Best Vacation Homes in Leeward
1600 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R24,429/Night
For 7 Nights R171,002
322.92 ft²
28 Guests
12 Bedrooms
13 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
R35,984/Night
For 7 Nights R251,886
R52,372/Night
For 7 Nights R366,604
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
R5,250/Night
For 7 Nights R36,750
R15,195/Night
For 7 Nights R106,368
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
R10,166/Night
For 7 Nights R71,167
753 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R12,606/Night
For 7 Nights R88,251
1938 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R13,623/Night
For 7 Nights R95,368
Leeward Luxury Rentals
10764 ft²
12 Guests
6 Bedrooms
6 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
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10764 ft²
12 Guests
6 Bedrooms
6 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
Unlock the Best Price
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
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10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
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6997 ft²
16 Guests
8 Bedrooms
8 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
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6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
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2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
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12 Guests
6 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
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Leeward Pet Friendly Vacation Rentals
6 Guests
3 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R36,655/Night
For 7 Nights R256,586
1076.39 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
R11,905/Night
For 7 Nights R83,334
2476 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R40,661/Night
For 7 Nights R284,620
1076.39 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
R8,399/Night
For 7 Nights R58,784
1600 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R32,149/Night
For 7 Nights R225,036
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Pet Friendly
R22,834/Night
For 7 Nights R159,835
770 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Pet Friendly
- Kitchen
R15,426/Night
For 7 Nights R107,985
1292 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Ocean View
- Balcony/Terrace
- View
R12,946/Night
For 7 Nights R90,618
Leeward Large Vacation Homes
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R34,911/Night
For 7 Nights R244,369
1184.03 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
R31,650/Night
For 7 Nights R221,552
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
R20,517/Night
For 7 Nights R143,618
1800 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R10,938/Night
For 7 Nights R76,568
1614.59 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
R16,727/Night
For 7 Nights R117,085
1345 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R10,319/Night
For 7 Nights R72,234
861 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Oceanfront
- Hot Tub
- Ocean View
R8,459/Night
For 7 Nights R59,217
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R23,901/Night
For 7 Nights R167,302
Why Choose Rent By Owner for your Leeward 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 Leeward
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here ensures you enjoy the best weather and local events, making your stay in this region truly memorable.
Peak Season Highlights
December to April
During the peak season, the area experiences ideal weather conditions, making it perfect for enjoying outdoor activities and exploring the region's natural beauty. This period attracts many travelers seeking a luxurious getaway in this exclusive destination.
Average Temperature Daytime: around 28°C (82°F) - Nighttime: around 22°C (72°F)
July to August
The summer months bring warm temperatures and lively atmosphere, appealing to visitors looking to indulge in festive events and vibrant nightlife. This is when the island sees a surge of vacationers seeking the prime moments of the year here.
Average Temperature Daytime: around 30°C (86°F) - Nighttime: around 24°C (75°F)
Off-Season Highlights
May to June
In these months, you can enjoy fewer crowds and more serene surroundings while still benefiting from warm weather. It's an ideal time for those looking for a quieter escape in the region's tranquil environment.
Average Temperature Daytime: around 27°C (81°F) - Nighttime: around 21°C (70°F)
September to November
As the region transitions into the off-peak period, expect lower prices and fewer visitors, offering a relaxed experience. The weather remains warm, though occasional showers are possible, providing a peaceful retreat.
Average Temperature Daytime: around 29°C (84°F) - Nighttime: around 23°C (73°F)
Weekly Weather Forecast for Leeward
How to Book Your Leeward 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 Leeward
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 a private outdoor swimming pool to relax while taking in scenic views of the region.
- Make the most of a spacious sun terrace or patio for lounging and soaking up the island’s warm climate.
- Benefit from an outdoor dining area perfect for alfresco meals amidst tropical surroundings.
- Take advantage of lush gardens or landscaped yards that enhance your outdoor experience.
- Utilize a BBQ grill station to prepare delicious meals in the fresh air.
- Access to a shaded gazebo or gazebo-style seating for outdoor lounging and gatherings.
- Discover outdoor fitness amenities such as yoga decks or open-air gym spaces to stay active during your stay.
Top Attractions Around Leeward
What attractions are nearby?
In this inviting destination, you can explore a variety of water-based activities and scenic excursions just steps from your vacation rental, making it easy to enjoy the natural beauty and vibrant atmosphere that characterize the region.
Family Activities
- Snorkeling at Happy Bay Beach: Discover vibrant marine life and calm waters perfect for family snorkeling adventures just minutes from your vacation rental.
- Exploring Flamands Beach: Enjoy a relaxing day on the expansive white sands of Flamands Beach, ideal for picnics and gentle shoreline activities suitable for all ages.
- Hiking in Lorient Bay: Embark on scenic trails along the coast that offer breathtaking views, providing a memorable outdoor experience for active families staying here.
- Visit to the Leeward Marine Park: Engage in educational and fun marine excursions designed to introduce children to the region’s rich aquatic ecosystem while highlighting sustainable practices.
Adult Activities
- Snorkeling Excursions: Discover the vibrant marine life just off the coast, making it a perfect activity to enjoy in this scenic area.
- Sunset Cruises: Experience breathtaking sunsets aboard a luxury boat, offering a relaxing way to take in the region’s natural beauty.
- Hiking Adventures: Explore scenic trails that weave through the landscape, providing stunning views and an opportunity for outdoor enthusiasts.
- Gourmet Dining: Indulge in exquisite cuisine at local restaurants, showcasing the region’s culinary delights and lively atmosphere.
Other Places to Stay in Leeward
Gustavia
Grande Vigie
Flamands Beach
Anse des Flamands
Saint-Jean
Anse des Lezards
Terre Neuve
Colombier
Anse des Cayes
Public
Le Palidor
Leeward Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: Research local beaches, dining, and outdoor options to maximize your time in this scenic destination.
- Select the Perfect Accommodation: Choose from a variety of vacation rentals that offer the comfort and amenities suited to your preferences for an authentic stay here.
- Make Use of Local Tips: Engage with hosts or neighbors for insider advice on hidden spots and best times to visit popular areas within the region.
- Respect the Environment: Be mindful of the natural beauty by following eco-friendly practices and respecting local conservation efforts during your visit.
Transportation Options
- Car Rental Services: Renting a car provides the flexibility to explore the region at your own pace, especially when staying near popular beaches and scenic spots.
- Taxis and Private Transfers: Taxis offer convenient transportation around here, making it easy to reach your rental property from the airport or other key locations in the area.
- Public Buses: Local bus services are an affordable option for getting around the destination, connecting you to various beaches and attractions nearby.
- Boat Charters and Ferries: Navigating the waters surrounding the region can be a scenic way to visit neighboring islands and enjoy the stunning coastline views.
Local Customs Options
- Respect for Local Traditions: You’ll find that embracing the customs here, such as greeting with a warm "Bonjour," is appreciated and helps you connect authentically with residents.
- Celebration of Saint Barts Festivals: Participating in local festivals allows you to experience the vibrant cultural expressions unique to this destination.
- Emphasis on Eco-Friendly Practices: You'll notice a strong community focus on sustainability, encouraging visitors to minimize environmental impact during their stay.
- Traditional Cuisine Etiquette: When enjoying local dishes, it's customary to share meals and engage respectfully with the culinary traditions that define the region's flavor.
Frequently Asked Questions About Leeward?
1. What are the top vacation rentals in Leeward?
There are a lot of options in Leeward. If you plan on staying in the Leeward area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Leeward:
- 🏝REAL VILLA ON THE BEACH !SURFSPOT🏝CLOSE TO FLAMANS-STJEAN BEACH .REST.BARS
- SUPERIOR WATERFRONT PRIVACY AVAILABLE MARCH AND APRIL DATES NOW
- VILLA PERCHOIR ST BARTS: PEACEFUL HAVEN OF YOUR DREAM VACATION
- Luxury villa with magnificent sea view
- Saint Barths: brand new, luxury, architect-designed villa
- Villa Lama, sea view, owner operated, credit cards, 2 or 3 bedroooms rate
- Villa VOGUE - Panoramic Ocean View - St Jean
- 2BR Villa - Full Comfort - Open Atlantic View - 23 ft Pool
- SUNSET VILLA ANGEL *
- Located on the famous island of St. Barts, Villa Eugenie is a charming house.
2. How many vacation rentals have private pools in Leeward?
There are 1912 vacation rentals with private pools near Leeward. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Leeward are best for families?
If you are looking for a family-friendly vacation home in Leeward, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Leeward:
4. How many Rentbyowner vacation rentals are available in Leeward?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2397 in the Leeward 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 Leeward.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the specific property you choose. To ensure a smooth planning process, please review the cancellation terms listed on the property’s page or contact the property owner directly for detailed information.
6. Are there any additional fees I should be aware of when booking a rental here?
Additional fees such as cleaning charges, service fees, or security deposits are typically noted on the listing. It's advisable to carefully read the property details or reach out to the owner for clarification before completing your reservation.
7. How do I know if the vacation rental has the amenities I need?
Amenities are detailed in the property description and photographs on the listing. If you have specific requirements, contacting the owner directly can help confirm the availability of essential amenities during your stay.
8. What is the check-in and check-out process for these rentals?
Check-in and check-out procedures vary by property. Specific instructions are provided upon booking confirmation. For any special requests or questions about the process, it’s best to communicate directly with the owner beforehand.
9. Is there a secure way to pay for my vacation rental booking here?
Payments are typically processed through the booking platform's secure system. For added security and peace of mind, ensure all financial transactions are completed via the official booking channels and consult the listing for accepted payment methods.
Leeward Top Rated Vacation Rentals
646 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R20,622/Night
For 7 Nights R144,352
3229 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R55,393/Night
For 7 Nights R387,754
538 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
R7,116/Night
For 7 Nights R49,817
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R24,168/Night
For 7 Nights R169,185
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R23,901/Night
For 7 Nights R167,302
1500 ft²
7 Guests
3 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Pool
- Ocean View
R69,259/Night
For 7 Nights R484,822
2153 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R18,259/Night
For 7 Nights R127,818
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R26,182/Night
For 7 Nights R183,269
