Bailey's Bay Holiday Rentals

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Holiday Rentals in Bailey's Bay

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. "
United States
Jennifer
The price is AU$581
includes taxes & fees
24 Oct - 25 Oct
Rosemont Guest Suites
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
10.0 out of 10, Exceptional, (3)
"Fantastic property- conveniently located and as advertised! "
Canada
Adam M.
The price is AU$1,175
includes taxes & fees
12 Nov - 13 Nov
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
Oceanfront 3Bed w/ Private Patio & Garden - 6B
10.0 out of 10, Exceptional, (2)
"Loved the home and location. Only suggestion is more information on water access should be given. Ladder was broken and several days we did not use water because of lack of information."
United States
Gail L.
The price is AU$1,213
includes taxes & fees
7 Nov - 8 Nov
Oceanfront 3Bed w/ Private Patio & Garden - 6B
Sea View Contemporary 3Bed Upper - 3A
10.0 out of 10, Exceptional, (6)
"This vacation rental was perfect for our group. The rooms of this unit overlooked the ocean. We had everything to our comfort. Walking distance to Dockyard with restaurants and some entertainment. We would definitely stay there again in the future."
United States
AudreyM
The price is AU$1,213
includes taxes & fees
7 Nov - 8 Nov
Sea View Contemporary 3Bed Upper - 3A
Explore Bermuda in an RV - The home away from home feel. Ideal for 4 people
2.0 star property
The price is AU$662
includes taxes & fees
29 Oct - 30 Oct
Explore Bermuda in an RV - The home away from home feel. Ideal for 4 people
Shared Pools & Private Beaches! Room w/Garden View
The price is AU$772
includes taxes & fees
2 Nov - 3 Nov
Shared Pools & Private Beaches! Room w/Garden View
Luxe 2 Bedroom Suite in Beachfront Resort
The price is AU$2,490
includes taxes & fees
2 Nov - 3 Nov
Luxe 2 Bedroom Suite in Beachfront Resort
"Poolside", Grape Bay Beach, Paget
The price is AU$1,807
includes taxes & fees
22 Oct - 23 Oct
"Poolside", Grape Bay Beach, Paget
Sea View Contemporary Upper 3Bed - 7A
10.0 out of 10, Exceptional, (2)
"A lovely property on the water and close to shops and dining at the dockyard. The apartment was clean, comfortable and the AC's worked great!! Thank you for a great stay in Bermuda. "
United States
Daniel S.
The price is AU$1,213
includes taxes & fees
7 Nov - 8 Nov
Sea View Contemporary Upper 3Bed - 7A
Oceanfront 3bed w/ Private Patio & Garden - 4B
10.0 out of 10, Exceptional, (4)
"The place was absolutely beautiful and very spacious. Being able to jump right in the water was great for our kids! The location is very convenient with the bus stop right in front and in walking distance to the Glass Beach and Dockyard. The concierge service was very helpful setting up the ride to and from the airport. "
United States
Tina M.
The price is AU$1,213
includes taxes & fees
7 Nov - 8 Nov
Oceanfront 3bed w/ Private Patio & Garden - 4B
Stunning Sea Views, Contemporary Upper 3Bed - 4A
9.4 out of 10, Exceptional, (3)
"Modern and clean. Great space for our family of 6. Close to ferry and bus transportation. We were able to explore the whole island. Loved the location with the deck and patio area that you can get into the water at. Across the street is a short walk to the beach! So quiet and private off season! Only downside was since we stayed off season there were limited ferry rides only to Hamilton. We took the bus all the way to St. George versus we intended to use the ferry. Suggest stopping at the...
United States
Christine S.
The price is AU$1,213
includes taxes & fees
7 Nov - 8 Nov
Stunning Sea Views, Contemporary Upper 3Bed - 4A
Stunning Sea Views, Contemporary Upper 3Bed - 5A
9.4 out of 10, Exceptional, (3)
"Great place, very clean and situated in a good spot in proximity to dockyard and beaches. The Bermudian people were the nicest and most accommodating, Jerome & Sylvia were great tour guides on our non bus travels. Anchor Bar fish sandwich and bonefish tacos were top notch."
United States
Brett G.
The price is AU$1,213
includes taxes & fees
7 Nov - 8 Nov
Stunning Sea Views, Contemporary Upper 3Bed - 5A
Stunning Sea Views, Contemporary 3Bed - 6A
8.8 out of 10, Excellent, (3)
"We enjoyed our stay. Could have been cleaner"
United States
Joseph V.
The price is AU$1,213
includes taxes & fees
7 Nov - 8 Nov
Stunning Sea Views, Contemporary 3Bed - 6A
Oceanview 3 Bed w/ Private Patio & Garden - 3B
9.0 out of 10, Wonderful, (8)
"Comfortable for 4 people. Well equipped apartment. Beautiful setting. Nice dock to relax on. No top sheets under the comforters, intermittent WiFi service, and thin towels. "
United States
William G.
The price is AU$1,227
includes taxes & fees
14 Nov - 15 Nov
Oceanview 3 Bed w/ Private Patio & Garden - 3B
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

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$581 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?

Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool 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.