Why Choose Rent By Owner for your Derricks Winter Rental?
What makes our Winter Rental special?
Best Times to Visit Derricks
When should you plan your Winter Rental stay?
To make the most of your stay in this destination, consider planning your vacation during the region's optimal weather months, when the sunny skies and warm temperatures create ideal conditions for enjoying the local beaches and outdoor activities.
Peak Season Highlights
December to April
This is the peak season when the weather in Derricks, St. James, Barbados is warm and sunny, making it ideal for enjoying outdoor activities and relaxing by the beach.
July to August
During these summer months, you can experience the warmest weather here, perfect for soaking up the sun and exploring the region’s scenic coastline.
Off-Season Highlights
May to June
The early summer months offer fewer crowds and pleasant weather, providing a more tranquil environment for your winter rentals in this destination.
September to November
Late summer and early fall tend to be quieter, with occasional showers, making it an excellent time for a peaceful getaway in the area.
Weekly Weather Forecast for Derricks
How to Book Your Derricks Winter Rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Derricks
Common Winter Rental Amenities
What amenities can you expect?
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
- Access to a private or shared outdoor swimming pool for relaxing in the sun.
- Well-maintained garden areas ideal for leisurely strolls and outdoor lounging.
- Comfortable outdoor dining spaces perfect for enjoying meals al fresco.
- Convenient outdoor shower facilities to rinse off after beach or pool visits.
- Spacious patios or verandas that offer scenic views of the surroundings.
- Outdoor grilling stations or barbeque areas to enhance your culinary experience.
- Secure parking with designated outdoor spaces for your convenience and peace of mind.
Top Attractions Around Derricks
What attractions are nearby?
Nearby, you can explore a variety of engaging activities in the area, from relaxing on the pristine beaches to enjoying water sports, golf, and vibrant local dining options that showcase the region's rich culture and natural beauty.
Family Activities
- Beach Days at Dover Beach: Spend quality time with your family relaxing and enjoying the calm, turquoise waters along this popular beach in the area.
- Island Safari Tours: Discover the natural beauty of the region on guided safaris that are perfect for families seeking adventure and scenic views.
- St. James Parish Church: Visit this historic church to appreciate the local architecture and learn about the area's cultural heritage.
- Harrison’s Cave Excursion: Experience an awe-inspiring underground tour through this spectacular limestone cave system, ideal for exploring with children.
Adult Activities
- Snorkeling and Diving: Discover vibrant marine life and coral reefs just offshore, offering a refreshing aquatic adventure during your stay.
- Beach Relaxation: Unwind on pristine sands along the coast, perfect for sunbathing, reading, or enjoying tranquil seaside views.
- Golfing: Play a round at nearby golf courses that showcase breathtaking ocean views, ideal for both beginners and seasoned players.
- Dining Experiences: Savor delicious local cuisine at beachfront restaurants that serve fresh seafood and Caribbean specialties.
Other Places to Stay in Derricks
Derricks Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Take time to research popular local spots and events near your winter rentals to maximize your experience in this region.
- Explore Local Cuisine: Sample authentic dishes at nearby restaurants or markets to get a true taste of the area’s vibrant culinary scene.
- Utilize Convenient Transportation Options: Consider renting a scooter or arranging local transfers to explore the surroundings effortlessly during your stay.
- Respect the Environment and Community: Be mindful of local customs and eco-friendly practices to ensure a sustainable visit that benefits the region's natural beauty and residents.
Transportation Options
- Public Buses: Accessible and budget-friendly, the local bus service offers reliable transportation for exploring the area and reaching nearby attractions.
- Private Taxis: Convenient and comfortable, private taxis provide door-to-door service for quick travel across the region.
- Car Rentals: For maximum flexibility, renting a vehicle allows you to explore at your own pace while enjoying the scenic views of the destination.
- Bicycle Rentals: A sustainable option, bicycle rentals are perfect for leisurely rides and discovering local sights within the vicinity.
Local Customs Options
- Respect for Local Greetings: When visiting here, it’s customary to greet locals with a warm smile and a friendly nod or handshake, reflecting the region's welcoming culture.
- Embracing the Island’s Music and Dance: Participating in or appreciating local music styles like calypso and reggae is a significant aspect of experiencing this destination’s vibrant community spirit.
- Understanding Traditional Attire: Visitors often observe that wearing modest and respectful clothing during cultural events or visits to community centers aligns with local customs.
- Honoring Local Cuisine Etiquette: When enjoying meals here, it’s polite to try traditional dishes and show appreciation by engaging with local dining customs, which often emphasize shared experiences and hospitality.
Frequently Asked Questions About Derricks Winter Rentals
1. What are the top Winter Rentals in Derricks?
There are a lot of options in Derricks. If you plan on staying in the Derricks area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Derricks:
- Ebbtide - Four Bedroom House, Sleeps 8
- Villa Seawards - Three Bedroom Villa, Sleeps 6
- Seawards, Beachfront, Fitts Village, St. James, Barbados
- Secret Cove 1 Luxury apartment
- Secret Cove 4 | Beach Front - Located in Tropical Saint James with House Cleaning Included
- Secret Cove 2 | Beach Front - Located in Exquisite Saint James with Private Chef Services
- Beachfront Bliss - Stunning 3-Bedroom Villa on Barbados’ West Coast
- Ocean views, spacious 3 bed apt in Fitts Village - 6 min walk to beach
- Brand New- Modern Sea' Ya Villa
- Charming house within walking distance to the beach, in Fitts Village, Barbados.
2. How many Winter Rentals are available in Derricks?
Currently, the total number of properties listed by RBO in 2026 is over 60 in the Derricks area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Derricks.


























