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Compare 35 Vacation Homes in Bailey's Bay with updated reviews, rates, and availability.

Two Bedroom with Private Dock near Golf and Beach
Property grounds

Two Bedroom with Private Dock near Golf and Beach

10.0 out of 10, Exceptional, (28)
"Well kept house overlooking sea; apartment on ground floor. Everything was exactly as we hoped for in every way. The apartment was spacious quiet and comfortable and very well equipped. The ownders werexexfe"
Two Bedroom with Private Dock near Golf and Beach
Stunning Views of Horseshoe Bay Beach. Enjoy the sounds of the lapping waves!
You too may find a rainbow from the comfort of the bar sitting area.

Stunning Views of Horseshoe Bay Beach. Enjoy the sounds of the lapping waves!

10.0 out of 10, Exceptional, (69)
"Can’t say enough great things about this property. We love Bermuda having been there several times staying at various resorts. This property brought a whole new charm to the island for us. A true Bermuda experience. Everything about this house is beautiful and charming while providing every modern convenience. Waking up to the sunset over Horseshoe Bay was amazing. Not enough space in this review to say all the great things I could about our stay. The hosts went way beyond to ensure...
Stunning Views of Horseshoe Bay Beach. Enjoy the sounds of the lapping waves!
Amazing Property Close To Beaches/Golf Course/Railway Trails
Exterior

Amazing Property Close To Beaches/Golf Course/Railway Trails

9.8 out of 10, Exceptional, (79)
"The property was perfect for us two couples for our 5 night stay. The host, Thomasina, is wonderful and will assist with any and all help you need. She was kind enough to set up our transportation to and from the airport and also assisted with the best places to dine and venture out to. We would definitely return to this property should we ever go back to Bermuda. We rented scooters for our time there and this property location is close to lots of beaches and dining which made it convenient...
Amazing Property Close To Beaches/Golf Course/Railway Trails
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style
Interior detail

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

9.4 out of 10, Exceptional, (30)
"We enjoyed our time at this property! As others have noted, a little outdated. I was actually surprised at how much space we had - was not as evident in the photos. We were there with our three kids (ages 3-9) and felt safe in the area. The location was fantastic and the kids loved having the beach so close. They were also particularly fond of the chickens that would sometimes venture over from next door. Elizabeth was super responsive and the offer to arrange for transport to/from the airport...
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style
Chateau Getaway 2 Bermy Style SLEEPS 2 1 Bed/Bath
Interior

Chateau Getaway 2 Bermy Style SLEEPS 2 1 Bed/Bath

9.4 out of 10, Exceptional, (6)
"Fantastic holiday, fantastic island, fantastic accommodation, lovely host very very helpful , great people, all in all perfect."
Chateau Getaway 2 Bermy Style SLEEPS 2 1 Bed/Bath
Large home at one of the highest in Tuckerstown, newly renovated.
Terrace/patio

Large home at one of the highest in Tuckerstown, newly renovated.

10.0 out of 10, Exceptional, (1)
"Very nice home in a great location in Tucker’s Point - the owner and the local team could not have been more helpful and went out of their way to ensure that we had a relaxing stay. Everything in the home is first class. We were very pleased with the whole experience - thank you!"
Large home at one of the highest in Tuckerstown, newly renovated.
Smugglers Cove - Walk to City of Hamilton
Pool

Smugglers Cove - Walk to City of Hamilton

10.0 out of 10, Exceptional, (32)
"This was our first visit to Bermuda and from the very first communication with the hosts to the taxi journey to the airport at the end of our stay, Rich and Alex were so thoughtful, helpful and friendly going above and beyond to ensure our every need was met. The property was gorgeous, set in a quiet residential area but within a 10 minute walk of Hamilton, great restaurants and lical supermarkets. Spotlessly clean and beautifully gurnished and equipped, the property catered to our every need...
Smugglers Cove - Walk to City of Hamilton
3 bedroom home with pool
Terrace/patio

3 bedroom home with pool

10.0 out of 10, Exceptional, (4)
"Charming family home kept extremely clean with fantastic kitchen & utensils. Very comfortable beds, great AC, large rooms with fabulous storage. Lovely host / family."
3 bedroom home with pool
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Stunning views from the Moongate believed to be good luck for newlyweds!

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

10.0 out of 10, Exceptional, (105)
"Very clean, great location, plenty of space, and unparalleled views! Highly recommend "
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Historic Belfield Beach Estate and cottage on Long Bay Beach-Close to Everything
House and cottage in foreground, long bay park and beach behind.

Historic Belfield Beach Estate and cottage on Long Bay Beach-Close to Everything

9.8 out of 10, Exceptional, (30)
"Loved the house. The guest house. The location. All the beach toys they have. You could hit a golf ball into the ocean from the yard. You walk through a little park that has a big playground for little kids on that beach the most crowded it was were eight people Down to none. Right down the street from a convenience store and the grocery store which is by the bus stop. It is far from the airport, but other than that the location is great not far from the ferry. Only one problem and that’s the...
Historic Belfield Beach Estate and cottage on Long Bay Beach-Close to Everything
#4 Laurel - Bermuda Getaway Studio
Living room with French doors

#4 Laurel - Bermuda Getaway Studio

8.4 out of 10, Very Good, (7)
"Very nice and spacious. Should remove old dishes and replace shower head. Other than that it’s a lovely space. I would definitely stay there again. "
#4 Laurel - Bermuda Getaway Studio
Rose Villa House
Living room

Rose Villa House

10.0 out of 10, Exceptional, (29)
"Really enjoyed the Rose Villa house. It has everything you need and lots of room for a great price in Bermuda! "
Rose Villa House
Wild Bird, Paget - Pool, Twizy charger, Kitchenette - Pets Welcome
Poolside!

Wild Bird, Paget - Pool, Twizy charger, Kitchenette - Pets Welcome

9.8 out of 10, Exceptional, (54)
"I am a regular business visitor to Bermuda (4 times a year) but this is the first time straying from the main business hotels. It will not be the last. Conveniently located for Hamilton but quietly tucked away near South Shore, it was the perfect spot to balance a busy week. The self-contained annexe has everything you need and Suzi is a lovely but unobtrusive host. "
Wild Bird, Paget - Pool, Twizy charger, Kitchenette - Pets Welcome
Waterfront luxury Villa - pool - Amazing views! xmas available - fall discounts
6 grey plastic wood adirondack chairs now on the balcony

Waterfront luxury Villa - pool - Amazing views! xmas available - fall discounts

10.0 out of 10, Exceptional, (34)
"What a wonderful stay! A well-equipped house, excellent communication with owner and property managers, and super clean and comfortable. We will stay here again."
Waterfront luxury Villa - pool - Amazing views! xmas available - fall discounts
Cozy stand alone cottage with Bermuda Character
Exterior

Cozy stand alone cottage with Bermuda Character

9.8 out of 10, Exceptional, (16)
"Stand alone is a very nice 3 bedroom, one bath cottage. It is very roomy with kitchen, living room and dining room. The map showed the cottage was in the town of St. George’s, which was incorrect. It is a half mile hilly walk to town which was a problem for my wife who has mobility issues. The main reason we booked it was its location. I guess I should have researched it more. I didn’t find out where it was located until two days before our trip. So we had to take taxis, which are expensive...
Cozy stand alone cottage with Bermuda Character
Bayshore - Charming 3 Bedroom Home, Great Location with a Pool
Property grounds

Bayshore - Charming 3 Bedroom Home, Great Location with a Pool

9.2 out of 10, Wonderful, (17)
"We chose this house based on its location and the fact that it had a pool. The location is in the middle of the island away from the resorts, so you get a more local experience- shopping at the grocery store, taking the bus, enjoying Bermudian favorites at Island Cuisine. The house is wonderfully quiet, comfortable, and well appointed. (Be sure to read the property info binder for tips on the house and great food and activity recommendations.)We especially loved our morning coffee and an...
Bayshore - Charming 3 Bedroom Home, Great Location with a Pool
Oceanfront "Dock of the Bay" Retreat in Beautiful Bermuda
Property grounds

Oceanfront "Dock of the Bay" Retreat in Beautiful Bermuda

Oceanfront "Dock of the Bay" Retreat in Beautiful Bermuda
Modern Townhouse Located Near To City, Public Transport, Restaurants And Beaches
Kitchen

Modern Townhouse Located Near To City, Public Transport, Restaurants And Beaches

9.6 out of 10, Exceptional, (35)
"The house itself was great. Very clean, nicely appointed. Our family of 5 enjoyed our time at the Odyssey. A couple things stopped me from rating it 5 stars. Probably the biggest issue was that the wi-fi at the house was not working. We rely heavily on the internet to plan out our days and figure out how to get around the island and not having internet for the entire stay was stressful. Communication with the host on this issue did not yield any results. I was able to use my cell phone to...
Modern Townhouse Located Near To City, Public Transport, Restaurants And Beaches
Two-bedroom cottage with lovely pool - central, near beaches, great location!
Rainbow's End - pot of gold at The Pool House!

Two-bedroom cottage with lovely pool - central, near beaches, great location!

9.6 out of 10, Exceptional, (14)
"Diana"
Two-bedroom cottage with lovely pool - central, near beaches, great location!
SeaView Bermuda
SeaView..... A Bermudiful Dream Home!

SeaView Bermuda

10.0 out of 10, Exceptional, (1)
"We arrived during a rain storm, so did not realize how amazing the house is. Sue met us and showed us around. The views cannot be beat, we spent most of the time on the back patio enjoying the view. The kitchen is well Equipped for cooking. Jen was so helpful and our needs were addressed immediately. I will definitely be back. Bermuda is one of the most beautiful places I have ever been. If I could give it 20 stars I would!"
SeaView Bermuda
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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Other property types in Bailey's Bay

Paradise at Limehouse
Private kitchen

Paradise at Limehouse

9.6 out of 10, Exceptional, (32)
"Loved location. Comfortable "
Paradise at Limehouse
Wyndham Water Views
Room

Wyndham Water Views

10.0 out of 10, Exceptional, (5)
"Good location fairly near the airport. Cottage on a hill with the bus a short walk away down the hill....back up then of course!! Cute cottage, clean, comfortable bed. We loved it!"
Wyndham Water Views
This spacious 2br home offers a comfortable retreat
Beautiful View of the Bay from the upper level driveway

This spacious 2br home offers a comfortable retreat

9.6 out of 10, Exceptional, (5)
"The home was beautiful. Great location. All amenities you need. Plenty of space with a large backyard "
This spacious 2br home offers a comfortable retreat
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.