Winter Rentals in Southampton:【 GREAT PRICES 】Rent By Owner

Southampton Winter Rental

Location! Location! SUMMER SAVINGS at 5 Cross Bay Estate, next to Horseshoe Bay

Highly Rated

Apartment

Location! Location! SUMMER SAVINGS at 5 Cross Bay Estate, next to Horseshoe Bay

10.0

Exceptional

(160 Reviews)

1 Bedroom 1 Bath 2 Guests 200 ft²

US $199/Night 7 Nights - US $1,391

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Highly Rated

Resort

The Reefs Resort and Club

9.1

Exceptional

(76 Reviews)

2 Baths 6 Guests 215.28 ft²

US $825/Night 7 Nights - US $5,775

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Highly Rated

Hotel

The Reefs Resort & Club

9.6

Exceptional

(1006 Reviews)

1 Bath

US $917/Night 7 Nights - US $6,421

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

Highly Rated

House

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

10.0

Exceptional

(129 Reviews)

4 Bedrooms 4 Baths 10 Guests 3500 ft²

US $2,191/Night 7 Nights - US $15,338

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Highly Rated

Resort

Pompano Beach Club

9.0

Exceptional

(129 Reviews)

3 Baths 13 Guests 425.17 ft²

US $1,160/Night 7 Nights - US $8,120

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Large studio apartment w/views. Close to beaches

Highly Rated

Apartment

Large studio apartment w/views. Close to beaches

10.0

Exceptional

(119 Reviews)

1 Bedroom 1 Bath 2 Guests 650 ft²

US $285/Night 7 Nights - US $1,995

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Charming , Comfortable Cottage Near Amenities

Highly Rated

Cottage

Charming , Comfortable Cottage Near Amenities

10.0

Exceptional

(104 Reviews)

1 Bedroom 1 Bath 3 Guests 625 ft²

US $247/Night 7 Nights - US $1,732

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'RIPPLE WATERS' - More for Less - Great One Bedroom Pool House

Price Dropped

Apartment

'RIPPLE WATERS' - More for Less - Great One Bedroom Pool House

10.0

Exceptional

(8 Reviews)

1 Bedroom 1 Bath 4 Guests

US $378/Night 7 Nights - US $2,648

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Panoramic Private Beachfront Home with Breathtaking Views

Highly Rated

House

Panoramic Private Beachfront Home with Breathtaking Views

9.8

Exceptional

(177 Reviews)

4 Bedrooms 2 Baths 8 Guests 2100 ft²

US $1,066/Night 7 Nights - US $7,459

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Spacious Beachfront and Private Resort living

Highly Rated

Apartment

Spacious Beachfront and Private Resort living

9.8

Exceptional

(143 Reviews)

1 Bedroom 1 Bath 2 Guests 570 ft²

US $397/Night 7 Nights - US $2,778

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House

Villa at Cedar Brae - Ocean Views & Private Pool

9.8

Exceptional

(45 Reviews)

4 Bedrooms 3 Baths 12 Guests

US $1,335/Night 7 Nights - US $9,346

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House

The Pool House 2-bedrm townhouse-10-15 min walk to Horseshoe Bay, golf. Sleeps 6

9.6

Exceptional

(16 Reviews)

2 Bedrooms 1 Bath 6 Guests 1800 ft²

US $523/Night 7 Nights - US $3,658

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More Top-Rated Winter Rental in Southampton Area

Why Choose Rent By Owner for your Southampton Winter Rental?

What makes our Winter Rental 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 Southampton

When should you plan your Winter Rental stay?

Choosing the right time to visit this destination ensures you enjoy its tranquil charm and favorable weather conditions, making your winter rentals in Southampton, Bermuda the perfect escape for relaxation and exploration during the cooler months.

Peak Season Highlights

Spring (March to May)

During this time, the region comes alive with vibrant natural beauty and mild weather, making it ideal for enjoying outdoor activities at a comfortable pace.

Average Temperature Daytime: around 75°F (24°C) - Nighttime: roughly 65°F (18°C)

Summer (June to August)

The warmest season offers warm temperatures and longer days, perfect for soaking up sunshine and experiencing the lively local atmosphere.

Average Temperature Daytime: about 85°F (29°C) - Nighttime: approximately 75°F (24°C)

Off-Season Highlights

Fall (September to November)

As the summer crowds dwindle, you'll find more tranquility and cooler weather, providing a peaceful setting for exploring the area’s scenic landscapes.

Average Temperature Daytime: around 78°F (26°C) - Nighttime: roughly 68°F (20°C)

Winter (December to February)

While the weather is cooler, this is the time when you can enjoy fewer visitors and a serene environment, ideal for seeking cozy accommodations here.

Average Temperature Daytime: about 65°F (18°C) - Nighttime: roughly 55°F (13°C)

Weekly Weather Forecast for Southampton

How to Book Your Southampton Winter Rental

What's our booking process?

Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Southampton

More Top-Rated Winter Rental in Southampton Area

Common Winter Rental Amenities

What amenities can you expect?

Our Winter Rental 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 seating areas perfect for relaxing and dining al fresco amid the scenic surroundings.
Take advantage of private or shared swimming pools to unwind after exploring this beautiful region.
Make the most of well-maintained gardens or lush green spaces that add to the tranquility of your stay.
Benefit from outdoor barbecue grills, ideal for hosting gatherings and savoring local flavors outdoors.
Embrace the warm climate with access to shaded patios or verandas for a comfortable outdoor experience.
Explore the nearby beaches or waterfronts that are often included in the outdoor amenities of these rentals.
Utilize available outdoor recreational facilities like tennis courts or walking trails integrated into the property grounds.

Top Attractions Around Southampton

What attractions are nearby?

During your stay in this destination, you'll find a variety of nearby activities to enjoy, including exploring pristine beaches, engaging in water sports, and experiencing local cultural sites, all conveniently accessible from your winter rentals here in Southampton, Bermuda, making it an ideal choice for a relaxing and adventure-filled getaway.

Family Activities

Snorkeling at Church Bay Beach Discover vibrant marine life and enjoy calm, clear waters perfect for engaging family snorkeling adventures.
Visit to Bermuda Aquarium, Museum & Zoo Explore diverse marine exhibits, interactive displays, and animal encounters that captivate children and parents alike.
Exploring the South Shore Park Spend quality time with outdoor picnics, playgrounds, and scenic walking trails along the coastline here in this inviting destination.
Historical tour of St. Anne’s Parish Church Introduce your family to local history while strolling through an iconic site rich with cultural heritage.

Adult Activities

Snorkeling and Diving: Explore the vibrant underwater world just off the coast, where you can discover colorful reefs and marine life in clear, calm waters.
Golfing Adventures: Tee off at renowned golf courses in the area that offer scenic views and challenging fairways suited for all skill levels.
Boat Tours and Sailing: Embark on a guided boat tour or sailing excursion to enjoy breathtaking vistas of the coastline and learn about local maritime history.
Relaxing at Beach Resorts: Unwind at luxurious beach resorts nearby, where pristine sands and tranquil surroundings create the perfect setting for rest and rejuvenation.

Other Places to Stay in Southampton

Southampton Travel Tips

How Can You Make the Most of Your Stay?

Explore local dining options: Sample authentic Bermudian cuisine at nearby restaurants to immerse yourself in the region’s culinary culture.
Plan outdoor activities: Take advantage of the area's pleasant winter climate by enjoying beach walks or scenic tours around the coastline.
Stay connected with amenities: Ensure your winter rentals include reliable Wi-Fi and essential comforts to make your stay relaxing and hassle-free.
Discover cultural events: Check for seasonal festivals or local gatherings that showcase the unique heritage and traditions of here.

Transportation Options

Public Ferry This affordable option allows you to enjoy scenic rides across the water, connecting to various parts of the region with ease.
Taxis and Ride-Sharing Services Convenient for quick trips around the area, these services provide reliable transportation directly to your winter rental.
Car Rentals Renting a vehicle offers flexibility and freedom to explore more remote parts of this destination at your own pace.
Bicycle Rentals An eco-friendly way to navigate the area, bicycle rentals are perfect for enjoying the scenic routes nearby.

Local Customs Options

Gombey Dancing: Participating in or observing the vibrant Gombey dance performances is a cherished tradition that reflects the area’s rich cultural heritage.
Fishing Customs: Engaging in local fishing practices, which have been an essential part of the community’s livelihood for generations, offers insight into the region’s maritime history.
Sea Turtles Conservation: Respect for sea turtle nesting sites and conservation efforts are integral to protecting the natural environment here.
Local Festivals: Attending seasonal festivals provides a glimpse into the area's cultural celebrations and community spirit rooted in Bermuda's traditions.

Frequently Asked Questions About Southampton Winter Rentals

1. What are the top Winter Rentals in Southampton?

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

2. How many Winter Rentals are available in Southampton?

Currently, the total number of properties listed by RBO in 2026 is over 34 in the Southampton area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Southampton. 

3. What is the cancellation policy for winter rentals in Southampton, Bermuda?

The cancellation policies vary by property and host. To ensure you understand the specific terms, please review the booking details on the listing or contact the property owner directly before confirming your reservation.

4. Are there any specific requirements or restrictions when booking winter rentals here?

Yes, each property may have its own set of requirements or restrictions, such as minimum stay durations, age limits, or pet policies. For detailed information, refer to the individual listing or reach out to the host for clarification.

5. How do I secure my booking for a winter rental during the peak season?

Securing your reservation typically involves submitting a booking request and paying a deposit or full amount, depending on the property's policies. Be sure to review the listing’s payment terms and contact the host if you have questions about the process.

6. Are utilities and amenities included in the rental price?

Utilities and amenities are outlined in each listing and can vary. To confirm what is included in your reservation, check the property description or contact the host directly for clarification.

7. What is the best way to communicate with property owners in this area?

The platform provides a messaging feature that allows you to contact hosts directly. Using this feature ensures clear communication about your booking, special requests, or any concerns about your stay.