Bailey's Bay Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Holiday Rentals in Bailey's Bay

Our top choices for Bailey's Bay holiday rentals

Paradise at Limehouse
Fridge, microwave, oven, stovetop

Paradise at Limehouse

9.4 out of 10, Exceptional, (38)
"The room clean and comfortable."
The price is HK$1,180
HK$1,797 total
includes taxes & fees
10 Sept - 11 Sept
Paradise at Limehouse
Rosemont Guest Suites
Outdoor pool

Rosemont Guest Suites

3.5 star property
8.6 out of 10, Excellent, (177)
"Comfortable "
The price is HK$2,493
HK$2,950 total
includes taxes & fees
23 Aug - 24 Aug
Rosemont Guest Suites
Seven Arches
Dining room

Seven Arches

3.0 star property
9.6 out of 10, Exceptional, (46)
"Nice property "
Seven Arches
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
Interior

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

9.8 out of 10, Exceptional, (125)
"The house had a great view, was comfortable, in a great area. We always felt safe. Bus stop in front of the shop was perfect, but was actually in the road. We waited for the bus in a driveway near the stop.This is an older house and right on the water causing it to need a lot of maintenance. I enjoyed it, but in all honesty it needed some love and attention. I was decorating it in my mind."
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
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, (39)
"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!
Entire Property House & Studio Cottage w/Pool, Near Beach, Trails, Shop, Bus Stp
Beach nearby, beach towels

Entire Property House & Studio Cottage w/Pool, Near Beach, Trails, Shop, Bus Stp

10.0 out of 10, Exceptional, (1)
"Fantastic property- conveniently located and as advertised! "
Entire Property House & Studio Cottage w/Pool, Near Beach, Trails, Shop, Bus Stp
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Exterior

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

9.8 out of 10, Exceptional, (159)
"3rd stay at this house, loved it again . Thanks Christine !"
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Windsong Guest Apartments
Property entrance

Windsong Guest Apartments

3.0 star property
8.8 out of 10, Excellent, (93)
"Very clean and beautifully built and maintained property with friendly hosts. Will definitely stay again. "
Windsong Guest Apartments
LOCATION! LOCATION! on Bermuda's Gold Coast of beautiful Beaches & Restaurants
Beach nearby

LOCATION! LOCATION! on Bermuda's Gold Coast of beautiful Beaches & Restaurants

10.0 out of 10, Exceptional, (143)
"⭐️💌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! on Bermuda's Gold Coast of beautiful Beaches & Restaurants
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
Interior

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

10.0 out of 10, Exceptional, (112)
"Truly enjoyed our stay. "
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Pool

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

10.0 out of 10, Exceptional, (119)
"This beautiful home truly exceeded all our expectations. Totally equipped with everything we needed. Amazing host who went above and beyond to be sure everything was perfect! The pictures are beautiful but it is even more spectacular in person. The rooms are huge and it is such a thoughtful layout. The deck is amazing with incredible biews of horshoe bay. Cannot wait to return!"
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
Interior

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

10.0 out of 10, Exceptional, (11)
"Access to the accomodation is downstairs. The rooms are very clean and spaceous, cool, airy, very well furnished and beautifully decorated. Austin is a very polite, thoughtful, and very friendly host who greets you on arrival and is there if you need him & when the time comes to leave.We enjoyed our time there and would certainly return there too."
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
3 bedroom home with pool
Beach nearby

3 bedroom home with pool

10.0 out of 10, Exceptional, (7)
"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
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
Property grounds

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

9.8 out of 10, Exceptional, (94)
"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!
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.
Beach nearby, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (98)
"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.
“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”
Outdoor pool

“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”

10.0 out of 10, Exceptional, (22)
"See other review - rented all units"
“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”
Brand New, modern, light, delightful small apartment packed with luxuries
Sun-loungers, beach towels

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

9.0 out of 10, Wonderful, (24)
"Property was great...good location close to a bus stop which made getting around the island pretty easy..."
Brand New, modern, light, delightful small apartment packed with luxuries
Sound Winds 5 bedroom waterfront estate w tennis court
Exterior

Sound Winds 5 bedroom waterfront estate w tennis court

9.8 out of 10, Exceptional, (11)
"Fantastic property directly on the water with a dock; facing west for beautiful sunsets. House is spacious with large windows and terrace that look onto the water. Tom and Anya who own the property are immediately responsive and very helpful."
Sound Winds 5 bedroom waterfront estate w tennis court
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style
Property grounds

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

9.2 out of 10, Wonderful, (38)
"I am local and I booked this cottage for family visiting for the first time. The location is across the street from my childhood beach. This made for some very happy visitors! The large window in the living room is gorgeous and was perfect for unwinding next to or watching thunderstorms. The kitchen was clean and stocked with everything you would need. The property is along a main bus route and just a few minutes away from some of my favourite restaurants, a wonderful nature preserve, and a...
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style
Spacious Beachfront and Private Resort living
On the beach, sun-loungers, beach towels

Spacious Beachfront and Private Resort living

9.8 out of 10, Exceptional, (132)
"Will be back for sure !Would give 6 stars if possible !!!Lorna was an amazing host & made us feel like family "
Spacious Beachfront and Private Resort living
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 St. Regis Bermuda Resort

The St. Regis Bermuda Resort

10/10 Excellent
"Amazing experience and very helpful and polite staff. Food is phenomenal and can easily dine 3-4 nights there without eating the same dish twice. The pool and beach is sublime and relaxing. Only gripe is there is a facility fee that we didn't notice until after we checked out "
Daniel 6-night trip
Posted 3 days ago
The St. Regis Bermuda Resort

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?

Entire Property House & Studio Cottage w/Pool, Near Beach, Trails, Shop, Bus Stp: 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.