Leeward Settlement vacation rentals

We found 298 vacation rentals — enter your dates for availability

Discover a selection of 46 homes, 160 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.

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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.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. By becoming a member of our travel rewards program, OneKey, you can immediately access exclusive savings and earn as well as use OneKeyCash on eligible reservations. Sign up today to start enjoying the benefits of saving.

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 in Leeward Settlement?
In Leeward Settlement, villas are the most popular type of vacation rental, with about 78 available throughout the area. These properties typically feature luxurious amenities such as private pools, expansive outdoor terraces, fully equipped kitchens, and spacious living areas, making them ideal for travelers seeking comfort and relaxation. Additionally, there are around 24 vacation houses, which often provide family-friendly spaces with multiple bedrooms and outdoor dining options. Several apartments, cottages, and condos are also available, offering travelers a range of choices that cater to different preferences and group sizes.
Are there any beach house rentals in Leeward Settlement?
In Leeward Settlement, there are approximately 167 beach house rentals available, making it a popular destination for vacationers seeking a tropical getaway. These beach houses typically offer spacious interiors with multiple bedrooms, fully equipped kitchens, and inviting living areas. Many properties also feature outdoor amenities such as private pools, patios, and direct access to the stunning beaches of Providenciales. The area is known for its beautiful turquoise waters and nearby attractions, including the serene Long Bay Beach and the vibrant Grace Bay, great for snorkeling and water sports.
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 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 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.
What are popular rental amenities in Leeward Settlement?
In Leeward Settlement, Providenciales, popular vacation rentals frequently come equipped with essential amenities that enhance the overall guest experience. Many properties offer fully equipped kitchens, allowing travelers to prepare their own meals and enjoy dining at their leisure. Additionally, private pools are a common feature, providing a refreshing retreat from the tropical heat. Guests can also expect outdoor spaces such as decks or patios, great for relaxing and taking in the beautiful surroundings. For those who enjoy a morning pick-me-up, rentals typically include coffee and tea makers, ensuring a comforting start to the day.
Can I find family house rentals in Leeward Settlement?
In Leeward Settlement, Providenciales, there are a substantial number of family-friendly vacation rentals available, totaling around 66. This area is known for its beautiful beaches and proximity to popular attractions like Long Bay Beach, which is superb for families looking to enjoy water activities. Many of these homes feature spacious living areas, fully equipped kitchens for convenient meal preparation, and outdoor patios or decks for enjoying the tropical climate.

Guests can also expect amenities such as private pools, game rooms, and easy access to nearby snorkeling spots, making it an excellent choice for those traveling with children.
Can I rent a vacation home with a pool or hot tub in Leeward Settlement?
In Leeward Settlement, Providenciales, there are plenty of vacation homes available for rent that feature both pools and hot tubs, with around 104 options for homes with pools and 17 options with hot tubs. This beautiful area is known for its stunning beaches and clear turquoise waters, making it a fantastic choice for travelers seeking relaxation and luxury.

Many of these rentals come equipped with private pools and hot tubs, offering a ideal setting for unwinding after a day of exploring the island. You'll also find amenities like spacious outdoor decks, barbecue areas, and fully equipped kitchens, allowing for seamless indoor-outdoor living.
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 travelers 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 book pet-friendly vacation rentals in Leeward Settlement?
In Leeward Settlement, Providenciales, there are several pet-friendly vacation rentals available for travelers. This charming area is known for its proximity to beautiful Grace Bay Beach, where visitors can enjoy stunning turquoise waters and soft white sands. Many of the vacation rentals in this region feature amenities such as private pools, outdoor patios, and fully equipped kitchens, making them superb for families or groups.

The Leeward Settlement area also offers easy access to a variety of outdoor activities, including snorkeling and kayaking, which are popular among visitors. Additionally, nearby local shops and restaurants provide convenient options for dining and entertainment.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Leeward Settlement for a vacation rental?
March marks the most popular time to visit Leeward Settlement, Providenciales, as the peak season runs from March to May. This period attracts travelers seeking sun-soaked beaches, crystal-clear waters, and a vibrant setting. With average temperatures ranging from the mid-70s to low 80s Fahrenheit, visitors can comfortably enjoy outdoor activities such as snorkeling, diving, and relaxing on the pristine shores.

During these months, Leeward Settlement offers a lively yet laid-back vibe, great for those looking to soak up the sun while exploring the stunning coral reefs and engaging in water sports. The area is well-equipped with convenient amenities, ensuring a straightforward experience for visitors keen on quality and comfort.

For those considering a more budget-friendly option, October is an excellent time to visit. While it falls outside the peak season, October still boasts warm weather and fewer crowds, allowing you to enjoy the beauty of the islands in a more tranquil setting. This quieter month provides opportunities for leisurely exploration and discovering the local culture without the hustle and bustle of high season.

Ultimately, the best time to book a vacation rental in Leeward Settlement depends on whether you prefer the vibrant setting of peak season or the peaceful charm of the shoulder months.
Are there any remote work vacation rentals in Leeward Settlement?
In Leeward Settlement, Providenciales, there are numerous remote work-friendly vacation rentals available, totaling around 107 options. This area is known for its stunning beaches and relaxed atmosphere, making it an ideal spot for those looking to blend work with leisure. Many of these rentals come equipped with essential amenities such as high-speed internet, free Wi-Fi, and dedicated desk spaces, allowing for a productive work environment.

Travelers can expect comfortable accommodations that often feature spacious living areas and fully equipped kitchens, superb for preparing meals during longer stays. Additionally, some properties may offer outdoor spaces where guests can unwind after work, with beautiful views of the surrounding landscapes. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
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 a range of attractions that highlight the area's natural beauty and vibrant culture. One of the main draws is Long Bay Beach, known for its soft, white sand and calm turquoise waters, superb for swimming and water sports. The area is ideal for kitesurfing, with many operators offering lessons and equipment rentals.

Another highlight is the nearby Sapodilla Bay, a tranquil spot suitable for families and those seeking a quieter beach experience. The shallow waters and stunning sunsets make it a picturesque location for relaxation.

For those interested in local culture, the Turtle Cove Marina offers dining options and the chance to book boat excursions, including snorkeling trips to explore the vibrant coral reefs.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 as applicable.

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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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