Leeward Beach Rentals by Owner

Why Choose Rent By Owner for your Leeward Beach vacation rental?

What makes our Rentals by Owner special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Leeward Beach

When should you plan your Rentals by Owner stay?

To make the most of your rental by owner experience here, consider visiting during the region’s shoulder seasons when the weather is pleasantly warm and popular times are less crowded, ensuring you enjoy a relaxing and authentic getaway in this sought-after destination.

Peak Season Highlights

spring
December to April

During this peak season, you will experience the warmest and most pleasant weather in the region, making it ideal for beach activities and exploring the area. This period attracts many visitors seeking a luxurious escape, which often results in higher rental prices.

Average Temperature Daytime: 85°F - Nighttime: 75°F
spring
July to September

This summer peak offers hot temperatures and lively conditions, perfect if you're looking to enjoy water sports and vibrant local events. Be prepared for increased demand for vacation rentals during these months, as many travelers flock to this destination for their holiday getaway.

Average Temperature Daytime: 88°F - Nighttime: 78°F

Off-Season Highlights

image
May to June

These months offer fewer crowds and more affordable rental options, making it a great time to relax on the beach and explore without the busy holiday rush. The weather remains warm and inviting, with less humidity and lower prices for your stay.

Average Temperature Daytime: 83°F - Nighttime: 73°F
image
October to November

The shoulder season features cooler temperatures and quieter beaches, providing a peaceful environment for your vacation. It's an excellent opportunity to enjoy the region's natural beauty at a more leisurely pace, with appealing rental rates available.

Average Temperature Daytime: 80°F - Nighttime: 70°F

Weekly Weather Forecast for Leeward Beach

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.

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 shaded lounging areas with comfortable outdoor furniture to relax after a day at the beach.
  • Take advantage of private or shared outdoor pools for refreshing swims in the warm Caribbean sun.
  • Make the most of fully equipped outdoor kitchens and barbecues for convenient al fresco dining.
  • Benefit from direct access to pristine beaches with sunbeds and umbrellas for ultimate comfort by the sea.
  • Utilize outdoor showers and changing areas to rinse off after swimming or water activities.
  • Explore well-maintained pathways and gardens that enhance your outdoor experience in this tropical destination.
  • Relax on spacious balconies or verandas offering scenic views of the surrounding region's natural beauty.
image
image

Family Activities

  • Snorkeling Adventures: Discover the vibrant marine life just off the shore, making it a perfect activity for families who enjoy exploring under the sea.
  • Beach Picnic Days: Pack a delicious meal and relax on the soft sands, enjoying quality family time in this scenic coastal setting.
  • Kids' Water Play Areas: Engage your children with nearby safe and fun water activities designed specifically for families visiting here.
  • Eco-Friendly Nature Tours: Embark on guided excursions that highlight the area's unique ecosystems, providing educational entertainment for the whole family.
image

Adult Activities

  • Spa and Wellness Retreats: Indulge in luxurious spa treatments and wellness experiences tailored for relaxation and rejuvenation, all conveniently accessible from your rental here.
  • Snorkeling and Diving Excursions: Explore vibrant coral reefs and marine life through guided snorkeling and diving trips that showcase the region's stunning underwater scenery.
  • Golfing Courses: Enjoy a round of golf at premier courses nearby, where you can take in scenic views while practicing your swing in a tranquil setting.
  • Luxury Yacht Charters: Experience the beauty of the area from the water by booking a private yacht charter, perfect for exploring the coastline and enjoying sunset cruises.

Leeward Beach Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Arrival Early: Arriving during daylight hours allows you to settle into your rental and explore the area with ease, making the most of your time here.
  • Utilize Local Resources: Take advantage of local guides and recommendations to discover hidden gems and authentic experiences unique to this coastal region.
  • Respect the Environment: Preserve the natural beauty of the area by sticking to designated paths and practicing eco-friendly habits during your stay.
  • Book with Confidence: Secure your vacation rental through Rent By Owner for a seamless experience, ensuring comfort and reliability at this popular destination.

Transportation Options

  • Rental Car Services: Renting a car provides the freedom to explore this destination and its surrounding areas at your own pace, with numerous local providers offering convenient pick-up options nearby.
  • Taxis and Chauffeur Services: Taxis are readily available for quick and reliable transfers around here, making it easy to reach popular spots without the need for personal transportation.
  • Public Transportation: Although limited, shared shuttle services and local buses serve key routes, offering an economical way to navigate within the region.
  • Bike Rentals and Scooters: For short trips and a more immersive experience, renting bikes or scooters allows you to easily explore the area’s scenic surroundings with convenience and flexibility.

Local Customs Options

  • Greetings and Respect: Visitors are encouraged to greet locals with a friendly "hello" or "good morning," reflecting the warm hospitality characteristic of this destination.
  • Dress Code for Religious Sites: Modest attire is appreciated when visiting churches or during religious ceremonies in the region, demonstrating respect for local traditions.
  • Beach Etiquette: It’s customary to keep the beaches clean by disposing of trash properly and respecting the quiet, laid-back atmosphere here.
  • Local Cuisine Etiquette: When dining at local eateries, sharing dishes and engaging politely with staff enhances your experience of the regional culture.

Frequently Asked Questions About Leeward Beach Rentals by Owner

2. How many Rentbyowner vacation rentals are available in Leeward Beach?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 957 in the Leeward Beach 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 Beach. 

3. What is the cancellation policy for a rental by owner in Leeward Beach?

Cancellation policies vary by individual host. You should review the specific listing details or contact the property owner directly to understand the terms related to cancellations and any applicable fees.

4. How do I communicate with the property owner before booking?

You can reach out to the owner through the messaging system provided on the Rent By Owner platform. This allows you to ask questions about the rental and confirm availability before making your reservation.

5. Are there any additional fees I should be aware of when booking a rental in the region?

Additional fees such as cleaning, security deposits, or service charges may apply. These will be specified in the listing details, so it's advisable to review all costs before completing your booking.

6. What amenities are typically included in vacation rentals here?

Most rentals in this destination offer amenities like Wi-Fi, fully equipped kitchens, air conditioning, and private outdoor spaces. Confirm the specific amenities with the owner to ensure they meet your needs.

7. Is there a minimum stay requirement for booking a rental by owner in the area?

Minimum stay requirements can vary depending on the property. Details about length of stay restrictions are usually listed on the property page, or you can inquire directly with the owner for clarification.

More Rentals You May Like Near Leeward Beach