Flamboyant Cottage: Your Gingerbread Perch on Booby Hill
A private two-bedroom cottage with pool and postcard views of Statia, St. Kitts, and Nevis
Why Go
Perched 1,500 feet above the Caribbean on the flanks of Booby Hill, Flamboyant Cottage is the kind of place you book once and then quietly recommend only to friends you actually like. It's a candy-colored gingerbread bungalow with a private plunge pool, a shaded gazebo, and a wraparound deck that stares straight out at three neighboring islands rising from the sea.
The Experience
Saba is already the Caribbean's most under-the-radar island, and Flamboyant Cottage doubles down on that quiet. You're a short walk from Windwardside's restaurants and shops, but tucked far enough up Booby Hill that the soundtrack is birds, tree frogs, and the occasional goat. The two-bedroom, two-bath layout means couples traveling together get real privacy, and the full kitchen plus outdoor dining gazebo make it easy to settle in for a week rather than treat it as a hotel. Days end with a swim in your own pool as the sun drops behind the Mount Scenery rainforest and the lights of Statia begin to flicker across the water.
What to Try
Start your morning with coffee on the tiled deck watching the clouds lift off Mount Scenery, then walk down into Windwardside for breakfast. Book at least one night to cook in — Saba's tiny grocery stores stock enough for a solid pasta-and-local-fish dinner in the gazebo. Use the Bluetooth speakers, pour something cold, and float in the pool for sundown; it's the single best seat on the island for the Statia–St. Kitts–Nevis skyline. Rinse and repeat.
Insider Tip
Book a rental car or arrange a taxi transfer in advance — Booby Hill is a genuine hill, and while Windwardside is technically walkable, the climb back up after dinner in flip-flops with a bag of groceries is a rite of passage you only need to do once. Also: bring reef-safe sunscreen and a light layer. At 1,500 feet the evening breeze actually gets cool, which is half the magic.
The Practical Stuff
Two bedrooms, two bathrooms, sleeps up to 4. Private pool, full kitchen, gazebo, tiled decks, ceiling fans, flat-screen TV, Wi-Fi, Bluetooth speakers. Location: Booby Hill, Windward Side (JQFC+CW4), a short uphill walk from Windwardside village. Self-catering rental — no on-site restaurant or daily housekeeping, so plan a grocery run on arrival. Contact the owner directly via flamboyantcottage.com or FlamboyantCottage@gmail.com for rates and availability.
Pair It With
- Angelina's Saba By OwAiChie — A short walk down into Windwardside for hearty local Saban plates when you don't feel like cooking in the gazebo.
- Amonhana Guide — Another nearby Windwardside spot to rotate through on multi-night stays — perfect for a laid-back dinner before the walk back up Booby Hill.
- Battery Corre Corre Guide — A historic coastal battery close by that makes an easy half-day outing between pool sessions.
- Barney's Ground Guide — A green, breezy hillside area nearby ideal for a stroll and photos of Saba's dramatic terrain.
- Big Rock Engineering Guide — Handy local transport contact for arranging island rides so you're not hiking back up to Booby Hill after dinner.
