Bailey's Bay Vacation Rentals from $207: Search Short-Term Rentals

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Vacation Rentals in Bailey's Bay

Kitchen features an oven, microwave, and sink, with ample countertop space and a tile floor.

"The room clean and comfortable."

$207 nightly

Jul 20 - Jul 21

Total includes taxes and fees

Relax in a serene garden with lush greenery and a patio area featuring two Adirondack chairs.

"Good location fairly near the airport. Cottage on a hill with the bus a short walk away down the hill....back up then of course!! Cute cottage, clean, comfortable bed. We loved it!"

Relax by the pool surrounded by comfortable lounge chairs and a shaded area.

"-Great views of the water -The owner gave us a ride when we couldn’t get a cab -Nice relaxing place"

$340 nightly

Jul 26 - Jul 27

Total includes taxes and fees

Enjoy meals in this stylish dining area with a central table, comfortable seating, and a large window.

"We loved this property! Clean, tranquil, great neighborhood within walking distance of pharmacy, convenience store, and bus stop. Would recommend and stay again!"

Experience the unique charm of WindSong Guest Arts, featuring a distinctive white facade with a yellow accent and a beautiful balcony with a bird sculpture.

"Properties great but away from the area I was having meetings. "

Situated on a rocky outcrop, this property offers a scenic ocean view from its covered patio area.

"We had a WONDERFUL stay and can't wait to go back. It is such a beautiful spot and we were so happy to discover that the fishing (and swimming) is excellent right from the rocks on the property. The hosts were wonderful and gave some great fishing tips as well!"

Relax in this stylish living room with a sofa, coffee table, and welcoming sign.

"Highly recommend. The location was central so the commute to any destination wasn't long. Very very clean and neat. A comfortable and enjoyable stay"

Guests can enjoy a view of the outdoor pool and lounge area from the comfort of their room.

"We loved our stay here. The place was very clean and conveniently located. The host even arranged pick up and drop-off to airport for us which that was super nice and convenient. Jody picked us up hes a great guy aho gave us good recommendations. We really enjoyed our stay. "

Enjoy a serene beach experience with a wide, sandy shoreline.

"Overall a very nice property. We like to be off the beaten track and it certainly was."

Enjoy breathtaking views of the turquoise sea and unspoiled beach.

"⭐️💌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"

Enjoy serene ocean views and access to a tranquil beach with rock formations.

"Lorna was a great host, very responsive with communications and provided transportation tips to/from airport. We basically had a private beach during our stay, easy walk to eat and other beaches, room nice and comfortable for our stay."

Enjoy a refreshing swim in the pool surrounded by lounge chairs and a beautiful ocean view.

"The property is a bit dated. Bed was comfortable. Linens clean. Beach a few minute walk away. Good location for many activities "

Guests can enjoy breathtaking ocean views from this beachfront location.

"I would recommend this AMOUR. Great service! Claudette is the best Host 😊. AMOUR has everything "

Guests can enjoy breathtaking ocean views from this serene beachside retreat.

"Charming family home kept extremely clean with fantastic kitchen & utensils. Very comfortable beds, great AC, large rooms with fabulous storage. Lovely host / family."

Stroll along the beachside walkway, offering a path to the sandy beach with a clear ocean view.

"Suzi was an excellent host and provided a lovely respite from our busy day-to-day lives in the gorgeous island paradise of Bermuda. Will be staying here again!"

Enjoy the serene beach scene with clear waters, rocky outcrops, and lush greenery.

"A pleasant stay, the unit is nice. Shower stall is a bit small, but quite comfortable over all."

Relax in comfort with a panoramic ocean view from the curved glass door, a cozy seating area, and a balcony.

"Property was great - great access - beautiful view."

Enjoy breathtaking ocean views from this beachfront property.

"The host, Claudette was absolutely wonderful. The location was great and the apartment was wonderful. A short walk got you to the number 7 bus which provided you transportation which connected to everything. Our host provided us a nice surprise one night of the makings for a great Bermuda fish sandwich. We really enjoyed our stay!!"

Stunning coastal home with a large lawn, pathways, and a dock overlooking the ocean.

"The property was beautiful! We spent our mornings on the large veranda enjoying the gorgeous view of Harrington Sound. The house is a bit tired, but you can not beat the location and the privacy. The house was large and accommodated our party of 8 easily. Location was central and easy to get to both St. George and Hamilton by bus, with the stop right at the end of the drive. We even were able to walk to John Smith Beach. The information packet included detailed information about the house,...

Enjoy a serene beach experience with access to the ocean.

"We just back from our vacation at Chan Mar. It was wonderful, cozy, and a great location. The views and the beaches were beautiful and relaxing. The hosts were very nice and accommodating. We are looking forward to returning in the near future."

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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 $207 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.

Recent reviews of Bailey's Bay properties

5/5 Excellent

"Absolutely stunning views of the truly aquamarine-colored water, tan and pink sand, and blue skies from the room as well as from the entire campus. Amazingly friendly and warm and attentive staff. Great beach access for swimming and even snorkeling. Room could use blackout shades to help us not wake up at the earliest sunrise. Bar drinks were a little small and a little expensive. The Surf Terrace menu's burger was fantastically juicy and ample while the charcuterie plate's meats were skimpy. Easy to hop on public busses to go anywhere on the island. A few different off-campus great restaurants were accessible by walking or short bus trips - Lost In The Triangle; Paraquet; and Ice Queen."

A verified traveler stayed at Azura Bermuda

Posted 2 days ago

Newstead Belmont Hills Golf Resort & Spa

5/5 Excellent

"Lovely staff and property! The hotel provides a shuttle to the beach + restaurants and a water taxi to Hamilton making moving around easy. Our room was spacious, quiet, and clean. Would absolutely stay here in the future!"

A verified traveler stayed at Newstead Belmont Hills Golf Resort & Spa

Posted 3 days ago

5/5 Excellent

"Pros: This is a beautiful resort with a private beach, restaurants with good view, spa room with good view, pools by the ocean, rooms with good view (although I might have gotten the worst view because my room is by the pool and it is on the first floor, so there're people outside by my balcony. I'm sure a room with pool view on the second floor or a room with ocean review will give you much better view and privacy). Cons: The location is relatively far from the city and you rely on the resort for restaurants. I found it far from the water activities too that Bermuda offers (the water sports company nearby only has jet ski on the weekends), so you need to do a bit travel for these (either by taxi or bus). In conclusion, it is a beautiful resort just to chill, relax, look at the ocean and do nothing or read a book with your sunglasses."

A verified traveler stayed at The Reefs Resort & Club

Posted 5 days ago

5/5 Excellent

"Very clean, spacious Habourview cottage with a breathtaking view of the harbour. The two storey, 2 bedroom, 2 bathroom, kitchen, living room was ideal for 3 of us. Generous supply of towels, even for the pools. Wall air conditioner in every room (which was essential and very comfortable.) Front desk staff very helpful for booking taxi tours and taxi to airport, and answering our many questions. Curtis, the shuttle driver, gave us a quick tour of the tip of the island as we were checking in early, prior to cottage being ready, and he drove us to the cottage with our luggage, then dropped us in town right at our restaurant for dinner. The shuttle was available Mon, Wed, Fri while we were there, and wish it were also available Tues and Thurs. Very close to small grocery stores - one about a one minute walk from the hotel. The walk away from the hotel is easy as it's downhill and takes mere minutes to walk into St George's where there are a variety of restaurants, some shops and a historical wharf. This is also where you catch the ferry to the Dockyards. But be forewarned that the walk back to the hotel is a steep incline to the lobby or there is also a set of stairs that can be accessed from Old Maid's Lane - I'm guessing about 75 steps. It was a wonderful stay and this hotel is a gem. Hope there are plans to reinstate the restaurant as it is currently closed."

A verified traveler stayed at St George's Club Hotel

Posted 8 days ago

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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?

Wild Bird, Paget - Pool, Twizy charger, Kitchenette - Pets Welcome: This vacation home rental outside of Bailey's Bay is located near the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

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.

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Vacation Rentals in Bailey's Bay

Paradise at Limehouse

Paradise at Limehouse

Wyndham Water Views

Wyndham Water Views

Rosemont Guest Suites

Rosemont Guest Suites

Seven Arches

Seven Arches

Windsong Guest Apartments

Windsong Guest Apartments

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

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

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

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

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

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

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

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

6 Days left at LOCATION! LOCATION! between Aug 15- 21, at a special 150 nightly!

6 Days left at LOCATION! LOCATION! between Aug 15- 21, at a special 150 nightly!

Spacious Beachfront and Private Resort living

Spacious Beachfront and Private Resort living

Clairfont, Jobson's Cove / Warwick Long Bay/ Horseshoe Beach - APARTMENT 4

Clairfont, Jobson's Cove / Warwick Long Bay/ Horseshoe Beach - APARTMENT 4

[A]MOUR AMOUR AMOUR The Heart of Hospitality

[A]MOUR AMOUR AMOUR The Heart of Hospitality

3 bedroom home with pool

3 bedroom home with pool

Wild Bird, Paget - Pool, Twizy charger, Kitchenette - Pets Welcome

Wild Bird, Paget - Pool, Twizy charger, Kitchenette - Pets Welcome

Sunset Paradise Oceanview 1Bedroom Lower Holiday Home Near Beaches

Sunset Paradise Oceanview 1Bedroom Lower Holiday Home Near Beaches

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

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

[A]MOUR AMOUR HEART OF HOSPITALITY!

[A]MOUR AMOUR HEART OF HOSPITALITY!

Sound Winds 5 bedroom waterfront estate w tennis court

Sound Winds 5 bedroom waterfront estate w tennis court

"Chan Mar" Tucker's Town Bermuda

"Chan Mar" Tucker's Town Bermuda

Find out more about Bailey's Bay

Find out more about Bailey's Bay

Recent reviews of Bailey's Bay properties

Recent reviews of Bailey's Bay properties

Azura Bermuda

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Explore a world of travel with Expedia

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