Holiday Rentals in Bailey's Bay

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Holiday Rentals in Bailey's Bay

Rosemont Guest Suites

3.5 star property
Pembroke Parish
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 €326
includes taxes & fees
21 Nov - 22 Nov
Rosemont Guest Suites

Seven Arches

3.0 star property
Warwick Parish
9.4 out of 10, Exceptional, (53)
"Excellent stay Will return "
United States
Sherri
Seven Arches

Windsong Guest Apartments

3.0 star property
Pembroke Parish
8.8 out of 10, Excellent, (93)
"Place was really clean and big, Roslyn was very caring and helpful. Great place to stay!!!!"
United States
Henry
Windsong Guest Apartments

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

Devonshire
9.8 out of 10, Exceptional, (127)
"Loved this rental! The owner is so nice, the location is beautiful, and the house is so spacious. Very chill environment, probably not great for anyone who want to be in the center of the action. My group had an amazing time, the ocean access got a little hairy because of the impending hurricane, but when the water was calm, it was perfection. Would definitely stay here again!"
United States
Constance f.
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

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

Somerset Village
9.8 out of 10, Exceptional, (167)
"As always, Perfect location. Perfect host. Perfect water. "
United States
LU S.
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....

Pool House Studio In A Garden Setting + EV chargers

Smiths
10.0 out of 10, Exceptional, (125)
"The hosts, Chris and Gail are wonderful. Tilly, their dog, is adorable. The pool house was perfect for us. We went to Bermuda for a wedding, and stayed for a week. We had plenty of room. You can’t beat the location. We highly recommend this property to anyone!"
United States
Dawn
Pool House Studio In A Garden Setting + EV chargers

Tiny Studio in fabulous Smith's Parish at John Smith's Bay Beach

Paget Parish
10.0 out of 10, Exceptional, (2)
"Location "
United Kingdom
clare a.
Tiny Studio in fabulous Smith's Parish at John Smith's Bay Beach

Wild Bird, Paget - Pool, Twizy charger, Kitchenette - non smoking property

Paget
9.8 out of 10, Exceptional, (64)
"It was a great place all the way around. "
United States
keith f.
Wild Bird, Paget - Pool, Twizy charger, Kitchenette - non smoking property

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

Smith's Parish
9.2 out of 10, Wonderful, (40)
"Property location is a 10! This house is directly across from John Smith's Bay, one of the best beaches in Bermuda. Beach chairs and umbrellas are provided in addition to all necessary kitchen/bath amenities. Bus stops are conveniently located close by. Well stocked grocery store is a quick bus ride away. Property could use some updating, but did not deter our wonderful vacation."
United States
Betty R.
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style

Pre-Thanksgiving, HALF PRICE SALE of 100 Daily, from November 9th. Just request!

5 Cross Bay Road
10.0 out of 10, Exceptional, (150)
"Wendell was an absolutely awesome host! Very friendly and willing to help whenever possible! You can’t beat a better location, just a short walk to the beach and the view is absolutely spectacular! We truly enjoyed our stay in Bermuda! Thank you, Wendell! "
United States
Jim M.
Pre-Thanksgiving, HALF PRICE SALE of 100 Daily, from November 9th. Just request!

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

Devonshire DV08
10.0 out of 10, Exceptional, (14)
"I travel to Bermuda on business several times a year and have stayed at a host of different places from resorts/hotels to rentals and this one is hands down the best so far.Spacious and clean with all of the necessary amenities to make my stay comfortable and enjoyable.The water pressure was the best I've experience on island and having a grocery store less than a 1/2 mile away was super convenient (although it is closed on Sundays).Austin was a great host and I plan on staying with him again!"
United States
Bill M.
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........

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

Sandy's
9.8 out of 10, Exceptional, (98)
"A well provisioned and conveniently located accommodation, with a charming and hospitable host."
Canada
Alix W.
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!

Tranquil, Roomy Getaway - Close to City of Hamilton

Pembroke
10.0 out of 10, Exceptional, (1)
"Clean, comfortable and exactly as advertised. Close to all amenities and a great location for all of the activities we had planned - good Bermuda value!"
Canada
Thomas W.
Tranquil, Roomy Getaway - Close to City of Hamilton

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

Southampton
10.0 out of 10, Exceptional, (74)
"We were all amazed at the beach view from the house. It was so perfect and we would all stay again there. Jessica was a great hostess who answered every and all our questions and requests. I give this hour a 10 out of 10Stay here, you won’t regret it. "
United States
jackie k.
Stunning Views of Horseshoe Bay Beach. Enjoy the sounds of the lapping waves!

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

Warwick
9.8 out of 10, Exceptional, (101)
"Perfect location, clean and Nice accommodation "
France
Olivier M.
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

Somerset village
10.0 out of 10, Exceptional, (41)
"Nice, spread out house that provides indoor and outdoor space to congregate but also privacy in bedrooms and bathrooms. 2 minute walk to beach with chairs and umbrellas and 5 minute walk to Somerset long bay beach. Walkable to good size grocery store, a few takeout restaurants and bus stop. The nooks and crannies of the property are amazing. Hammock, moon gate, benches, outdoor showers, so many birds and gorgeous lush foliage surround the house. "
United States
Heather D.
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment

Sandys
10.0 out of 10, Exceptional, (93)
"Great sunset from the lawn, great snorkeling, and a comfortable bed. "
United States
James W.
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment

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

Southampton
10.0 out of 10, Exceptional, (123)
"Amazing property and amazing host "
United States
Robert C.
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

[A]MOUR AMOUR HEART OF HOSPITALITY!

Hamilton
10.0 out of 10, Exceptional, (41)
"Nice views and location. "
United States
Adriaan
[A]MOUR AMOUR HEART OF HOSPITALITY!

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

Hamilton Parish
10.0 out of 10, Exceptional, (25)
"Beautiful place and off the normal tourist path. Wayne was great to deal with! "
United States
Kevin M.
“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”
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, apart-hotels, 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 favorite 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 depends 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 €326 per night. Entering your travel dates in the search wizard 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 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?

Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!: This holiday 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 that 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 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.