
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.

VillaKendara~SALE 3/28-4/4~OnSea~Private~Gate~View
Private~Gated~Beachfront~Convenient~Panoramic Water Views~Beautiful by Nature~A+ Sunrises/Sunsets~Swim in Pool or Sea, Snorkel~5 min to Grace Bay Hub & Beaches, Restaurants, Stores, Marina~Exclusive "Johnson Guide to Provo"~Fully Equipped with GMT Kitchen, Amenities, Supplies, AC, Fans, Wi-Fi, TV, DVD, Phone, Safe & LOFT FOR KIDS~CoralStone Deck, Pergola for Shade, BBQ~Snorkel Gear, Portable Beach Chairs & Umbrella~Island Partner Discount for Car Rental, Water Sports/Eco-Tours, Cruise, Massages

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.

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.

Pelican View #4 amazing beach views
Pelican View apartments offers unrivalled beach access and a truly unique and tranquil way to experience Providenciales. Located in the neighbourhood of Blue Hills you’ll quickly be lulled into the local rhythm of island life. From Blue Hills it’s an easy 15 minute drive east to the heart of the tourist mecca of Grace Bay; if you travel west you’ll find the best national parks and nature reserves that Turks & Caicos has to offer, often overlooked gems in this island paradise.

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.

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.

Beach Bungalow Steps from Ocean!
THIS IS BUNGALOW #2 PLEASE SEE NUMBERED AERIAL PHOTO FOR REFERENCE! Simply put PARADISE! Swaying Palms is a set of (9) luxurious romantic single bedroom Beachfront Bungalows located on beautiful Long Bay Beach. Our Bungalows share a generous 554 feet of beachfront making it the lowest density resort on the island. While still being in a quiet and romantic spot, only a 5-minute drive to Grace Bay and all the restaurants, grocery stores, shops, and Casino.

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.

"Captain's Quarters" Suite with a View!, King Bed
Captain’s Quarters is a newly renovated guest suite attached to our home, overlooking the Thompson Cove canal and within a 3 minute walk to the beach. You will enjoy your own private entrance, private terrace and private deck overlooking the canal. You are welcome to use our SUPs and kayaks, which are located on our guest dock. Book today for an ideal tropical escape to a tranquil area in Provo, TCI!

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

Sunny Daze - Condo By the Water

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

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

Metopium - 2/1 Secluded Getaway

3 Bed Beach Oasis on Flamingo Lake w/Private Pool

Coastal Vibes Villa Near Sapodilla Beach

NEW Water Access! Luxe Villa, Infinity Pool& Views

Blue Tang Villa (2 Bedroom)
Waterfront apartment rentals

Oceanview Lux Penthouse - 2 Bedroom @ Yacht Club

Located in heart of Grace Bay Villa Renaissance

Barefoot Luxury/Beachfront Condo

Ocean and Pool Front 2 king beds 2 Bath Condo

Ocean view paradise

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

Luxury Condo Somerset on Grace Bay!

Luxury Large 2 Bed 2 Bath at the Yacht Club
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 $268 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
- House rentals Leeward
- Rentals with a hot tub Leeward
- Rentals with a firepit Leeward
- Rentals with outdoor seating Leeward
- Rentals with beach access Leeward
- Rentals with a washing machine and dryer Leeward
- Pet-friendly rentals Leeward
- Fitness-friendly rentals Leeward
- Rentals with a patio Leeward
- Rentals with a kayak Leeward
- Rentals with pools Leeward
- Luxury rentals Leeward
- Beachfront rentals Leeward
- Villa rentals Leeward
- Waterfront rentals Providenciales
- Waterfront rentals Caicos Islands
- Waterfront rentals Turks and Caicos Islands




