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Holiday rentals in Leeward

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Top-rated holiday rentals in Leeward

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

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Top guest favourite
Villa in The Bight Settlement
4.98 out of 5 average rating, 131 reviews

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.

Superhost
An outdoor deck features a private pool surrounded by tropical foliage. Lounge chairs are positioned near a table shaded by a large umbrella. A view of beachside structures and palm trees can be seen in the background under a clear blue sky.
Flat in Long Bay Hills
5 out of 5 average rating, 3 reviews

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.

Guest favourite
An outdoor pool area is illuminated by natural sunlight, featuring lounge chairs with blue cushions arranged around the pool. Palm trees provide shade, while ocean views extend in the background, showcasing the vibrant blue water and greenery of the hillside.
Apartment in Turtle Cove
4.95 out of 5 average rating, 197 reviews

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝

🏖 NEWLY RENOVATED, SPACIOUS one bedroom condo with an ocean view at La Vista Azul Condo Resort. Located hillside in the exciting area of Turtle Cove, Providenciales, the unit is close to several excellent restaurants, cafes, bars, a casino, and a marina. Most notably, the studio is a 10 minute walks to Smith's Reef in the Princess Alexandra Park National beach. Smith’s Reef is located near Turtle Cove on the north coast of Providenciales, and about 3.5 miles (5.6 km) from Grace Bay 🏝

Top guest favourite
A rooftop terrace features multiple sun loungers and circular seating areas, complemented by blue umbrellas providing shade. The water of the pool reflects the sky above, creating a calming atmosphere. Lush greenery and distant rooftops are visible in the background, adding to the serene setting.
Apartment in The Bight Settlement
4.95 out of 5 average rating, 117 reviews

Oasis | 1 BR Condo | Blue View | Pool & Wifi

Peaceful Palm Trees with a peek of Ocean View! 10 min walk to the beach or 10 min drive to Grace Bay. Located on 2nd floor of the higher buildings, this condo is a spacious studio with Queen Bed, full kitchen, living room, bathroom, washer and dryer, Wifi and free parking. The large balcony has a pretty view over soothing palm trees dancing in the breeze, with a peek at the ocean in the distance. A great place for morning coffee or relax after long day at the beach or by the pool.

Superhost
Apartment in Grace Bay
4.81 out of 5 average rating, 134 reviews

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.

Top guest favourite
An outdoor area features a rectangular swimming pool with clear water, surrounded by a deck area with lounge chairs. A striped umbrella provides shade, while views of the ocean and sandy beach create a serene backdrop. Lush greenery frames the space, enhancing the coastal ambiance.
Villa in Providenciales
4.99 out of 5 average rating, 120 reviews

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.

Top guest favourite
An infinity edge pool is visible on a spacious deck, overlooking stunning views of Juba Sound. The sunset casts warm hues across the sky, reflecting on the calm waters below. Lush greenery surrounds the area, enhancing the natural beauty of the landscape.
Guest house in Long Bay Hills
4.99 out of 5 average rating, 184 reviews

Juba Sunset

Waterfront Private apartment that is fully furnished. Private deck. fantastic views overlooking Juba Sound. within 7mins to Grace Bay, world famous Grace Bay Beach and shops. Very quiet and safe area. Infinity edge pool included. Glorious sunsets. BBQ on the waterfront. Only a couple of mins away from popular Kite Surfing spot. There is also a Kayak available for guests use down on the waterfront. This is the only rental unit on property, you will be the only guests.

Top guest favourite
Guest house in Leeward Settlement
4.97 out of 5 average rating, 117 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.

Guest favourite
An aerial view of a modern villa surrounded by lush greenery. The exterior features large glass windows and a private pool, accompanied by sleek lounge chairs on the deck. The open layout invites natural light, showcasing the villa's seamless connection to its outdoor surroundings.
Home in Providenciales
4.96 out of 5 average rating, 359 reviews

Modern Villa with Pool Minutes to Grace Bay 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

Superhost
Cottage in Leeward Settlement
4.91 out of 5 average rating, 128 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
A modern living area is shown, featuring a gray couch with green decorative pillows. A light-colored coffee table is positioned in front of the couch. Two framed pieces of wall art enhance the space. A chair is also visible, contributing to the open layout.
Flat in Grace Bay
4.8 out of 5 average rating, 182 reviews

Crescent 4 - Grace Bay 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 studio because of the neighbourhoods and quiet area. Studio apartment has open concept, only door for the bathroom. Place is good for couples, solo adventurers and business travellers.

Superhost
An inviting interior space combines a comfortable green sofa with a vibrant orange wall. A queen bed is visible in the background, surrounded by natural light from glass doors. Decorative pillows add color, while a ceiling fan and art piece enhance the cozy atmosphere.
Guest house in Leeward Settlement
4.91 out of 5 average rating, 150 reviews

Pelican Cottage -Mins. to the Beach!

Nestled in the tranquil, gated community of Leeward, just minutes from the Grace Bay area and Grace Bay Beach, frequently ranked “The Best Beach in the World”. This exclusive enclave offers both privacy and convenience. Leeward is only a 5–8 minute drive from the Grace Bay shopping and restaurant district, which includes a large grocery store and many other amenities.

Popular amenities for Leeward holiday rentals

Frequently Asked Questions

  • How much does it cost to stay in condo rentals in Leeward Settlement?

    Experience the best of Leeward Settlement with our condo rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Leeward Settlement apartment rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 apartment rentals with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there house rentals with a dedicated workspace in Leeward Settlement?

    Yes! Work meets play with ease at over 20 house rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do villa rentals in Leeward Settlement have a bbq area?

    Absolutely! We offer over 60 villa rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Leeward Settlement?

    Leeward Settlement has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Leeward Settlement have wifi?

    Absolutely! We offer over 80 house rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Leeward Settlement have a gym?

    Absolutely! We offer over 20 villa rentals with a gym in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Leeward Settlement have air conditioning?

    Absolutely! We offer over 130 villa rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Leeward Settlement?

    Four-legged friends are welcome in Leeward Settlement. Choose from more than 10 house rentals for guests traveling with pets.

  • What are the most popular amenities for House Rentals in Leeward Settlement?

    Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with wifi, over 80 homes with air conditioning, over 100 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Leeward

  • Total holiday rentals

    Explore 320 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at $115 SGD per night before taxes and fees

  • Verified guest reviews

    Over 7,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    230 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    270 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wifi availability

    310 of Leeward holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Leeward rentals

  • 4.8 Average rating

    Leeward stays are highly rated by guests – averaging 4.8 out of 5!