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

15 mins walk to restaurants and beach
Welcome to Peaceful Hideawayâyour serene escape designed for rest and renewal. Step into a calming space equipped with air conditioning, Wi-Fi, a cozy bed, and kitchen to make you feel instantly at home. Just moments away, youâll discover the breathtaking turquoise waters of Grace Bay Beach. With restaurants, grocery stores & nightlife all within easy reach, convenience meets tranquility here. Iâm truly delighted to host you and hope your stay is as relaxing and memorable as the island itself.

Endless Honeymoon Villa
Luxurious Gated Villa near Grace Bay Beach â Private Pool & Jacuzziâ¨ď¸ 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, & 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 todayđ´

2 Bedroom Spectacular Views
Kick back and relax in this calm, stylish space. This modern 2-bedroom, 2-bathroom home is nestled along the serene Chalk Sound, offering peaceful seclusion with breathtaking views. FAR from the hustle and bustle of Grace Bay, it caters to guests looking to relax and reset. Enjoy spacious living, stylish finishes, and stunning water views from almost every roomâperfect for those seeking comfort and tranquility. 15 mins to airport 20 mins to Grace Bay 5 mins to Taylor Bay & Sapoddila Bay Beach

Ideal private getaway villa | 250 yds to the beach
The perfect getaway villa, just 250 yards from Grace Bay beach, Gracehaven Getaway is tucked away from passing traffic in a little garden oasis of its own. It is an ideal venue to celebrate anniversaries, birthdays, or honeymoons, or just for a couple seeking a romantic, private setting. Enjoy your own private pool hidden away from main roads and just a 2-minute walk to the Grace Bay beach and Coral Gardens Reef. Easily walk to local restaurants or visit the nearby supermarket for groceries.

Luxury Spacious 1 Bed Condo close to the Beach
Just renovated: 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 925 sqft luxury 1 bedroom, freshly renovated (Jan 2023), provides all necessary amenities for your home away from home.

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.

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.

VILLA INFINI..PLUNGE POOL.đ´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!!

"The Nest Cozy Cottage"
âThe Nestâ 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, itâs perfect for honeymooners or if youâre 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.

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 in your 6-seater Golf Cart or pedal along with the (2) provided pedal bikes. Or relax out by the pool in your private back yard! Book your villa now for an unforgettable experience in paradise!

â â â â â Modern Condo | Amazing Pool | On Site Spa
⢠Located in the exclusive Northern section of Grace Bay ⢠Ground level with direct pool access ⢠Hot tub ⢠Highest Rated Spa on Island onsite ⢠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 ⢠Porta-Crib ⢠WiFi ⢠Beach toys, coolers, DVD collection, & games ⢠Take-one/leave-one liquor cabinet ⢠Buy Travel Insurance

Sandpiper Cottage, minutes from the beach
Kick back and relax in this delightful modern one bedroom cottage in the high end residential gated community of Leeward. Grace Bay Beach, most recently voted âThe best in the worldâ is only a 4 minute walk away! This cozy cottage is perfect for a couple, wanting to relax and have some downtime. Complete with full kitchen, washer/dryer/ BBQ, high speed internet with cable TV and all amenities needed for the perfect getaway.
Popular amenities for Leeward holiday rentals
Other great holiday rentals in Leeward

sugar apple

3 Bed Condo in Leeward! 5 minute walk to the beach

Blue Diamond Villa

Gabriella Luxury Villa - Opening Special Rates

Hopewell Villa East/Pool & walk to Gracebay Beach

Lush 2-Story Villa, Poolside Bliss Near Beach

Canal Access - SUP - Kayak -Swim. 2BR Guesthouse

Cocodemer, a short walk to secluded Pelican Beach.
Frequently Asked Questions
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 $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Leeward Settlement?
Yes! Work meets play with ease at over 120 vacation rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Leeward Settlement apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 apartment rentals with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in Leeward Settlement?
Leeward Settlement has more than 240 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly vacation rentals in Leeward Settlement?
Four-legged friends are welcome in Leeward Settlement. Choose from more than 20 vacation rentals for guests traveling with pets.
Do apartment rentals in Leeward Settlement have air conditioning?
Absolutely! We offer over 40 apartment rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Do villa rentals in Leeward Settlement have wifi?
Absolutely! We offer over 140 villa rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Leeward Settlement have a bbq area?
Absolutely! We offer over 100 house rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Leeward Settlement have a gym?
Absolutely! We offer over 20 house rentals with a gym in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Guesthouse Rentals in Leeward Settlement?
Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Leeward

Total holiday rentals
Explore 330 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at $126Â AUD per night before taxes and fees

Verified guest reviews
Over 7,640 verified reviews to help you choose

Family-friendly holiday rentals
240 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
280 properties feature pools

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
330 of Leeward holiday 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 guestsâaveraging 4.8 out of 5!
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