Best Vacation Homes in Leeward Islands
377 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Ocean View
- Balcony/Terrace
- View
R4,472/Night
For 7 Nights R31,299
538.2 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Balcony/Terrace
- Parking
- Internet
R2,039/Night
For 7 Nights R14,266
R4,815/Night
For 7 Nights R33,707
1076 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
Ski Chalet
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,651/Night
For 7 Nights R39,554
2152.78 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
House
- Balcony/Terrace
- View
- Parking
R5,352/Night
For 7 Nights R37,457
560 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
R1,802/Night
For 7 Nights R12,611
2153 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
R8,840/Night
For 7 Nights R61,877
2691 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
R8,583/Night
For 7 Nights R60,076
Leeward Islands Luxury Rentals
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
Unlock the Best Price
753.47 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
Villa
- Private Beach
- Oceanfront
- Ocean View
R116,444/Night
For 7 Nights R815,101
5382 ft²
12 Guests
6 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R56,356/Night
For 7 Nights R394,489
R35,490/Night
For 7 Nights R248,427
R21,082/Night
For 7 Nights R147,569
1439.67 ft²
26 Guests
9 Bathrooms
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Spa
R18,753/Night
For 7 Nights R131,272
888.02 ft²
4 Bathrooms
Free Cancellation
Hotel
- Private Beach
- Oceanfront
- Spa
R11,961/Night
For 7 Nights R83,726
R11,918/Night
For 7 Nights R83,431
Leeward Islands Pet Friendly Vacation Rentals
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
R5,468/Night
For 7 Nights R38,276
565.11 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Bed & Breakfast
- Oceanfront
- Pool
- Ocean View
R3,131/Night
For 7 Nights R21,914
861 ft²
6 Guests
2 Bedrooms
4 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,162/Night
For 7 Nights R22,127
R2,498/Night
For 7 Nights R17,476
538.2 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Balcony/Terrace
- View
- Pet Friendly
R1,214/Night
For 7 Nights R8,500
107.64 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Balcony/Terrace
- View
- Pet Friendly
R1,547/Night
For 7 Nights R10,826
258.33 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Pet Friendly
- Parking
- Internet
R973/Night
For 7 Nights R6,813
387.5 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Balcony/Terrace
- View
- Pet Friendly
R1,776/Night
For 7 Nights R12,431
Leeward Islands Large Vacation Homes
8 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
Villa
- Air Conditioner
- Internet
- Child Friendly
R7,329/Night
For 7 Nights R51,313
2690.98 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Balcony/Terrace
- View
- Parking
R4,030/Night
For 7 Nights R28,204
1023 ft²
10 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Ski Chalet
- Balcony/Terrace
- Kitchen
- Air Conditioner
R7,073/Night
For 7 Nights R49,512
775 ft²
25 Guests
10 Bedrooms
5 Bathrooms
Free Cancellation
House
- Oceanfront
- Ocean View
- Balcony/Terrace
R3,855/Night
For 7 Nights R26,992
2734 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Hot Tub
- Ocean View
- Balcony/Terrace
R11,473/Night
For 7 Nights R80,319
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Air Conditioner
- Internet
- Child Friendly
R10,777/Night
For 7 Nights R75,439
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Kitchen
- Parking
- Air Conditioner
R7,197/Night
For 7 Nights R50,380
2045 ft²
8 Guests
2 Bedrooms
1 Bathroom
Ocean View
Villa
- Ocean View
- Balcony/Terrace
- View
R8,105/Night
For 7 Nights R56,735
Why Choose Rent By Owner for your Leeward Islands 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 Islands
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination ensures you enjoy its stunning scenery and pleasant weather, making your stay in the Leeward Islands seamless and memorable.
Peak Season Highlights
June to August
During these months, you'll enjoy the warmest weather with abundant sunshine, perfect for exploring and relaxing on the beaches of this destination.
Average Temperature Daytime: approximately 85°F to 88°F - Nighttime: around 75°F to 78°F
December to April
This period offers ideal conditions with plenty of sunshine and minimal rainfall, making it a popular choice for travelers seeking optimal beach weather.
Average Temperature Daytime: roughly 82°F to 86°F - Nighttime: about 73°F to 76°F
Off-Season Highlights
May and November
These shoulder months experience slightly lower visitor numbers and occasional rain showers, providing a more peaceful setting to enjoy your stay.
Average Temperature Daytime: around 80°F to 84°F - Nighttime: approximately 72°F to 75°F
September and October
The region sees increased chance of tropical showers during these months, but you can still find sunny periods and fewer crowds for a more relaxed visit.
Average Temperature Daytime: about 81°F to 83°F - Nighttime: roughly 71°F to 74°F
Weekly Weather Forecast for Leeward Islands
How to Book Your Leeward Islands 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 Islands
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 swimming pool to cool off and relax under the sun.
- Take advantage of an outdoor dining area perfect for savoring meals with scenic views.
- Relax in a shaded lounge or cabana to unwind and soak up the island atmosphere.
- Explore lush gardens or landscaped yards that add to your outdoor experience.
- Access to a barbecue grill for preparing delicious meals during your stay.
- Spend leisurely hours on a spacious patio or veranda overlooking the surroundings.
- Utilize outdoor showers or hammocks to enjoy the tropical climate at your own pace.
Top Attractions Around Leeward Islands
What attractions are nearby?
In this stunning destination, you can explore a variety of outdoor activities such as snorkeling, diving, and sailing, all conveniently accessible from your nearby vacation rentals in the Leeward Islands region.
Family Activities
- Snorkeling at Coral Gardens: Discover vibrant marine life and colorful coral reefs just off the coast, perfect for family adventures in the region.
- Exploring Local Markets: Visit bustling markets to sample fresh tropical produce and handcrafted souvenirs, offering an authentic taste of the area's culture.
- Beach Day at Matira Point: Relax on pristine sands and enjoy calm waters, making it an ideal spot for families seeking leisure and gentle swimming.
- Guided Eco Tours: Join family-friendly eco excursions to experience the region's lush landscapes and learn about its unique ecosystem.
Adult Activities
- Sailing and Yacht Charters: Experience the thrill of exploring crystal-clear waters and secluded coves by booking a private yacht or sailboat for an unforgettable day on the ocean.
- Snorkeling and Diving Excursions: Discover vibrant coral reefs and diverse marine life through guided snorkeling and diving tours, offering an immersive experience in the region's underwater ecosystems.
- Cultural Tours and Local Markets: Immerse yourself in Polynesian culture by visiting local markets and participating in authentic cultural experiences that showcase the area's rich heritage.
- Hiking and Nature Walks: Explore scenic trails and lush landscapes to enjoy breathtaking views and encounter native flora and fauna across this island paradise.
Other Places to Stay in Leeward Islands
Teahupoo
Taha'a
Mont Temehani
Society Islands
Vaitoare
Champon Pearl Farm
Tehurui
Raiatea
Uturoa
Tevaitoa
Leeward Islands Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: By scheduling your excursions and activities in advance, you ensure access to the best experiences this destination has to offer, making your stay more enjoyable and stress-free.
- Explore Local Dining Options: Take the opportunity to sample regional cuisine at local eateries or markets to truly immerse yourself in the area's vibrant culinary scene.
- Utilize Water Transportation: Make the most of boat rentals or ferries to discover nearby islands and hidden beaches that provide unforgettable scenic views and peaceful retreats.
- Choose a Strategic Location: Select vacation rentals situated near key attractions or beaches to maximize your leisure time and enjoy the region's natural beauty fully.
Transportation Options
- Domestic Flights: You can easily explore this destination by taking advantage of the regional flights that connect the islands, offering quick and convenient travel between key locations.
- Ferry Services: The region boasts reliable ferry services that provide scenic and affordable transportation options between the islands, ideal for exploring multiple areas during your stay.
- Private Water Taxis: For a more personalized experience, private water taxis are available to transfer you directly to your vacation rentals along the coastlines or beaches.
- Car Rentals: Renting a car is a practical choice for navigating the area at your own pace, especially when accessing remote or less accessible vacation rentals within the region.
Local Customs Options
- Respect for the Tārava Ceremony: Participating in or observing traditional ceremonies like the Tārava is an important way to honor local customs and cultural heritage here.
- Greetings with 'Ia Orana': When interacting with locals, using the greeting of 'Ia Orana' shows respect and appreciation for the region's Polynesian hospitality.
- Respect for the Marae: Visiting sacred sites called marae requires careful behavior and reverence, reflecting the deep spiritual significance they hold in this area.
- Traditional Tattooing Customs: Understanding and respecting the islanders' traditional tattooing practices offers insights into their history and cultural identity in this destination.
Frequently Asked Questions About Leeward Islands?
1. What are the top vacation rentals in Leeward Islands?
There are a lot of options in Leeward Islands. If you plan on staying in the Leeward Islands 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 Islands:
2. How many vacation rentals have private pools in Leeward Islands?
There are 2 vacation rentals with private pools near Leeward Islands. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Leeward Islands are best for families?
If you are looking for a family-friendly vacation home in Leeward Islands, 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 Islands:
4. How many Rentbyowner vacation rentals are available in Leeward Islands?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 296 in the Leeward Islands 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 Islands.
5. What is the cancellation policy for vacation rentals in this destination?
Cancellation policies vary depending on the specific property and owner. To understand the details, please review the cancellation terms listed on the property’s page or contact the owner directly for clarification.
6. How do I ensure my booking is secure when reserving a vacation rental here?
Reservations are secured through trusted booking platforms that offer secure payment options. It's recommended to confirm your reservation through the official listing and follow the platform's guidelines to ensure a safe booking process.
7. Are there any additional fees I should be aware of when booking a vacation rental in this region?
Additional fees, such as cleaning fees, service charges, or local taxes, are typically outlined in the listing. Review the detailed price breakdown before finalizing your reservation or contact the owner for specific fee information.
8. What amenities are usually included with vacation rentals in this area?
Most properties offer amenities like Wi-Fi, kitchen facilities, air conditioning, and outdoor spaces. For a complete list of features, refer to the property description or reach out to the host directly.
9. What should I know about check-in and check-out procedures for vacation rentals here?
Check-in and check-out times are set by each property owner and may vary. Details will be provided in the listing or upon confirmation. Contact the owner beforehand if you have special requests or need assistance with your arrival or departure.
Leeward Islands Top Rated Vacation Rentals
R7,726/Night
For 7 Nights R54,081
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Private Pool
- Pool
- Kitchen
R2,178/Night
For 7 Nights R15,248
807 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Pool
- Balcony/Terrace
- Kitchen
R7,033/Night
For 7 Nights R49,233
538.2 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Pool
- Balcony/Terrace
- View
R1,873/Night
For 7 Nights R13,103
R10,173/Night
For 7 Nights R71,213
291 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Pool
- Ocean View
- Balcony/Terrace
R2,282/Night
For 7 Nights R15,969
430.56 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Oceanfront
- Pool
- Ocean View
R2,624/Night
For 7 Nights R18,377
861.11 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Private Beach
- Oceanfront
- Pool
R4,692/Night
For 7 Nights R32,839
