Vacation rentals in Bailey's Bay

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Top-rated vacation rentals in Bailey's Bay

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Top guest favourite

A vibrant green lawn stretches towards the water, framed by lush trees. A tall palm tree towers above, while the shoreline and ocean are visible in the background under a clear blue sky scattered with fluffy white clouds.

Home in Southampton

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.

4.98 out of 5 average rating, 255 reviews

Top guest favourite

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

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.

4.95 out of 5 average rating, 148 reviews

Top guest favourite

A serene beach scene is depicted, showcasing clear turquoise waters and a sandy shoreline. A yellow floating structure is visible in the background, with a few individuals enjoying the gentle waves. Lush greenery and palm trees frame the landscape under a bright blue sky.

Apartment in Town of St. George's

Tobacco Bay beachfront Traditional apartment

If you love the beach ,sunsets ,casual walks, fishing , the Beach front apt is for you. the apt is a large lower fully equipped apt . with a beach natacal decor there is also a large upper yard with a picnic table and barbecue ,the beach front apt is located at the Entrance of Tobacco Bay Beach. guests also get discounts at the beach for food and lounge chairs the beachfront apt is in the historic Town of St Georges walking distance to forts ,beaches ,St Regis 5 forts golf course.

4.98 out of 5 average rating, 143 reviews

Top guest favourite

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

"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

4.98 out of 5 average rating, 237 reviews

Top guest favourite

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 Town of St. George's

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

4.97 out of 5 average rating, 156 reviews

Top guest favourite

A bright living area is showcased, featuring a comfortable seating arrangement with dark blue sofas and an ottoman. A wooden coffee table is present in the center, while a television is mounted on a wooden console. Large windows lined with dark blinds allow natural light to fill the space.

Apartment in Smith's

Cozy Cartwheel Cottage 2BR Apt.

This charming two bedroom one bathroom upper unit in a quiet residential area in Smith's Parish offers scenic ocean view from the balcony. Located just minutes away from John Smith's Bay Beach , Spittal Pond Nature Sanctuary, Tuckers' Point Golf Club, Crystal Caves and Harrington Hundreds Grocery, there is much to do in close proximity of the apartment. A fifteen minute bus ride will get you into Hamilton for business , shopping excursions and sightseeing tours.

4.93 out of 5 average rating, 105 reviews

Top guest favourite

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

"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.

4.97 out of 5 average rating, 189 reviews

Top guest favourite

Apartment in Hamilton

Sugar Shack | Your cozy vacay home w/ ocean views!

Wake up in Bermuda and enjoy your breakfast watching the sunrise over the ocean from a cozy patio in a local, Bermudian neighborhood. Sugar Shack is a short 10-minute drive from Bermuda's airport and provides easy access to transportation, convenience and grocery stores, Bermuda's famous Railway Trail, and a short bus ride to the beautiful Shelly Bay Beach. It comes with all the standard amenities a modern traveler needs to have a comfortable stay.

5.0 out of 5 average rating, 11 reviews

Top guest favourite

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

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.

4.99 out of 5 average rating, 223 reviews

Top guest favourite

A comfortable living area features a plush gray sofa adorned with decorative pillows. A matching ottoman is placed in front, and a round dining table sits nearby. A painting of sailboats hangs on the wall, complemented by natural light streaming through window treatments.

Condo in Hamilton

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.

4.94 out of 5 average rating, 52 reviews

Guest favourite

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

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.

4.93 out of 5 average rating, 148 reviews

Top guest favourite

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

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!

4.96 out of 5 average rating, 342 reviews