Apartment • 13 People • 5

• 6

•

From

€

7,758 /night

Min Stay 1 night

Messina, Italy

€ 7,758 /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

€

6,129 /night

Min Stay 1 night

Messina, Italy

€ 6,129 /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

€

5,620 /night

Min Stay 1 night

Messina, Italy

€ 5,620 /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

€

4,818 /night

Min Stay 1 night

Messina, Italy

€ 4,818 /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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Giardini Naxos, Apartment for rent

Apartment • 20 People • 10

• 11

•

From

€

3,169 /night

Min Stay 1 night

Giardini Naxos, Italy

€ 3,169 /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 • 16 People • 7

• 6

•

From

€

2,842 /night

Min Stay 1 night

Messina, Italy

€ 2,842 /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 • 12 People • 6

• 6

•

From

€

2,818 /night

Min Stay 1 night

Messina, Italy

€ 2,818 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Sicilian Heights

This villa is all about the views. Perched on Sicily’s east coast, it looks out over the Ionian Sea, with Mount Etna rising in the distance. Days are spent padding between the pool, shaded terraces, and sun-drenched loungers. Inside, it’s all cool marble floors, clean lines, and a kitchen made for long, lazy meals – whether you’re perched at the breakfast bar or gathered around the table. Taormina is just 7km away, but here you’ll enjoy the same cinematic backdrop without the crowds. And when the beach calls? It’s only 4km from your door. *Cleaning is included here for four hours every other day. Towels and linen will also be changed midweek. *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. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There's parking onsite. Air Conditioning Barbeque Beach / Pool Towels Ca...More Details

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Messina, Apartment for rent

Apartment • 12 People • 6

• 5

•

From

€

2,668 /night

Min Stay 1 night

Messina, Italy

€ 2,668 /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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Messina, Apartment for rent

Apartment • 7 People • 4

• 4

•

From

€

2,419 /night

Min Stay 1 night

Messina, Italy

€ 2,419 /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, House for rent

House • 10 People • 5

• 5

•

From

€

2,269 /night

Min Stay 1 night

Messina, Italy

€ 2,269 /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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Messina, House for rent

House • 12 People • 6

• 7

•

From

€

1,927 /night

Min Stay 1 night

Messina, Italy

€ 1,927 /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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Messina, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,475 /night

Min Stay 1 night

Messina, Italy

€ 1,475 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Where Lemons Grow

Wake up to the sound of the Tyrrhenian Sea each morning from this sublime villa set in the bustling seaside resort of Capo d'Orlando. It even boasts direct access to the pebbly beach. Glistening white from top to toe, and offering up next-level sea views from nearly every room, terrace and poolside, this place has got rest and reset written all over it. Outside, a year-round relaxation pool is prime for soaking up the rays in style. And through a charming white picket gate, there's the glorious beach with sunbeds and umbrellas at the ready for cooling dips. Inside, across the cool herringbone stone floors, discover four bedrooms, each as spacious and light-filled as the next, and each offering en-suites for a little extra privacy. And did we mention there's a spa with a Jacuzzi, sauna and a chromotherapy shower that leads out onto a sun terrace where you can drip-dry beneath the Sicilian sun? Now we're talking. ...More Details

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Messina, Apartment for rent

Apartment • 8 People • 4

• 5

•

From

€

1,381 /night

Min Stay 1 night

Messina, Italy

€ 1,381 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Palazzo Approach

This luxurious villa is a stunning base in east Sicily. It’s just above the seaside town of Letojanni and is close to Taormina, with beaches nearby. The villa boasts truly glorious views over the Ionian Sea and Taormina, which can be admired from inside as well as outside, thanks to floor-to-ceiling sliding French doors. Inside, the decor is crisp and clean, and you’ll find everything you need to enjoy a comfortable, relaxing stay. There’s even a gym and a sauna. Outside, the infinity pool is the main focus – aside from the views. The pool has a hydromassage area, and there’s a separate Jacuzzi. We love the alfresco dining area – there’s a barbecue to cook on too. *There’s private parking at this home. *The pool is open to guests all year round *This home is split between the main villa and a separate one-bedroom space that is only accessible from the pool area. *There are stairs to climb at this home so it may not be suitable for th...More Details

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Messina, Apartment for rent

Apartment • 8 People • 4

• 4

•

From

€

1,294 /night

Min Stay 1 night

Messina, Italy

€ 1,294 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Villagonia Blue

Located in the hilltop town Taormina, this villa offers stunning views of the sprawling cliffs which drop down to Ionian, sea-forming coves and powdery sand beaches. With stretches of green garden and encumbering mountain views, this peaceful spot has everything you need for a blissful coastal break. With prime Sicilian temperatures, it’s not surprising this home promotes outdoor living. This home has a hydromassage pool as well as a pristine swimming pool, a four-poster daybed for siestas under the shade and a cool, curtained patio which is perfect for balmy, alfresco dinners prepared by a private chef if you so wish. When you need a repose from the sun, retreat to the inside where you’ll find an oasis of amenities. The natural design aesthetic blends with minimal leather furnishings and cooling glass accents to create a laid-back energy that synchronises with the outside’s coastal spirit. The white sofas are a perfect spot to read ...More Details

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Messina, Apartment for rent

Apartment • 8 People • 5

• 4

•

From

€

1,216 /night

Min Stay 1 night

Messina, Italy

€ 1,216 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

As Sweet as Candy

Nestled into the hills, gazing lovingly out over Taormina, this elegant villa provides the most serene escape for a Sicilian stay. The private pool is likely to entice you in straight away, with the cooling waters hard to resist in the heat of the day. Suitably refreshed, you can settle down on a sun lounger to while away a few hours with your summer read at the ready. With just the quiet notes of birdsong around you, it’s a peaceful way to spend the day. On the upper level of the villa, you’ll find the living area which boasts such an expanse of floor-to-ceiling glass, you’ll feel the Ionian Sea wrapping itself around you even when you’re indoors. Step out onto the terrace, and you can still enjoy the view with the addition of a gentle sea breeze – it’s the perfect spot for after-dinner drinks. Speaking of dinner, when it’s time for a meal, light the barbecue and dine poolside under the candy-striped gazebo. With your loved ones gathe...More Details

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Messina, House for rent

House • 10 People • 5

• 4

•

From

€

1,208 /night

Min Stay 1 night

Messina, Italy

€ 1,208 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Sweet Melody

This lovely villa is located on the edge of the charming village of Savoca, just a few kilometres north of Taormina. The property boasts a stunning view over the surrounding landscape, Mount Etna and the Ionian Sea. It features great amenities such as a salt-water swimming pool and an outdoor kitchen area – ideal for alfresco dining with your loved ones. The home is within easy reach of several seaside towns such as Santa Teresa di Riva and Sant'Alessio, as well as the impressive Alcantara Gorges. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. The pool is only available for use between 1st March and 30th November. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s private parking here. Air Conditioning Barbeque Beach Essentials Blender Child Friendly Coffee Maker Cot / Crib Dishwasher Dryer Espresso Machine Free Parking On...More Details

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Messina, Apartment for rent

Apartment • 12 People • 6

• 5

•

From

€

1,145 /night

Min Stay 1 night

Messina, Italy

€ 1,145 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Prosecco on the Pebbles

Beach lovers will be blown away by this incredible Italian villa, based in the heart of the Nebrodi mountain range, and surrounded by 15 hectares of private land. Made up of two separate villas connected by a courtyard with a gorgeous private pool, this home offers large groups lots of room to enjoy both social celebrations and solitary bliss. Inside features simple Italian style, with touches of charming decor that make every space feel characterful and inviting. We love the large dining area, ideal for feasting on pizza and pasta with your loved ones. Go on a wander around the grounds and you’ll come across the home’s private woods and lake – the perfect place to have a stroll in the shade of the lush treetops when the Italian heat turns up. Summer evenings can be spent sipping on Prosecco while you take the short 400m walk down to your own private pebble beach, where you’ll find your own beach chairs where you can relax and watch th...More Details

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Messina, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

1,111 /night

Min Stay 1 night

Messina, Italy

€ 1,111 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Head Full of Flowers

If you’re looking for views, you’ve come to the right place. This contemporary villa is based on the most beautiful stretch of south-eastern Sicily’s coast, with iconic vistas over the sea and Mount Etna. Large windows frame the panorama perfectly and flood the living space with natural light. Outside you’ll find a hydro-massage mini pool (with counter-current for getting those lengths in), a lush array of flowering plants and a sunbathing area for soaking up those Sicilan rays. You’re just 1km away from the sandy beach at Giardini Naxos and spectacular Taormina isn’t much further, for a taste of the dolce vita. The large veranda with its sail-like cover is the place to be, come sundown. Rustle up an Italian feast in the outdoor kitchen, or just kick back and take in those views. *The pool is open from the last Saturday of April to the first Saturday in October *There’s parking at the entrance for one car *Electricity is charged separ...More Details

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Messina, Apartment for rent

Apartment • 8 People • 4

• 5

•

From

€

1,101 /night

Min Stay 1 night

Messina, Italy

€ 1,101 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Shades of Tangerine

Nestled along the cliffs of Taormina, this orange-sherbert-hued villa offers impressive views of the rocky precipices that drop down to the Ionian, sea-forming coves and the golden beaches of Isola. With encumbering mountain views, enjoy tranquil moments amidst the Mediterranean fauna and flora that fragrances the air. With a private pool, bright traditional living space and a spectacular view of the surrounding landscape, this Sicilian villa ticks all the boxes for a coastal retreat. With prime Sicilian temperatures, it’s not surprising this home promotes outdoor living. This home has a hydromassage pool, sleek daybeds for siestas under the shade of the palm trees and a cool, covered patio which is perfect for balmy, alfresco dinners. When you need a repose from the sun, retreat to the inside where you’ll find an oasis of amenities. The traditional design aesthetic blends with minimal modern furnishings and pops of orange to create a...More Details

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Messina, House for rent

House • 10 People • 5

• 5

•

From

€

1,076 /night

Min Stay 1 night

Messina, Italy

€ 1,076 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Aeolian Song

This home in Sicily is postcard-worthy without a doubt. Its grounds are home to a villa that comes complete with a saltwater pool, impressive views of the Tyrrhenian coast, oodles of privacy, an outdoor hot tub, and lots of dining areas, too. Inside, you'll find a mélange of classic charm and modern comfort. Each bedroom comes complete with its own en-suite, and there are different hangout areas and dining arrangements to suit every mood. Hop in the car and discover the beach just three kilometres away. Or, if you're in the mood for a day trip further afield, the coastal city of Cefalù is a great choice. *The pool is open from the 1st of March until the 30th of November. The jacuzzi is open year-round. *If you're travelling with little ones, your host can provide a cot and a high chair for free. You'll need to request them in advance. *There is a seven-night minimum stay at this villa between the 21st of June and the 29th of August. T...More Details

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

Found 45 Messina holiday homes for rent

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Giardini Naxos, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

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

Found 45 Messina holiday homes for rent

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Giardini Naxos, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina, Italy

Messina Property for rent