
Holiday rentals with beach access in Leeward
Find and book unique rentals with beach access on Airbnb
Top-rated rentals with beach access in Leeward
Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

"Dive Shop" Guesthouse, Easy Walk to Beach, Kayaks
The " Dive Shop " is located in the quiet residential neighbourhood of Thompson Cove. Our property is canalside with a dock available for guests including SUPs and Kayaks. We are also just a 3 minute walk to the beach. Please note that these water toys are shared with other guests in our other units. Amenities include a kitchenette, outdoor patio, outdoor shower, BBQ, reliable WiFi, Smart TV, Netflix Book now for this private little hideaway + kayak, SUP & snorkeling fun in Provo, TCI!

Grace Bay villa | Pool | 3min walk to Beach & Reef
A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

Luxury Spacious 1 Bed Condo close to the Beach
Just renovated: 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 925 sqft luxury 1 bedroom, freshly renovated (Jan 2023), provides all necessary amenities for your home away from home.

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.

PERIWINKLE | Charming Island Home|Near to Beach
Nestled in the Gated Upscale community of Leeward at the end of a quiet cul-de-sac is Periwinkle. Experience the true flavor of the Islands with us. Be cradled and relax in the lush native vegetation and enjoy the view from the many windows which decorate the home. Periwinkle is a short stroll away from the magnificent soul quenching Leeward Beach and a five minute drive to the heart of Grace Bay for great shopping and dining experiences. Escape to the quieter side of 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.

"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.

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!

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

Sea View Villa — Private Pool & Grace Bay Beach
Wake up to Caribbean sea views, then spend your days by your private pool in this gated two-story villa in Long Bay Hills. Optional services — from a private chef and in-house massages to private yacht experiences — are available to make your stay effortless. Long Bay Beach is 5 minutes away, and Grace Bay is just a 10-minute drive. Ideal for groups and families, with complimentary airport transfers for stays of 5 nights or more.

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.
Popular amenities for rentals with beach access in Leeward
Apartment rentals with beach access

Grace Bay Escape II, walk to beach & restaurants!

1 BR Starfish Stay in the Heart of Grace Bay

OCEAN ORCHID

The Old Beach House

"Soleil" - Updated Luxury Studio-TurtleCove

Oceanview Studio: Steps away to Grace Bay Beach

Serene Caribbean Deluxe Beach Front Studio w/ Pool

Grace Bay Studio
House rentals with beach access

Sea Shell Villa 2.

Sea Chelles Villa TCI

Beach Bungalow Steps from Ocean!

Waterfront Turtle Tail Villa | Pool & Kayaks

Hopewell Villa East/Pool & walk to Gracebay Beach

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views

SunSeaSand 3Bdrm Oceanview Home -Long Bay Hills

Guest House 2B&2B near Grace Bay Beach & Long Bay
Apartment rentals with beach access

Allies Rest - Seaflowers townhome

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝

Grace Bay Luxury Gated 1400 sq ft 2 Bedroom Condo

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞

Shore to Please - Large Studio Condo with Patio

Paradise Stay Studio-Beaches-Nature-Relax-Central

Sea Dreams - Jr 1 bdrm with Panoramic Ocean views!

Inn by the Beach, Grace Bay
Quick stats about holiday rentals with beach access in Leeward

Total holiday rentals
Explore 140 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at $179 SGD per night before taxes and fees

Verified guest reviews
Over 3,500 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
120 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
140 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!
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