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.

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Superhost
The image showcases a modern villa with a private pool in the foreground. Lounge chairs are arranged around the pool, while an outdoor dining area and BBQ are visible under a shaded structure. Large glass doors lead into the bright interior space.
Home in Leeward Settlement
4.94 out of 5 average rating, 18 reviews

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!

Top guest favorite
The villa's modern architecture is highlighted by multiple levels and a rooftop terrace. Lush greenery surrounds the property, with palm trees framing the outdoor seating area. Soft lighting emanates from the interior, creating a welcoming atmosphere as dusk falls.
Villa in Grace Bay
4.96 out of 5 average rating, 47 reviews

Ideal Honeymoon Villa

Luxurious Gated Villa near Grace Bay Beach– Private Pool & Jacuzzi♨️ Escape to this luxury villa, just 2 minutes by car or a 10-min walk from Grace Bay Beach. Relax in your private infinity pool or rooftop jacuzzi with ocean view. The villa features 2 outdoor balconies, a modern kitchen with new appliances, and fast fiber internet. Perfect for 2 guests, this private retreat offers comfort, style, and Super host service. Close to dining, shopping, and activities. Book your dream vacation today🌴

Top guest favorite
The modern villa features a two-story design with a spacious ground-level patio. A private pool reflects the blue sky, surrounded by tropical landscaping. Comfortable outdoor seating is visible on the terrace, offering a quiet space for relaxation.
Villa in The Bight Settlement
4.98 out of 5 average rating, 140 reviews

Grace Bay villa | Pool | 3min walk to Beach & Reef

A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

Top guest favorite
An inviting outdoor area showcases a natural-shaped pool with a heated spa, surrounded by tropical landscaping. The open design features ample seating areas, dining spaces, and large sliding doors that provide a view of the main house and patio.
Villa in Leeward Settlement
4.98 out of 5 average rating, 46 reviews

Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool

*Great for couples and families - Pool - Heated SPA - On the canal - Sups - 5 min to the beach* Piccolo Ponte is an elegant 3 bedroom canal front Caribbean property that sits on an acre of private tropical garden where friends and family gather together to relax and enjoy a laid-back vacation island-style. Located directly on the clear and turquoise canals of the prestigious Leeward Settlement, just a few minutes away from Blue Haven Marina and many beach accesses and watersports operators.

Guest favorite
The expansive resort pool area features multiple sections, including a large main pool with a central gazebo. Vibrant palm trees surround the space, enhancing the tropical atmosphere, while sun loungers and umbrellas are positioned nearby for guest relaxation.
Condo in Providenciales
4.92 out of 5 average rating, 248 reviews

★★★★★ 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

Guest favorite
A well-appointed bedroom features a king size bed with a plush headboard and decorative pillows. Natural light fills the room through sliding glass doors that open to a private outdoor patio. Light-colored walls and glossy tile flooring contribute to a spacious feel.
Apartment in Leeward Settlement
5 out of 5 average rating, 72 reviews

Luxury Paradise 1 Bedroom condo+pool in Grace Bay

The perfect 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 890 sq. ft. luxury one bedroom, freshly renovated condo (in Nov 2022), provides all necessary amenities for your home away from home.

Top guest favorite
A serene outdoor space features a sparkling pool surrounded by lush tropical plants and palm trees. Soft lighting illuminates the area, enhancing the inviting atmosphere. A shaded lounge chair rests nearby, offering a comfortable spot to relax and enjoy the peaceful surroundings.
Apartment in Leeward Settlement
4.95 out of 5 average rating, 241 reviews

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.

Guest favorite
A picturesque entrance leads to a light blue house surrounded by lush tropical vegetation. A smooth driveway, lined with palm trees and native plants, leads up to the home, providing a sense of privacy and tranquility. The clear sky enhances the inviting atmosphere.
Home in Leeward Settlement
4.95 out of 5 average rating, 85 reviews

PERIWINKLE | Charming Island Home|Near to Beach

Nestled in the Gated Upscale community of Leeward at the end of a quiet cul-de-sac is Periwinkle. Experience the true flavor of the Islands with us. Be cradled and relax in the lush native vegetation and enjoy the view from the many windows which decorate the home. Periwinkle is a short stroll away from the magnificent soul quenching Leeward Beach and a five minute drive to the heart of Grace Bay for great shopping and dining experiences. Escape to the quieter side of Paradise.

Superhost
A modern villa is showcased, with its sleek design complemented by lush tropical landscaping. A private plunge pool is visible, surrounded by wooden decking and lounge chairs. A small outdoor dining area and a barbecue grill are also present, creating a relaxing outdoor living space.
Villa in Long Bay Hills
4.92 out of 5 average rating, 129 reviews

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!!

Top guest favorite
The infinity edge pool reflects the vibrant colors of the sunset, overlooking Juba Sound. Lush greenery surrounds the area, enhancing the serene atmosphere. The horizon features a calm waterway and the setting sun, creating a picturesque evening view.
Guesthouse in Long Bay Hills
4.99 out of 5 average rating, 178 reviews

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.

Top guest favorite
An airy studio features a king size bed adorned with a patterned comforter, complemented by hardwood flooring. A compact kitchen area with a small fridge, microwave, and stove is visible in the background. A flat-screen TV is mounted on the wall opposite a small dining table with blue chairs.
Guest suite in Leeward Settlement
4.95 out of 5 average rating, 82 reviews

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.

Top guest favorite
Guesthouse in Leeward Settlement
4.97 out of 5 average rating, 114 reviews

"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

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 ﺩ.ﺇ331 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!