Discover Your Perfect Front Street Vacation Homes

Best Vacation Homes in Front Street

Apartment
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 2 Guests 325 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
R8,602/Night 7 Nights - R60,220
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Bed & Breakfast
Map-icon
like-icon9.7
Exceptional
(135 Reviews)
4 Bedrooms 4 Baths 8 Guests 263.71 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R5,497/Night 7 Nights - R38,476
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Apartment
Map-icon
like-icon10.0
Exceptional
(8 Reviews)
1 Bedroom 1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R2,910/Night 7 Nights - R20,370
House
Map-icon
like-icon9.8
Exceptional
(98 Reviews)
2 Bedrooms 2 Baths 6 Guests 1500 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R5,790/Night 7 Nights - R40,530
Apartment
Map-icon
like-icon9.5
Exceptional
(15 Reviews)
2 Bedrooms 1 Bath 4 Guests 645.83 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R6,467/Night 7 Nights - R45,266
Apartment
Map-icon
like-icon9.6
Exceptional
(4 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
R5,105/Night 7 Nights - R35,744
Apartment
Map-icon
like-icon9.0
Exceptional
(48 Reviews)
1 Bedroom 1 Bath 5 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R4,953/Night 7 Nights - R34,677
House
Map-icon
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
R3,460/Night 7 Nights - R24,217

Front Street Luxury Rentals

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Hotel
Map-icon
like-icon9.2
Exceptional
(56 Reviews)
1 Bath
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
R17,232/Night 7 Nights - R120,619
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Hotel
Map-icon
like-icon8.4
Excellent
(69 Reviews)
6 Baths 378.53 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R15,845/Night 7 Nights - R110,919
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Hotel
Map-icon
like-icon8.6
Fabulous
(83 Reviews)
4 Baths 355.21 ft²
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
More amenities
R15,358/Night 7 Nights - R107,508
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Hotel
Map-icon
like-icon8.6
Fabulous
(241 Reviews)
10 Baths 569 ft²
  • Private Pool
    Private Pool
  • Private Beach
    Private Beach
More amenities
R13,814/Night 7 Nights - R96,708
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Bed & Breakfast
Map-icon
like-icon9.3
Exceptional
(135 Reviews)
7 Bedrooms 2 Baths 4 Guests 242.19 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R13,742/Night 7 Nights - R96,191
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Resort
Map-icon
like-icon9.2
Exceptional
(1001 Reviews)
1 Bath
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
R13,720/Night 7 Nights - R96,045
House
Map-icon
1 Bedroom 2 Baths 6 Guests
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R12,933/Night 7 Nights - R90,533
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Hotel
Map-icon
like-icon8.7
Fabulous
(155 Reviews)
18 Baths 1031.18 ft²
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
More amenities
R12,691/Night 7 Nights - R88,835

Front Street Pet Friendly Vacation Rentals

Cottage
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 4 Guests 794 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R7,081/Night 7 Nights - R49,567
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Apartment
Map-icon
like-icon8.9
Fabulous
(22 Reviews)
2 Bedrooms 2 Baths 6 Guests 1302.43 ft²
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
More amenities
R3,346/Night 7 Nights - R23,425
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Apartment
Map-icon
like-icon8.6
Fabulous
(193 Reviews)
1 Bedroom 1 Bath
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
R7,006/Night 7 Nights - R49,049
Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 2 Guests 440 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R6,743/Night 7 Nights - R47,206
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Apartment
Map-icon
like-icon8.8
Fabulous
(28 Reviews)
2 Bedrooms 1 Bath 6 Guests 3003.13 ft²
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
More amenities
R5,909/Night 7 Nights - R41,370
Apartment
Map-icon
like-icon9.8
Exceptional
(123 Reviews)
1 Bedroom 1 Bath 2 Guests 600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
R7,059/Night 7 Nights - R49,421
Cottage
Map-icon
like-icon9.8
Exceptional
(108 Reviews)
2 Bedrooms 2 Baths 7 Guests 1600 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R11,958/Night 7 Nights - R83,710
Cottage
Map-icon
like-icon9.8
Exceptional
(90 Reviews)
2 Bedrooms 2 Baths 7 Guests 1600 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R13,240/Night 7 Nights - R92,683

Front Street Large Vacation Homes

Cottage
Map-icon
like-icon10.0
Exceptional
(17 Reviews)
4 Bedrooms 4 Baths 11 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R22,056/Night 7 Nights - R154,391
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Apartment
Map-icon
like-icon9.0
Exceptional
(167 Reviews)
14 Bedrooms 2 Baths 7 Guests 5704.87 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R5,254/Night 7 Nights - R36,779
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 4 Baths 11 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R27,518/Night 7 Nights - R192,624
House
Map-icon
like-icon8.5
Fabulous
(88 Reviews)
5 Bedrooms 5 Baths 11 Guests 10.76 ft²
  • Oceanfront
    Oceanfront
  • Skiing
    Skiing
More amenities
R3,041/Night 7 Nights - R21,291
Villa
Map-icon
like-icon5.0
Average
(1 Review)
3 Bedrooms 4 Baths
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
R47,465/Night 7 Nights - R332,255
House
Map-icon
3 Bedrooms 6 Baths 12 Guests 2700 ft²
  • Oceanfront
    Oceanfront
  • Ocean View
    Ocean View
More amenities
R27,532/Night 7 Nights - R192,721
House
Map-icon
2 Bedrooms 2 Baths 16 Guests 5980 ft²
  • Oceanfront
    Oceanfront
  • Ocean View
    Ocean View
More amenities
R26,157/Night 7 Nights - R183,102
House
Map-icon
4 Bedrooms 8 Baths 16 Guests 2700 ft²
  • Child Friendly
    Child Friendly
R36,714/Night 7 Nights - R257,000

Why Choose Rent By Owner for your Front Street Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Front Street

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you enjoy the best weather and local events, making your experience in this vibrant destination truly memorable.

Peak Season Highlights

spring
Spring (April to June)

During this period, you'll enjoy the lively atmosphere and warm weather that make this destination ideal for exploring and relaxing on the region's scenic shores.

Average Temperature Daytime: around 75°F to 80°F - Nighttime: around 65°F to 70°F
winter
Winter (December to February)

This time offers a pleasant escape from colder climates, with comfortable temperatures that encourage outdoor activities and sightseeing in the area.

Average Temperature Daytime: around 70°F to 75°F - Nighttime: around 60°F to 65°F

Off-Season Highlights

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Summer (July to September)

While this is the peak of the warm season, it’s also when the area sees fewer visitors, making it perfect for those seeking tranquility and more affordable rates.

Average Temperature Daytime: around 85°F to 90°F - Nighttime: around 75°F to 80°F
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Autumn (October to November)

The shoulder season features mild weather and fewer crowds, providing a peaceful environment to enjoy the natural beauty without the peak season rush.

Average Temperature Daytime: around 70°F to 75°F - Nighttime: around 60°F to 65°F

Weekly Weather Forecast for Front Street

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.

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 a private outdoor patio or balcony to relax and take in the scenic views of the area.
  • Take advantage of on-site outdoor swimming pools available at many Bermuda vacation rentals.
  • Stroll through beautifully maintained shared gardens, perfect for morning walks or leisurely afternoons.
  • Utilize outdoor barbecue grills for hosting cookouts and enjoying local cuisine outside.
  • Make the most of nearby beaches with easy access to sun loungers and beach umbrellas often included in rentals.
  • Benefit from outdoor dining areas that allow you to dine al fresco while soaking up the island atmosphere.
  • Access outdoor fitness spaces or tennis courts typically found close to many rental properties in this destination.
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Family Activities

  • Bermuda Aquarium Museum and Zoo: Discover marine life, exotic animals, and interactive exhibits that are perfect for engaging young minds in this family-friendly attraction.
  • Queen Elizabeth Park: Enjoy a leisurely stroll through lush gardens, play areas, and scenic views that make this park an ideal spot for picnics and outdoor fun with children.
  • Front Street Shopping and Dining: Experience the vibrant atmosphere of this bustling street, offering diverse shops and casual eateries where you can relax and explore as a family.
  • Crystal Caves Bermuda: Venture into these awe-inspiring caves to witness stunning stalactites and stalagmites, making it a memorable educational adventure for everyone.
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Adult Activities

  • Shopping at Front Street: Explore the vibrant boutiques and international shops that line this bustling street, perfect for unique finds and souvenirs.
  • Dining in Hamilton: Indulge in a variety of local and international cuisines at the acclaimed restaurants nestled along the waterfront on this destination's main thoroughfare.
  • Strolling Along the Waterfront: Enjoy picturesque views and relaxing walks along the harbor, immersing yourself in the lively atmosphere of this area.
  • Cultural Experiences: Discover museums and art galleries nearby that showcase Bermuda’s rich history and contemporary creativity, adding depth to your visit.

Other Places to Stay in Front Street

Front Street Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the local dining scene: Savor authentic Bermudian cuisine at nearby eateries to immerse yourself in the area's vibrant culinary culture.
  • Take advantage of waterfront views: Choose accommodations with scenic harbor or ocean vistas to enhance your stay and enjoy relaxing sunsets here.
  • Plan your transportation options: Utilize public transit, taxis, or walk to easily access attractions and maximize your time exploring this destination.
  • Visit the local shops and markets: Stroll through the area’s boutiques and markets to find unique souvenirs and experience the region's lively atmosphere.

Transportation Options

  • Public Ferries: You can enjoy scenic crossings along the harbor using the local ferry services that connect the area with other parts of Bermuda, offering a convenient and picturesque way to explore.
  • Bus Services: The region is well-served by an efficient bus network that provides affordable transportation throughout Hamilton and surrounding neighborhoods, making it easy to navigate the area.
  • Taxis and Rideshare: Taxis and rideshare options are readily available for direct travel within the city center and to nearby attractions, offering comfort and flexibility during your stay.
  • Car Rentals: For more independence, car rental services are accessible here, allowing you to explore the broader region at your own pace from your vacation rental base.

Local Customs Options

  • Respect for Local Heritage: When visiting here, you'll notice that Bermudians deeply honor their history, and it's customary to show appreciation for local customs and cultural sites.
  • Greeting Etiquette: A friendly handshake or a warm "Good morning" is appreciated when meeting residents or fellow visitors in the area.
  • Dress Code for Religious and Cultural Sites: Modest attire is often expected at churches and cultural venues, so packing appropriate clothing will help you blend in seamlessly.
  • Celebration of Festivals: Participating in local festivals involves joining in traditional music, dance, and community events that highlight the area's vibrant culture.

Frequently Asked Questions About Front Street?

1. What are the top vacation rentals in Front Street?

There are a lot of options in Front Street. If you plan on staying in the Front Street area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Front Street:

2. How many vacation rentals have private pools in Front Street?

3. Which vacation homes in Front Street are best for families?

If you are looking for a family-friendly vacation home in Front Street, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Front Street:

4. How many Rentbyowner vacation rentals are available in Front Street?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 207 in the Front Street 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 Front Street. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies depending on the specific rental property. You should review the individual listing details or contact the owner directly to understand the terms and any applicable fees before booking.

6. How do I determine if a vacation rental in Hamilton offers flexible check-in and check-out options?

Flexible check-in and check-out times depend on each property’s policies. It’s best to read the listing descriptions carefully or reach out to the host to confirm availability and special arrangements.

7. Are there any specific amenities or services included with rentals in this part of Bermuda?

Amenities and services vary from one property to another. To ensure your needs are met, review the detailed listing information or contact the owner for clarification about what’s included in your stay.

8. What are the parking options available near vacation rentals in the vicinity?

Parking facilities differ based on the location of the property. Check the property listing for details on parking availability or contact the owner to inquire about nearby parking options.

9. How close are these Bermuda vacation rentals to local attractions and transportation hubs?

Properties are typically situated near key points of interest and transit options within the region. For precise distances and accessibility information, refer to the listing details or ask the owner directly.

Front Street Top Rated Vacation Rentals

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Hotel
Map-icon
like-icon8.9
Fabulous
(105 Reviews)
4 Baths 301.39 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R9,158/Night 7 Nights - R64,117
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Hotel
Map-icon
like-icon8.9
Fabulous
(58 Reviews)
2 Baths 597.39 ft²
  • Private Beach
    Private Beach
  • Pool
    Pool
More amenities
R10,508/Night 7 Nights - R73,558
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Hotel
Map-icon
like-icon8.4
Excellent
(154 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R3,072/Night 7 Nights - R21,502
Bed & Breakfast
Map-icon
like-icon7.5
Very Good
(43 Reviews)
11 Bedrooms 3 Baths 8 Guests 175.81 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R8,979/Night 7 Nights - R62,856
Apartment
Map-icon
4 Bedrooms 3 Baths 7 Guests 1937.5 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R5,012/Night 7 Nights - R35,081
House
Map-icon
like-icon10.0
Exceptional
(57 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R5,280/Night 7 Nights - R36,957
Cottage
Map-icon
like-icon10.0
Exceptional
(23 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R5,650/Night 7 Nights - R39,560
Apartment
Map-icon
like-icon10.0
Exceptional
(22 Reviews)
1 Bedroom 1 Bath 3 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R6,121/Night 7 Nights - R42,841