Holiday houses in Leeward

Endless 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, & 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🌴

CoCo Lingo Guest Cottage

The CoCo Lingo Guest Cottage is ideal for couples or small families. It sleeps up to 4 guests and offers a relaxing and peaceful retreat in the most beautiful place on earth. The cottage sits behind a private residence and shares a pool but has a very private feel. The area is quiet and conveniently located near to the island's best amenities. The world-famous Grace Bay beach is just a short 10 minute walk away and the famous shops and restaurants of Grace Bay are just a 4-5 minute drive away.

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.

Large Luxury Modern Condo + pool + close to 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.🌴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!!

Leeward Condo - Sleeps 4

Welcome to Palm Grove Villa! This beautifully decorated 1-bedroom, 1.5-bath condo in Leeward sleeps 4 and is a short stroll from Leeward and Grace Bay Beaches. Enjoy modern décor, a cozy king bedroom, and a queen pullout sofa in the open living area. The fully equipped kitchen and private patio/balcony make it ideal for relaxing. Amenities include a sparkling pool and grilling area. With nearby beaches, restaurants, and shops, this condo is the perfect island escape!

"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.

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!

Private Luxury Villa with Pool 5 Min to GB Beach

Villa Cocuyo offers complete privacy, comfort, and consistent 5⭐️ hospitality. Couples love the safe and secure , peaceful setting, private solar heated pool, modern interior, and garden oasis. Enjoy fast WIFI, premium amenities, and a spotless space designed for true relaxation. Our 5-star reviews reflect our dedication to exceptional hosting, attention to detail, and a worry-free, private island getaway close to everything including beach

★★★★★ 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