Winter Sun

Welcome to our handpicked collection of villas, perfect for your winter sun escape.

Whether you’re seeking the tranquil beaches of the Caribbean, the historic charm of Europe, or the exotic allure of Asia, our villas offer an ideal retreat from the winter chill. Imagine lounging by your private pool under the Mediterranean sun, exploring vibrant Caribbean cultures, or unwinding in the serene landscapes of Asia.

Each villa is handpicked by our travel experts for its exceptional comfort, style, and prime location, making for an unforgettable holiday. From sun-drenched beachfront paradises to hillside havens, our diverse selection caters to every taste and desire. Indulge in luxury, privacy, and personalised service as you create lasting memories in some of the world’s most stunning destinations.

Dive into our collection and embark on a winter holiday where warmth, relaxation, and adventure await.

Why take a villa holiday in winter?

Escape the cold and boost mental health
Winter can be harsh and gloomy in many parts of the world. Escaping to a sunny destination can provide much-needed exposure to sunlight which helps boost serotonin levels, mood and energy.

Enjoy outdoor activities in comfortable weather
In winter, many sun-soaked destinations offer the perfect climate for outdoor activities minus the sweltering heat. Whether it’s relaxing on pristine beaches, wandering scenic nature trails, or diving into water sports, the mild and pleasant weather opens a world of unforgettable experiences.

Experience different cultures and off-season advantages
Travelling to sunny destinations in winter often means visiting places during their off season, meaning reduced crowds, lower costs and authentic experiences.

Handpicked Winter Sun Destinations

Why stay with us?

Oliver’s Travels’ handpicked luxury villas exude style and character in every corner, perfect for your ultimate winter sun escape.

Our destination experts know the ins and outs of all our regions, handpicking the very best of unique homes in extraordinary locations.

Whether you’re looking for tips on local restaurants, advice on key attractions to visit, or help with – think of our concierge team as your holiday genie, helping with planning and recommendations.

Are you dreaming of a white Christmas? If you’re more pine tree than palm tree, then we have a gorgeous collection of Christmas cottages in the UK and France, perfect for cosy picture-book moments straight out of a snow globe.

Where to go for Winter Sun

Winter sun holidays provide a wealth of exciting activities across Europe, the Caribbean, and Asia. In Europe, enjoy outdoor adventures like hiking scenic trails, exploring picturesque coastal paths, or participating in water sports in warm climates. Embrace cultural experiences with historic site tours, local markets, and vibrant festivals.

The Caribbean offers an array of thrilling activities including snorkeling or diving in crystal-clear waters, relaxing on beautiful beaches, and exploring lush rainforests. Engage in local cultural experiences such as lively music and dance, or take part in traditional cooking classes.

In Asia, bask in the warmth while indulging in wellness retreats or yoga sessions set against stunning landscapes. Explore bustling markets, ancient temples, and vibrant city life. Outdoor enthusiasts can enjoy activities like surfing, jungle treks, or beachside adventures. For a more tranquil experience, unwind with spa treatments or savour local cuisine in idyllic settings.

Each region presents a blend of relaxation and adventure, ensuring winter sun holidays are filled with diverse activities, from exploring natural wonders to immersing in local cultures.

Contact our friendly concierge team for more ideas on how to spend a sunshine-filled getaway during the winter months. The team will be happy to share some local knowledge and assist in booking experiences.

Extra experiences when you rent with Oliver's Travels

World-class dining: Our concierge Team can recommend some of the world’s best restaurants and out-of-the-way eateries and book on your behalf.

Private guides and tours: Visit some of the most famous sites, natural wonders, and museums with a friendly and knowledgeable local guide.

Spa services: slow down and gift yourself a well-deserved pampering. We can help organise massage therapists and yoga instructors and spa packages including all sorts of tempting treatments.

Additional experiences: There are so many unique experiences that you can choose from, depending on the chalet you stay in, from fitness sessions to wine experiences.

Winter Sun in Europe

Spread your wings and head south for the winter with an escape to the far reaches of Europe for some sunshine and warm climes. Bask in the Mediterranean sunshine on beautiful beaches or in lush vineyards where a perfect blend of relaxation, adventure, and cultural experiences means that rain, snow and cloud cover are a distant memory.

Cyprus

Visit Cyprus in winter for mild weather, serene beaches, and fewer crowds. Explore ancient ruins in Paphos, hike the scenic Troodos Mountains, and wander around quaint towns and villages. The island’s rich history, picturesque scenery and unique cuisine make it a perfect winter sun destination, blending relaxation with cultural exploration.

Canary Islands

Escape to the Canary Islands in winter for sunny weather and diverse landscapes. Enjoy Tenerife’s beaches, hike Gran Canaria’s scenic trails, relax among the sand dunes of Fuerteventura and explore Lanzarote’s volcanic wonders. With mild temperatures, vibrant festivals, and fewer tourists, the islands offer a perfect blend of relaxation and adventure during the winter months.

Turkey

The Aegean and Mediterranean shorelines meet in a rich tapestry of history and flavours on Turkey’s Turquoise Coast. This region invites you to relax on pristine beaches, explore historic treasures and savour exquisite regional cuisine. If you seek adventure and cultural immersion, this region is home to two of the Seven Wonders of the Ancient World – the Temple of Artemis and the Mausoleum at Halicarnassus.

Madeira

Travelling to Madeira in winter offers mild temperatures, lush landscapes, and fewer tourists. The island’s unique levada walks (narrow mountain tracks with irrigation channels), vibrant festivals, and breathtaking scenery make it a serene escape. Enjoy whale watching, hiking and hearty local cuisine, perfect for a rejuvenating winter getaway.

Rome

Visiting Rome during the cooler months means fewer crowds, pleasant weather, and shorter lines at iconic sites like the Colosseum, the Roman Forum and the Vatican. Enjoy the festive atmosphere with holiday markets and seasonal cuisine. This time of year offers a unique charm, allowing you to explore the city’s rich history and culture at a more leisurely pace.

Barcelona

With highs of 16c even around New Year, Barcelona is the ideal destination for urban exploration in the off-season. Fewer crowds mean the top sights are more enjoyable and you can really indulge in the flavours and colours of the city. Christmas markets, the festive Three Kings Parade (January), and the lively Santa Eulalia Festival (February) are all well worth seeing.

Winter Sun in the Caribbean

Discover the Caribbean for winter sun, where endless sandy beaches, crystal-clear waters, and vibrant island culture create the ultimate tropical escape. From December to April, the region enjoys warm temperatures, low humidity, and minimal rainfall, making it perfect for beach outings and outdoor activities. The dry season also means clearer skies and calm seas, ideal for snorkelling, diving, and exploring tropical terrain.

Barbados

Escape the winter chill by heading to Barbados, where warm sun, pristine beaches, and turquoise waters await. Indulge in the island’s rich culture, savour fresh seafood, and explore vibrant nightlife. Barbados promises a perfect tropical getaway with friendly locals, lush landscapes, and endless sunshine, making it an ideal winter destination.

St. Lucia

Stunning St. Lucia guarantees a tropical paradise experience. Discover the island’s breathtaking beaches, lush rainforests, and the majestic Pitons. Engage in thrilling adventures like snorkelling and hiking, relax in luxury resorts, and enjoy vibrant local culture. St. Lucia promises an unforgettable escape with its natural beauty and warm hospitality.

Jamaica

Jamaica promises a vibrant blend of stunning sandy stretches, verdant forests, and rich cultural experiences. Enjoy reggae rhythms, savour delicious jerk cuisine, and explore natural wonders like waterfalls and jungle. With warm weather year-round, friendly locals, and diverse activities, Jamaica offers a perfect tropical escape for any traveller.

Turks & Caicos

Visiting Turks and Caicos in winter provides a perfect exotic retreat with sunny skies and warm temperatures. Enjoy stunning beaches, crystal-clear waters, and world-class diving spots. The serene atmosphere and luxurious resorts offer a peaceful escape, ideal for relaxation and water activities away from the winter chill elsewhere.

Dominican Republic

For a diverse and colourful experience featuring stunning shorelines, buzzing cities, and lush landscapes, Dom-Rep is your go-to. Discover the historic capital of Santo Domingo, relax on Punta Cana’s white sand beaches, and venture into the incredible tropical rainforest of Jarabacoa. With electric nightlife, and outdoor adventures, there’s no doubting this island’s captivating charm.

Antigua

With its 365 gorgeous beaches – one for each day of the year – you might never want to come home from Antigua. Enjoy vibrant marine life, explore historic Nelson’s Dockyard, and experience the island’s lively festivals. With its warm climate, mountainous terrain, and charming atmosphere, Antigua offers a perfect getaway from the gloom of winter.

Winter Sun in Asia

The best time to visit Southeast Asia is the ‘winter’ time. Warm climates with little rain, stunning festivals, delicious street food, colourful markets, and serene spaces await your exploration. This season provides ideal conditions for sightseeing, outdoor adventures, and experiencing the region’s rich heritage before the monsoons of summer roll in.

Thailand

Frenetic cities, picture-postcard beaches, and lush jungles… Thailand is a world away from sleet and snow. Explore Bangkok’s bustling markets and temples, relax on Phuket’s picturesque shores, and discover the cultural charm and elephant sanctuaries of Chiang Mai. Enjoy delicious food made with exotic spices and fresh fruit, otherworldly landscapes, and warm hospitality in this diverse and captivating destination.

Vietnam

Vietnam offers a blend of natural beauty and cultural richness. Explore Hanoi’s historic charm and striking architecture, cruise through beautiful Ha Long Bay’s limestone islands, and wander the lantern-lit ancient streets of Hoi An. Shop bustling markets, try delicious street food, and walk in awe among swaying palms. Vietnam promises a journey filled with unforgettable experiences and warm hospitality.

Bali

Ever-inviting Bali provides a canvas of thrilling experiences. Explore terraced rice paddies, hike active volcanoes, and take a moment of quiet in ancient temples. Ride the waves on some of the world’s best surf spots, unwind in tranquil yoga retreats, and indulge in the tantalising flavours of local cuisine. Bali’s warm climate and rich traditions offer a captivating and rejuvenating escape for all types of traveller.