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Expert advice for exceptional stays. For over 25 years, WhereToStay.com has been the go-to source for luxury villa rentals in the Caribbean and beyond.
Our global travel experts help you to find the
perfect villa, complimented by a tailor made experience for your dream vacation. With over 2,000 hand-selected villas across 22 islands, plus our recent expansion into Europe through Edge Retreats, we bring you the best vacation homes at the best prices. We’re not just a booking site—we’re villa experts who personally visit and vet every property, en
💫Wishing you and your loved ones a Merry Christmas - From the WhereToStay family. 🎄✨️
12/16/2025
🎄Last Minute Christmas Week Promotion!!🏖️
💫Escape the cold and head to St. Martin for a Caribbean Christmas! Casa de la Playa in St. Martin is offering 50% off for Christmas Week🌟
🤩What we love:
🌊Beachfront location
🎆Plenty of space for entertaining
☀️The Indoor/Outoor space merges seamlessly
🌴Perfect for large families!
Tap our link in the bio for more information on this villa.
📞Call or DM us today📩
12/09/2025
☀️Trade snowflakes for salt waves! - Caribbean winter anyone?⛱️
💫Marahuyo Villa in Grace Bay is crafted for effortless relaxation and unforgettable escapes. Its coveted beachfront setting, striking black lava stone pool with ocean views, and expansive outdoor lounging areas create an atmosphere of refined seaside luxury.✨️🏖️
What we love:
🌊 Exclusive oceanfront location - Immaculate white sand, vibrant turquoise water, and a serene stretch of coastline on Grace Bay to call your own.
🌞 Private swimming pool – With views that stretch effortlessly toward the beach.
🏓 Pickleball court – For active moments and a touch of friendly competition.
SAVE 15% during the month of February. Call us today for more details.
👉️Tap or link in bio to view more about this luxury villa in Turks and Caicos.
📩DM our team to secure your 2026 dates.
12/02/2025
✨ Villa Gamberaia: Where Tuscan Dreams Come Alive ✨
☀️A masterpiece of Italian elegance, Villa Gamberaia blends historic grandeur with modern luxury. Wander through frescoed salons, sunlit loggias, and gardens that unfold like living art—parterres, fountains, and cypress-lined paths overlooking the Florence skyline. From peaceful mornings by the reflecting pools to golden sunsets on the terrace, every moment here is pure Tuscan magic. 🌿💛
💫 Tap the link in bio for more information on Villa Gamberaia
📩 DM our sales experts to check availability on this or other Tuscan Villas.
11/27/2025
💫Wishing you and your family a Happy Thanksgiving.🦃
💫Cruz on Inn Villa has it all ... beachfront location, large swimming pool and spa, lush vegetation offering seclusion, and plenty of outdoor space to enjoy the views. 🏖️
😍 What We Love:
⚡️Gated Estate perfect for couples or families traveling together
🏝️Location - Located minutes from the North Shore Beaches and walking distance to restaurants☀️
✨ All bedrooms can be accessed from the interior of home. (Perfect for groups traveling with children.)
👀Tap the link in bio for more information on Cruz on Inn Villa.
📩 DM our sales experts to check availability on this or other St. John Villas.
11/12/2025
💫 Exclusive. Serene. Unforgettable. L’Oasis in St. Martin is where luxury meets the sea! 🌊
✨ Dreaming of a Christmas escape? 🎄 Celebrate the season at L’Oasis, a luxury beachfront villa perfect for entertaining!
⚡️ Save 20% for your Christmas and New Year stay
What We Love:
🏖️ Located on the infamous Baie Rouge Beach
🧑🍳 Chef Services = Gourmet dining without lifting a finger
🌅 Lots of outdoor lounge spaces- all with views!
☀️Tap the link in bio to see more.
📩 DM us to connect with our sales experts.
💫The Last Resort Villa has it all … panoramic views, infinity edge pool, lush landscaping, and is close to Cruz Bay and the North Shore Beaches!🏝️☀️
🧡Tap our link in bio to learn more about this beautiful estate.
🦃 Last minute availability over Thanksgiving!
📩 DM our sales experts to r4serve your dates.
💫Discover your personal paradise at Valhalla, St. John! Indulge in luxury, savor ultimate privacy, and feast your eyes on the endless views. Dive into dual swimming pools, explore the hidden grotto, and lose yourself in the lush landscapes surrounding the villa. 🌴⛱️
☀️Tap our link in bio to discover Valhalla
📩 DM our island experts for more information
10/15/2025
Celebrate the Holidays in Paradise 🎄 -
Celebrate the Holidays in Paradise 🎄 Luxurious beachfront villa on a secluded, pristine, white beach. Perfect for a family or group as well as for a wedding or party.
Click here to claim your Sponsored Listing.