Holiday rentals in Bailey's Bay

Sea Breeze Mews on the Little Sound

Cozy & compact, this delightful 1 bedroom/2 story waterfront hideaway affords a panoramic view of the Little & Great Sounds. On the water (walk across the lawn and jump in) with a large dock suitable for swimming, snorkeling & spectacular sunsets. "Sea Breeze Mews" is only a 10 minute walk to picturesque Church Bay beach & a short bus ride to all the magnificent South Shore Beaches. Restaurants and award winning Golf courses are only a few minutes away. Public transportation right outside gate.

Historic Waterfront Cottage in Flatts Village

Westport is a fully refurbished, historic cottage on the water in Flatts Village. The interior has all of the modern conveniences for comfort with an old world charm. Ideal for an individual or couple, this unique building is more spacious than one would think. The verandah overlooks the manicured lawn and Flatts Inlet. Westport is perfectly located between Hamilton and the airport (12 mins in either direction) and 2 of the most popular restaurants (Rustico & V Pantry) are across the street

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.

"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.

High & Dry Bermuda

Enjoy the peace and tranquility of Bermuda while still being just a short drive away from all the island's attractions. Located within walking distance to the popular Blue Hole Hill in Hamilton Parish, High and Dry Bermuda is a cozy two-bedroom/2 bath villa with stunning panoramic views of Grotto Bay and St. George’s. This peaceful and secluded home can accommodate up to four adult guests, as well as children and pets.

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.

Oceanfront Romance Haven — Poolside Bliss + Kayaks

This is a very quaint unit, and has been well received by guests who have stayed there. As you look out of the front door of the entrance to the unit, you can see the pool which is 5 feet away. You will also be able to see the clear blue ocean from your bed as you look out. It is a very romantic unit with its blue walls which blends in with its environment.