Bailey's Bay holiday homes

We found 215 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Bailey's Bay to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include a fireplace and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The beachside setting of Bailey's Bay is ready to explore

Enjoy the museums and other features of Bailey's Bay. This romantic city is known for its beaches, restaurants and sporting events. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Bailey's Bay

Are you hoping to find attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Bailey's Bay a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Tucker's Point Golf Club (1.5 mi / 2.5 km)
  • Bermuda Aquarium Museum and Zoo (BAMZ) (1.9 mi / 3.1 km)
  • Mid Ocean Golf Club (2 mi / 3.3 km)
  • Fairmont Southampton Golf Club (9 mi / 14.4 km)
  • Port Royal Golf Course (10.7 mi / 17.2 km)
  • Five Forts Golf Club (4 mi / 6.4 km)

Exploring the natural landscape of Bailey's Bay

Whether you're looking for adventure or just want to spend some time taking in the scenery, Bailey's Bay is a great place to get outside. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Crystal Caves (0.4 mi / 0.7 km)
  • Blue Hole Park (0.7 mi / 1 km)
  • Windsor Beach (2.6 mi / 4.1 km)
  • Frick's Beach (2.8 mi / 4.4 km)
  • Nonsuch Island Nature Reserve (3.5 mi / 5.6 km)
  • Clearwater Beach (3.7 mi / 6 km)

Transport to and around Bailey's Bay

Book a flight to St. George's (BDA-L.F. Wade Intl.), the closest airport, located 1.5 mi (2.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Bailey'S Bay when booking a holiday rental?
When considering a holiday rental in Bailey's Bay, Bermuda, the area around the bay itself is highly recommended. This picturesque neighbourhood boasts a charming coastal atmosphere, making it great for those looking to relax by the sea. The scenic views and tranquil surroundings are ideal for a peaceful getaway.In Bailey's Bay, you'll find a variety of properties, ranging from cosy cottages to more luxurious accommodations, ensuring there's something to suit every traveller's needs. One of the main attractions in the area is the stunning beach, which offers excellent opportunities for swimming, snorkelling, and sunbathing. Additionally, the nearby Crystal Caves are a must-visit, showcasing breathtaking underground formations that are sure to impress.Staying in this area not only provides easy access to these attractions but also allows you to enjoy the natural beauty and laid-back lifestyle that Bermuda is renowned for.
What are the top attractions in Bailey'S Bay?
In Bailey's Bay, Bermuda, visitors can enjoy a selection of popular attractions that highlight the area's natural beauty and cultural heritage. The picturesque beaches, such as the nearby John Smith's Bay, are superb for sunbathing and swimming, while the crystal-clear waters offer excellent opportunities for snorkelling and diving.The Bermuda Aquarium, Museum and Zoo, located a short drive away in Flatts Village, showcases a variety of marine life and is a fantastic educational experience for families. For those interested in local history, the nearby St. George's, a UNESCO World Heritage site, features well-preserved historic architecture and historical landmarks, including the St. Peter's Church and the Town Hall.Nature enthusiasts can explore the lush landscapes of the nearby Spittal Pond Nature Reserve, which is ideal for hiking and birdwatching.
Are all fees included in the Bailey's Bay holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Bailey's Bay holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Bailey's Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Bailey's Bay holiday homes?
You can find great discounts on holiday homes in Bailey's Bay on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Bailey's Bay holiday home booking on Bookabach?
To find Bailey's Bay holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Bailey's Bay?
A long-stay holiday home in Bailey's Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Bailey's Bay holiday home?
Book your Bailey's Bay holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Bailey's Bay?
Prices for holiday homes in Bailey's Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Bailey's Bay to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.