Italy

€ 2,474 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Lapping Waves

With direct sea access, a private swimming pool overlooking an outcrop of lava rock and the sea, a wrap-around balcony terrace with panoramic views of the seascape, plus two floors of beautiful interior designs and luxury living – what more could you want from a villa in Sicily? Stylish and refined, this place exudes cool – we love its contemporary aesthetic alongside quirky accessories and artworks that inject character into the space with elegance. Access to the first floor is reachable by an external staircase which leads to a large living area, dining space, kitchen and five luxurious bedrooms with en-suite bathrooms. Meanwhile, on the ground floor, you'll find a second living room with a kitchen and dining area and a further three bedrooms with en-suite bathrooms alongside a games room (featuring table tennis, table football and a punching bag). Beyond the villa's sublime interiors, you'll find a well-kept garden with a swi...More Details

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Sicily, Apartment for rent

Apartment • 10 People • 5

• 7

•

From

€

2,470 /night

Min Stay 1 night

Sicily, Italy

€ 2,470 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Sea Dream

From the inspiring views to the minimalist aesthetic and luxurious features, every detail of this home sings with the warmth and beauty of Sicily. And just a fifteen-minute drive from the beaches of Fondachello and Giardini Naxos, this is the perfect setting for an immersive retreat into the heart of Italian living. Set across two expansive floors connected by an external staircase, the villa provides ample space for relaxing, socialising and spending quality moments together. Inside, you’ll find both floors feature a private kitchen and living room as well as serene bedrooms. And with the addition of a sauna and jacuzzi, this is the kind of space that transports you to the height of rejuvenation. Open the glass doors and you’ll discover the idyllic garden and swimming pool set the tone for a truly relaxing stay. From quiet mornings under the shaded pergola to dreamy golden-hour drinks and barbecue meals, there’s everything you co...More Details

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Syracuse, Apartment for rent

Apartment • 16 People • 8

• 7

•

From

€

2,393 /night

Min Stay 1 night

Syracuse, Italy

€ 2,393 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Sicilian Sky

If you’re visiting in a group, this is the spot. There are two villas on this property, so your cohort will have plenty of space to unwind solo and socialise over a pitcher of Aperol spritz. The designs are minimal, which allows those sea vistas to really shine. Speaking of, you’ll have direct beach access here – and even when you don’t feel like sand, you can watch the waves from your private pool. For dinners out, head into the charming fishing village of Marzamemi to sample the local cuisine, or spend a day soaking up some culture in Noto, a short drive away. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There's parking here.\n *This estate is made up of two modern villas, just a few metres from each other. Each villa features a kitchen and living room and sleeps eight guests. To access the top floors of each villa, you'll need to climb an external staircase. \n *Your host will provide a ...More Details

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Syracuse, House for rent

House • 8 People • 4

• 4

•

From

€

2,355 /night

Min Stay 1 night

Syracuse, Italy

€ 2,355 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Sea in Bloom

Located just by the sea in the protected natural area of Plemmirio, this exclusive villa complex is a rare find. Split between the main home and a separate annexe, you’ll find peace and tranquillity here, with plenty of opportunities for socialising and enjoying the fantastic outdoor space. With three swimming pools, an additional natural pool, outdoor games and an alfresco dining area, this home is designed for relaxation. Your host also provides snorkelling masks for those who feel like exploring the turquoise waters. The interior is just as impressive, guaranteeing comfort with the four luxurious bedrooms, each coming with an en-suite bathroom. Note that you’ll need a car to reach the sandy beaches and the port city of Syracuse, located approximately a ten-minute drive away. *This home is split between the main villa and a separate annexe which features a double bedroom and an en-suite bathroom. Note that the villa is spread across...More Details

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Messina, House for rent

House • 10 People • 5

• 5

•

From

€

2,318 /night

Min Stay 1 night

Messina, Italy

€ 2,318 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Bella Sicilia

Nestled in the heart of Taormina, within a twenty-minute walk of Corso Umberto and the Teatro Antico di Taormina – the ancient Greek theatre still used today – it’s not hard to see why this home caught our eye. Step inside, and you’re met with traditional Sicilian decor that mixes seamlessly with modern touches, such as the big screen in the living room, perfect for movie nights. Sun worshipers will love the outdoor space. Whether you’re drinking in the distant sea views from the balcony, relaxing on the terrace, or swimming in the private pool, this villa makes the most of the Mediterranean climate. *While not all bathrooms are fully photographed, expect the style and quality to be consistent with the rest of the home. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. *There are open-tread, open-sided stairs here. If you're bringing children, they'll n...More Details

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Syracuse, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

2,299 /night

Min Stay 1 night

Syracuse, Italy

€ 2,299 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Villa Oltremare

Overlooking the glimmering blue of the Ionian Sea, this charming whitewashed villa boasts a prime location, plenty of outdoor space, and chic interiors. You’ll have plenty of peace and privacy here: the house is surrounded by 4000m2 of manicured gardens, which lead down to a large outdoor pool and plenty of deck chairs for relaxing in after a refreshing dip. Large whitewashed pillars support the covered terrace that wraps around the house. Fire up the audio system while you make drinks and snacks in the outdoor kitchen, or throw some meats on the barbecue for an alfresco lunch. The rooms inside are characterised by high ceilings and dark wooden beams that contrast with the whitewashed walls. Sleek, minimalist furniture is compounded by statement pieces: we love the sunken living area with the towering ultramarine ornamental fireplace. The villa is just 50 metres from the sea, and there are beautiful sandy beaches within easy reach. ...More Details

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Messina, House for rent

House • 12 People • 6

• 7

•

From

€

2,246 /night

Min Stay 1 night

Messina, Italy

€ 2,246 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Sicilian Salt

This contemporary villa is located in Taormina, just a short drive from the historic centre and the beaches of Giardini Naxos, Isola Bella and Mazzarò. With modern touches throughout this home, you’ll want for nothing – it’s an ideal base for an extended family getaway or a group of friends. But for us, the outdoor space steals the show. Boasting views out to sea, Taormina, Castelmola, and Mount Etna, along with a private pool and sun-drenched terraces, it ticks all our holiday boxes. *While not all bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. *The swimming pool isn't fenced and there are open tread stairs here. If you're bringing children, they'll need to be supervised at all times. *We recommend hiring a car to get the most out of your stay. *Ho...More Details

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Sicily, House for rent

House • 10 People • 5

• 6

•

From

€

2,184 /night

Min Stay 1 night

Sicily, Italy

€ 2,184 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Ancient Jewel

This showstopper of a villa near Santa Venerina is surrounded by manicured gardens, terracotta terraces and Mediterranean cacti. Once a historic winery, it's now a relaxing escape complete with a gym, sauna and Turkish baths. Outside, there's a heated pool (with plenty of sunbeds for everyone), there's also an outdoor kitchen and a barbecue for alfresco dinners under the shaded, vine-covered pergolas. There's more than enough to keep you busy, but if you feel like exploring, the city of Catania and the coastline are less than thirty minutes' drive away. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There's free parking on the driveway. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. Air Conditioni...More Details

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Syracuse, Apartment for rent

Apartment • 30 People • 14

• 9

•

From

€

2,175 /night

Min Stay 1 night

Syracuse, Italy

€ 2,175 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The High Tone

This sprawling estate is a collection of five separate villas, all a short walk from each other. Four of the villas have private swimming pools and the fifth has a hot tub for long soaks, and all have covered terraces for dining, reclining and unwinding. Of course, between five separate buildings, you’ve got five full kitchens and living rooms and one of the villas is all on one floor, so may suit those with limited mobility. Apart from having oodles of space for massive groups to spread out, this complex is just two kilometres from the beautiful Baroque town of Noto for days out. *This home consists of five independent villas a short walk away from each other. \n *One of the bedrooms has a set of bunk beds and three of the bedrooms have triple beds, so would be best suited to children sharing. In the triple rooms, two beds can be joined to make a double and a single. \n *Your host can provide a cot and high chair for infants, just as...More Details

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Luxury Rentals Sicily Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 638 Sicily holiday homes for rent

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Syracuse, Italy

Giardini Naxos, Italy

Messina, Italy

Catania, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Catania, Italy

Sicily, Italy

Syracuse, Italy

Syracuse, Italy

Messina, Italy

Syracuse, Italy

Messina, Italy

Sicily, Italy

Syracuse, Italy

Luxury Rentals Sicily Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 638 Sicily holiday homes for rent

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Syracuse, Italy

Giardini Naxos, Italy

Messina, Italy

Catania, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Catania, Italy

Sicily, Italy

Syracuse, Italy

Syracuse, Italy

Messina, Italy

Syracuse, Italy

Messina, Italy

Sicily, Italy

Syracuse, Italy

Sicily Property for rent