Discover Your Perfect Leeward Settlement Vacation Homes

Best Vacation Homes in Leeward Settlement

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Leeward Settlement Luxury Rentals

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Leeward Settlement Pet Friendly Vacation Rentals

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Leeward Settlement Large Vacation Homes

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Why Choose Rent By Owner for your Leeward Settlement Vacation Rental Homes?

What makes our Vacation Rentals special?

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

Best Times to Visit Leeward Settlement

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you enjoy the region’s best weather and vibrant local events, making your stay in Leeward Settlement, Providenciales, Turks and Caicos, truly unforgettable.

Peak Season Highlights

spring
December to April

During these months, the area experiences its peak tourist season, attracting visitors seeking warm weather and clear skies. You'll enjoy perfect conditions for outdoor activities and relaxing on the beaches of Providenciales.

Average Temperature Daytime: around 85°F (29°C) - Nighttime: around 75°F (24°C)
spring
June to August

The summer months bring high season with lively events and bustling beaches. Expect warm days ideal for water sports and exploring the region's natural beauty, making it a popular time for vacation renters.

Average Temperature Daytime: around 88°F (31°C) - Nighttime: around 79°F (26°C)

Off-Season Highlights

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May and November

These shoulder months offer a quieter experience with fewer visitors. The weather remains pleasant, providing a relaxed atmosphere perfect for enjoying the area's tranquil side.

Average Temperature Daytime: around 83°F (28°C) - Nighttime: around 74°F (23°C)
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September to October

This off-peak period falls within the hurricane season, so you may encounter less predictable weather. However, you'll benefit from lower prices and less crowded beaches during this time.

Average Temperature Daytime: around 87°F (31°C) - Nighttime: around 77°F (25°C)

Weekly Weather Forecast for Leeward Settlement

How to Book Your Leeward Settlement 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 Settlement

More Top-Rated Vacation Rentals in Leeward Settlement Area

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 access to a private outdoor swimming pool, perfect for relaxing under the sun.
  • Take advantage of lush garden or yard areas ideal for outdoor dining or leisurely strolls.
  • Make use of a fully furnished patio or veranda to unwind while soaking in the scenic surroundings.
  • Benefit from on-site barbecue grills, allowing you to host outdoor meals with family and friends.
  • Utilize available outdoor showers or rinse stations, especially useful after beach activities nearby.
  • Experience the comfort of shaded pergolas or cabanas designed for leisure and privacy outdoors.
  • Leverage easy access to nearby beaches or outdoor recreation spots, often included with the property.

Top Attractions Around Leeward Settlement

What attractions are nearby?

Within this tropical destination, you can enjoy a variety of activities such as snorkeling, boating, and relaxing on pristine beaches just minutes from your accommodation in Leeward Settlement, Providenciales, Turks and Caicos.

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Family Activities

  • Snorkeling at Smith's Reef: Explore the vibrant marine life just off the coast, an engaging activity perfect for families seeking adventure in the clear waters of the area.
  • Sunset Beach visits: Enjoy relaxing family walks and picture-perfect sunsets along this popular nearby beach known for its soft sands and gentle waves.
  • Island hopping tours: Embark on guided excursions to surrounding islands, offering memorable experiences and opportunities for snorkeling, swimming, and exploring local culture.
  • Wildlife watching in the region: Discover the area's rich natural habitats by observing native bird species and marine creatures in their protected environments.
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Adult Activities

  • Snorkeling and Diving Tours: Explore the vibrant coral reefs nearby, where you can discover diverse marine life just off the coast of this destination.
  • Golfing at Local Courses: Enjoy a round of golf on scenic courses that offer picturesque views and challenging fairways in the region.
  • Sailing and Boat Charters: Experience the tranquility of the sea with private sailing excursions or boat charters available here, providing stunning coastal vistas.
  • Spa and Wellness Retreats: Indulge in luxurious spa treatments designed to relax and rejuvenate amidst the serene surroundings of this area.

Other Places to Stay in Leeward Settlement

Leeward Beach
Leeward Beach Vacation Rentals
Provo Conch Farm
Provo Conch Farm Vacation Rentals
More Places to Stay Near Leeward Settlement

Leeward Settlement Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Activities: Book your preferred activities in advance to ensure you experience the best of what the area has to offer without last-minute surprises.
  • Choose a Well-Located Property: Opt for vacation rentals near key beaches and dining options to maximize your relaxation and convenience during your stay here.
  • Explore Local Dining: Indulge in authentic cuisine at nearby restaurants to enjoy the region's flavors and make the most of your visit.
  • Respect Natural Beauty and Environment: Practice eco-friendly habits and follow guidelines to help preserve the pristine environment that makes this destination so special.

Transportation Options

  • Personal Car Rentals: Renting a car provides the flexibility to explore this destination and the surrounding region at your own pace.
  • Taxi Services: Taxis are readily available for quick, convenient transportation around the area and to nearby attractions.
  • Public Transportation: Local buses offer an economical way to navigate here, connecting key points within the region efficiently.
  • Airport Transfers: Shuttle and private transfer services facilitate seamless arrivals and departures from nearby airports, ensuring a stress-free start and end to your stay.

Local Customs Options

  • Respect for Local Festivals: You should participate in or observe the area's traditional festivals, which often celebrate Caribbean culture and heritage, providing an authentic experience during your stay.
  • Greetings and Etiquette: When meeting locals here, a friendly handshake or a warm smile is customary, reflecting the region’s welcoming spirit.
  • Dress Modestly for Religious Sites: When visiting churches or religious ceremonies, it’s respectful to wear modest clothing that covers shoulders and knees as a sign of reverence.
  • Environmental Respect: Protecting the pristine beaches and natural surroundings by disposing of waste properly and avoiding harm to marine life is highly valued in this destination.

Frequently Asked Questions About Leeward Settlement?

1. What are the top vacation rentals in Leeward Settlement?

There are a lot of options in Leeward Settlement. If you plan on staying in the Leeward Settlement 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 Settlement:

2. How many vacation rentals have private pools in Leeward Settlement?

There are 162 vacation rentals with private pools near Leeward Settlement. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Leeward Settlement are best for families?

If you are looking for a family-friendly vacation home in Leeward Settlement, 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 Settlement:

4. How many Rentbyowner vacation rentals are available in Leeward Settlement?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 363 in the Leeward Settlement 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 Settlement. 

5. What is the cancellation policy for vacation rentals in Leeward Settlement, Providenciales?

Cancellation policies vary by property, so it's important to review the specific listing details or contact the owner directly to understand the terms and any applicable fees.

6. How do I book a vacation rental in this destination securely?

Booking is streamlined through a trusted platform that verifies listings and provides secure payment options. Be sure to read the property's description and communicate with the owner if you have any questions before confirming your reservation.

7. Are there any additional fees I should be aware of when reserving here?

Additional fees such as taxes, cleaning charges, or security deposits may apply depending on the property. Details are typically outlined in the listing, so review all terms carefully before booking.

8. What amenities can I expect from vacation rentals in this area?

Properties usually include amenities like Wi-Fi, air conditioning, fully equipped kitchens, and outdoor spaces. Specific offerings are listed in each property’s details, allowing you to choose accommodations that suit your needs.

9. Is there a minimum stay requirement for booking here?

Minimum stay requirements vary by property and season. To find out the exact policy, consult the listing details or contact the host directly before completing your reservation.

Leeward Settlement Top Rated Vacation Rentals

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