
Waterfront holiday rentals in Leeward
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Leeward
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

Pelican View #3 unrivalled beach views
Pelican View apartments offers unrivalled beach access and a truly unique and tranquil way to experience Providenciales. Located in Blue Hills you’ll quickly be lulled into the local rhythm of island life as you sit on your 2nd floor terrace enjoying the spectacular views and listening to the waves crashing on shore. This 2-bed, 1-ba apartment is comfortably appointed with true up-cycled charm. Peppered throughout are some treasured vintage pieces to make it feel like your home away from home.

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.

“Sail Loft Port”, Duplex with a Pool, Beach Access
Sail Loft Port is the left side of our purpose-built guest duplex. Our Sail Loft duplex features two separate but identical efficiency suites, each one equipped with a King Sized bed, bath and kitchenette. The pool is shared with guests who may be staying in the other side. Wander down to the dock and use our SUPs and kayaks in the canal where you are guaranteed to see turtles. Fast WiFi lets you work from home if you must. Smart TVs with Netflix help you wind down after a day of fun.

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.

Best deal on island! On the water w/pool!
♥♥ The studio is a secluded get-away place apart from the tourist areas. It overlooks the lake of Juba Sound National Park. The studio is only a 10-minute drive to the world-famous Grace Bay Beach and Longbay Beach (kiteboarding beach)! Restaurants and nightlife are also close by. The studio is in a secure, quiet location where you can relax and enjoy your vacation. This studio is ideal for singles, couples, and kiteboarders. You will need to rent a car for better convenience and freedom!

Beautiful Sunset Villa with Infiniti Pool
Beautiful Sunset Villa is nestled in the heart of Chalk Sound, Providenciales where guests are guaranteed a home away from home experience. It enjoys unique trade winds in a private and safe community close to restaurants and the beach. Beautiful Sunset Villa provides views of the famous Chalk Sound turquoise waters, featuring a private Infiniti pool, extensive pool deck, a dedicate kitchen and dining area with full air conditioning. View the video below! https://youtu.be/13YyhYECZQA

The Yacht Club-Relaxed Vibe-1 BR-Pool-Beach
This spacious, comfortable, well-designed one-bedroom poolside apartment is in a private gated community—The Yacht Club. Couples and small families will appreciate the gorgeous grounds, stunning multi-level saltwater pool, relaxed vibe, and local restaurants. A five-minute walk will take you to one of the best beaches on the island, which features a snorkeling reef. The property is next to one of the largest marinas on the island with boat cruises, fishing & a variety of water sports.

Villa DelEvan 4B / 1-bedroom 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.

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.

Luxe Home / 2 bedroom (5 minute walk to beach)
Large 1200 square feet / top floor oversized END UNIT condo sophisticated elegance in Grace Bay - 2 large bedrooms/ queen size beds, 2 full bathrooms. Thoughtful design - makes all the difference. Short walk to beach. Pool and parking onsite. 4 Beach chairs and beach umbrella included along with beach towels. Fitness room in development with bike machine, elliptical and treadmill - no free weights. 2 yoga mats in our condo. We do not provide bath soap and shampoo.

Romantic Escape with Stunning Pools & Sunset Views
Welcome to our private island paradise. This is a light, charming, one bedroom unit in a quiet setting with a view over the terraced pools & into Turtle Cove & the marina. Its 1091 square feet bring a spacious open plan living/dining/kitchen/balcony. The patio door opening spans 16 ft. The large bedroom has a king bed, walk-in closet, another TV & beautiful ensuite bath w/ large shower. Please note, elevator is currently under repair.

Spacious contemporary private villa
This beautiful and well appointed property was constructed in 2011. It has contemporary appliances, over 1400sq/ft of internal space with high '"loft" ceilings along with two large external deck areas and a private garden / yard. Located in walking distance to the main supermarket and gracebay west beaches (Bight Park), it makes the perfect island getaway.
Popular amenities for waterfront rentals in Leeward
Waterfront apartment rentals

Yacht Club Marina Condo

Oceanview Studio: Steps away to Grace Bay Beach

1-Bed Suite – Kitchen, Pool & Steps to Grace Bay

High Rock Hideaway Estates #2

Exquisite Yacht Club Townhome

Spectacular view 2 bedroom condo-The Grandview 205

Seache’ Escape

NEWLY remodeled Dec 2025 - near Beach, Golf, Food
Waterfront house rentals

Brighter Days Villa

Tropical Paradise: Pool, Beaches & 360° Views

Secluded Escape, Ocean Views, Pool and Hot Tub

Coastal Vibes Villa Near Sapodilla Beach

NEW Water Access! Luxe Villa, Infinity Pool& Views

Blue Tang Villa (2 Bedroom)

Enjoy Secluded Cottage w/ Pool Jacuzzi Beach Front

Vision Kite- Longbay beach house
Waterfront apartment rentals

Oceanview Lux Penthouse - 2 Bedroom @ Yacht Club

Located in heart of Grace Bay Villa Renaissance

Ocean and Pool Front 2 king beds 2 Bath Condo

Ocean view paradise

Newly Renovated 2 Bedroom/2 Bath Beach Front Condo

2 Bdrm Stunning Marina View at The Yacht Club C5

Couple’s retreat- ocean view, pool and hot tub!

BEST BEACH, BEST LOCATION IN GRACE BAY - PH 305
Quick stats about waterfront rentals in Leeward

Total holiday rentals
Explore 70 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at $269 SGD per night before taxes and fees

Verified guest reviews
Over 990 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
60 of Leeward holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Leeward rentals

4.9 Average rating
Leeward stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Santo Domingo Holiday rentals
- Las Terrenas Holiday rentals
- Santiago De Los Caballeros Holiday rentals
- Santo Domingo Este Holiday rentals
- Puerto Plata Holiday rentals
- Sosúa Holiday rentals
- Cabarete Holiday rentals
- Juan Dolio Holiday rentals
- Jarabacoa Holiday rentals
- Boca Chica Holiday rentals
- Bonao Holiday rentals
- Río San Juan Holiday rentals
- Family-friendly rentals Leeward
- Flat rentals Leeward
- Rentals with a washing machine and dryer Leeward
- Rentals with a kayak Leeward
- Rentals with a hot tub Leeward
- Luxury rentals Leeward
- Villa rentals Leeward
- Rentals with pools Leeward
- House rentals Leeward
- Rentals with a firepit Leeward
- Rentals with outdoor seating Leeward
- Rentals with beach access Leeward
- Rentals with a patio Leeward
- Beachfront rentals Leeward
- Pet-friendly rentals Leeward
- Fitness-friendly rentals Leeward
- Waterfront rentals Providenciales
- Waterfront rentals Caicos Islands
- Waterfront rentals Turks and Caicos Islands




