Best Vacation Homes in Bailey's Bay
280 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Pool
- Ocean View
ZA R4,527/Night
For 7 Nights ZA R31,694
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R2,954/Night
For 7 Nights ZA R20,681
450 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Pool
- Oceanfront
- Fireplace/Heating
ZA R4,021/Night
For 7 Nights ZA R28,149
1013.96 ft²
37 Guests
88 Bedrooms
12 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Spa
ZA R30,714/Night
For 7 Nights ZA R214,999
900 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R4,338/Night
For 7 Nights ZA R30,365
280 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
ZA R4,098/Night
For 7 Nights ZA R28,691
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
ZA R9,047/Night
For 7 Nights ZA R63,323
Bailey's Bay Luxury Rentals
16 Guests
8 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
ZA R92,100/Night
For 7 Nights ZA R644,703
5000 ft²
9 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Balcony/Terrace
ZA R85,760/Night
For 7 Nights ZA R600,321
4000 ft²
9 Guests
5 Bedrooms
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Parking
ZA R69,622/Night
For 7 Nights ZA R487,347
9 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
ZA R64,265/Night
For 7 Nights ZA R449,859
8 Guests
4 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
ZA R61,810/Night
For 7 Nights ZA R432,674
3000 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
ZA R51,456/Night
For 7 Nights ZA R360,193
3003.13 ft²
10 Guests
5 Bedrooms
6 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
ZA R41,034/Night
For 7 Nights ZA R287,235
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
ZA R37,852/Night
For 7 Nights ZA R264,962
Bailey's Bay Pet Friendly Vacation Rentals
4000 ft²
8 Guests
4 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Spa
ZA R36,749/Night
For 7 Nights ZA R257,248
3003.13 ft²
9 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
ZA R22,322/Night
For 7 Nights ZA R156,256
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
ZA R9,848/Night
For 7 Nights ZA R68,936
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
Villa
- Fireplace/Heating
- Pool
- Ocean View
ZA R33,555/Night
For 7 Nights ZA R234,892
1343.95 ft²
53 Guests
43 Bedrooms
13 Bathrooms
Free Cancellation
Hotel
- Private Beach
- Oceanfront
- Spa
ZA R8,453/Night
For 7 Nights ZA R59,170
650 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Pet Friendly
- Kitchen
ZA R4,460/Night
For 7 Nights ZA R31,218
5027 ft²
5 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
ZA R5,163/Night
For 7 Nights ZA R36,142
Bailey's Bay Large Vacation Homes
3000 ft²
18 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Cottage
- Oceanfront
- Hot Tub
- Fireplace/Heating
ZA R23,492/Night
For 7 Nights ZA R164,446
753.47 ft²
8 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- Parking
- Air Conditioner
ZA R18,981/Night
For 7 Nights ZA R132,867
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Air Conditioner
- Child Friendly
- Laundry
ZA R32,584/Night
For 7 Nights ZA R228,081
2203 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Pool
- Ocean View
- Balcony/Terrace
ZA R28,723/Night
For 7 Nights ZA R201,064
Why Choose Rent By Owner for your Bailey's Bay Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Bailey's Bay
When should you plan your Vacation Rentals stay?
To make the most of your stay in this charming destination, consider visiting during the shoulder seasons when the region offers pleasant weather and fewer crowds, ensuring a relaxing and enjoyable vacation experience here.
Peak Season Highlights
Spring (April to June)
During spring, the region experiences warm weather ideal for outdoor activities and exploring the local scenery in Bailey's Bay and surrounding areas.
Average Temperature Daytime: around 75-80°F - Nighttime: about 65-70°F
Fall (September to November)
Early fall offers pleasant temperatures and fewer crowds, making it a great time to enjoy the peaceful atmosphere of this Bermuda destination.
Average Temperature Daytime: approximately 78-82°F - Nighttime: around 68-72°F
Off-Season Highlights
Summer (July to August)
This period sees the highest influx of visitors thanks to warm weather and holiday festivities, which may lead to some busy attractions and higher rental rates.
Average Temperature Daytime: roughly 85-90°F - Nighttime: around 75-80°F
Winter (December to February)
The cooler winter months bring milder temperatures, offering a quieter experience if you prefer avoiding the peak tourist season while still enjoying comfortable weather.
Average Temperature Daytime: about 65-70°F - Nighttime: roughly 60-65°F
Weekly Weather Forecast for Bailey's Bay
How to Book Your Bailey's Bay Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Bailey's Bay
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a fully equipped patio or BBQ area, perfect for savoring meals with scenic views of the region.
- Relax beside a private or shared swimming pool, offering a refreshing escape in the warm Bermudian climate.
- Take advantage of well-maintained garden spaces and lush landscaping to unwind amidst natural beauty.
- Access nearby beaches or waterfront areas with outdoor seating, ideal for sunbathing, picnicking, or watching stunning sunsets.
- Benefit from outdoor shower facilities that provide convenience after a day spent exploring the outdoor scenery.
- Make use of outdoor recreational amenities such as tennis courts, golf courses, or walking trails available in the area.
- Utilize covered verandas or balconies to enjoy panoramic views and breathe in the fresh air whenever you desire.
Top Attractions Around Bailey's Bay
What attractions are nearby?
While staying here, you'll have the opportunity to enjoy a variety of nearby activities in Bailey's Bay, Hamilton Parish, Bermuda, including exploring scenic coastal walks, engaging in water sports, and discovering local beaches just moments from your vacation rental.
Family Activities
- Snorkeling at the Coral Reefs: Explore the vibrant underwater world just off the coast, where you can observe colorful marine life ideal for family adventures in this part of Bermuda.
- Spending the Day at Blue Halo Beaches: Relax and enjoy the pristine sands and gentle waters perfect for children and adults alike in the scenic surroundings of this region.
- Harbor Kayaking Tours: Discover the calm waters with guided kayaking excursions that provide a fun and educational experience for the whole family.
- Visit to Bermuda Aquarium, Museum & Zoo: Engage with local wildlife and learn about Bermuda’s natural history in a family-friendly setting right here in the area.
Adult Activities
- Sailing Excursions: Explore the pristine waters surrounding this destination with a sailing trip, offering stunning vistas and a chance to unwind on the Atlantic Ocean.
- Snorkeling Adventures: Discover the vibrant marine life in local coral reefs, making snorkeling a must-do activity here for an unforgettable underwater experience.
- Historic Shipwreck Tours: Learn about the area's maritime history while exploring preserved shipwreck sites that lie just off the coast of this region.
- Golfing at Premier Courses: Tee off at world-class golf courses nearby, where scenic fairways and challenging holes await passionate golf enthusiasts visiting here.
Other Places to Stay in Bailey's Bay
Bermuda Perfumery
Abbot's Cliff Park
Bailey's Bay Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Beaches: Take advantage of the pristine shoreline nearby by visiting local beaches to relax and enjoy the region's natural beauty, making your stay more memorable.
- Experience Water Activities: Engage in water-based adventures such as snorkeling or kayaking to fully immerse yourself in the coastal charm of this destination.
- Discover Regional Cuisine: Savor the authentic flavors of Bermuda by trying out local eateries and sampling regional specialties during your visit.
- Plan Day Trips: Use this area as a base to explore surrounding attractions, ensuring you make the most of your vacation experience in the region.
Transportation Options
- Bus Services: Public buses offer an economical way to explore the area and access key attractions from your vacation rental.
- Taxis and Rideshare Services: Convenient taxis and rideshare options like Uber provide quick and direct transportation around here.
- Car Rentals: Renting a car gives you the flexibility to independently discover the region at your own pace.
- Bicycle Rentals: For eco-friendly travel, bicycle rentals let you enjoy the scenic views and reach nearby spots comfortably.
Local Customs Options
- Respect for the Local Fishing Traditions: You’ll notice that fishing is a cherished activity here, with many residents upholding traditional methods and local customs in their daily routines.
- Greeting Etiquette: When visiting here, it’s customary to greet neighbors and shop owners with a friendly hello or a warm smile, reflecting the region's welcoming spirit.
- Celebration of Heritage Festivals: Participating in or observing regional festivals offers a glimpse into the area's cultural heritage and community values during your stay.
- Environmental Consciousness: Locals often emphasize eco-friendly practices, so adopting responsible behavior when exploring ensures the preservation of this beautiful destination.
Frequently Asked Questions About Bailey's Bay?
1. What are the top vacation rentals in Bailey's Bay?
There are a lot of options in Bailey's Bay. If you plan on staying in the Bailey's Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Bailey's Bay:
- Pool House Studio In A Garden Setting + EV chargers
- Water Front property with great views, pool, use of Kayaks, & strong Wi-Fi.
- Charming New Waterfront One Bedroom Loft Apartment On Mullet Bay St. George’s
- Las Brisas apartment with pool and walk to beach + EV chargers
- “Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”
- Cozy stand alone cottage with Bermuda Character
- "Chan Mar" Tucker's Town Bermuda
- Extraordinary Bermuda retreat w/large cave, panoramic pool and viewing deck.
- Luxury 3 bedroom Townhome
- The Boathouse: Large Waterfront Cottage on Harrington Sound – Sleeps 4+
2. Which vacation homes in Bailey's Bay are best for families?
If you are looking for a family-friendly vacation home in Bailey's Bay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Bailey's Bay:
3. How many Rentbyowner vacation rentals are available in Bailey's Bay?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 80 in the Bailey's Bay area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Bailey's Bay.
4. What is the cancellation policy for vacation rentals in Bailey's Bay, Bermuda?
The cancellation policies vary depending on the individual listing. It is recommended to review the specific rental details and contact the property owner directly for the most accurate information regarding cancellations.
5. How do I find the best vacation rental deals in this region?
To secure the best deals, consider filtering your search based on your preferred dates, amenities, and budget. Additionally, reading host reviews and reaching out with questions can help ensure a smooth stay in this area.
6. Are there any special requirements or house rules to be aware of when booking here?
Each property may have its own house rules and requirements. Check the rental listing carefully and communicate with the host if you have any specific needs or questions before confirming your reservation.
7. What amenities should I expect from vacation rentals in this destination?
Most properties offer essential amenities such as Wi-Fi, air conditioning, and kitchen facilities. To find accommodations that match your preferences, review the detailed amenities listed in each rental profile.
8. How far in advance should I book my accommodation for peak season?
It's advisable to book several months ahead during peak seasons to secure availability and the best rates. Contacting the property owner early can also provide additional flexibility and personalized assistance for your stay.
Bailey's Bay Top Rated Vacation Rentals
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Fireplace/Heating
- Pool
ZA R4,500/Night
For 7 Nights ZA R31,497
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
ZA R3,968/Night
For 7 Nights ZA R27,772
ZA R14,427/Night
For 7 Nights ZA R100,992
ZA R17,062/Night
For 7 Nights ZA R119,440
ZA R8,362/Night
For 7 Nights ZA R58,530
355.21 ft²
24 Guests
188 Bedrooms
8 Bathrooms
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
ZA R19,696/Night
For 7 Nights ZA R137,873
ZA R9,077/Night
For 7 Nights ZA R63,536
1150 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Spa
- Pool
- Balcony/Terrace
ZA R17,142/Night
For 7 Nights ZA R119,999
