Holiday rentals in Bailey's Bay

Charming Beachfront chill spot

Welcome to our beautiful beachside studio, the Ledges. It’s located on over an acre of property in the rustic west of Bermuda. Take strolls on our country road to the local farm. The bus stop is steps away to take public transportation to Dockyard or to Hamilton. Or spend your days on the property at one of 2 private beaches. The Ledges studio is an architectural gem with exposed beamed ceilings, a cozy fireplace for chilly evenings, and a modern fully equipped kitchen. The studio has its own private, large upper deck for entertaining or relaxing where the sunsets are just stupendous!!! Airport pick-ups and island tours can be arranged through your host.

Cozy Studio across from beach

This Cozy studio is located directly across from one of Bermudas most family friendly beaches. There is a large field with a walking track and an outdoor basketball court across the street, and bus stops are easily accessible. Eve's pond nature reserve is a two-minute walk away and you can get there along scenic walking trails. A mile away is Flatts Village which is home to restaurants, and the Bermuda Aquarium and Zoo. A mile in the opposite direction are restaurants and a large supermarket.

Modern Ocean Front Studio w/ Panoramic View

Modern, clifftop, ocean front studio with breathtaking panoramic views of the exquisite turquoise waters off the rugged south shore. Bright and airy with a relaxed, minimalist island vibe. Well appointed kitchenette, perfect for prepping morning coffee or small, simple meals to enjoy in the comfort of the studio or on the patio in the fresh ocean air. Central location 10-15 mins drive from the town of Hamilton and close to many of Bermuda's best beaches, restaurants and attractions.

High & Dry Bermuda (lower east apt)

Located just five minutes from L.F. Wade International Airport, this newly renovated, private one- bedroom apartment features a queen-sized bed, an oversized pull-out sectional sofa, dual split-unit air conditioning, and two 55-inch Smart TVs. For seamless connectivity, both nightstands include integrated smart-charging outlets for your phone, smartwatch, laptop, and wearable tech. On-site e-bike rentals are also available to enhance your stay—please inquire for details.

A Quiet Oasis at Havannah Night

Relax and reconnect in this charming Bermuda studio. Escape the hustle and bustle at this peaceful studio retreat, just 4 minutes from the airport! Immerse yourself in the charm of Bermuda with a private haven featuring a spacious outdoor area, perfect for unwinding with a glass of wine. Explore the nearby beaches, caves, and restaurants, all within a walking distance. This cozy studio is ideal for those seeking a getaway. Book your peaceful escape today!

"Del-Lita"

This apartment is fully furnished and has a 'Queen' size bed + a 'Foldaway' cot + an Air Bed suitable for an extra person. It is located 2/3 miles from the Airport. Has its own private porch in a garden setting. Nearby is the Crystal Caves, Blue Hole Park, The Swizzle Inn, The Grotto Bay Hotel, The Railway /Walking trail, The Ice Cream Parlor, A Cycle Livery, Nearby convenience store and several Scenic Bus routes to the City of Hamilton and popular Beaches.

Cow Polly: Coastal luxury, featured in CN Traveler

Recently featured in Condé Nast Traveler, Cow Polly is a high-end luxury oceanfront cottage with spectacular views of Bermuda’s North Shore in a contemporary, beautifully decorated space. Guests enjoy premier amenities and elegantly appointed furnishings in an airy beach cottage setting. Along with its sister property, Top Shell (https://www.airbnb.com/h/top-shell) -- conveniently located next door -- it's like no other vacation rental on the island.

Pepper Tree Cottage one bedroom.

This charming newly renovated, one bedroom in Pepper Tree Cottage, is literally a stones throw from beautiful Dolly’s Bay. Your private garden area is the perfect place to enjoy the gorgeous views of the bobbing boats or a paddle in the kayak. Please note, there are many steps down to this unit. The very quaint old town of St. George's where you will find local hangouts and some lovely restaurants, only a 15 minute bus, car or bike ride away.

Stylish, harbour view apt in historic St George

Newly renovated and perfectly perched above Bermuda’s charming old town, this 1-bedroom, 1-bathroom apartment offers breathtaking views of the harbour — all just a minute’s stroll from the vibrant town square. Whether you’re in the mood to dine waterside, explore the historic streets, or simply relax and watch the boats drift by from your bedroom window, this spot offers the perfect blend of comfort, character, and convenience.

Simdell - Lower

Welcome to your home away from! This spacious one-bedroom is nestled in a peaceful neighborhood, just minutes from the beach, a grocery store, and a scenic nature trail. You’ll also be a short walk or drive away from great spots to grab a quick bite to eat. Whether you’re here to unwind by the shore, explore the outdoors, our place offers the ideal blend of comfort and convenience.

Chic 3BR w/ Dock + Hot Tub + Lounge Vibes

Welcome to Banana Cottage, your private island hideaway nestled on a lush, private estate in Hamilton Parish. This beautifully designed 3-bedroom, 2-bathroom home offers the perfect blend of comfort and coastal charm, with stunning views of Harrington Sound, a private dock, and a hot tub shaded by swaying palms. Just minutes from Bermuda’s best natural attractions and fine dining.

Ocean front Loft living with unobstructed view

OCEAN LOFT BERMUDA Newly built, bright and spacious loft living in a desirable neighborhood. Our drinking water goes through a 3-stage filtering system. Public transit is just steps away from the property. Ample parking with an EV charger available for guests preferred car rental. Restaurants and Bermuda’s nature railway trails are minutes away from the property.