
Vacation rentals in Leeward
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Top-rated vacation rentals in Leeward
Guests agree: these stays are highly rated for location, cleanliness, and more.

Leeward Landing Villa
Escape to paradise at Beach Landing Villa nestled in the heart of Leeward TCI. This luxurious villa is just minutes away from the pristine award-winning Grace Bay Beach offering a perfect blend of relaxation and adventure. Conveniently cruise your community with the provided pedal bikes. Lounge in the backyard in your private pool or relax indoors with the brilliant large screened TV equipped with all the latest streaming services. Book your villa now for an unforgettable experience in paradise!

Flame Tree Cottage|Ocean view&pool.Walk to beach
Built in 2013. 1 bedroom 2 bathroom cottage with PRIVATE POOL. Sunrise & ocean view from the front deck and only 1/4 mile to the beach. Perfect for 2, but can sleep up to 6. Full kitchen, 2 bathrooms + outdoor shower. No bathtub. Propane Grill. AC in master bedroom. WIFI throughout & local cell provided. This quaint clutter-free 1200 square foot home is surrounded by indigenous foliage, cactus', succulents and native stonework. A rental car is recommended to explore all the island has to offer!

Cozy Studio Near Beaches w/ Gym & Pool Access
Welcome to your idyllic island retreat! Our centrally located unit offers the perfect blend of convenience and tranquility. Nestled at the heart of the island, you're just minutes away from pristine beaches, supermarkets, cultural hotspots and the airport. Unwind in our thoughtfully designed space, boasting island-inspired decor. Whether you seek adventure or relaxation, this rental is your gateway to a memorable island experience. Book now and make our home yours during your island getaway!

★★★★★ Modern Condo | Amazing Pool | On Site Spa
• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub (under consrtuction until mid-Nov) • Highest Rated Spa on Island • Fully equipped kitchen • Private front patio • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝
🏖 NEWLY RENOVATED, SPACIOUS one bedroom condo with an ocean view at La Vista Azul Condo Resort. Located hillside in the exciting area of Turtle Cove, Providenciales, the unit is close to several excellent restaurants, cafes, bars, a casino, and a marina. Most notably, the studio is a 10 minute walks to Smith's Reef in the Princess Alexandra Park National beach. Smith’s Reef is located near Turtle Cove on the north coast of Providenciales, and about 3.5 miles (5.6 km) from Grace Bay 🏝

Luxury 1Bed Large ModernCondo, close to Grace Bay
The perfect large condo, and only 3 minutes from the famous Grace Bay Beach! Located in the exclusive Leeward area, a gated, secure residential area where all the major luxury villas are. The beach is a short stroll away & the main Grace Bay shopping / resort area is 5 minutes by car. The condo boasts a large pool, stunning modern finish and appliances. This 925 sq. ft. luxury one bedroom, freshly renovated in Feb 2023, provides all necessary amenities for your home away from home.

Oasis | 1 BR Condo | Vista Azul | Pool & Wifi
Peaceful Palm Trees with a peek of Ocean View! 10 min walk to the beach or 10 min drive to Grace Bay. Located on 2nd floor of the higher buildings, this condo is a spacious studio with Queen Bed, full kitchen, living room, bathroom, washer and dryer, Wifi and free parking. The large balcony has a pretty view over soothing palm trees dancing in the breeze, with a peek at the ocean in the distance. A great place for morning coffee or relax after long day at the beach or by the pool.

Romantic Apartment few steps from beach
Wake up to the soothing melody of a mockingbird in the garden, as gentle sunlight filters through the lush greenery. Sip your morning coffee on the balcony, overlooking the tropical garden and sparkling crystal-clear pool, where the peaceful ambiance sets the tone for a romantic escape. Afterward, take a leisurely stroll through the vibrant garden or wander just a few minutes to the nearest beach with turquoise waters and soft white sands, perfect for a tranquil start to your day.

VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY
Take it easy at this dreamy, unique and tranquil getaway. Villa Infini brings privacy and relaxation all in one. Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway. Bali like plunge pool that can create amazing insta-worthy moments. Located in Long Bay! A 5 minute walk to Long Bay Beach, a 5 minute drive to the nearest grocery store and a 5 minute drive to Grace Bay Beach. Everything is 5 minutes away!!

Juba Sunset
Waterfront Private apartment that is fully furnished. Private deck. fantastic views overlooking Juba Sound. within 7mins to Grace Bay, world famous Grace Bay Beach and shops. Very quiet and safe area. Infinity edge pool included. Glorious sunsets. BBQ on the waterfront. Only a couple of mins away from popular Kite Surfing spot. There is also a Kayak available for guests use down on the waterfront. This is the only rental unit on property, you will be the only guests.

Erisa Studio - cozy studio close to GraceBay Beach
Erisa Studio is a bright, comfortable studio with a king bed, high ceilings, AC, ceiling fan, 32" TV, and a large 3-door patio slider. It includes a small kitchen and a spacious bathroom. Just a 15-min walk or 3-min drive to Grace Bay Beach, shops, and restaurants. Next to Provo Golf Club and a short drive to Long Bay Beach. Beach towels, beach chairs, sunbrella and cooler provided. Bike rental available for $10/day, but we highly recommend a car. Private entrance.

"The Nest Cozy Cottage"
“The Nest” Spacious and modern 1 bedroom cottage sits amongst a well-manicured garden with majestic swaying palms. Less than 150 steps away from the famous Grace Bay Beach. This cozy sanctuary is quiet and bears the true beauty of itself, it’s perfect for honeymooners or if you’re just seeking for some quiet and down time. Complete with high-speed internet, cable TV and all amenities one need for the perfect vacation, The Nest is where you want to be.
Popular amenities for Leeward vacation rentals
Other great vacation rentals in Leeward

Sea Sun Relax - villa 5 min walk to Grace Bay

NEW *2 BR Villa Maya- BBQ- Golf- Pool in Grace Bay

Lovely Studio#D in Venetian Road

Dreamy Suite Getaway with Pool and Beach Access

NEW Water Access! Luxe Villa, Infinity Pool& Views

2 Bedroom Stunning Views

55 Oasis Cottage Nearby World's #1 Grace Bay Beach

Welcome to Artemis Retreat!
Frequently Asked Questions
Are there Leeward Settlement house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 80 house rentals with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Leeward Settlement?
Experience the best of Leeward Settlement with our condo rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there apartment rentals with a dedicated workspace in Leeward Settlement?
Yes! Work meets play with ease at over 10 apartment rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do villa rentals in Leeward Settlement have a bbq area?
Absolutely! We offer over 60 villa rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly villa rentals in Leeward Settlement?
Leeward Settlement has more than 140 family-friendly villa rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do condo rentals in Leeward Settlement have wifi?
Absolutely! We offer over 10 condo rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Do villa rentals in Leeward Settlement have a gym?
Absolutely! We offer over 30 villa rentals with a gym in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Leeward Settlement have air conditioning?
Absolutely! We offer over 10 condo rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly house rentals in Leeward Settlement?
Four-legged friends are welcome in Leeward Settlement. Choose from more than 10 house rentals for guests traveling with pets.
What are the most popular amenities for Villa Rentals in Leeward Settlement?
Enhance your stay in our Villa Rentals with the most popular amenities: over 140 homes with air conditioning, over 140 homes with wifi, over 60 homes with a bbq area, over 30 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Leeward

Total vacation rentals
Explore 310 vacation rentals in Leeward

Nightly prices starting at
Leeward vacation rentals start at R1,544 ZAR per night before taxes and fees

Verified guest reviews
Over 6,530 verified reviews to help you choose

Family-friendly vacation rentals
230 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
260 properties feature pools

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wi-Fi availability
310 of Leeward vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Leeward rentals

4.8 Average rating
Leeward stays are highly rated by guests—averaging 4.8 out of 5!
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