Vacation rentals in Bailey's Bay

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Top-rated vacation rentals in Bailey's Bay

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Guest favorite

Rental unit in Hamilton Parish

4.89 out of 5 average rating, 144 reviews

Great Relaxing Pool and Ocean View With Kayaks

Welcome to 'Neston'! Picture yourself on 2 acres of lush property nestled in a serene, tucked-away neighborhood. Immerse yourself in the breathtaking views of Harrington Sound, one of Bermuda's most enchanting inlets. Step into your private paradise with access to a dock – swim to secluded islands or paddle away on kayaks at your leisure. Savor the tranquility as you bask in the beauty of the crystal-clear azure waters. Wander along the longest, safest trail just 8 minutes away from your haven.

Guest favorite

Rental unit in St.George's

4.95 out of 5 average rating, 112 reviews

The Windsor, your quaint and cozy getaway.

Nestled just off Turkey Hill, St. George’s, in the UNESCO World Heritage Site, you will find THE WINDSOR. The Windsor is a quaint and cozy vacation rental unit that is within walking distance to the town center, grocery store, restaurants and shops. It is a short walk to public transportation and beaches. The Windsor, which has been tastefully furnished, is non-smoking, comfortable and cozy and can sleep up to 3 persons. This Airbnb is part of Richard Allen AME Church. Be you and enjoy!

Guest favorite

Rental unit in Saint George's

4.97 out of 5 average rating, 104 reviews

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 there is also a Snow cone stand at the upper yard which is open in the peak season the beach front apt is located at the Entrance of Tobacco Bay Beach with in the historic Town of St Georges walking distance to forts ,beaches ,St Regis 5 forts golf course.

Guest favorite

Rental unit in Ferry Reach

4.98 out of 5 average rating, 168 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

Guest favorite

Rental unit in Devonshire

4.95 out of 5 average rating, 191 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.

Guest favorite

Place to stay in St. David's Island

4.99 out of 5 average rating, 185 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. 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. Please note that since Covid, breakfast is no longer available.

Guest favorite

Rental unit in Hamilton Parish

4.97 out of 5 average rating, 142 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.

Guest favorite

Guest suite in Hamilton

4.96 out of 5 average rating, 314 reviews

Little Arches Studio close to town

The unit is a self-contained studio apartment within my house. It consists of a bedroom and en-suite bathroom and has its own entrance via french doors onto the patio and garden. It has a fridge, microwave and Keurig coffee machine. It is air-conditioned, has WIFI and cable TV. Hamilton is only a five minute walk with shops and restaurants, bus station and ferry terminal. The central location makes it a convenient place from which to explore Bermuda.

Guest favorite

Rental unit in Smith's

4.96 out of 5 average rating, 134 reviews

Pool, Private Gym, Serenity,Tranquility it's here!

Embrace the tranquility & privacy as you relax in our garden snuggled with your favorite book. Cook outdoors on our BBQ & dine el-fresco, then take a dip in our swimming pool. Fully equipped recreation room. Our property is conveniently located to beaches, restaurants, Flatts Village & other tourist spots. If shopping is on your list visit the city of Hamilton, The Ole' towne of St. George's or venture west to The Royal Naval Dockyard.

Guest favorite

Home in Bermuda

4.99 out of 5 average rating, 255 reviews

Contemporary Oceanfront Apartment with shared pool

A contemporary oceanfront apartment located at the end of a quiet lane on the south shore between Whale Bay and Church Bay. Ideal for those looking to relax, with great ocean views from every room We also have a 3 Bed Contemporary Oceanfront Villa with private horizon pool approximately a mile down the road perfect for larger groups and family gatherings! Can be booked together for groups up to 8! https://www.airbnb.com/rooms/23767162

Guest favorite

Rental unit in St.George's

4.84 out of 5 average rating, 103 reviews

Domiche's Apt - Water Front Paradise

Fully renovated lower-level, water-front apt with stainless steel appliances, all household amenities & out door shower to rinse off after a swim. 12-15 minute drive from airport. Walking distance to small market/liquor store/gas stn & walking distance to Clearwater Beach & Cooper's Island Nature Reserve. Use of BBQ, paddle-board, kayak and other amenities (snorkeling fins/water toys, etc)... are complimentary.

Guest favorite

Rental unit in Pembroke Parish

5 out of 5 average rating, 233 reviews

Paradise Awaits on the water’s edge, walk to town!

Welcome to your piece of Paradise, where you can wine and dine under the stars in your private garden with 180 degree unobstructed water views. Snorkel on your private reef directly in front of your apartment. Hamilton is just a 15 - 20 minute stroll away, or a 5 minute bus or cab ride. A convenience store is only a 2 minute walk. You have a full bathroom, fully equipped kitchen, and a king size bed.