Bailey's Bay Vacation Rentals

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Check prices for these dates

Tonight
Dec 5 - Dec 6
Tomorrow
Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Bailey's Bay

Outdoor pool
Rosemont Guest Suites

Rosemont Guest Suites

3.5 star property
Pembroke Parish
8.6 out of 10, Excellent, (183)
"Great little quaint local property, clean, a quiet and walkable to Front street shops and restaurants. "
United States
Jennifer
The price is ￥44,818
￥53,341 total
includes taxes & fees
Dec 17 - Dec 18
Rosemont Guest Suites
Property grounds
West End Gem | Homestead at Moresby House | Sleeps 9+

West End Gem | Homestead at Moresby House | Sleeps 9+

2.0 star property
Sandys
10.0 out of 10, Exceptional, (1)
"Our expectations at the Moresby home in Homestead were exceeded. From the very first day upon our arrival our family was truly blown away at how beautiful the home was with incredible views from every window and door. The accommodations for a family of 9 were very comfortable and we felt there was plenty of space for all. Movie time on the big screen in the theater was a hit along with ping pong tournaments in the living space. We will definitely plan to return."
United States
VernonH
The price is ￥211,044
￥293,584 total
includes taxes & fees
Dec 11 - Dec 12
West End Gem | Homestead at Moresby House | Sleeps 9+
Property grounds
Oceanfront 3Bed w/ Private Patio & Garden - 6B

Oceanfront 3Bed w/ Private Patio & Garden - 6B

Sandys
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 ￥60,746
￥123,204 total
includes taxes & fees
Dec 6 - Dec 7
Oceanfront 3Bed w/ Private Patio & Garden - 6B
Terrace/patio
Sea View Contemporary 3Bed Upper - 3A

Sea View Contemporary 3Bed Upper - 3A

Sandys
10.0 out of 10, Exceptional, (6)
"Restful, clean, lovely view, very spacious. (be a little careful on the stairs.)"
United States
Barbara N.
The price is ￥60,726
￥124,405 total
includes taxes & fees
Dec 13 - Dec 14
Sea View Contemporary 3Bed Upper - 3A
Beach
"Poolside", Grape Bay Beach, Paget

"Poolside", Grape Bay Beach, Paget

Paget Parish
The price is ￥139,572
￥186,096 total
includes taxes & fees
Dec 8 - Dec 9
"Poolside", Grape Bay Beach, Paget
Pool
Luxe 2 Bedroom Suite in Beachfront Resort

Luxe 2 Bedroom Suite in Beachfront Resort

Sandys Parish
The price is ￥117,433
￥157,381 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxe 2 Bedroom Suite in Beachfront Resort
Private kitchen
Explore Bermuda in an RV - The home away from home feel. Ideal for 4 people

Explore Bermuda in an RV - The home away from home feel. Ideal for 4 people

2.0 star property
Warwick Parish
The price is ￥50,492
￥65,718 total
includes taxes & fees
Dec 19 - Dec 20
Explore Bermuda in an RV - The home away from home feel. Ideal for 4 people
An infinity pool
Shared Pools & Private Beaches! Room w/Garden View

Shared Pools & Private Beaches! Room w/Garden View

Sandys Parish
The price is ￥50,572
￥67,852 total
includes taxes & fees
Dec 23 - Dec 24
Shared Pools & Private Beaches! Room w/Garden View
Exterior
Stunning Sea Views, Contemporary Upper 3Bed - 5A

Stunning Sea Views, Contemporary Upper 3Bed - 5A

Sandys
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 ￥60,746
￥123,204 total
includes taxes & fees
Dec 6 - Dec 7
Stunning Sea Views, Contemporary Upper 3Bed - 5A
Exterior
Sea View Contemporary Upper 3Bed - 7A

Sea View Contemporary Upper 3Bed - 7A

Sandys
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 ￥60,746
￥123,204 total
includes taxes & fees
Dec 6 - Dec 7
Sea View Contemporary Upper 3Bed - 7A
Exterior
Stunning Sea Views, Contemporary Upper 3Bed - 4A

Stunning Sea Views, Contemporary Upper 3Bed - 4A

Sandys
9.4 out of 10, Exceptional, (3)
"We really enjoy staying on this side of the island. The bus stop is close and walking distance to the dockyard. The home was clean and our bed was comfortable. It was also nice having a laundry room available."
United States
Jenny W.
The price is ￥60,746
￥123,204 total
includes taxes & fees
Dec 6 - Dec 7
Stunning Sea Views, Contemporary Upper 3Bed - 4A
Exterior
Oceanfront 3bed w/ Private Patio & Garden - 4B

Oceanfront 3bed w/ Private Patio & Garden - 4B

Sandys
8.4 out of 10, Very Good, (5)
"A handsome, well kept place with spacious rooms and friendly staff, put us a short walk from the dockyard. The island is a bit pricey but absolutely beautiful and full of friendly people."
United States
Mark B.
The price is ￥60,746
￥123,204 total
includes taxes & fees
Dec 6 - Dec 7
Oceanfront 3bed w/ Private Patio & Garden - 4B
Terrace/patio
Stunning Sea Views, Contemporary 3Bed - 6A

Stunning Sea Views, Contemporary 3Bed - 6A

Sandys
8.8 out of 10, Excellent, (3)
"We enjoyed our stay. Could have been cleaner"
United States
Joseph V.
The price is ￥60,726
￥124,405 total
includes taxes & fees
Dec 13 - Dec 14
Stunning Sea Views, Contemporary 3Bed - 6A
Exterior
Oceanview 3 Bed w/ Private Patio & Garden - 3B

Oceanview 3 Bed w/ Private Patio & Garden - 3B

Sandys
9.0 out of 10, Wonderful, (8)
"Our teenage daughters and us stayed for 6 lovely nights. Bus stopped across the street and easy walk to ferry and shops. Lovely condo and very clean and comfortable with everything you need. Would definitely go back. "
United States
simon f.
The price is ￥60,726
￥124,405 total
includes taxes & fees
Dec 13 - Dec 14
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

The Loren at Pink Beach

The Loren at Pink Beach

10/10 Excellent
"The Loren is fantastic...........the staff are all amazing and friendly.........the room we had was beautiful with a fantastic ocean view and amazing balcony.......the restaurant was also amazing - we mostly ate breakfast here but also had two dinners and the food was amazing. Cant say enough good things about this hotel - we will definitely be back for another stay! it truly is a first class hotel!!"
Mark 7-night trip
Posted 2 days ago
The Loren at Pink Beach

Find out more about Bailey's Bay

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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?

Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!: This vacation home rental outside of Bailey's Bay is located by the ocean and has a patio, a selection of games, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.