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Vacation Rentals in Bailey's Bay

"The room clean and comfortable."

￥33,854 total

includes taxes & fees

Sep 10 - Sep 11

"This was a great property. We really enjoyed our stay. The access to the railway walking path was really nice and the views were spectacular. "

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

￥55,563 total

includes taxes & fees

Aug 20 - Aug 21

"Nice property "

"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."

"3rd stay at this house, loved it again . Thanks Christine !"

On the beach, sun loungers, beach towels

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

"Very clean and beautifully built and maintained property with friendly hosts. Will definitely stay again. "

"⭐️💌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"

"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. "

"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."

"Jessica is wonderful.Very knowledgeable and super pleasant.Took a tour of East part of Bermuda with Jessica. Fun times. Wahoo!!!!"

"We cannot wait to return. We didn’t even wanna go to the wedding that we were there for because we enjoyed our host. The recommendations are host gave us the beach probably the only negative thing we could say is we didn’t understand the coffee pot and would like to have more coffee whenever we wake up because we drink a lot of coffee at the beach, but other than that, this is the only place that we will stay every single time we return and we hope that the host will keep our numbers in their...

"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! "

Beach nearby, sun loungers, beach towels

"Sand Dollar was exactly what we needed for our week in Bermuda - amazing beach & accommodations and great access to the bus line too "

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

"See other review - rented all units"

"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."

"Will be back for sure !Would give 6 stars if possible !!!Lorna was an amazing host & made us feel like family "

"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...

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Top Bailey's Bay Hotel Reviews

Hamilton Princess & Beach Club - a Fairmont Managed Hotel

10/10 Excellent

"Can’t go wrong with the Princess!"

Pompano Beach Club

10/10 Excellent

"I had a great stay at this resort. It reminds me of an old catskills resort from the 60’s…. but on the beach! It’s not upscale fancy, it’s warm, friendly and the staff make you feel like family. If you want fancy, this is not your place, if you liked the movie Dirty Dancing, book it! Did not have one bad meal and the food was delicious! Not a lot for kids to do, but it’s a great place to ditch the cell phones and play some board games. Accommodations are not really updated but are clean! No complaints. Staff are always helpful. I will go back! "

Find out more about Bailey's Bay

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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?

Entire Property House & Studio Cottage w/Pool, Near Beach, Trails, Shop, Bus Stp: This vacation home rental outside of Bailey's Bay is located next to a golf course and has an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 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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Bailey's Bay Vacation Rentals

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Vacation Rentals in Bailey's Bay

Paradise at Limehouse

Wyndham Water Views

Rosemont Guest Suites

Seven Arches

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

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

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

Windsong Guest Apartments

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

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

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

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

Petite & Peaceful Studio by the Beach

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

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

3 bedroom home with pool

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

Sound Winds 5 bedroom waterfront estate w tennis court

Spacious Beachfront and Private Resort living

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

Top Bailey's Bay Hotel Reviews

Hamilton Princess & Beach Club - a Fairmont Managed Hotel

Fourways Inn

Azura Bermuda

The St. Regis Bermuda Resort

Grotto Bay Beach Resort

Newstead Belmont Hills Golf Resort & Spa

Pompano Beach Club

Cambridge Beaches Resort & Spa

Hamilton Princess - Fairmont Gold Experience

Find out more about Bailey's Bay

Frequently asked questions