Vacation rentals in Bailey's Bay

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Top-rated vacation rentals in Bailey's Bay

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Top guest favorite

A decorative coral sculpture stands prominently on a marble surface, framed by large windows that overlook an expansive ocean view. Soft blue waters meet the horizon under a bright sky dotted with clouds, creating a serene coastal ambiance.

Cottage in Smith's

4.98 out of 5 average rating, 104 reviews

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.

Top guest favorite

A bright turquoise exterior showcases a welcoming entrance with a white door beneath a decorative awning. Vibrant red flowers and potted green plants are situated beside the door, enhancing the inviting appearance of the studio unit's entrance.

Apartment in Ferry Reach

4.98 out of 5 average rating, 191 reviews

"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

Top guest favorite

A lush yard is visible, featuring a well-maintained lawn and surrounded by tropical palm trees. A small shed is positioned in the background, with a glimpse of a beach and colorful recreational activities visible in the distance.

Apartment in Hamilton

4.95 out of 5 average rating, 101 reviews

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.

Top guest favorite

An aerial view showcases the studio's clifftop location alongside rocky shoreline and clear turquoise waters. The gentle waves lap against the rugged coast, while lush greenery surrounds the property, emphasizing its private setting near the ocean.

Apartment in Smiths

5 out of 5 average rating, 116 reviews

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.

Top guest favorite

A stately gray building sits atop a stone-walled terrace, surrounded by lush greenery and palm trees. A white railing outlines the terrace, and the entrance is marked by steps leading up from the road, showcasing the welcoming exterior.

Apartment in St.George's

4.98 out of 5 average rating, 110 reviews

Roxbury Studio - in St. George

Enjoy this affordable studio rental unit near the historic Towne of St. George. Lovely views of St. George's Harbor and a peaceful neighborhood with close proximity to restaurants, shops, bus and ferry transportation. Tobacco Bay Beach and St. Catherine's Beach are a short distance away (20 minute walk). Only 10 minute drive from the L.F. Wade Airport. (Twizzy and Rugged Electric) car rental across the street as well as 'Temptations', a very good breakfast and lunch restaurant

Guest favorite

A two-story house is surrounded by lush greenery, featuring a covered porch adorned with colorful prayer flags. The outdoor seating area invites relaxation, while tropical plants create a serene atmosphere. The structure’s light green exterior complements the natural setting.

Apartment in Devonshire

4.95 out of 5 average rating, 206 reviews

Spirit House Bermuda

We are a small spiritual community center in the middle of the island of Bermuda. Our cosy bedroom (which consists of a queen bed and two bunk beds, plus desk and love seat) will be solely yours unless you bring friends or family with you. It offers a comfortable retreat where you can choose to spend time on your own or join in and become part of the community if there is an event going on. You are also welcome to attend classes upstairs for a fee directly to the teachers.

Top guest favorite

A two-story white building is set against a clear blue sky. Features include an inviting garden area with well-maintained greenery and sun loungers. A driveway leads to the entrance, while a staircase can be seen on the side of the building.

Apartment in Hamilton Parish

4.98 out of 5 average rating, 165 reviews

"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.

Top guest favorite

The bedroom features a queen-sized bed with a blue headboard, complemented by light bedding. Two bedside lamps are mounted on the wall, and a circular mirror sits above the bed. A colorful seahorse painting adds a touch of decor, while a fan is installed on the ceiling.

Place to stay in St. David's Island

4.99 out of 5 average rating, 197 reviews

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.

Top guest favorite

A covered balcony showcases a wooden bar table with two stools, offering views of Harrington Sound and lush surroundings. Bright green walls complement the natural light filtering through the windows, creating a relaxed outdoor space for morning coffee or evening cocktails.

Cottage in Smiths

4.96 out of 5 average rating, 146 reviews

Quaint and charming cottage on the Water

Ship Shape is a charming stand-alone cottage on Harrington Sound. Wake up to the peace of the Sound lapping under the porch where you have morning coffee or enjoy a picturesque sunset. A five-minute walk to Flatt's village with three restaurants. We are 20 minutes from the airport and a ten-minute drive to the City of Hamilton for nightlife. The closest beach is John Smith's Bay, which is a 5-minute moped ride away or a 15-minute walk.

Guest favorite

A serene view from a doorway showcases a tranquil pool surrounded by lush palm trees, with a backdrop of Harrington Sound and gentle hills. The clear sky reflects on the water, creating a peaceful atmosphere.

Apartment in Hamilton Parish

4.96 out of 5 average rating, 114 reviews

Romantic, Ocean and Pool View

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.

Top guest favorite

The exterior of a charming pink cottage is framed by natural wood accents. A spacious covered porch features wooden railings and a table with chairs, inviting relaxation and outdoor dining. Lush greenery surrounds the entrance, enhancing the cottage's cozy appeal.

Home in Flatts Village

4.96 out of 5 average rating, 318 reviews

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!

Top guest favorite

The exterior of a cottage is shown, featuring a light-colored facade and a distinctive arched window. A covered porch extends outward, providing a shaded area. Surrounding greenery and textured plants enhance the natural setting, with a clear blue sky in the background.

Home in Baileys Bay

4.95 out of 5 average rating, 221 reviews

Bird's Nest Cottage

Bird's Nest cottage is a historically listed seaside cottage perched at the waters edge, overlooking Bailey's Bay. The cottage has been restored and includes modern conveniences necessary for a comfortable stay. It's the perfect getaway for up to four guests, with 2 bedrooms with double beds.