Vacation rentals in Bailey's Bay

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.

Pool house in a garden setting (+ EV chargers)

The pool house has a queen bed and its own bathroom + shower. It is next to our house in a spacious yard in a quiet residential neighbourhood. Bus stop is a 3 minute walk, John Smith's Bay beach 5 minutes and grocery store 12 minutes away. We also have a Labrador that roams the property. There's cable tv (includes HBO and Showtime) free wifi. Please see our other rental on the property "Las Brisas apartment with a pool" as an alternative (has a full stove) or if you are travelling with friends.

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.

"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. We are 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! 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

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.

Smuggler's Cove - Walk to City of Hamilton

** Early check-in is guaranteed on flight arrival with Bermuda Covid entry requirements. ** Fully furnished, newly renovated, Bermuda themed, one bedroom, one bathroom, two story townhouse located on Rosemont Avenue. Interior Queen bed Bath with shower Split unit air-conditioning and heating Full kitchen with Nespresso machine All dining and cookware Laundry Desk 2 Flat screen TV’s Cable, Wifi and local phone Exterior Private patio/BBQ/outdoor dining Shared pool

“Long Bay” Studio Overlooking Bermuda

Nestled in the heart of Somerset Village, our contemporary studio offers breathtaking views of Long Bay from one of Bermuda's highest point. Wake up to serene ocean vistas and enjoy your morning coffee on the private balcony. The studio features a comfortable queen-sized bed, a fully equipped kitchenette, and modern bathroom facilities. Just a short walk away, explore scenic walks on the trail ways, restaurants and the pristine beaches Bermuda is renowned for.

"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.

The Pool House w/ Heated Pool (Nov. 1)

Take a step back in time for a refreshingly sophisticated island holiday at the Ledgelets Cottage Colony. The serene atmosphere instantly lulls you into a soothing, restful state of relaxation. Wake to the chirping birds, and fall asleep to the choral tree frogs. The refurbished cottage interiors and pool terrace have been created with a modern vintage, boho-luxe vibe. To us, nostalgia is a very cool thing. Welcome, Pool House cottage awaits.

Bungalow 41

Visiting Bermuda for the first time? Look no further. Bungalow 41 is a private studio pool cottage located in the heart of Paget and within walking distance of the city of Hamilton, Bermuda Botanical Gardens, Bermuda National Trust headquarters, Pomander Gate Tennis Club and Royal Hamilton Amateur Dinghy Club. Easy access to all bus routes and the main ferry terminal for those not wanting to rent a scooter or small electric car.

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.