Smile Upon You villa exterior with infinity pool and terraces, Pyrgos, Cyclades Islands, Greece

This Cycladic-style villa cascades down a hillside with an infinity pool, multiple shaded terraces, and uninterrupted views across the Aegean Sea.

Smile Upon You living room with gold pendant lights and staircase, Pyrgos, Cyclades Islands, Greece

The open-plan living space features sculptural gold leaf pendant lights suspended above a glass balustrade staircase, with natural light flooding through floor-to-ceiling windows.

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Smile Upon You

VILLA • PYRGOS, CYCLADES ISLANDS, GREECE

5 Bedrooms • 5 Bathrooms • Sleeps 10

Private PoolPrivate ChefSea ViewConciergeBBQ

Smile Upon You is a five-bedroom luxury villa in Pyrgos, Santorini, commanding spectacular views of the sparkling Aegean Sea from its prime hillside position. The 2,153 square foot property accommodates up to 10 guests across five beautifully appointed bedrooms, each with its own bathroom, making it ideal for families or groups seeking both space and privacy. The villa's infinity swimming pool appears to merge seamlessly with the azure horizon beyond, whilst the covered balcony provides shaded respite from the Mediterranean sun. Inside, the open-plan living space combines stark white walls with gold oversized light fixtures and a striking collection of artwork, creating a distinctly contemporary aesthetic. The fully equipped kitchen features glossy white surfaces that balance style with functionality. Private chef and concierge services are included, alongside daily housekeeping and airport transfers, ensuring a truly pampered experience. The traditional village of Pyrgos lies just a 15-minute walk away, offering authentic Santorinian architecture, local shops and restaurants, plus a medieval castle. The seaside town of Kamari with its volcanic black sand beach is merely a 10-minute drive from the property. This villa successfully combines the tranquillity of an elevated position with convenient access to Santorini's most compelling attractions, making it an excellent choice for discerning travellers seeking both luxury and authentic Greek island experiences.

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Best time to visit

summer

22-28°Cjun · jul · aug

peak crowdpremium value

Summer provides the perfect combination of guaranteed sunshine for pool enjoyment, warm sea temperatures for swimming at nearby beaches, and the long daylight hours essential for experiencing Santorini's legendary sunsets from the villa's elevated position.

peak crowdpremium value

Late spring through early autumn offers the best conditions, with May to September providing reliably warm weather and calm seas ideal for the infinity pool experience. July and August bring peak crowds and premium pricing, whilst June and September offer excellent value with fewer visitors but equally spectacular weather.

winter

dec · jan · feb

Mild and occasionally wet with temperatures suitable for sightseeing but too cool for swimming. The heated pool remains usable with spectacular winter light for photography.

12-16°C

low crowdexcellent value

Many restaurants and tourist facilities close during winter months. Verify the villa's accessibility and confirm that preferred restaurants will be open before booking.

spring

mar · apr · may

Increasingly warm and sunny with wildflowers blooming across the island. Perfect for outdoor exploration with comfortable temperatures and excellent visibility.

16-22°C

moderate crowdgood value

Late spring offers excellent value before summer prices take effect. Book early as availability increases significantly from May onwards.

summer

Recommended

jun · jul · aug

Hot, dry and reliably sunny with minimal rainfall. Perfect for pool and beach activities with long daylight hours ideal for sunset viewing.

22-28°C

peak crowdpremium value

Peak season requires booking 6-12 months ahead, particularly for July and August. Expect premium pricing and busy tourist sites during daylight hours.

autumn

sep · oct · nov

Warm and pleasant in early autumn, cooling as winter approaches. September offers ideal conditions whilst October provides excellent value with mild weather.

18-24°C

moderate crowdexcellent value

September offers the perfect balance of summer weather and reduced crowds. October provides excellent value though some tourist facilities begin reducing hours.

Why we chose it

The infinity pool creates the most perfect visual illusion we've encountered on Santorini, appearing to pour directly into the Aegean Sea from this elevated vantage point. Unlike many Santorinian villas that compromise on interior space for dramatic views, Smile Upon You delivers both: 2,153 square feet of thoughtfully designed living space that feels genuinely spacious rather than cramped. The inclusion of private chef and concierge services at this price point sets it apart from most comparable properties, where such amenities typically command significant additional fees. Most importantly, its position in Pyrgos offers something increasingly rare on the island: proximity to authentic village life without sacrificing the commanding sea views that define a premium Santorinian experience.

Reviewed by The Chosen Stay · 2026

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01The Architecture

The villa employs traditional Cycladic architecture updated with contemporary touches, featuring the classic white-rendered walls and clean geometric lines synonymous with Santorinian design. The building takes full advantage of its hillside position through strategic placement of floor-to-ceiling windows that frame the sea views whilst maintaining the privacy essential to luxury living. The outdoor spaces are designed as extensions of the…

02The Interior

The interior design philosophy centres on a sophisticated monochrome palette of stark white walls punctuated by carefully chosen gold accents. Oversized light fixtures serve as sculptural elements whilst providing functional illumination for the open-plan living spaces. A curated collection of contemporary artwork adds personality and visual interest without overwhelming the clean aesthetic. The kitchen features high-gloss white surfaces that reflect…

03The Outdoor

The infinity swimming pool serves as the outdoor space's centrepiece, positioned to maximise the dramatic sea views whilst providing respite from the Aegean sun. The pool's heated system ensures year-round usability, essential given Santorini's cooler spring and autumn temperatures. Multiple lounging areas accommodate both sun-seekers and those preferring shade, with the covered balcony offering all-day comfort. A barbecue area enables…

04The Location

Pyrgos occupies a unique position amongst Santorini's villages, elevated enough to command sweeping sea views yet retaining an authentic character often lost in the island's more touristic areas. The villa sits approximately 15 minutes on foot from the village centre, where medieval castle ruins and traditional tavernas provide genuine local atmosphere. The strategic location offers quick access to Kamari's black…

05Ideal For

The property excels for groups of friends or extended families seeking luxury with authentic Greek island character. The five separate bedrooms with individual bathrooms provide privacy for multi-generational groups, whilst the included chef and concierge services appeal to guests prioritising relaxation over self-catering.

Amenities

Private PoolWiFiParkingSea ViewGarden ViewBBQBalconyPrivate ChefConciergeHousekeepingDishwasher

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TheChosenStay's Guide

dining

Metaxi Mas

This authentic hillside restaurant serves traditional Greek dishes with sea views, offering friendly service and exceptional value compared to the tourist-focused establishments in Oia and Fira.

4 minutes by car

dining

Aroma Avlis

Experience high-quality Greek cuisine in a peaceful setting with excellent local wine selection. The restaurant's commitment to authentic flavours attracts discerning local diners alongside visitors.

13 minutes by car

experience

Estate Argyros

This family-run winery offers exceptional tastings of Santorini's distinctive volcanic wines, including the rare dessert wine Vinsanto, with knowledgeable staff explaining the island's unique viticulture.

16 minutes by car

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Frequently Asked

Click the booking link to be taken directly to our booking partner, where you can check availability and complete your reservation.

The villa includes a private chef and concierge service as part of the rental. Daily housekeeping and airport transfers are also included in the cost.

The villa accommodates up to 10 guests across five bedrooms, with six beds and five bathrooms providing ample space and privacy for all guests.

Santorini National Airport is approximately 20 minutes by road and serves both commercial flights and smaller private aircraft. For larger private jets, Athens International Airport offers helicopter connections to Santorini.

No, pets are not permitted at this property.

Yes, the villa welcomes children and infants. The heated swimming pool and multiple outdoor spaces provide safe entertainment, though the property spans two storeys which may require supervision for very young children.

May to September offers the best weather for enjoying the villa's pool and outdoor spaces. June and September provide excellent value with fewer crowds, whilst July and August offer guaranteed sunshine but attract peak visitor numbers.

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