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Leeward Settlement vacation rentals

We found 302 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Leeward Settlement by choosing from 50 houses, 25 apartments, and other vacation rentals. 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.

Vacation rentals with weekly discounts - Leeward Settlement

Showing deals for:Sep 19 - Sep 26
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Find out more about Leeward Settlement

Find out more about Leeward Settlement

Why visit Leeward Settlement

  1. Stunning Beaches: Enjoy pristine sands at Leeward Beach and Pelican Beach, perfect for sunbathing and relaxation.
  2. Outdoor Activities: Explore scenic trails and engage in water sports like snorkeling and diving in vibrant coral reefs.
  3. Serene Atmosphere: Experience a laid-back vibe ideal for romantic getaways or family vacations amid tropical beauty.
  4. Vibrant Culture: Discover local culture and traditions by exploring nearby areas and engaging with the community.
  5. Diverse Accommodations: Choose from luxurious villas to cozy condos, ensuring a perfect stay tailored to your needs.

Popular types of accommodation in Leeward Settlement

If you're looking for the perfect getaway in Leeward Settlement, you're in the right place! Our vacation rentals offer a range of options, from luxurious villas to comfortable condos and houses. Whether you desire a lavish escape or a cozy retreat, our Leeward vacation rentals provide everything you need for an unforgettable stay. Explore our selection of luxury villas and make your dream vacation a reality!

  • Villas: The top choice for vacation rentals in Leeward Settlement, offering luxurious accommodations and stunning views.
  • Condos: A popular option for travelers seeking modern amenities and easy access to the beach.
  • Houses: Ideal for families or groups wanting a home-like atmosphere with added privacy.
  • Apartments: A convenient choice for those looking for comfortable living spaces in a central location.
  • Cottages: Charming and cozy, these rentals provide a quaint escape in a beautiful setting.**

Top attractions near Leeward Settlement

Leeward Settlement in Providenciales, Turks and Caicos, is a paradise for beach lovers and outdoor enthusiasts. With its stunning beaches like Leeward Beach and Pelican Beach, visitors can enjoy scenic trails and breathtaking views. Whether you're seeking relaxation or adventure, this area is perfect for creating unforgettable memories while exploring its beautiful reefs and nearby island resorts.

  1. Grace Bay Beach: Renowned for its pristine white sand and turquoise waters, Grace Bay Beach is the perfect spot for relaxation and sunbathing. Enjoy beach vibes while soaking in stunning views and indulging in water sports.
  2. Coral Gardens Reef: A vibrant underwater paradise, Coral Gardens Reef offers excellent snorkeling opportunities. Experience breathtaking scenery and marine life while enjoying the beach atmosphere nearby.
  3. Little Water Cay: This protected island is a haven for wildlife, particularly iguanas. Explore its natural beauty and outdoor activities while enjoying the serene beach vibes.

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

When planning your trip, whether you're traveling with a group, family, pets, or seeking longer stays, it's important to prioritize your filters effectively. Here are some valuable Vrbo booking tips to help you.

  • Traveling to Leeward Settlement with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas 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 be demanding. 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 complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Leeward Settlement: If you're seeking vacation rentals with special offers 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 features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Leeward Settlement

Leeward Settlement in Providenciales offers a delightful Caribbean getaway perfect for beach lovers and outdoor enthusiasts. This charming village boasts stunning scenery and a relaxed atmosphere, making it ideal for romantic escapes or family-friendly vacations. Explore nearby areas to experience the vibrant culture and breathtaking landscapes that define this tropical paradise. Whether you're seeking adventure or relaxation, Leeward Settlement is your gateway to an unforgettable vacation experience.

  • Grace Bay: Grace Bay is a picturesque village located 2 miles from Leeward Settlement, renowned for its stunning beach and vibrant outdoor atmosphere. Visitors flock to Grace Bay for a relaxing seaside experience, where the soft, powdery sands meet crystal-clear waters. The area is well-equipped with amenities, including shopping centers and luxurious resorts. Highlights include the beautiful marina and water features that enhance the scenic views. Grace Bay is perfect for those seeking both leisure and adventure, with opportunities for water sports and exploration of the local culture.
  • Grace Bay Hills: Just 2 miles away from Leeward Settlement, Grace Bay Hills offers a serene neighborhood experience that complements the vibrant atmosphere of nearby Grace Bay. This area is known for its stunning beaches and breathtaking scenery, making it an ideal spot for relaxation and outdoor activities. With easy access to local marinas and picturesque water features, travelers can enjoy a peaceful retreat while still being close to the lively attractions of Grace Bay. Grace Bay Hills is perfect for those looking to unwind while soaking in the natural beauty of the region.
  • Long Bay: Long Bay is a charming village situated 2 miles from Leeward Settlement, famous for its breathtaking beaches and outdoor recreational opportunities. Visitors to Long Bay can enjoy a range of activities, from shopping at local centers to relaxing on the beautiful shoreline. The area is known for its marina and stunning water features, making it a great destination for both adventure seekers and those looking to relax by the water. Long Bay’s tranquil atmosphere, combined with its proximity to other attractions, makes it a must-visit for a well-rounded vacation experience.

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 a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your needs!

Unlock savings with One Key

Secure a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire reservation. It truly benefits you to take on the role of planner! When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and accumulate OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board feature offers you a convenient space to plan new trips, pick up right where you left off, or manage your travel arrangements. You can easily access properties you’ve previously saved or booked under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-ca/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.

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