Family-friendly holiday rentals in Leeward

Follow Your Dreams Villa!

Follow Your Dreams – Private Villa Escape to this stylish villa designed for one or two couples. Enjoy a private pool surrounded by palms, a 65" TV, and a fully equipped kitchen with dishwasher and laundry. Located behind Coco Bistro/Coco Van and just 2 minutes by car to Grace Bay Beach, it offers a mix of privacy and convenience. Private villa perfect for a tropical getaway🌴 *As per March 6th, neighbours started construction, possible construction noise during the day mostly week days only *

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.

OCEAN ORCHID

This fabulous penthouse apartment is located within the exclusive Turtle Tail Marina and next to the late singer Prince's house. This newly built 3 large en suite bedroom apartment offers beautiful ocean and marina views from every room and balconies. The outdoor BBQ area has views of the ocean and Flamingo Lake where you can socialize, chill and spot the odd pink flamingo. There is a large pool with loungers and a hammock for relaxing, kayaks are available to explore the small cays and beach.

Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks

Classic Caribbean 3 Bedroom canal front villa in Leeward. Cotton House has been designed in the timeless, traditional Caribbean aesthetic and is solar powered. Located in the gated Leeward community (25 min from PLS airport - 8 min to Grace Bay), this canal front home exudes an easy living elegance. Each bedroom opens to a central courtyard, the serene heart of the home featuring fountain, ferns, climbing vines, and tropical trees. *Ask us about our 4 and 5 Bedroom options for this villa.

Tropical Carabas Villa!

Peaceful Villa Near Grace Bay Beach 🌴 Escape to this serene villa just minutes from Grace Bay Beach and steps from Coco Bistro. Enjoy a private pool, air-conditioned bedrooms, a fully equipped kitchen, and an outdoor grill for relaxing meals. Lounge with beach towels and chairs, stay connected with strong Wi-Fi, and soak in the lush tropical surroundings. The perfect mix of comfort, convenience, and tranquility for your getaway! 🌴 12% government tax is included in the listed price.

Villa DelEvan 4A / 1-bedrm Beach front villa

Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.

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!!

Luxury Spacious 1 Bed Condo close to the Beach

This 925 sqft luxury 1 bedroom, recently renovated condo provides all necessary amenities for your home away from home. 3 minutes drive 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. We recommend renting a car.

"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!

★★★★★ 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 “The best in the world” 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.