Bailey's Bay Holiday Rentals

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Holiday Rentals in Bailey's Bay

Our top choices for Bailey's Bay holiday rentals

Paradise at Limehouse

9.4 out of 10, Exceptional, (40)
"Excellent stay. Goodwin was very helpful too."
Paradise at Limehouse

Wyndham Water Views

9.0 out of 10, Wonderful, (10)
"This was a great property. We really enjoyed our stay. The access to the railway walking path was really nice and the views were spectacular. "
Wyndham Water Views

Rosemont Guest Suites

3.5 star property
8.6 out of 10, Excellent, (181)
"Great little quaint local property, clean, a quiet and walkable to Front street shops and restaurants. "
The price is AU$572
includes taxes & fees
26 Sept - 27 Sept
Rosemont Guest Suites

Seven Arches

3.0 star property
9.4 out of 10, Exceptional, (50)
"Nice property "
Seven Arches

Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach!

10.0 out of 10, Exceptional, (1)
"Fantastic property- conveniently located and as advertised! "
Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach!

Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!

10.0 out of 10, Exceptional, (115)
"Amazing place Jody has set up! My fiance and I had a wonderful time!"
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!

Stunning sunsets, turtle watching, longtails wheeling and glow worms ....

9.8 out of 10, Exceptional, (163)
"Once again, we really enjoyed our stay. This has to be the best little cottage in Bermuda. Thank you and see you soon. Jo and Ed"
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....

Windsong Guest Apartments

3.0 star property
8.8 out of 10, Excellent, (93)
"Place was really clean and big, Roslyn was very caring and helpful. Great place to stay!!!!"
Windsong Guest Apartments

Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

10.0 out of 10, Exceptional, (41)
"Overall a very nice property. We like to be off the beaten track and it certainly was."
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

10.0 out of 10, Exceptional, (122)
"We really enjoyed our stay. Beautiful location and great home for large family gathering. Jessica was immediately responsive in answering questions and helping us when needed. Kids loved the pool, and the nearby beach."
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

9.8 out of 10, Exceptional, (126)
"the views are breath taking house needs some work but being on the water will beat any property up"
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

Spacious Beachfront and Private Resort living

9.8 out of 10, Exceptional, (135)
"Fantastic stay. Accurate description. Right on bus route and basically a beautiful private beach. Wonderful hosts. We will come again. "
Spacious Beachfront and Private Resort living

Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment

10.0 out of 10, Exceptional, (91)
"This place is fabulous, just like in the pictures. You get your private balcony to watch the sunsets, and walk right down to the ocean for swimming and snorkeling. The owners are super nice and very helpful. The is room comfy and the bed is nice and firm. We would definitely stay here again. Small word of awareness, it is down a steep road, and can be tricky to navigate. Also it requires some up and down hilly walking to the ocean and room, just keep that in mind. Other than that, it's paradise,...
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment

Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!

9.8 out of 10, Exceptional, (96)
"We loved our time at this property! The unit was beautifully setup, amazing view all day long, convenient access to bus, walkable to beach and Breezes restaurant. And to top it off the host is great too and even coordinated our transportation to and from airport. Highly recommend! "
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!

Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........

10.0 out of 10, Exceptional, (13)
"We had the best stay with Austin. His home is lovely and fully equipped with everything you need. Never had a host take such great care of us. He went above and beyond. Would definitely stay with him again Thanks Austin we had a great time. The Luersens."
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........

Location! Location! HALF PRICE SALE @ 100 Daily, Sep 25 - Oct 10 & Oct 27- Nov 1

10.0 out of 10, Exceptional, (146)
"⭐️💌TOP HOST & LOCATION⭐️💌Perfect 4 Couples Looking for Serenity & a Secure Sanctuary💌⭐️40+YEAR HOST Hospitality & Guidance if Needed💌⭐️PRIVATE ACCESS TO THE BEST SOUTH SHORE~CROSS BAY BEACH⭐️💌Full Amenities on Property w/Transportation Available⭐️💌KINDNESS MATTERS as this is what Host Wendell & his family are all about💓Lynn&Mark, June 2025"
Location! Location! HALF PRICE SALE @ 100 Daily, Sep 25 - Oct 10 & Oct 27- Nov 1

Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

9.8 out of 10, Exceptional, (99)
"Sand Dollar was exactly what we needed for our week in Bermuda - amazing beach & accommodations and great access to the bus line too "
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

“Boathouse” Large one Bed cottage on Harrington Sound

10.0 out of 10, Exceptional, (11)
"Not only is Bermuda beautiful- staying at the Boathouse wonderful! Great beach, dock- the views- awesome. could not have been closer to bus stops… both ways! Comfortable wonderful week at the Boathouse!"
“Boathouse” Large one Bed cottage on Harrington Sound

Brand New, modern, light, delightful small apartment packed with luxuries

9.2 out of 10, Wonderful, (25)
"Love it! It was great staying here. Patrick was amazing & attentive. Definitely coming back!"
Brand New, modern, light, delightful small apartment packed with luxuries

Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style

9.2 out of 10, Wonderful, (38)
"Property location is a 10! This house is directly across from John Smith's Bay, one of the best beaches in Bermuda. Beach chairs and umbrellas are provided in addition to all necessary kitchen/bath amenities. Bus stops are conveniently located close by. Well stocked grocery store is a quick bus ride away. Property could use some updating, but did not deter our wonderful vacation."
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bailey's Bay Hotel Reviews

Find out more about Bailey's Bay

Find out more about Bailey's Bay

Everything you need to know about Bailey's Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bailey's Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bailey's Bay holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Bailey's Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bailey's Bay. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bailey's Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bailey's Bay holiday rentals we have selected for you start as low as AU$572 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Bailey's Bay rentals

At Expedia, we put the best Bailey's Bay holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Bailey's Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bailey's Bay holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bailey's Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Bailey's Bay?

Yes, there are holiday rentals close to the most popular sights in Bailey's Bay, or you can select a more secluded option if you're looking for a relaxing stay. Bailey's Bay is known for its beaches and restaurants. Make sure you have time to check out the sporting events and shopping during your trip.

What are some of the best holiday rentals that Bailey's Bay has to offer?

Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach! : This holiday home rental outside of Bailey's Bay is located next to a golf course, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

What’s there to see and do in Bailey's Bay?

Explore the area and family-friendly sights such as Bermuda Aquarium Museum and Zoo (BAMZ), or get out into nature at a spot like Abbot's Cliff Park. In the wider area, you’ll find Bermuda Perfumery and Crystal Caves.

What’s a holiday rental in Bailey's Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bailey's Bay. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.