Bailey's Bay Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Tonight
Oct 29 - Oct 30
Tomorrow
Oct 30 - Oct 31
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in Bailey's Bay

Outdoor pool
Rosemont Guest Suites
Rosemont Guest Suites
3.5 star property
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
$340 nightly
The price is $377
Nov 7 - Nov 8
Total with taxes and fees
Rosemont Guest Suites
Apartment | Dining room
Seven Arches
Seven Arches
3.0 star property
9.4 out of 10, Exceptional, (52)
"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!
9.8 out of 10, Exceptional, (127)
"the views are breath taking house needs some work but being on the water will beat any property up"
United States
bill f.
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
Exterior
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
9.8 out of 10, Exceptional, (166)
"Once again, we really enjoyed our stay. This has to be the best little cottage in Bermuda. Thank you and see you soon. Jo and Ed"
United States
JOANN L.
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Property entrance
Windsong Guest Apartments
Windsong Guest Apartments
3.0 star property
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
On the beach, sun loungers, beach towels
Spacious Beachfront and Private Resort living
Spacious Beachfront and Private Resort living
9.8 out of 10, Exceptional, (135)
"This is a lovely property that has all basic features and amenities for a casual comfortable stay. The location is out of this world-overlooking the ocean with just steps down to a secluded beach that feels almost like a private beach. The hosts are very welcoming and accommodating. We look forward to booking with them again. It was an absolutely incredible summer vacation. "
United States
Elena T.
Spacious Beachfront and Private Resort living
Interior
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
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.........
Beach nearby, beach towels
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
10.0 out of 10, Exceptional, (3)
"Fantastic property- conveniently located and as advertised! "
Canada
Adam M.
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
Property grounds
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
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!
Outdoor dining
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
9.4 out of 10, Exceptional, (30)
"Loved the uniqueness of the cottage. Comfortable and cozy. "
United States
Dorothy L.
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
Beach nearby
Location! Location! HALF PRICE SALE @ 100 Daily, November 9th - December 9th ASK
Location! Location! HALF PRICE SALE @ 100 Daily, November 9th - December 9th ASK
10.0 out of 10, Exceptional, (148)
"⭐️💌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"
United States
Lynn
Location! Location! HALF PRICE SALE @ 100 Daily, November 9th - December 9th ASK
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!
10.0 out of 10, Exceptional, (41)
"Overall a very nice property. We like to be off the beaten track and it certainly was."
United States
Underpressure S.
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
Property grounds
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
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
Interior
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
10.0 out of 10, Exceptional, (117)
"The apartment was very good, clean and handy to bus stops"
Canada
Helen Yee Wun
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
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
10.0 out of 10, Exceptional, (122)
"Loved the property, the incredible views and the responsiveness of host. Great location on the island. "
United States
Martha L.
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Exterior
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger
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!
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!
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.
9.8 out of 10, Exceptional, (100)
"Beautiful cottage, stunning views, lovely beach. We will definitely be returning!"
United States
Anonymous traveler
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.
Sun loungers, beach towels
Pool House Studio In A Garden Setting + EV chargers
Pool House Studio In A Garden Setting + EV chargers
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
Outdoor pool
“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”
“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”
10.0 out of 10, Exceptional, (25)
"This property is in a beautiful location and was exceptionally clean upon arrival. The pool was a highlight, providing endless hours of fun and relaxation for my family. We had a fantastic stay and would definitely return!"
United States
Krysta S.
“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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bailey's Bay Hotel Reviews

Hamilton Princess & Beach Club - a Fairmont Managed Hotel

Hamilton Princess & Beach Club - a Fairmont Managed Hotel

10/10 Excellent
"Everything was fantastic. Staff was super friendly and helpful. The restaurant intrepid was off the charts!! it was so good, We had to go back multiple times."
Dawn Marie 4-night trip
Posted 2 days ago
Hamilton Princess & Beach Club - a Fairmont Managed Hotel

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.