Holiday houses 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.

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. Come and experience Cow Polly for yourself.

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.

"By Faith" Vacation Rental Unit

You’ll love our place because of the coziness. It’s a non-smoking studio unit that is suited for two persons or solo travelers. It is about a 6 minute walk to the bus stop and located about 10 minutes by bus from the UNESCO World Heritage Site, a grocery store and restaurants in St. George's town! We are less than 15 minutes by vehicle to beaches in St. George's! It's a 5 minute walk to (BIOS) Bermuda Institute for Ocean Sciences. We are about a 45 minute bus ride to Hamilton. Sofa is a bed

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.

Little Loft-Central location-Beaches nearby

A tiny loft cottage just comfortable and cozy enough for one or two people. Includes an outside garden space under the pergola with Adirondack chairs and fire pit, lovely for relaxing. We are situated close to Admiralty House and Deep Bay where you can swim, explore caves and cliff jump. Approximately 7 minute drive to Hamilton. Bus #4 Airbnb guests only allowed on the property, no parties or outside guests. Safety concern with stairs for children below age of twelve.

"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.

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.

Ocean Side Studio Cottage - Condé Nast Recommended

"Saltine" is an exquisite cottage overlooking Hungry Bay in Paget. In July 2025 Condé Nast Traveler selected Saltine as one of the top 11 AirBNBs in Bermuda and selected it as the top pick for Local Charm. With stunning views across south shore with magnificent sunrise, enjoy the nature, beauty & tranquility of Hungry Bay, while being a short distance from the City of Hamilton.

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.

Your Own Beautiful Bermuda Cottage

WE'RE OPEN! Dean Hall Nursery is your own charming and welcoming home away from home. Perfectly appointed, stocked full of complimentary extras and well-situated, discover for yourself why this open-plan cottage has consistently been the most highly recommended vacation rental in beautiful Bermuda!