14 Greek Island Getaways You’ll Want To Book Now

The weather is so wonderful in the Greek Isles that people often dwell in caves, but this Exotic Cave Suite is a little more luxe. Nestled in a secluded spot, this Vrbo offers a rare combination of breathtaking views and privacy. Soak in the scenery from the jetted tub and marvel at the awe-inspiring sights of Oia. Leave your cares behind as you traverse the cobbled steps leading to your very own sanctuary, then unwind on the sun bed on the spacious private terrace.

Wake up to the stunning beauty of Santorini at Grand Canava. This meticulously restored 1868 winery offers uninterrupted views of the caldera and volcano. Immerse yourself in the tranquility and enjoy ultimate relaxation with a large outdoor private pool, sunbathing deck, and a hydromassage hot tub. Each living area has its own entrance, ensuring privacy for up to 12 guests. Follow the main promenade to see one of the most famous sunsets in the world!

Experience the breathtaking beauty of Oia by staying at the newly renovated Terracotta Cave House. Located near the Venetian castle, this traditional cave house offers panoramic views of the caldera, volcano, and the entire village. Enjoy privacy and tranquility while being just a 2-minute walk from the main street bustling with restaurants and shops. Admire stunning views from the private courtyard. Daily cleaning service is provided for your convenience.

Explore the pedestrian village of Oia on foot and venture out to the rest of the island by car, bus, taxi, or organized tours. With personalized and discreet service from Nicoletta and her team, your stay at Terracotta Cave House guarantees a carefree and enjoyable holiday.

Experience pure enchantment at Kallisti Sunset in Oia, one of Santorini’s most picturesque and renowned locations. Take in unrivaled views of the blue Aegean and the world’s most captivating sunset from the spacious veranda and plunge pool private Jacuzzi. Porch or living room? You decide from the porch swing in the living room. Staff is available 24/7 to ensure your stay is nothing short of extraordinary.

Sea View Apartment boasts direct access to an idyllic beach. Soak in the Aegean breeze from the private terrace. Its cliffside location provides magnificent Caldera views and easy access to the sea. Dive into the crystal-clear waters from the dock and unwind on your private terrace, marveling at the sailing boats passing by.

Traveling with a crowd, hosting a workshop, or tying the knot? Sea Horse Residence can accommodate up to 20 guests with a truly unforgettable experience in Fira. Immerse yourself in the charm of traditional Cycladic architecture at this recently renovated property just a short walk from Santorini’s capital. Within easy reach of the island’s archaeological sites and stunning beaches, this Vrbo offers both convenience and beauty. Its prime location allows guests to enjoy breathtaking panoramic views of the caldera, stretching from Oia to Akrotiri, and the volcano. The play of light and colors will leave you in awe from day to night. Breakfast is prepared fresh by the resident cook.

Located in a former winery, Canava Villa #1 offers a peaceful and private retreat. Soak in the double bathtub indoors, or head outside to take advantage of the private jet plunge pool and Jacuzzi. Enjoy views of the black beach Perivolos and the picturesque Medieval village of Emporio.

Just steps from the beach, this wonderful villa can be found in the exclusive area of Orkos, Naxos. In addition to breathtaking views of the Aegean Sea, it features a spacious terrace with a private swimming pool, a gorgeous hexagonal pergola, and a charming dining area surrounded by beautiful gardens. The upstairs bedroom boasts its own terrace with spectacular views. The villa is equipped with tilt-and-turn doors and windows, air conditioning, and mosquito nets throughout.

Escape to the stunning island of Naxos and experience the perfect getaway at Seaside Naxos. Yes, that gorgeous pool and pergola-shaped lounge are private. The upstairs bedroom has its own private terrace overlooking the Aegean Sea, too. Let the hosts help personalize your vacay by suggesting hidden gems, from sandy beaches and picturesque villages to hikes and restaurants.

Escape to the idyllic St. Nicholas Beach Villa in Corfu, where tranquility and natural beauty meet. Nestled on a peninsula and surrounded by the sea, this beachfront retreat offers unparalleled privacy and breathtaking views. A large heated pool, indoor paddle pool, sauna, steam room, fully equipped gym, and o-zone therapy spa are there for a little self-care. Explore the enchanting gardens and follow a path through a “rainforest” to discover two secluded beaches. Unwind on a sun lounger by the pool, go snorkeling around the nearby islet, or find a cozy corner to savor a glass of wine and enjoy the captivating sunset.

A haven of relaxation and privacy, Golden Beach Villa is a serene retreat near the peaceful village of Drios on the enchanting island of Paros. Wake to the sparkling sea and distant islands, then sip your Greek coffee outside on the expansive private veranda by the private swimming pool.

Only 5 minutes away by car, the renowned Golden Beach is a must-visit, but numerous sandy beaches can be found nearby. The airport, Parikia (the main city port), and Naousa, a charming town brimming with vibrant bars, restaurants, and shops, are all within a half-hour’s drive. Explore the delightful village of Drios, swim in its picturesque bay, and enjoy authentic Greek cuisine and fresh seafood at the serene beachfront tavernas.

During spring and autumn, nature lovers can explore a variety of walking routes, including the Lefkes Byzantine Trail and Paros Park Walking paths, where the untouched beauty of the natural landscape awaits. These footpaths are accessible to individuals of all ages and physical abilities, offering a serene and immersive experience. Embark on a memorable retreat at Golden Beach Villa and create cherished moments on the captivating island of Paros.

With gorgeous stone inside and out, Alexandros Luxury Private Villa features a cozy living room with a fireplace. Step into the outdoors and immerse yourself in the lush garden and its tranquil sunbathing area. Two outdoor tables make it easy to dine al fresco, even for large groups. With a capacity of 10, this villa is the perfect getaway for a couple of families. Guests also enjoy access to the swimming pool.

Escape to paradise at this newly built Luxury Villa in Paros, a true embodiment of traditional Cycladic architecture. Step into luxury as you soak in the private pool and relax on the expansive covered terrace, complete with a barbecue area and surrounded by elegant marble columns and stone. Prepare to be mesmerized by the panoramic sea view and the enchanting sight of neighboring islands from the terrace. The garden is adorned with a charming Cycladic stone oven, adding a touch of authenticity to your experience.

Nestled in the tranquil northern part of Andros, Villa Elissavet offers a secluded oasis just 20 minutes from Gavrio port. Designed with love and creativity, the villa combines luxury and comfort with Cycladic charm. Immerse yourself in the surrounding nature, wander along beautiful paths, and discover the breathtaking wild beaches of Zorgos and Peza. Experience the soothing sound of the wind and unwind on the expansive veranda, where you can enjoy panoramic views of the mountains, ravine, and the deep blue sea.

Take a dip in the inviting pool and witness the magnificent sunset that paints the sky with vibrant colors. Incorporating natural materials and repurposed objects throughout, the villa is a testament to the host’s commitment to sustainability. As you explore the estate, you can even gather fresh vegetables from the garden for a refreshing salad.