Bailey's Bay Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

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, (182)
"Great little quaint local property, clean, a quiet and walkable to Front street shops and restaurants. "
United States
Jennifer
$340 nightly
The price is $377
Nov 30 - Dec 1
Total with taxes and fees
Rosemont Guest Suites
Apartment | Dining room
Seven Arches

Seven Arches

3.0 star property
Warwick Parish
9.4 out of 10, Exceptional, (53)
"Excellent stay Will return "
United States
Sherri
Seven Arches
Interior
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

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

Devonshire
9.8 out of 10, Exceptional, (128)
"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!
Property entrance
Windsong Guest Apartments

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

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 ....
Sun loungers, beach towels
Pool House Studio In A Garden Setting + EV chargers

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
On the beach, sun loungers, beach towels
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

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!
Microwave, oven, stovetop
Charming 1-bedroom apartment centrally located to all that Bermuda has to offer

Charming 1-bedroom apartment centrally located to all that Bermuda has to offer

Devonshire
10.0 out of 10, Exceptional, (3)
"It is an amazing place**so many amenities.Joe and Florence are Very nice and Helpful!!!Highly recommended them and the apartment ; } "
Canada
Garth W H G.
Charming 1-bedroom apartment centrally located to all that Bermuda has to offer
Fridge, microwave, oven, stovetop
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style

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
On the beach, sun loungers, beach towels
Spacious Beachfront and Private Resort living

Spacious Beachfront and Private Resort living

Southampton
9.8 out of 10, Exceptional, (136)
"Perfect location - lovely stay - great hostess - thank you Lorna x"
United Kingdom
Susan H.
Spacious Beachfront and Private Resort living
Pool
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

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
Outdoor dining
Tranquil, Roomy Getaway - Close to City of Hamilton

Tranquil, Roomy Getaway - Close to City of Hamilton

Pembroke
10.0 out of 10, Exceptional, (2)
"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
Beach nearby, sun loungers, beach towels
Tiny Studio in fabulous Smith's Parish at John Smith's Bay Beach

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
Beach nearby
LOCATION! LOCATION! - Whispering Waves Apt, at Cross Bay Private Estate & Beach

LOCATION! LOCATION! - Whispering Waves Apt, at Cross Bay Private Estate & Beach

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.
LOCATION! LOCATION! - Whispering Waves Apt, at Cross Bay Private Estate & Beach
Exterior
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger

Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger

Southampton Parish
9.2 out of 10, Wonderful, (7)
"A small, clean, well-equipped apartment that is a great jumping off point for exploring the wonders of Bermuda."
United States
Claire A.
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger
Property grounds
Stunning Views of Horseshoe Bay Beach. Enjoy the sounds of the lapping waves!

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

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!
Beach nearby, sun loungers, beach towels
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

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

Warwick
9.8 out of 10, Exceptional, (102)
"Perfect location, clean and Nice accommodation "
France
Olivier M.
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.
Property grounds
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment

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
Property grounds
'Panatola' Studio with Breathtaking Views - Close to beach

'Panatola' Studio with Breathtaking Views - Close to beach

Southampton
9.8 out of 10, Exceptional, (46)
"A delightful apartment with local character, lovely views in the middle of a beautiful island. The host was very welcoming and helpful. Would recommend."
United Kingdom
Charlotte
'Panatola' Studio with Breathtaking Views - Close to beach
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

Coco Reef Bermuda

Coco Reef Bermuda

10/10 Excellent
"Beautiful place and views"
Stephen 3-night trip
Posted 5 days ago
Coco Reef Bermuda

Find out more about Bailey's Bay

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 $377 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.

Explore a world of travel with Expedia

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.