Spyglass Hill Villa: A Private Perch Above Road Bay
A four-bedroom clifftop hideaway with the most commanding views on Anguilla.
Why Go
Perched high on North Hill with Road Bay's yacht-dotted harbor spread out below, Spyglass Hill is the rare Anguillan villa that trades beachfront for something arguably better: a 360-degree sweep of Caribbean blue, offshore cays, and Sandy Ground's twinkling waterfront lights after dark. Rented to just one party at a time, the whole three-story property becomes yours.
The Experience
You arrive to what feels like a private Mediterranean-West Indian estate ΓÇö bamboo floors underfoot, a roofless interior courtyard pulling in the trade winds, and an infinity-edge pool that dissolves into the horizon over Road Bay. Mornings are for coffee on a private patio off one of the twin upstairs master suites, each with its own outdoor shower and Jacuzzi. Afternoons drift between the pool deck, the fitness suite, and the entertainment room's billiard table. When you're ready for the island, Sandy Ground's beach bars, seafood shacks, and boat charters are a five-minute descent down the hill ΓÇö but most guests find themselves lingering just to watch the sun sink behind the cays.
What to Try
Book a sunset cocktail hour on the upper terrace ΓÇö the westward orientation over Road Bay makes it one of the best sundown perches on the island. Then walk down to Sandy Ground for dinner at Roy's Bayside Grill or grilled crayfish at Elvis' Beach Bar, and arrange a day-charter to Sandy Island or Prickly Pear Cays straight from the harbor below.
Insider Tip
Ask the villa team to stock the kitchen from Albert Lake Marketplace and arrange a private chef for at least one night ΓÇö the sunset view from the villa's dining terrace is worth staying in for, and Anguilla's chef-at-home scene is genuinely world class. Also request a car: North Hill is beautiful but steep, and you'll want wheels for beach-hopping to Meads Bay, Shoal Bay East, and Rendezvous Bay.
The Practical Stuff
Four bedrooms across three floors, sleeps up to eight. Located on North Hill, AI-2640, roughly five minutes by car to Sandy Ground and 15ΓÇô20 minutes to Anguilla's marquee beaches. Whole-villa rental only (single party at a time). Contact +1 (264) 497-3666 or info@spyglasshillanguilla.com. Rental car recommended; the villa can arrange transfers from Clayton J. Lloyd International Airport (AXA) or the Blowing Point ferry terminal from St. Martin.
Pair It With
- Sandy Ground / Road Bay — The village directly below the villa ΓÇö beach bars, live music at Elvis' and The Pumphouse, and the launching point for boat charters to nearby cays.
- Sandy Island — A tiny, palm-dotted sandbar a short boat ride from Road Bay with grilled lobster and rum punch ΓÇö an essential Anguilla day trip visible from the villa's terrace.
- Meads Bay — Anguilla's iconic powder-white beach, about 10 minutes away, with standout beach-club lunches at Blanchards Beach Shack and Straw Hat.
- Prickly Pear Cays — Uninhabited cays with snorkeling and beach-shack lunches, easily reached by charter from Road Bay Harbor right below the villa.