Saba Island Properties
Cliffside villas and hideaway cottages on Booby Hill, a short stroll from Windwardside
Why Go
Forget cookie-cutter resorts — this is Saba, and Saba does things differently. Saba Island Properties hands you the keys to a private villa or cottage tucked into the rainforest above Windwardside, where the only neighbors are hummingbirds, goats, and the occasional passing cloud. Perched 1,200+ feet above the Caribbean on Booby Hill, these homes trade lobbies and buffets for hammocks, outdoor showers, and jaw-dropping ocean panoramas that shift with every hour of light.
The Experience
Booby Hill is Saba at its most quietly cinematic — a ridge of lush hillside just outside the storybook village of Windwardside, dotted with red-roofed white cottages that feel plucked from a Dutch fairytale. Properties in the portfolio range from ultra-private cliff-edge villas like Spyglass and Hummingbird to intimate hideaways like Compass Cottage in the Johnny's Ground enclave, each with its own personality but sharing that same slow, salt-air rhythm. Mornings mean coffee on the deck watching frigate birds ride the trade winds; evenings usually involve an easy walk down the hill for dinner, then a walk back under a sky so dark you'll actually see the Milky Way. There's no beach club here, no swim-up bar, no crowds — just you, the mountain, and the sea unfolding forever.
What to Try
Book a villa with a private plunge pool or hot tub — the elevation means cool evening breezes and you'll want to soak while watching the sunset paint the Caribbean pink. Ask for a property on the seaward side of the ridge for uninterrupted views toward St. Eustatius on clear days. If you're traveling as a group or family, the larger villas like Troy or Spyglass give you the space of a private estate for less than what a mid-tier hotel room costs elsewhere in the Caribbean. Cook one night in — the fully equipped kitchens are a treat after a day of diving or hiking Mt. Scenery.
Insider Tip
Rent a car (or arrange one through the property manager on arrival) even if you think you won't need it. The walk from Booby Hill down to Windwardside is charming going down but a proper cardio workout coming back up — and Saba's roads, though famously steep, are short and easy to master. Also: bring layers. At this elevation the trades can turn a Caribbean night surprisingly cool, and most villas skip AC because they simply don't need it.
The Practical Stuff
Located on Booby Hill, Windwardside — roughly a 10–15 minute walk (uphill on return) or 3-minute drive to the village's restaurants, shops, and dive operators. About 15 minutes by car from Juancho E. Yrausquin Airport and 20 minutes from Fort Bay harbor. Contact Albert Pensis at Saba Island Properties (+599-416-2777 or +1-631-604-4435) to inquire about specific villas, minimum stays, and shoulder-season rates. Payment, cleaning fees, and check-in logistics are handled directly with the property manager.
Pair It With
- Amonhana Guide — A short walk down the hill for a relaxed dinner in Windwardside — perfect for your first or last night when you don't want to drive.
- Angelina's Saba By OwAiChie — Easy, satisfying local food and drinks nearby — great for a casual lunch between hikes or dives.
- Barney's Ground Guide — One of the classic Booby Hill trailheads — lace up and explore straight from your villa's doorstep.
- Big Stone Guide — A nearby activity spot that captures Saba's wild, volcanic character — an easy add-on for guests who want to hike beyond Mt. Scenery.
