Best Vacation Homes in Leeward Islands
House
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
Private Pool
Pool
Kitchen
Air Conditioner
CA $268/Night
7 Nights - CA $1,876
Bed & Breakfast
10.0(36 Reviews)
1 Bedroom
1 Bath
4 Guests
538.2 ft²
Balcony/Terrace
Parking
Internet
Child Friendly
CA $175/Night
7 Nights - CA $1,222
CA $137/Night
7 Nights - CA $958
Bed & Breakfast
2 Bedrooms
1 Bath
4 Guests
Ocean View- Balcony/Terrace
View
Breakfast
CA $269/Night
7 Nights - CA $1,886
Villa
10.0(2 Reviews)
1 Bedroom
1 Bath
6 Guests
2690.98 ft²
- Balcony/Terrace
- View
- Parking
- Air Conditioner
CA $345/Night
7 Nights - CA $2,416
Ski Chalet
10.0(7 Reviews)
2 Bedrooms
3 Baths
6 Guests
1076 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $501/Night
7 Nights - CA $3,505
House
10.0(5 Reviews)
1 Bedroom
1 Bath
3 Guests
560 ft²
Oceanfront- Ocean View
- Balcony/Terrace
- View
CA $168/Night
7 Nights - CA $1,179
Villa
10.0(4 Reviews)
2 Bedrooms
3 Baths
6 Guests
2691 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $794/Night
7 Nights - CA $5,559
Leeward Islands Luxury Rentals
Villa
3 Bedrooms
3 Baths
6 Guests
753.47 ft²
Private Beach- Oceanfront
- Ocean View
- Balcony/Terrace
CA $9,976/Night
7 Nights - CA $69,830
Resort
9.7(177 Reviews)
9 Baths
26 Guests
1439.67 ft²
- Private Beach
- Oceanfront
Spa- Pool
CA $2,019/Night
7 Nights - CA $14,135
Hotel
9.3(3 Reviews)
4 Baths
888.02 ft²
- Private Beach
- Oceanfront
- Spa
Fireplace/Heating
CA $1,025/Night
7 Nights - CA $7,173
Hotel
9.6(143 Reviews)
3 Baths
1130.21 ft²
- Private Beach
- Oceanfront
- Spa
- Ocean View
CA $1,018/Night
7 Nights - CA $7,126
Villa
9.6(20 Reviews)
4 Bedrooms
3 Baths
9 Guests
2475.7 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $912/Night
7 Nights - CA $6,384
Villa
7.4(12 Reviews)
4 Bedrooms
3 Baths
10 Guests
2690.98 ft²
- Private Beach
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $856/Night
7 Nights - CA $5,991
New
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
8 Guests
1614.59 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
CA $826/Night
7 Nights - CA $5,782
Villa
9.5(2 Reviews)
5 Bedrooms
3 Baths
9 Guests
1829.86 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $739/Night
7 Nights - CA $5,172
Leeward Islands Pet Friendly Vacation Rentals
House
9.2(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $468/Night
7 Nights - CA $3,279
Bed & Breakfast
9.6(235 Reviews)
2 Bedrooms
2 Baths
4 Guests
565.11 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $268/Night
7 Nights - CA $1,877
House
4.0(1 Review)
2 Bedrooms
4 Baths
6 Guests
861 ft²
- Balcony/Terrace
Pet Friendly- Kitchen
- Internet
CA $271/Night
7 Nights - CA $1,896
House
9.3(27 Reviews)
4 Bedrooms
1 Bath
4 Guests
247.57 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $214/Night
7 Nights - CA $1,497
Apartment
9.1(76 Reviews)
1 Bedroom
1 Bath
2 Guests
538.2 ft²
- Balcony/Terrace
- View
- Pet Friendly
- Parking
CA $104/Night
7 Nights - CA $728
House
9.1(32 Reviews)
1 Bedroom
1 Bath
2 Guests
107.64 ft²
- Balcony/Terrace
- View
- Pet Friendly
- Kitchen
CA $119/Night
7 Nights - CA $836
Apartment
9.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
258.33 ft²
- Pet Friendly
- Parking
- Internet
CA $83/Night
7 Nights - CA $584
House
8.7(11 Reviews)
1 Bedroom
1 Bath
2 Guests
387.5 ft²
- Balcony/Terrace
- View
- Pet Friendly
- Parking
CA $152/Night
7 Nights - CA $1,065
Leeward Islands Large Vacation Homes
Villa
10.0(4 Reviews)
2 Bedrooms
3 Baths
6 Guests
2153 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $766/Night
7 Nights - CA $5,360
House
9.8(65 Reviews)
10 Bedrooms
5 Baths
25 Guests
775 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $319/Night
7 Nights - CA $2,231
CA $1,021/Night
7 Nights - CA $7,148
Villa
10.0(4 Reviews)
2 Bedrooms
1 Bath
8 Guests
2045 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
CA $694/Night
7 Nights - CA $4,860
Cabin
9.7(109 Reviews)
2 Bedrooms
2 Baths
10 Guests
592.02 ft²
- Private Beach
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $340/Night
7 Nights - CA $2,381
Villa
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
CA $767/Night
7 Nights - CA $5,368
Villa
10.0(2 Reviews)
6 Bedrooms
5 Baths
12 Guests
5382 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $5,034/Night
7 Nights - CA $35,241
Apartment
10.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
1346 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
CA $681/Night
7 Nights - CA $4,764
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 314 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
Ski Chalet
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
538.2 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $222/Night
7 Nights - CA $1,555
House
9.9(81 Reviews)
1 Bedroom
1 Bath
2 Guests
430.56 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $225/Night
7 Nights - CA $1,574
Apartment
9.9(38 Reviews)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Private Beach
- Oceanfront
- Pool
- Ocean View
CA $386/Night
7 Nights - CA $2,700
House
9.9(32 Reviews)
2 Bedrooms
1 Bath
4 Guests
484.38 ft²
- Pool
- Balcony/Terrace
- View
- Parking
CA $203/Night
7 Nights - CA $1,421
Apartment
9.7(55 Reviews)
1 Bedroom
1 Bath
4 Guests
861.11 ft²
- Private Beach
- Oceanfront
- Pool
- Ocean View
CA $402/Night
7 Nights - CA $2,813
Apartment
9.7(33 Reviews)
3 Bedrooms
1 Bath
10 Guests
1130.21 ft²
- Private Beach
- Oceanfront
Hot Tub- Spa
CA $543/Night
7 Nights - CA $3,797
Villa
9.5(16 Reviews)
3 Bedrooms
2 Baths
6 Guests
1291.67 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $266/Night
7 Nights - CA $1,863
House
9.4(93 Reviews)
5 Bedrooms
5 Baths
10 Guests
419.79 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
CA $239/Night
7 Nights - CA $1,674
