Leeward Settlement vacation rentals

We found 295 vacation rentals — enter your dates for availability

Welcome to the enchanting Leeward Settlement, where stunning beaches meet vibrant coral reefs, creating a paradise for sun-seekers and adventure enthusiasts alike. Dive into the crystal-clear waters or explore the colorful underwater world while snorkeling, and don’t miss the local animal farm, a delightful experience for families. With a selection of luxurious villas and cozy condos, your group can enjoy comfort and convenience, making this vacation rental the perfect home-away-from-home for unforgettable memories.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Leeward Settlement

Why visit Leeward Settlement

  • Beautiful Beaches: Enjoy the stunning Leeward Beach with its crystal-clear waters, perfect for relaxation and sunbathing.
  • Vibrant Marine Life: Explore vibrant reefs, ideal for snorkeling and diving enthusiasts eager for underwater adventures.
  • Outdoor Activities: Engage in various outdoor activities, from kayaking to paddleboarding, ensuring an adventurous getaway.
  • Charming Accommodations: Choose from luxurious villas to cozy condos, offering comfort and essential amenities for every traveler.
  • Serene Atmosphere: Experience a tranquil environment, perfect for families or couples seeking a romantic escape.

Popular types of accommodation around Leeward Settlement

Discover the charm of Leeward Settlement with our selection of vacation rentals. From luxurious villas and cozy condos to spacious houses, we have the perfect fit for every traveler. With essential amenities and a focus on guest satisfaction, our rentals ensure a comfortable stay. Whether you're seeking relaxation or adventure, your ideal vacation home is waiting for you in Leeward Settlement. Happy guests are our priority.

  • Villas: The top choice for travelers in Leeward Settlement, villas offer luxurious accommodations with stunning views and private amenities.
  • Condos: A popular option, condos provide a comfortable stay with convenient access to local attractions and shared facilities.
  • Houses: Ideal for families or groups, these homes offer a homey atmosphere with ample space and privacy.
  • Apartments: A practical choice for solo travelers or couples, apartments deliver essential comforts in a compact setting.
  • Cottages: For a charming and quaint experience, cottages offer a cozy escape amidst beautiful surroundings.**

Top attractions near Leeward Settlement

Leeward Settlement in Providenciales, Turks and Caicos, is perfect for a beach and outdoor getaway, offering stunning scenery and a variety of attractions. Visitors can enjoy the beautiful Leeward Beach, explore vibrant reefs, and engage in exhilarating outdoor activities. Whether you're looking to relax by the water or seek adventure, Leeward Settlement has something for everyone, with plenty of nearby points of interest to enhance your vacation experience.

  • Grace Bay Beach: Renowned for its powdery white sand and turquoise waters, Grace Bay Beach provides a quintessential Caribbean experience. Relax under swaying palm trees or indulge in water sports, all while soaking up the vibrant beach vibes.
  • Coral Gardens Reef: A stunning underwater paradise, Coral Gardens Reef invites snorkelers and divers to explore its colorful marine life and breathtaking scenery. Experience the thrill of swimming alongside tropical fish in this vibrant and serene setting.
  • Little Water Cay: A beautiful island known for its pristine beaches and outdoor adventures, Little Water Cay offers opportunities for hiking, birdwatching, and observing the local wildlife, making it a perfect spot for nature enthusiasts.

Things to do recommended for couples

Ready for a romantic getaway in Leeward Settlement? Enjoy a sunset dinner on the beach, take a private boat tour to explore hidden cays, or relax with a couples' spa day at a local resort. Embrace the island's beauty together for an unforgettable experience.

Things to do recommended for families

Families vacationing in Leeward Settlement can enjoy a day at the beautiful Grace Bay Beach, known for its soft sand and clear waters. Kids will love snorkeling at Coral Gardens, and exploring the nearby nature trails offers a perfect blend of adventure and relaxation for everyone.

Things to do recommended for groups

Explore the vibrant Regent Village Shopping Mall and Salt Mills Plaza, both 2 miles from Leeward Settlement, for shopping and entertainment. For a unique experience, visit Turk’s Head Brewery, located 7 miles away, where you can enjoy a romantic atmosphere and craft brews with your group.

*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 traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your needs with the right filters. Here are some helpful booking tips for using Vrbo.

  • Traveling to Leeward Settlement with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Leeward Settlement with young kids: Traveling with young kids can present some challenges. It’s important to prioritize their comfort and safety, as well as look for amenities suitable for their age, 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 wouldn’t feel complete without their furry companions. If this resonates with you, explore Vrbo listings that are pet-friendly. Most of these properties come equipped with feeding bowls and beds, ensuring that everyone, including your pet, 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 filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Leeward Settlement

Leeward Settlement in Providenciales is a tropical paradise perfect for beach lovers and outdoor enthusiasts. Explore stunning beaches with crystal-clear waters, enjoy breathtaking views, and discover affordable accommodations that make your stay comfortable. Venture into the nearby remote areas for a relaxing getaway, ideal for families or couples seeking romance. With its sunny weather and serene atmosphere, Leeward Settlement promises an unforgettable vacation experience.

  • Providenciales: Providenciales, often referred to as Provo, is the main city in the Turks and Caicos Islands, and Leeward Settlement is nestled within its borders. This vibrant destination attracts travelers for its stunning beaches, outdoor adventures, and breathtaking scenery. Visitors can enjoy a variety of activities, including shopping at local centers and malls, engaging in thrilling water sports, or simply relaxing on the pristine beaches. Key attractions include the picturesque marina and beautiful water features that enhance the area's natural charm.
  • Grace Bay: Located 2 miles from Leeward Settlement, Grace Bay is a world-renowned neighborhood celebrated for its powdery white sands and crystal-clear waters. This coastal paradise is perfect for beach lovers and outdoor enthusiasts alike. Grace Bay offers a plethora of activities, from upscale shopping at local centers to luxury resort experiences. Visitors can soak in the scenic beauty while enjoying nearby landmarks like the beach, marina, and captivating water features, making it a must-visit location during your stay.
  • Grace Bay Hills: Also situated 2 miles from Leeward Settlement, Grace Bay Hills is a charming neighborhood that offers an idyllic escape for those seeking relaxation and natural beauty. Known for its serene beaches and outdoor attractions, this area provides an excellent setting for leisurely strolls and sunbathing. Visitors can explore the nearby marina and experience the stunning water features that define this picturesque landscape, contributing to the overall allure 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.

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 a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, booking a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly area to plan new trips, resume your previous plans, or manage your travel itinerary. You can easily access your saved or booked properties, which are organized into categories such as Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Barefoot luxury in Leeward Settlement

Set on the northern tip of Providenciales, Leeward Settlement is your ticket to a tropical paradise. The laidback community is a gateway to the Turks and Caicos Islands, a string of sandy cays fringed by sugar-white beaches, swaying palms and translucent water. While Grace Bay Beach makes a dreamy first impression, Leeward Settlement is just as enchanting. A favorite with longtime vacationers, Leeward Settlement vacation rentals champion barefoot luxury. Take your pick from condos, cottages and spacious villas.

Conch and cocktails in Leeward Settlement

Most visitors arrive on Providenciales in search of well-deserved R&R. Leeward Settlement vacation rentals deliver, with oceanfront infinity pools and sun-drenched decks. Throw in sunset cocktails and you'll quickly find yourself slipping into island time. When you've had your fill of gorgeous beaches and swaying hammocks, why not check out attractions like the Caicos Conch Farm? It cultivates conch for the entire Bahamian Archipelago, with tours offering a behind the scenes glimpse at the entire process, from shell to seafood restaurant.

Tropical winters in Leeward Settlement

Winter is high season in the Turks and Caicos Islands, when the archipelago enjoys clear skies, calm waters and balmy temperatures. Expect bigger crowds over busy periods like Christmas and the winter school break. Planning a family getaway to the tropics? With spacious living areas and affordable price tags, self-contained Leeward Settlement vacation rentals run circles around hotels. If you don't mind the occasional rain shower, consider visiting in April or May. This is considered a sweet spot, with quieter beaches and highs that hover around the 80s. You'll also sidestep Atlantic hurricane season, which rolls from June to November.

Aquamarine lagoons in Leeward Settlement

Leeward Settlement is perched on the northernmost tip of Providenciales, the most populated island in the Turks and Caicos. The Atlantic archipelago is made up of 40 low-lying coral islands encircled by barrier reefs and underwater sea walls. As well as a myriad of ravishing beaches, Providenciales is also home to gems like Chalk Sound National Park. The lagoon stretches for 3 miles and is strewn with tiny islets that rise up from the turquoise-hued water. Visit in winter and you'll catch 1000s of humpbacks cruise through the Turks and Caicos Islands on their annual migration.

Transportation options to and around Leeward Settlement

Fly into Providenciales Intl. Airport (PLS), the closest airport, located 8.3 mi (13.4 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Leeward Settlement?
Villas are the most popular style of vacation rental in Leeward Settlement, according to our data. Even if you've got a different idea about what you'd like, Vrbo has vacation homes in all sizes and shapes. Take a look at our options to find your perfect fit.
How much does it cost to rent a vacation rental in Leeward Settlement?
Several things determine what you'll pay for your vacation rental in Leeward Settlement, such as the length of stay, type of property and season. However, all our vacation homes have something in common — unbeatable value. Simply add your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Leeward Settlement?
Prices for beach houses in Leeward Settlement vary depending on the size and type of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and how many guests to view your vacation rental options and prices. From there you can use the filters to tailor your search by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Leeward Settlement?
Yes. There are. Take your pick of 173 vacation rentals that allow pets in Leeward Settlement on Vrbo. Our furry best friends also deserve a getaway, so simply use our search function for pet-friendly vacation rentals to find a perfect property where your doggie can lap up the good times.
Can I rent a house with a pool in Leeward Settlement?
Grab your swimming gear and pool noodle, because there are 134 houses with a private pool in Leeward Settlement. Make a booking at one of these terrific vacation homes and you'll enjoy pool days every day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the ideal place for a splashing good time!
What are popular rental amenities in Leeward Settlement?
A nearby river, a fireplace and ski-in/ski-out facilities rank as the most popular rental amenities in Leeward Settlement. Whether you plan to travel on your own, with your spouse or as a family, Vrbo can help you find a vacation rental that matches your tastes with all the features you need.
Are there large group vacation rentals in Leeward Settlement?
You'll discover 67 vacation rentals in Leeward Settlement that can host 10 or more guests. Whether you're organizing a get-together with extended family or a celebration like a birthday, there's ample space to get your favorite people together under the same roof.
Are there vacation rentals in Leeward Settlement that welcome kids?
Bring the entire group together for the adventure of a lifetime in Leeward Settlement at one of our 163 family-friendly vacation rentals. Many of these stays offer conveniences that are just perfect for trips with youngsters, like dining rooms, multiple bedrooms and swimming pools. Simply check the "Properties good for families" filter and pick your favorite.
Are there one-bedroom vacation rentals in Leeward Settlement?
Take your pick from 25 one-bedroom rentals in Leeward Settlement. Whether you're looking for a townhouse or a fancy condo, Vrbo's one-bedroom properties are just right if you don't need a lot of space. One of the perks of having your own pad? You won't ever have to share your adventure with strangers.
Can I find two-bedroom vacation rentals in Leeward Settlement?
Take off with your besties and enjoy peace, privacy and comfort in one of the 21 two-bedroom vacation properties Leeward Settlement has to offer.
Are there vacation rentals with WiFi in Leeward Settlement?
Take your pick of 75 vacation rentals with WiFi in Leeward Settlement. If you'd like to disconnect from daily life on your vacation, but still need to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Leeward Settlement?
You can choose from 154 Vrbo vacation homes with air conditioning in Leeward Settlement offering that cool, cool breeze and extra bit of comfort. Simply enter your preferred dates of travel and then make use of our filter tool to locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Leeward Settlement?
The minimum age can vary across properties on Vrbo, so be sure to check the rules of the vacation home in Leeward Settlement you're considering. But in general, it's 16, 18 or 21.
How long can I rent a vacation rental in Leeward Settlement for?
It's down to the Leeward Settlement property. To view a list of options offering extended stays, just type your dates and guest number into the Vrbo search page. You can look forward to having the entire place to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and a yard where the kids can burn off energy. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Leeward Settlement?
Whether you're after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to find some incredible deals and discounts on Vrbo. From short stays to extended vacations, we've got the ideal space for your next Leeward Settlement escape.

More Vacation Ideas