Leeward Settlement vacation rentals

We found 294 vacation rentals — enter your dates for availability
Discover a selection of 50 homes, 174 villas, and vacation rentals in Leeward Settlement that are perfect for your trip. Vacation rentals offer the best amenities for your stay with friends, family, or just your pet, such as parking and a fireplace. You're sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

Find out more about Leeward Settlement

Why visit Leeward Settlement

  • Stunning Beaches: Leeward Beach offers pristine sands and crystal-clear waters, perfect for sunbathing and family-friendly activities.
  • Outdoor Adventures: The warm tropical atmosphere is ideal for various outdoor pursuits such as snorkeling and kayaking.
  • Vibrant Reefs: Explore vibrant coral reefs teeming with marine life, making it a paradise for snorkelers and divers.
  • Charming Neighborhoods: Discover the unique charm of Leeward Settlement and its surrounding areas, ideal for leisurely exploration.
  • Diverse Accommodations: A variety of holiday rentals cater to all types of travellers, ensuring a comfortable stay.

Popular types of accommodation around Leeward Settlement

Discover the charm of Leeward Settlement with a variety of holiday rentals that cater to every traveler's needs. Whether you're looking for a spacious villa, a cozy condo, or a private holiday home, you'll find the perfect accommodation to suit your getaway. With transparent information and great savings, exploring holiday rentals in Leeward Settlement has never been easier. Enjoy your next adventure in this beautiful destination.

  • Villas: Luxurious private residences offering ample space and upscale amenities, perfect for families or groups seeking comfort and privacy.
  • Condos: Modern, self-contained units that provide a blend of convenience and style, ideal for those wanting a home-away-from-home experience.
  • Private Holiday Homes: Spacious homes that allow for a personalized stay, featuring full kitchens and outdoor areas for relaxation.
  • Apartments: Cozy living spaces that offer essential amenities, suitable for couples or solo travelers looking for simplicity and affordability.
  • Cottages: Charming and quaint accommodations that provide a rustic feel, perfect for a peaceful retreat amidst nature.**

Top attractions near Leeward Settlement

Leeward Settlement in Providenciales is the perfect destination for those seeking a beach holiday filled with outdoor adventures and stunning scenery. Visitors can enjoy various attractions such as the beautiful Leeward Beach and vibrant reefs. Whether you're looking for exhilarating outdoor activities or simply want to relax by the water, Leeward Settlement offers a variety of experiences that cater to all types of travellers, making it an ideal spot for your getaway.

  • Grace Bay Beach: A stunning stretch of soft white sand and turquoise waters, Grace Bay Beach is perfect for sunbathing, swimming, and enjoying the vibrant beach atmosphere. Its picturesque views and tranquil vibe make it an ideal spot for relaxation.
  • Coral Gardens Reef: This beautiful reef offers excellent snorkeling opportunities with vibrant marine life and stunning underwater scenery. The shallow waters make it accessible for all skill levels, providing an unforgettable aquatic experience.
  • Little Water Cay: A serene island sanctuary, Little Water Cay boasts beautiful beaches and lush landscapes, perfect for outdoor enthusiasts. Explore its unique wildlife and enjoy hiking trails amidst captivating natural beauty.

Things to do recommended for couples

For a romantic getaway in Leeward Settlement, enjoy a sunset beach picnic on Grace Bay, sail together on a private catamaran, or indulge in a couples' spa day. Don't miss the chance to explore vibrant coral reefs while snorkelling hand-in-hand—it's a perfect blend of adventure and intimacy.

Things to do recommended for families

Families visiting Leeward Settlement can enjoy a day at the beautiful Grace Bay Beach, where kids can build sandcastles and swim in the clear waters. Explore the nearby Coral Gardens for some excellent snorkeling, or take a leisurely kayak tour through the stunning mangroves for a unique adventure.

Things to do recommended for groups

Explore the stunning Grace Bay Beach, perfect for group relaxation and water sports. Take a guided tour of the local coral reefs for snorkelling, or enjoy a sunset cruise along the beautiful coastline to soak in the breathtaking views together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Leeward Settlement

If you're planning a trip with a group, family, or pets, or if you're interested in extended stays, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Leeward Settlement with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Leeward Settlement with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Leeward Settlement: For many families, a vacation isn't truly fulfilling without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Leeward Settlement: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider including amenities like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Leeward Settlement

Leeward Settlement, nestled in the heart of Providenciales, offers a picturesque escape with its stunning beaches and lush scenery. Visitors can bask in the sun at Leeward Beach, perfect for relaxation and family-friendly activities. The area boasts a warm, tropical atmosphere ideal for outdoor adventures, making it a delightful destination for those seeking a romantic getaway or a serene retreat. Explore the charm of Leeward Settlement and its surrounding neighborhoods for an unforgettable holiday experience.

  • Grace Bay: Grace Bay is a stunning neighborhood located approximately 3km from Leeward Settlement, known for its pristine beaches and crystal-clear waters. Visitors flock to this area for its picturesque scenery and outdoor experiences, including sunbathing, swimming, and water sports. The vibrant atmosphere is complemented by shopping centres and local markets, offering a mix of boutique shopping and dining options. With nearby attractions including beautiful beaches, a charming marina, and water features, Grace Bay is a perfect spot for relaxation and adventure alike.
  • Grace Bay Hills: Just 3km from Leeward Settlement, Grace Bay Hills is a serene neighborhood that captivates visitors with its breathtaking natural beauty. This area is celebrated for its outdoor experiences, where travellers can enjoy scenic walks and beach activities. Grace Bay Hills is close to stunning beaches and water features, making it an ideal destination for nature lovers. The proximity to a national park adds to the allure, offering opportunities for exploration and connection with the island’s unique flora and fauna.
  • Long Bay: Located approximately 3km from Leeward Settlement, Long Bay is known for its expansive beaches and tranquil atmosphere. This neighborhood is a popular choice for those seeking outdoor adventures, as it provides access to a variety of water sports and recreational activities. Visitors can explore shopping centres nearby for local crafts and cuisine, while the area's stunning beaches and water features create a relaxing backdrop. Long Bay is also near a national park, offering a chance to immerse yourself in the natural beauty of the Turks and Caicos Islands.

Best time to go to Leeward Settlement

If you're planning a trip to Leeward Settlement, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs from January to March, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January77.0°F (25.0°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
February76.6°F (24.8°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March76.1°F (24.5°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
April77.7°F (25.4°C)No Rain (Dry)Mostly SunnyAverageAverage
May79.5°F (26.4°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.6°F (28.1°C)Light RainMostly SunnyAverageAverage
August83.1°F (28.4°C)Light RainMostly SunnyAverageSlightly Low
September83.3°F (28.5°C)Light RainMostly SunnyModerately LowSlightly Low
October82.6°F (28.1°C)Light RainMostly SunnyModerately LowSlightly Low
November80.2°F (26.8°C)Light RainMostly SunnyModerately LowAverage
December78.6°F (25.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save some dollars on your upcoming journey? One helpful tip is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to utilize our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform where you can plan new trips, resume your previous ones, or manage your travel arrangements. You’ll find your saved or booked properties neatly organized under the sections for Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a vacation home in Leeward Settlement?
Prices for vacation rentals in Leeward Settlement vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Leeward Settlement to more spacious homes.
Are there any discounts for Leeward Settlement vacation house rentals?
You can find great discounts on house rentals in Leeward Settlement on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Leeward Settlement vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Leeward Settlement with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Leeward Settlement?
A long-stay vacation rental in Leeward Settlement is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Leeward Settlement for a vacation rental?
March is the most popular time to visit Leeward Settlement, as it marks the beginning of the peak season that lasts from March to May. This period lures sun-seekers and adventure enthusiasts alike, all eager to bask in the islands' stunning beaches and enjoy a variety of water sports. The warm temperatures, typically ranging from 24 to 30 degrees Celsius, create ideal conditions for outdoor activities, whether it's snorkelling, paddleboarding, or simply lounging by the turquoise waters.During these months, you'll find a vibrant setting with plenty of opportunities to explore the local culture and cuisine. However, if you're looking for a more tranquil experience and better value, consider planning your trip in October. This month offers pleasant weather and fewer crowds, allowing you to fully appreciate the beauty of Leeward Settlement without the hustle and bustle of peak tourist season.Ultimately, the best time to book a vacation rental in Leeward Settlement hinges on your preferences—whether you desire the lively energy of the peak season or the peaceful charm of the quieter months.
How early should I book a Leeward Settlement vacation rental?
Book your Leeward Settlement vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Leeward Settlement, Providenciales, Turks and Caicos?
In Leeward Settlement, Providenciales, visitors can enjoy several top attractions that highlight the natural beauty of the area. The stunning Grace Bay Beach, renowned for its powdery white sand and crystal-clear waters, is easily accessible and great for sunbathing, swimming, and various water sports. Nearby, the Coral Gardens and the Barrier Reef offer excellent opportunities for snorkelling, where guests can explore vibrant marine life in a tranquil setting.The local dining scene features a mix of beachfront restaurants and casual eateries, where you can savour fresh seafood and Caribbean cuisine. In addition, the Leeward Settlement area is close to the unique Mudjin Harbor on North Caicos, which, though a bit further, presents breathtaking views and an opportunity for adventure through hiking and exploring the coastline.For those interested in local culture, the nearby island of Providenciales offers the opportunity to visit the Conch Farm, the world's only conch farm, where visitors can learn about this unique marine creature and its importance to the local economy and ecosystem.
Can I change or cancel my Leeward Settlement home rental booking on Vrbo?
To find Leeward Settlement vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Leeward Settlement vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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