Holiday rentals with a pool 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 *

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🌴

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.

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.

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.

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.

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.

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.

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.

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!