Holiday rentals in Leeward Settlement

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Leeward Settlement

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Apartment in Leeward Settlement

4.93 out of 5 average rating, 14 reviews

Buttonwood 1 BR Updated Condo - BEACH -POOL - WIFI

*New listing* Welcome to Buttonwood - A Newly renovated condo, with pool and grill, only 8 min walk from Leeward Beach. Nestled in the peaceful, sought-after gated community of Leeward, Buttonwood Suite is a charming 1BR Condo perfect for singles or couples seeking a tranquil escape or an island adventure! With a new decor and thoughtful design, this boutique condo offers a cozy and comfortable stay with all the amenities you need for a delightful vacation by the beach. Highlights below:

Guest favourite

Flat in Leeward Settlement

4.98 out of 5 average rating, 60 reviews

Large Luxury Modern condo, close to beach, w/ pool

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 890 sq. ft. luxury one bedroom, newly renovated condo (in May 2023), provides all necessary amenities for your home away from home.

Guest favourite

Flat in Leeward Settlement

4.95 out of 5 average rating, 234 reviews

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.

Guest favourite

Home in Grace Bay

4.94 out of 5 average rating, 162 reviews

Follow Your Dreams Villa!

Follow Your Dreams – Private Villa Escape to this stylish villa designed for one couple. 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. This totally private villa is perfect for two guests seeking a serene and unforgettable tropical getaway. Book now to make your dream vacation a reality!

Superhost

Villa in Long Bay Hills

4.92 out of 5 average rating, 118 reviews

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!!

Guest favourite

Apartment in Providenciales

4.92 out of 5 average rating, 238 reviews

★★★★★ 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 • 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 • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Top guest favourite

Guest house in Leeward Settlement

4.97 out of 5 average rating, 114 reviews

"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.

Top guest favourite

Flat in Long Bay Hills

5 out of 5 average rating, 63 reviews

Jade@Long Bay Retreat-Luxury Stay near Grace Bay

Nestled in Long Bay, Turks & Caicos, this luxurious apartment is minutes from Long Bay and Grace Bay Beaches. It boasts an expansive Infiniti Edge Pool, offering a sublime relaxation space. Inside, Balinese furniture and a luxury bathroom with high-end finishes create an elegant retreat. The serene, upscale location provides privacy while keeping island attractions within reach. Perfect for those seeking tranquility and luxury in a tropical paradise.

Guest favourite

Cottage in Leeward Settlement

4.93 out of 5 average rating, 112 reviews

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.

Superhost

Guest house in Leeward Settlement

4.9 out of 5 average rating, 146 reviews

Pelican Cottage -Mins. to the Beach!! Car 4 Rent!

Nestled in the tranquil gated community of Leeward, on the heels of the Grace Bay area and the Grace Bay Beach, most recently ranked as the “The Best Beach in the World!”. The upscale Leeward community is within a 5-8 minute drive to the Grace Bay shopping and restaurant district, with about two dozen businesses, including a large grocery store, banks, liquor store, café, phone company, and bookstore.

Superhost

Flat in Grace Bay

4.84 out of 5 average rating, 141 reviews

Crescent 6 (beach 2 min walk)

My place is just a two minute walk to one of the most beautiful beaches in the world, Grace Bay beach. Absolutely great spot to walk to many restaurants, bars, casino, grocery store and shopping centre at Salt Mills. You’ll love my place because of the neighbourhoods and quiet area. Place is good for couples, solo adventurers, families and business travellers.

Superhost

Loft in Providenciales and West Caicos

4.89 out of 5 average rating, 71 reviews

Cozy Loft Condo Great Location w/Pool

Located in the perfect spot, Just minutes away from Grace Bay Beach, Restaurants, Supermarkets and attractions, this loft style apartment is the perfect couple's getaway to come enjoy and relax in the beautiful Turks and Caicos Islands. Apartment was newly renovated in September 2022.