Luxury rentals in Santorini caldera

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Top-rated vacation rentals in Santorini caldera

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Villa in Pyrgos Kallistis

5.0 out of 5 average rating, 3 reviews

Christou Estate

Please note: This property can be booked with less bedrooms. Contact a Trip Designer for updated pricing. Christou Estate is one of the finest contemporary luxury properties on the Greek island of Santorini, situated just a short walk from the medieval town of Pyrgos. Comprising three distinct villas (two of which, Saligari and Chelona, can be rented individually), the estate is an outstanding choice for multiple families, groups of friends, or destination wedding guests seeking privacy, consummate style, and a prime location on these spectacular Aegean shores. Each villa features exquisite interior and alfresco living spaces—combining classic Cycladian simplicity with outstanding contemporary art and design—while shared amenities, including fitness facilities and a Hamman, provide a resort-like experience. Stunning, panoramic sea views grace the property. Villa Saligari is the estate's largest and most well-appointed villa. In addition to a private swimming pool, the terrace features a gorgeous Jacuzzi hot tub with expansive views, while a beautiful dining table and rustic grill await you beneath the dreamy canopy. Indoors, the luminous living room, with fireplace and large TV, adjoins a stunning, sea-view dining area, while the fully equipped kitchen includes espresso and coffee makers. Three superb bedrooms accommodate six guests, with two of the bedrooms enjoying access to the terrace. Villa Chelona, the second-largest villa, likewise features a private swimming pool, an ample terrace with breathtaking views, and a barbeque grill. The superb alfresco dining area includes a lovely table and comfortable lounge bench for savoring meals and cocktails in the dreamy breeze. Indoors, the fully equipped kitchen includes an espresso machine and coffee maker, while the living room is perfect for relishing fine Greek wine in the evening. Two superb bedrooms accommodate four guests. Villa Kota features the largest bedroom on the estate: a beautiful primary king suite. Its terrace enjoys a private pool, lovely sun loungers and shaded armchairs, and a yard with dining area. Indoors, a kitchenette adjoins a gorgeous living area. The Christou Estate is wonderfully located for enjoying the heavenly island of Santorini. Just ten minutes down the road is the medieval city of Pyrgos, with incredible, panoramic views of the island from its hilltop apex, along with lovely restaurants and cafés lining the charming streets. The port of Santorini, Perissa Beach, and Kamari Beach are minutes away by car. Copyright © Luxury Retreats. All rights reserved. Saligari Villa • Bedroom 1 - Primary: Queen size bed, Access to hall bathroom with stand-alone shower, Television, Air conditioning, Access to shared balcony • Bedroom 2: Queen size bed (or Two single size beds), Access to hall bathroom with stand-alone shower, Television, Ceiling fan, Access to shared balcony • Bedroom 3: Two single size beds, Access to hall bathroom with stand-alone shower, Television, Ceiling fan Chelona Villa • Bedroom 4 - Primary: Double size bed, Ensuite bathroom with stand-alone shower, Air conditioning • Bedroom 5: Queen size bed (or Two single size beds), Access to hall bathroom with shower/nath combo, Ground fan Kota Villa • Bedroom 6 - Primary: King size bed, bathroom with stand-alone shower, Air conditioning FEATURES & AMENITIES • Wine fridge • More under “What this place offers” below OUTDOOR FEATURES • Terrace • Hammam STAFF & SERVICES Included: • Welcome wine & fruits • Hostess (2 hours daily) • Pool maintenance • Hammam use (one hour daily) • More under “Add-on services” below Extra cost (advance notice may be required): • Activities and excursions

Aug 20 – 27

G$570,490 GYD per night

Villa in Vourvoulos

5.0 out of 5 average rating, 3 reviews

Tramountana

Poised on a hillside surveying the topaz Aegean Sea, Tramountana is an architecturally inspiring traditional Greek villa that looks as if it could have been fashioned out of snow. Generous outdoor areas and a high-quality interior finish lend it an air of laid-back luxury, blessed by breathtaking sea views. A separate entrance shields it from the road and there’s enclosed parking if you travel by car. Your accommodation includes complimentary car rental, third party insurance and unlimited mileage as well as transfers to and from the airport. Stepping inside Tramountana, you’re immediately struck by its uncluttered simplicity. Modern furnishings are offset by some older pieces and the décor is tastefully subtle. The main entrance leads to a bright and spacious open-plan living and dining area. Comfortably cushioned sofas invite you to take a break from the sun and choose from a selection of movies and music. A flat-screen TV, DVD player, sound system and high-speed wireless internet access makes it easy to stay in touch with the world. If you’d rather switch off, a picture window offers bewitching views of the ever-changing ocean. Fix yourself a cool drink or snack in the fully equipped kitchen and step out onto the pool terrace. Outside, a sculpted infinity pool mirrors the sea beyond and you can spend many hours just drifting and dreaming. Curvaceous sun loungers beckon you to take your place in the sun and an outdoor jetted tub promises to massage the tension from your shoulders. A well-stocked garden borders the villa and you are invited to help yourself to herbs and seasonal vegetables. Welcome shade can be found under the pergola, where you can cluster with friends for a leisurely lunch or tasty evening barbecue before retiring to the outdoor lounge for a nightcap. A second dining area at the other end of the terrace offers opportunities for more romantic dinners under the stars. Three air-conditioned, simply furnished bedrooms are brightened by vibrant bedspreads and prints. Bedrooms one and two are both en-suite and are positioned on the ground floor with access to a private terrace, while a third bedroom occupies the loft. Mosaic-tiled modern bathrooms with tubs and showers complete the ensemble. Massage treatments, yoga sessions and beauty care can all be provided at extra cost, and if you’re tempted to explore the locality you’re within walking distance of the beach, shops and nearest town. It’s 10km to the airport. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Family Suite Bedroom 1: King size bed, Ensuite bathroom with stand alone shower, Safe, Desk, Bedroom 2: Queen size bed, Ensuite bathroom with stand alone shower, Safe, Desk, Terrace Loft Bedroom 3 - located above bedroom 2 : Double bed, Accces to ensuite bathroom in bedroom 2 FEATURES & AMENITIES • More under “What this place offers” below Included: • Bottle of Santorini wine on arrival • Complimentary 3rd party insurance & unlimited kilometers • More under “What this place offers” below At Extra Cost – advance notice may be required: • Activities and excursions • Theme dinner nights • Event fee • Mobile phone rental • More under “Add-on services” below

Nov 26 – Dec 3

G$242,156 GYD per night

Villa in Thira

4.63 out of 5 average rating, 8 reviews

Olia Villa

Tucked away on a hillside in beautiful Imerovigli, far away from the tourist crowds, Villa Estelle offers contemporary clean and compact living with sensational views. Ideal for families and small groups, this lovely home from home can also host intimate weddings and social occasions (event fee applies). Fill your lungs with fresh ozone as you gaze across the deep blue of the Aegean Sea to the mysterious Santorini volcano and magical island of Thirasia. A villa manager and concierge will make sure your vacation lives up to your dreams and a daily housekeeper will keep everything neat and tidy. There is not a sharp angle within curvaceous Villa Estelle. The building - and even one of the nightstands - has been crafted from snow-white stone and the kitchen fits snugly into a rounded alcove. Its splendid waterfront location is mirrored by the softly lit heated plunge pool and you can enjoy fabulous views from the roof garden, day or evening. Lavender sunsets are a Santorini spectacle and an alfresco poolside dining table enhanced by candles means you can gather with friends or family and talk long into the night. Indoors, a homely living room opens out onto the sun terrace. Cushion-stacked sofas invite you to put your feet up and enjoy all the entertainments on offer. Pick a movie from the collection and play it on your DVD player. There’s a satellite television and games console. Staying connected with the outside world is also an option with Wi-Fi. Prepare yourself a fresh juice or strong coffee in the compact kitchen and enjoy it from your lounger as you soak up the morning sun. Later, you might fancy cooking up a feast on the gas grill. Drowsy from all the sea air and sunshine, you’ll be looking forward to a sound night’s sleep and Villa Estelle’s three air-conditioned king-size bedrooms can offer just that. All the home comforts are here, from LCD televisions and the finest linen to modern en-suite bathrooms with showers. There are also two sofa beds, ideal for teens and one of the rooms boasts a writing desk, perfect for penning postcards home. If you feel like exploring the area, a five minute walk will take you to a church, restaurant and grocery store in the nearby town. It’s a 8.2 km drive to the airport and nearest beach. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: King size bed, En-suite bathroom with shower, Air conditioning, Safe, LCD television • Bedroom 2: King size bed, En-suite bathroom with shower, Air conditioning, LCD television • Bedroom 3: King size bed, En-suite bathroom with shower, Air conditioning, LCD television • Additional Bedding: 2 Sofa beds ideal for teens FEATURES & AMENITIES • More under “What this place offers” below Included: • Concierge service • More under “What this place offers” below At Extra Cost – advance notice may be required: • Activities and excursions • Event fee • Baby equipment • More under “Add-on services” below

Jun 15 – 22

G$255,306 GYD per night

Villa in Santorini

Villa Cloud

Crisp white and rounded off by its roofline, this deceptively simple villa floats above the Santorini coast. Built into the hillside’s volcanic soil, it’s been remodeled into a futuristic lair—and a hole cut from the ceiling to let the Greek-island sunshine filter through the hot tub and ripple on the walls. It’s a short drive to Thera and the seafood-restaurant-lined shores of Exo Yalos Beach. Start each morning of your holiday at this vacation rental with the complimentary breakfast, then bring a book or headphones out to the furnished balcony overlooking the sea. There’s both a jetted plunge pool and a hot tub where you can soak while watching boats ply the waters below. And while the villa may have started as a cave, it’s fully in the 21st century with its smart TV, sound system, and Wi-Fi. Wall-to-wall glass lets light pour into the open-concept living area—as does a skylight cut beneath the upper-level hot tub. The sunshine bounces off the polished concrete floors and white walls around a dining table for 4, a fully equipped kitchen hidden behind folding doors, and a sitting area with a sculptural coffee table. Thanks to the open-plan layout, even the intimate bedroom at the back of this luxury property has ocean views. It also has a queen bed and a private ensuite bathroom, making it just right for a couple on their honeymoon or looking to relive it while in Greece. The villa is a short drive from Thera, the island’s main town, where you can wander amid whitewashed houses, peer over the breathtakingly high cliffs at the edge of the city, or take a cable car down to the water’s edge. It’s also an easy trip to the volcano-dark sand of Exo Yalos Beach, where you can rent a lounger or dine on fresh fish and squid at a waterfront restaurant, and the family-friendly waters of Monolithos Beach. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: Queen size bed, Ensuite bathroom with stand-alone rain shower, Desk, Safe, Air conditioning, Ocean view FEATURES & AMENITIES • Fully equipped kitchen • Formal dining area with seating for 4 • Nespresso • Wi-Fi • Smart TV • Sound system OUTDOOR FEATURES • Ocean view • Terrace • Jetted plunge pool - heating included • Hot tub - heating included • Outdoor furniture STAFF & SERVICES Included: • Daily housekeeping - 11am-2pm • Breakfast included Extra Cost (advance notice may be required): • Pre-stocking • Airport transfer • Activities & excursions • Private chef • Spa services LOCATION Points of Interest • 1.8km to Thera • 6.1km to Pyrgos Kallistis • 9.3km to Athinios Port Santorini • 12.8km to Akrotiri Beach Access • 4.2km to Exo Yalos Beach • 7.6km to Monolithos Beach • 9.2km to Kamari Beach Airport • 7.3km to Santorini National Airport (JTR)

Nov 22 – 29

G$241,619 GYD per night

Villa in Imerovigli

5.0 out of 5 average rating, 5 reviews

Erossea Villa

Panoramas of sea, sky and spectacular sunsets are on view from Erossea Villa. Set on the west side of Santorini in the picturesque village of Imerovigli, this west-facing vacation rental looks out across the brilliant blue waters of the Aegean. Reserve this newly renovated three-bedroom property for a honeymoon-worthy romantic getaway or a relaxed family holiday in the sun. Your stay at this luxury villa begins with an airport transfer and includes breakfast each day. Take in the vistas from outdoor living spaces with a heated pool, hot tub, loungers in the sun, and shaded sitting and dining areas. A wireless speaker means you can listen to a favorite playlist indoors and out, and Wi-Fi makes it easy to share photos from your trip. Taking inspiration from the traditional Greek village scenes on postcards, the villa is built into the hillside at the top of the caldera. Fresh white stucco forms the backdrop for the open-plan living and dining areas, which are flooded with sunlight from glass doors leading to the terrace and furnished with chic mid-century-style pieces. A fully equipped kitchenette is tucked into the open-concept space as well. Erossea Villa has two bedrooms with queen beds in the main villa—one with an en-suite bathroom and one with a hall bathroom—and one in a guest suite with its own queen bed and en-suite bathroom. Accessed via an exterior staircase, the guest suite is a private retreat within the property. From the villa’s setting in the village of Imerovigli, it’s a short drive to the island’s capital and several beaches, including the pebbled shores of Kamari and the black sands of Perissa. Don’t miss the chance to glimpse Santorini’s long history on a walk through the ruins at nearby Ancient Thira. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main Villa • Bedroom 1: Queen size bed, Access to hall bathroom with stand-alone shower, Television, Safe • Bedroom 2: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Safe Guest Suites (access from Main Villa via exterior staircase) • Guest Suite I: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Safe Additional Bedding • Guest Suite II: 2 Single size beds, Ensuite bathroom with stand-alone shower, Television, Safe • Guest Suite III: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Safe FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • View of the caldera • Sunset views • More under “What this place offers” below STAFF & SERVICES Included: • Daily housekeeping • Daily pool cleaning • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Apr 9 – 16

G$612,734 GYD per night

Villa in Thira

Milos

Enjoying dramatic views of the Santorini coastline, the 2-bedroom Milos villa sits proudly within the beautiful Villa Fabrica estate. Milos comfortably sleeps four guests and can be rented alone, although larger families and groups may consider combining it with the neighboring Canava and Katikia villas or as part of the complete four-unit estate. Complimentary services include a welcome tour, seasonal breakfast hamper and daily housekeeping. Fashioned from a former factory, this stylish vacation home maintains a few historic elements, among them the preserved machinery on display below the loft bedroom. The open plan living area opens onto a shared terrace, which neighbors the estate’s main pool area. Here you can find a welcome retreat from the heat in the shaded pool, and test the strength of your stroke against its countercurrent system. Fix yourself an industrial-strength morning coffee to start your day and drink in the sensational views from a comfortable sun lounger. Return to the terrace as the light fades and admire a glorious Santorini sunset over the rim of your glass. Sheer white is the theme indoors and out at Milos. Its minimalist design, contemporary furnishings and unusual spaces, all bathed in natural light, will clear your mind and fill you with deep tranquility. If you crave entertainment, there’s a satellite TV, DVD and CD player. Or you can stretch out on the sofa and lose yourself in a good book. If you like to cook, you can rustle up a feast or snack in the compact but fully-equipped kitchen before choosing whether to savor it inside at the dining table or outside at the breakfast bar. The services of a cook can be arranged at extra cost. However you choose to spend your long days in the Greek sunshine, it’s a relief to know that you can come back to a comfortable bed. Rest and relaxation are given priority in your air-conditioned island home and there’s little to distract you from a good night’s sleep. A ladder from the kitchen takes you to the double loft bedroom and master bedroom which share a bathroom. Hiring a rental vehicle is recommended if you’re going to explore the island. It’s an 8 minute drive to the nearest beach and 5km to the capital town of Fira and the bustling ferry port in Athinios. The town of Pygros Tallisti is within walking distance and it’s 6km to Santorini International Airport. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 2: Double size bed

Apr 18 – 25

G$112,756 GYD per night

Cycladic home in Thira

5.0 out of 5 average rating, 7 reviews

Villa Etheras

The quintessential rock, sea and sky of the Greek islands appear in all their glory at Villa Etheras. This cliffside Santorini vacation rental was named for ether, believed by the ancient Greeks to be the mystical fifth element from which the world was created along with air, fire, earth and water—and, in their mythology, the pure air breathed by the gods. When you sample its panoramic views, gorgeous terrace and chic interiors, you may enjoy a spiritual experience, too. Set into the rock of the hillside, the villa’s private oceanfront terrace commands views over the caldera and along the coast. Gather around the shaded dining table, stretch out on a seat in the sun or cool off in the infinity pool, which features a lounging platform that appears to be floating on the water’s surface. Inside, a TV, sound system, DVD player, Wi-Fi and air conditioning round out the amenities at this luxury property. The white stucco walls so characteristic of the islands are carried into Villa Etheras, where they wind around an open-concept living room and kitchen. A sleek fireplace surround and polished marble coffee table contrast with the soft slipcovered sofa in the living room; in the fully equipped kitchen, a rock slab is a rugged counterpoint to the minimalist cabinets and breakfast bar. The villa’s two bedrooms are the perfect size for a small family or two couples on holiday together—or even for an indulgent honeymoon in the Santorini sun. Both bedrooms have king beds, en-suite bathrooms and sea views. With a location in the quiet village of Firostefani, Villa Etheras is a short drive from the larger town of Fira and scenic, unpretentious Exo Yalos beach. When it’s time to leave your island retreat, plan on a 7-mile drive from the villa to the ferry docks at Athinios Port Santorini. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: King size bed, Ensuite bathroom with shower/bathtub combo, View of the sea • Bedroom 2: King size bed, Ensuite bathroom, Rain Shower, Television, View of the sea FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • View of the caldera • More under “What this place offers” below STAFF & SERVICES Included: • Daily housekeeping • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Sep 7 – 14

G$593,980 GYD per night

Villa in Akrotiri

5.0 out of 5 average rating, 4 reviews

Summer Lovers Villa

Rejuvenate in one of 3 hot tubs while you gaze upon the Aegean Sea and Santorini Caldera from this eco-friendly Greek villa in Akrotiri. Pick your favorite spot in the shade to catch up on some reading or work on your tan in one of the sun loungers. At peak afternoon heat, hop into the swimming pool and recharge your batteries. At night, head to town for dinner, it’s only a 10-minute walk. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Gold Suite • Bedroom 1: King size bed, Shared access to hall bathroom with bedroom 2, Stand-alone shower, Television, Air conditioning, Desk, Safe, Sea view • Bedroom 2: King size bed, Shared access to hall bathroom with bedroom 1, Stand-alone shower, Television, Air conditioning, Safe, Sea view Silver Suite • Bedroom 3: King size bed, Access to hall bathroom with stand-alone rain shower, Dual vanity, Television, Air conditioning, Desk, Safe, Kitchenette, Lounge area, Direct access to pool area, Sea view • Bedroom 4: King size bed, Access to hall bathroom with stand-alone rain shower, Television, Air conditioning, Safe, Kitchenette, Sea view Bronze Suite • Bedroom 5: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Air conditioning, Safe, Lounge area, Private entrance FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • View of the Aegean Sea • More under “What this place offers” below STAFF & SERVICES Included: • Linen & towel change - weekly • Housekeeping - once a week (4 hrs per 2 housekeepers) • Electricity consumption • Final cleaning and washing latest upholstery • More under “What this place offers” below Extra Cost (advance notice may be required): • Concierge • Grocery shopping services • Activities and excursions • Laundry services • More under “Add-on services” below

Oct 19 – 26

G$284,171 GYD per night

Villa in Santorini

Cellaria Estate Exclusive

Fragrant olive trees, glittering sea views, and sleek curved architecture greet you at this sprawling Santorini estate. A clean and crisp design scheme flows throughout with sunlight igniting the interior. The capacious pool is the perfect place to float beneath the stars. Spend the day sunbathing or snorkeling at the beach before indulging in a taste of authentic Greek eateries along the shore. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & jetted bathtub, Walk-in closet, Television • Bedroom 2: King size bed, Double size sofa bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 3: Queen size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 4: Queen size bed, Ensuite bathroom with shower/bathtub combo, Television Guest House: • Bedroom 5: Queen size bed, Shared access to hallway bathroom with stand-alone shower, Television STAFF & SERVICES Included: • Concierge services Extra Cost (advance notice may be required): • Activities and excursions • Breakfast - Daily • Masseuse • Event space

Oct 27 – Nov 3

G$371,058 GYD per night

Villa in Santorini

Samsara

The clear, bright, island-in-Greece sunlight turns pergolas into patterns and glitters on the water at this modern Santorini retreat. Stone and stucco evoke traditional island architecture, while clean-lined pieces add modern edge. Make a short drive through the countryside to the picturesque village of Pyrgos Kallistis and the popular, promenade-lined black-sand Kamari Beach. Copyright © Luxury Retreats. All rights reserved BEDROOM & BATHROOM • Bedroom 1 - Primary: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Safe, Air conditioning, Direct access to terrace • Bedroom 2: Queen size bed, Shared access to hallway bathroom with bedroom 3, Stand-alone shower, Television, Air conditioning, Safe, Mountain view • Bedroom 3: Queen size bed, Shared access to hallway bathroom with bedroom 2, Stand-alone shower, Television, Air conditioning, Direct access to terrace, Ocean view FEATURES & AMENITIES • Wine fridge • More under “What this place offers” below Extra Cost (advance notice may be required): • Activities & excursions • More under “Add-on services” below

Mar 30 – Apr 6

G$103,399 GYD per night

Villa in SANTORINI (Thira)

4.83 out of 5 average rating, 6 reviews

Villa Dio

The arches of classic Santorini architecture contrast with the bowl of the caldera in the views from this cliffside home. An infinity pool and terrace with loungers and outdoor dining seem to jut out of the rock over the sea. Stone tables and built-in sofas lend a minimalist-chic look inside the cool white rooms. The surrounding village of Firostefani is about a 10-minute walk to bustling Fira. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Television, Terrace • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Television, Ocean view • Bedroom 3: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Television, Terrace, Ocean view STAFF & SERVICES Included: • Concierge services • More under “Add-on services” below Extra Cost (advance notice may be required): • Activities and excursions • Pool maintenance

Jul 15 – 22

G$652,983 GYD per night

Place to stay in Pirgos Kallistis

Summit Villa at Santorini Heights

Situated atop the Santorini Heights Complex to capture soaring natural landscapes and endless sea views, this eco-focused villa shows off the land's raw materials, blending seamlessly with its UNESCO-protected location. Spend sunny afternoons by the pool, evenings on wood-deck watching the sunset, and late nights warming up in the hot tub. In the morning, sip tea in the herb garden. Copyright © Luxury Retreats. All rights reserved.

Aug 25 – Sep 1

G$187,926 GYD per night