Vacation rentals in Leeward

Large Luxury Modern Condo + pool + close to beach

*Pool closed 09/11 to 10/03 2026 for maintenance* This 925 sqft luxury 1 bedroom, recently renovated condo provides all necessary amenities. 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.

Location · Value · Decor

Villa Kendara~50% 9/26-10/3 ~Beach~Privt~Gate~View

Private~Gated~Beachfront~Convenient~Panoramic Water Views~Beautiful by Nature~A+ Sunrises/Sunsets~Pool~Snorkeling~5 min to Grace Bay Hub & Beaches, Dining, Stores, Marina~Exclusive "Johnson Guide to Provo"~Fully Equipped Gourmet Kitchen~Lots of Amenities/Supplies~AC, Fans, Wi-Fi, TV, DVD, Phone, Safe~LOFT FOR KIDS~CoralStone Deck (3 Seating Areas, Pergola for Shade)~BBQ~ Snorkel Gear~Portable Beach Chairs & Umbrella~Island Partner Discount for Car Rental, Water Sports/Eco-Tours, Cruise, Massages

Family · Value · Check-in

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 *

Location · Family · Comfort

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🌴

Value · Location · Parking

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 room—perfect for those seeking comfort and tranquility. 15 mins to airport 20 mins to Grace Bay 5 mins to Taylor Bay & Sapoddila Bay Beach

Family · Location · Backyard

Apt with private pool and direct beach access

Discover an intimate oasis perched just steps from the turquoise waters of Long Bay. Our newly added Oceanfront One-Bedroom Apartment at Swaying Palms offers the perfect blend of privacy, luxury, and resort-style amenities—ideal for couples, solo travelers, or anyone craving a secluded tropical retreat. This space features a full kitchen, private pool & spacious outdoor deck overlooking the turquoise sea. Your very own private umbrella/lounge chairs will be placed daily at the water's edge.

Location · Check-in · Bathroom

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.

Value · Location · Shared spaces

Gated Condo in Grace Bay/ Short Walk to Everything

This studio in Grace Bay offers comfort and convenience. It's a few minutes walk to the beach, grocery stores, restaurants, activities, and a medical center. The Caicos Key condo is new and includes a 55-inch smart TV with Fire Stick, fast Wi-Fi, a dishwasher, and a washer/dryer combo. For your security, the property has a smart lock and is gated. Guests can also use the swimming pool and BBQ area. We aim to make your stay comfortable and can provide anything you need on demand.

Family · Value · Air conditioning

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!!

Location · Family · Outdoor spaces

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.

Family · Location · Laundry

1BR Island Retreat | 100 Steps to Pelican Beach

Welcome to The Nest, a private one-bedroom cottage less than 100 steps from beautiful Pelican Beach. Surrounded by a peaceful tropical garden, it’s a quiet place to slow down and enjoy island life. Spend your days swimming in turquoise water, then head to your private rooftop deck for a BBQ, evening drinks and peaceful nights under the island sky. High-speed Wi-Fi makes it easy to work remotely when needed—though the beach may be a little distracting.

Value · Location · Comfort

Channel Villa - Elegant Canal-Front Retreat

Welcome to Channel Villa, a beautifully refurbished four-bedroom canal-front retreat in the sought-after Leeward area, just moments from Blue Haven Marina & Resort. Designed for relaxed luxury and effortless island living, with a large covered patio, private swimming pool, and tropical landscaping that enhances privacy and tranquility. Channel Villa offers a serene waterfront atmosphere while remaining close to world-class beaches, dining and boating.

Family · Location · Quiet