Bailey's Bay Vacation Rentals

Vacation Rentals in Bailey's Bay

Private kitchen | Fridge, microwave, oven, stovetop
Paradise at Limehouse
9.6 out of 10, Exceptional, (22)
"It was just me staying for a couple nights before getting on a boat. There is a bus stop 3 houses away from the property. A walking path along the ocean which was amazing. Swizzle Inn only a mile away......I walked! The place is perfect for a couple or single. Has everything you need and then some!"
The price is $131
$206 total
includes taxes & fees
Jun 2 - Jun 3
Paradise at Limehouse
Private kitchen
This spacious 2br home offers a comfortable retreat
8.0 out of 10, Very Good, (1)
"Very nice property. Space is good in this 2 bedroom home with 3 baths and a den/office. Important to know but not clear upon booking...they have 2 coffee makers. One traditional and a French press. They do have all kitchen conveniences. There is an iron and ironing board. Very convenient to bus stops! Great view at the end of driveway and nice walking bridge. You can also walk down to a small beach across the street. Driveway very steep! And there is a flight of stairs down to get to this home....
This spacious 2br home offers a comfortable retreat
Living area
Wyndham Water Views
10.0 out of 10, Exceptional, (1)
"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
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Outdoor pool
Rosemont Guest Suites
3.5 star property
8.6 out of 10, Excellent, (133)
"This was the 2nd time that we stayed at the Rosemont, and we were NOT disappointed !! Excellent location to downtown Hamilton (easy walk). Excellent service. Very friendly staff. We will be returning."
Rosemont Guest Suites
Aerial view
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
9.8 out of 10, Exceptional, (129)
"Book it right now. The yard is unreal, 270 degree water views, your own beach basically, take the kayak out the little islands during low tide.. you can pull up on a deserted beach and walk in the ocean. Great host. Did fire pit every night. Can walk to woodys (so much fun) and the restaurants at Cambridge resort, we also walked to the market, to a local gym, wine store, didn’t even use the bus. I couldn’t complain about any minor thing if there were any, with a view like that.. spectacular"
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Apartment | Dining room
Seven Arches
3.0 star property
9.2 out of 10, Wonderful, (26)
"Great accommodations "
The price is $173
$283 total
includes taxes & fees
Jun 2 - Jun 3
Seven Arches
Property entrance
Windsong Guest Apartments
3.0 star property
8.8 out of 10, Excellent, (77)
"Great Location. Friendly host and staff"
Windsong Guest Apartments
On the beach
Spacious Beachfront and Private Resort living
9.8 out of 10, Exceptional, (102)
"Beautiful view! Loved the beach access. Comfortable bed. Lorna was a wonderful host!"
Spacious Beachfront and Private Resort living
Beach nearby
3 bedroom home with pool
10.0 out of 10, Exceptional, (2)
"Great place to stay! Beautiful house, great beds and comfortable furniture to relax on. The pool off the back door is perfect when you want to skip the beach. The bus stops are a quick walk and after a day or two we were able to figure transportation out. Market across the street came in handy! Leila really went all out for us! She made sure we were comfortable and got in ok. After we asked about transportation from the airport she booked taxi both way! Leila is a great host! We will be back to...
3 bedroom home with pool
Interior
Welcome To Paradise 'AAA' - Private Romantic Getaway!
10.0 out of 10, Exceptional, (92)
"Fantastic location in the village, beautiful view of Mangrove Bay. Very clean with amenities close by. As well, the bus is across the street to take you to Hamilton or Dockyard. Jody is a wonderful host and very attentive. We’ve stayed here 2 years in a row and look forward to returning again. Highly recommend."
Welcome To Paradise 'AAA' - Private Romantic Getaway!
Beach nearby, sun loungers, beach towels
Sunset Paradise Oceanview 1Bedroom Lower Holiday Home Near Beaches
9.6 out of 10, Exceptional, (8)
"We had a fantastic stay. They had all the amenities that we could stay in or all the maps and attraction pamphlets needed to keep busy everyday. Public transportation was near the stores so it was easy to pick up what you need and walk about a block and a half to get back home. We found a restaurant right across the street that made the best fish sandwiches. As someone mentioned the shower is a little small but you can work with it. Over all I recommend this is the place to stay I look forward...
Sunset Paradise Oceanview 1Bedroom Lower Holiday Home Near Beaches
Property grounds
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
9.8 out of 10, Exceptional, (70)
"Was wanting to stay in the Somerset area for 3 weeks so this was a perfect location for our needs. Well set up for a longer term stay with great kitchen facilities, balcony, close to buses etc. would highly recommend for anyone - especially a longer term stay."
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
Beach nearby, sun loungers, beach towels
Two Bedroom with Private Dock near Golf and Beach
10.0 out of 10, Exceptional, (17)
"Rosalyn and Marshall's home is in an excellent location in Southampton. It is close to beaches, the Dockyard, Watson's farm, and golf, all of which we could access either by bus or by taxi driven by a person referred by Rosalyn. We will definitely recommend this property to friends and relatives who are considering a trip to Bermuda."
Two Bedroom with Private Dock near Golf and Beach
Sun loungers, beach towels
Las Brisas apartment with pool and walk to beach + EV chargers
10.0 out of 10, Exceptional, (64)
"The studio is fully equipped and is well stocked including kitchen basics, toiletries and towels. Gail and Chris are easy going hosts, point you in the right direction and don’t hover. Notes from former guests are welcome. The only issue for us was transportation as we were relying on the bus system which runs from stops just down the hill but doesn’t run at night. Taxis or an electric car rental, both expensive, necessary at times. John Smith Bay Beach with a very good casual bar/grill is...
Las Brisas apartment with pool and walk to beach + EV chargers
Sun loungers, beach towels
Pool House Studio In A Garden Setting + EV chargers
10.0 out of 10, Exceptional, (99)
"Upon arrival we were met by the host, Chris who welcomed us back to the island and answered questions. Pool house is extremely cute and has all necessary things. There is a Lab on the property, Tilly. She is smart and well behaved. Great location! Lovely property and sweet hosts!"
Pool House Studio In A Garden Setting + EV chargers
Pool
Clairfont, Jobson's Cove / Warwick Long Bay/ Horseshoe Beach - APARTMENT 5
9.8 out of 10, Exceptional, (10)
"Completely satisfied, clean & comfy apt & excellent staff, perfect location! Can't wait to come back!"
Clairfont, Jobson's Cove / Warwick Long Bay/ Horseshoe Beach - APARTMENT 5
Terrace/patio
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
9.2 out of 10, Wonderful, (15)
"We loved our stay at Sage Cottage. The house is magical. Fresh flowers awaited us in the kitchen and living room on our arrival - we found everything we needed for the rest of our stay. Thank you Tom and Victoria! Beth"
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
On the beach, sun loungers, beach towels
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
10.0 out of 10, Exceptional, (24)
"We had a ball"
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
Pool
Luxury Villa with Stunning Views of Horseshoe Bay on the Fairmont Hotel Grounds
10.0 out of 10, Exceptional, (95)
"The property was beautiful."
Luxury Villa with Stunning Views of Horseshoe Bay on the Fairmont Hotel Grounds
Beach | Beach nearby
MEMORIAL DAY WEEKEND SALE at Whispering Waves HALF PRICE of 100 Daily, BOOK NOW
9.8 out of 10, Exceptional, (119)
"Wendell greeted us warmly. We arrived a bit early from airport. The grounds were tidy. The actual room was older, needing some updates. There were some leftover personal care item’s left in a bathroom drawer with a chunk of old dried up bread. But bathroom was clean otherwise. Floors were clean which is important. The a/c worked well. We typically spend very little time in our room, we are not real particular. We would possibly stay again for future visits."
MEMORIAL DAY WEEKEND SALE at Whispering Waves HALF PRICE of 100 Daily, BOOK NOW
Don't see what you're looking for?
See all available properties in Bailey's Bay
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.

Baileys Bay Vacation Rental Travel Info

Number of vacation rentals
4
Popular accommodation
Bailey's Bay apartments
Known landmarks
Bermuda Aquarium Museum and Zoo, Crystal Caves and Blue Hole Park
International airport
St. George's (BDA-L.F. Wade Intl.)

Other types of properties in Bailey's Bay you may be interested in

Private kitchen | Fridge, microwave, oven, stovetop
Paradise at Limehouse
9.6 out of 10, Exceptional, (22)
"It was just me staying for a couple nights before getting on a boat. There is a bus stop 3 houses away from the property. A walking path along the ocean which was amazing. Swizzle Inn only a mile away......I walked! The place is perfect for a couple or single. Has everything you need and then some!"
The price is $131
$206 total
includes taxes & fees
Jun 2 - Jun 3
Paradise at Limehouse
Private kitchen
This spacious 2br home offers a comfortable retreat
8.0 out of 10, Very Good, (1)
"Very nice property. Space is good in this 2 bedroom home with 3 baths and a den/office. Important to know but not clear upon booking...they have 2 coffee makers. One traditional and a French press. They do have all kitchen conveniences. There is an iron and ironing board. Very convenient to bus stops! Great view at the end of driveway and nice walking bridge. You can also walk down to a small beach across the street. Driveway very steep! And there is a flight of stairs down to get to this home....
This spacious 2br home offers a comfortable retreat
Living area
Wyndham Water Views
10.0 out of 10, Exceptional, (1)
"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
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.

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bailey's Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bailey's Bay vacation 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 low season months. For more hustle and bustle, you may prefer to visit Bailey's Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $131 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bailey's Bay rentals

At Expedia, we put the best Bailey's Bay vacation 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 vacation.

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 vacation rentals in Bailey's Bay?

Yes, you can find vacation rentals near top points of interest in Bailey's Bay, or you can select a more remote option if you're looking for relaxation. 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's the top vacation rental that Bailey's Bay has to offer?

Rose Villa House: This vacation home rental outside of Bailey's Bay has laundry facilities and WiFi to help you feel perfectly comfortable in your new surroundings.

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 larger area, you’ll find Bermuda Perfumery and Crystal Caves.

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

Vacation rentals are privately owned properties where you can stay for a long or short time in Bailey's Bay. Vacation rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.

Recent reviews of Bailey's Bay properties
Expedia verified reviews

Willowbank Resort

Willowbank Resort

5/5 Excellent
"Very Quaint, Clean, Roomy, Friendly, helpful Staff."
A verified traveler stayed at Willowbank Resort
Posted 16 hours ago
Willowbank Resort