Luxury rentals in Pyrgos Kallistis

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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

$3,730 CAD 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

$1,687 CAD 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)

Apr. 19 – 26

$1,755 CAD per night

Cycladic homes 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

$4,401 CAD per night

Villa in Anavissos

5.0 out of 5 average rating, 7 reviews

Villa Take Off

Gaze upon panoramic seaside views, and breath in the crisp ocean air at this stylish Athenian villa. Find the perfect spot to watch the sunset on the pool deck, multi-level balconies, or through floor-to-ceiling windows in the living room. For a closer look, drive 4-km to Palea Fokea Beach. After a swim, grab a spot for dinner at one of the local taverns lining the sand. No matter which bedroom you’ve chosen, you’ll wake up to a view of Saronic Bay. Swing open the patio doors to enjoy the fresh sea breeze and linger in bed just a few extra minutes. Then, make your way downstairs, prepare breakfast, and relax amongst the minimalistic decor and designer furnishings. When the evening nears, don’t be afraid to invite new friends over, there’s parking for 7 at this gated-property. And, both the formal and alfresco settings offer scenic vistas. After you’ve eaten, move the party to the row of lounge chairs on the terrace and watch over Anavissos while you sip cocktails. If you’re in the mood for a late-night snack, fire up the barbecue or whip something up in the outdoor kitchen. If you’d rather hit the town, Athens is about 40-km from home. The Exarchia neighborhood is perfect for bar hopping and dinner, with lots of local favorites lining their winding streets. If you’re in the mood to dance, the Gyzi area is where you’ll find some of the world’s hottest nightclubs. And, make sure to explore the Acropolis Museum while you’re in town. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: Queen size bed, Ensuite bathroom with stand-alone shower, Direct access to patio • Bedroom 2: King size bed, Shared access to hall bathroom with bedroom 3, Shower/bathtub combo, Television, Desk, Direct access to patio • Bedroom 3: King size bed, Shared access to hall bathroom with bedroom 2, Shower/bathtub combo, Television, Desk, Direct access to patio • Bedroom 4 - Nanny Suite: 2 Twin size beds (can be converted into a king), Ensuite bathroom with stand-alone shower, Kitchenette, Television, Desk FEATURES & AMENITIES Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Feb. 27 – Mar. 6

$1,045 CAD per night

Villa in Mikonos

5.0 out of 5 average rating, 3 reviews

Villa Aloni

A picture-perfect bay view is just one of the attractive aspects of this stylish and fully-equipped villa, located just a few minutes’ drive from Mykonos town. A stone courtyard, sheltered terrace, pool and distinctive, heritage-conscious white exterior is paired with a spotless, modern interior and contemporary decor. Beaches, Ano Mera village, historic ruins and great nightlife are all close by. Lounging by the pool in the soft light of the sunset, guests at Villa Aloni can take in a striking view of rugged hillsides, stars glimmering above, and soft waves breaking on the northern Mykonos shore. Inside, other guests can prepare for an evening out in sumptuous ensuite bedrooms, sample a meal made with local ingredients in the fully-equipped kitchen, or relax with a drink in hand around the TV and entertainment system. Villa Aloni is ideally placed on the border between the quiet hinterland of the island and the more happening main town. This allows quick access to the tranquil lanes, sandy beaches, and sea views of Mykonos’s western half, as well as the seafood restaurants, cocktail bars and energetic nightclubs of the town itself. Other attractions, like the ruined temples and classic mosaics of Delos, are just a short distance away via local ferry. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Private balcony, Air conditioning • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Private balcony, Air conditioning • Bedroom 3: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Direct access to terrace, Air conditioning • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower, Television, Private entrance, Air conditioning FEATURES & AMENITIES • Heated floors • More under “What this place offers” below STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • Personal trainer • Laundry service

Mar. 6 – 13

$1,477 CAD 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

$1,857 CAD 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

$4,797 CAD per night

Villa in Santorini

5.0 out of 5 average rating, 5 reviews

Eolia Senior Villa

Offering a gorgeous view of the rugged Santorini coast, this hillside villa offers inventive design and interiors, plus abundant comfort. Embrace the shaded balcony love-seat and blue pool, which sharply contrast with the volcanic scene beyond. The sun-reflecting white exterior houses a dream sitting room and plush bedrooms, with Ancient Thera and black pebble beaches close by. Copyright © Luxury Retreats. All rights reserved.

Jan. 10 – 17

$819 CAD per night

Villa in Tourlos

5.0 out of 5 average rating, 4 reviews

Villa Opal

Indulge in a realm of lavish comfort within the exquisite Villa Opal, meticulously designed, to create an atmosphere of opulence. Whether it's a brilliant celebration, a corporate retreat, or an intimate family reunion, this exquisite villa stands as a testament to modern grandeur, offering the ultimate haven for your exclusive group gatherings, where refined elegance, harmonises with the timeless allure of the Aegean Sea.

Aug. 29 – Sep. 5

$7,820 CAD per night

Villa in Kastro

5.0 out of 5 average rating, 6 reviews

Villa Fleur de Sel

Feel the sun’s white-hot heat beating down and bouncing off the white and stone villa. The cooling aqua blue waters of the infinity pool beckon. Music drifts and floats along with an exotic mix of suntan lotions. Ice cubes rattle against glasses. It’s the start of a summer day in this hillside villa just 2.6 miles from Mykonos City. Copyright © Luxury Retreats. All rights reserved.

Sep. 25 – Oct. 2

$2,458 CAD per night

Villa in Porto Cheli

Rafaella Porto Heli

Villa Rafaella, with its imposing Mediterranean neoclassical character is a dreamlike combination of luxury, quality and beauty for an ideal holiday destination. Its excellent location on the southeastern cape of the Peloponnese, in Agios Aimilianos, just 1.8 miles across the cosmopolitan Spetses Island and 5 km from Porto Heli, makes it a unique reference point.

Oct. 14 – 21

$3,033 CAD per night