Photo by Staci Partlo

Leeward Settlement holiday lettings

We found 278 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Leeward Settlement by choosing from 48 houses, 26 apartments and other holiday rentals. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as Wi-Fi and a pool. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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Why visit Leeward Settlement

  • Pristine Beaches: Enjoy the stunning Leeward Beach, perfect for sunbathing and relaxation.
  • Water Activities: Engage in a variety of water sports, including snorkelling and kayaking in vibrant reefs.
  • Luxurious Accommodation: Choose from a range of upscale villas and stylish condos for a comfortable stay.
  • Scenic Exploration: Discover charming spots that embody the romantic tropical vibe of Turks and Caicos.
  • Outdoor Adventures: Experience a blend of relaxation and adventure amidst beautiful natural surroundings.

Popular types of accommodation around Leeward Settlement

You've chosen Leeward Settlement for your next getaway, and now it’s time to find the perfect accommodation. Discover a range of options, from luxurious villas and stylish condos to charming private holiday homes. With a variety of Leeward Settlement holiday rentals available, you're sure to find the ideal spot to unwind and create unforgettable memories. Explore the best Leeward Settlement vacation rentals to make your stay truly special.

  • Villas: The top choice for holidaymakers in Leeward Settlement, these luxurious properties offer spacious living and stunning views.
  • Condos: A close second, these modern accommodations provide comfort and convenience in a vibrant setting.
  • Houses: Ideal for families or groups, these homes offer a home-away-from-home experience.
  • Apartments: A practical option, apartments provide essential amenities and easy access to local attractions.
  • Cottages: Charming and quaint, cottages are perfect for a peaceful getaway in a picturesque environment.**

Top attractions near Leeward Settlement

Leeward Settlement in Providenciales, Turks and Caicos, offers a perfect getaway for beach lovers and outdoor enthusiasts. With stunning beaches, vibrant reefs, and luxurious island resorts, visitors can enjoy a variety of scenic attractions. Whether you're seeking relaxation or adventure, there are plenty of local points of interest to explore in and around Leeward Settlement, making it an ideal destination for a memorable holiday.

  • Grace Bay Beach: Renowned for its powdery white sands and crystal-clear waters, Grace Bay Beach is perfect for sunbathing and leisurely strolls. It offers a vibrant beach atmosphere, ideal for relaxation and enjoying picturesque sunsets.
  • Coral Gardens Reef: A stunning underwater paradise, Coral Gardens Reef boasts vibrant marine life and beautiful coral formations. Accessible for snorkelling, it offers breathtaking scenery and the chance to encounter colourful fish in their natural habitat.
  • Little Water Cay: This unspoilt island is a haven for nature lovers, featuring beautiful beaches and outdoor adventures. You can explore its scenic trails and observe the native iguanas in their natural environment, making it a unique experience.

Things to do recommended for couples

For a romantic getaway in Leeward Settlement, enjoy a sunset beach picnic on the pristine sands, indulge in a couples’ spa treatment, or take a private boat tour to explore the stunning cays. Experience the local cuisine at charming seaside restaurants for an unforgettable evening.

Things to do recommended for families

Families can explore the beautiful Grace Bay Beach, renowned for its powdery sand and calm waters, or embark on a thrilling boat trip to Half Moon Bay, where children can snorkel among vibrant marine life. Enjoy a delightful day at the local Conch Farm for a unique experience!

Things to do recommended for groups

Explore the vibrant Regent Village Shopping Mall and Salt Mills Plaza, both a mere 1.2km from Leeward Settlement, offering a mix of shopping and entertainment. For a unique twist, visit Turk’s Head Brewery, 4.3km away, where you can enjoy a taste of local craft beers in a charming atmosphere.

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

If you're travelling with a group, as a family, bringing your pets, or seeking longer stays, it's important to filter your options according to your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Leeward Settlement with a group: Think about how many bedrooms you’ll require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Leeward Settlement with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your location in relation to family-friendly attractions is advisable.
  • Taking your pets with you to Leeward Settlement: For many families, a holiday wouldn't be the same without their beloved pet by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. The majority of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Leeward Settlement: If you're in search of holiday rentals with 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 include additional preferences such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Leeward Settlement

Leeward Settlement in Providenciales offers a delightful escape for beach lovers and outdoor enthusiasts alike. With its stunning Leeward Beach, this neighbourhood is perfect for soaking up the sun and enjoying a relaxing atmosphere. Just a stone's throw away, you can explore charming spots that encapsulate the romantic, tropical vibe of the Turks and Caicos. Whether you're planning a family holiday or a romantic getaway, Leeward Settlement is an ideal base for your next adventure.

  • Grace Bay: Grace Bay is renowned for its stunning expanse of powdery white sand and crystal-clear turquoise waters, situated a mere 1.2km from Leeward Settlement. This idyllic neighbourhood offers a perfect blend of relaxation and adventure, making it a popular destination for beach lovers and outdoor enthusiasts. Visitors can indulge in a variety of activities, from sunbathing on the beach to exploring vibrant local shops within the shopping centre and mall. Key attractions include the picturesque marina and beautiful water features, making Grace Bay a must-visit location for anyone looking to experience the natural beauty of the Turks and Caicos.
  • Grace Bay Hills: Just 1.2km away from Leeward Settlement, Grace Bay Hills offers a serene escape for those seeking a quieter beach experience. This charming neighbourhood is surrounded by stunning landscapes and is perfect for enjoying leisurely strolls along the beach or engaging in outdoor activities. Visitors can discover local attractions such as the nearby marina and water features, all while soaking in the breathtaking scenery. Grace Bay Hills is an excellent choice for travellers looking to unwind and appreciate the natural beauty of the area.
  • Long Bay: Located 1.2km from Leeward Settlement, Long Bay is a picturesque neighbourhood that attracts visitors with its tranquil beaches and outdoor scenery. This area is perfect for those wanting to engage in watersports or simply relax by the shore. Long Bay is also home to a shopping centre and mall, providing a variety of shopping options. Nearby attractions, including beautiful beaches, marinas, and water features, make Long Bay a delightful destination for both adventure seekers and those looking for a peaceful retreat.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 cut costs on your upcoming holiday? It may be beneficial to remain flexible with your travel dates, as prices can vary considerably. Additionally, opting for a longer stay often results in significant savings. To discover the perfect Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for you to craft new journeys, resume your planning, or manage your existing arrangements. You can easily access your saved or booked properties, neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Leeward Settlement?
In Leeward Settlement, villas are the most popular type of holiday rental, with around 71 available in this picturesque area. These luxurious properties often feature private pools, spacious outdoor terraces, and stunning ocean views, making them ideal for relaxation and entertaining. Many come with fully equipped kitchens and multiple bedrooms, suiting families or larger groups seeking a comfortable stay.
Are there any beach house rentals in Leeward Settlement?
In Leeward Settlement, Providenciales, there are around 165 beach house rentals available, making it a popular choice for visitors seeking a tropical getaway. These beach houses often come with stunning ocean views and direct access to the pristine beaches of Grace Bay. Many properties feature spacious living areas, fully equipped kitchens, and outdoor terraces or decks where guests can enjoy the beautiful Caribbean sunsets. Amenities typically include private pools, air conditioning, and sometimes even direct beach access, providing a superb retreat for families or groups. Find your rental near the beach in Leeward Settlement.
How much does it cost to rent a holiday home in Leeward Settlement?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Leeward Settlement holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday rentals in Leeward Settlement?
A long-stay holiday 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 holiday rental?
March is the most popular month to visit Leeward Settlement, where travellers flock to enjoy the stunning beaches and vibrant culture of Providenciales. The peak season, which runs from March to May, is characterised by warm, sunny days and a lively atmosphere, making it an ideal time for those seeking both relaxation and adventure. With temperatures hovering around 28-30 degrees Celsius, outdoor activities such as snorkelling, diving, and exploring the lush surroundings are highly enjoyable.

During this peak period, the area thrives with tourists, so you can expect a bustling yet festive environment. It's a great time for beach lovers to soak up the sun and partake in watersports, all while being surrounded by breathtaking ocean views.

If you're looking for a more cost-effective option, consider visiting in October. Although this month falls within the low season, it offers a unique charm. With fewer crowds, October allows for a more intimate experience of the island, where you can explore the local culture and enjoy the tranquil beaches without the hustle and bustle. Plus, the weather remains pleasantly warm, making it a lovely time for sightseeing and relaxation.
Are there any remote work holiday rentals in Leeward Settlement?
In Leeward Settlement, Providenciales, there are numerous holiday rentals suitable for remote work, with around 93 options available. This area is known for its stunning beaches and crystal-clear waters, making it an ideal setting for those looking to blend work and leisure. Many properties come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated office spaces, desk chairs, and even computer monitors, ensuring a productive environment while enjoying the tropical surroundings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Leeward Settlement holiday rental?
Book your Leeward Settlement holiday 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 holiday 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?
In Leeward Settlement, visitors can enjoy a variety of attractions centred around its stunning beaches and vibrant marine life. Grace Bay Beach, renowned for its powdery white sands and crystal-clear waters, is a major highlight, with numerous water sports and sunbathing options available. Holiday rentals in this area often provide easy access to the beach, allowing for a seamless beach experience.

The nearby Coral Gardens is a popular snorkelling spot where guests can explore the rich underwater ecosystems filled with colourful fish and coral. For those interested in local culture, the area offers proximity to the quaint shops and restaurants that showcase the island's cuisine and hospitality.
Can I change or cancel my Leeward Settlement home rental booking on Vrbo?
To find Leeward Settlement holiday 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Leeward Settlement holiday 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.