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

Grace Bay Luxury Gated 1400 sq ft 2 Bedroom Condo
Welcome to your own peaceful, safe and secure luxury condo in the heart of Grace Bay, Providenciales! This contemporary two bedroom suite on the second floor facing NW enjoys gorgeous sunsets. Located in the heart of Grace Bay means you are a very short walk to every amenity you could possibly need on your vacation. Three minutes to a full service grocery store, a multitude of restaurants and shops, pharmacy and casinos, not to mention a five minute walk to the worlds #1 ranked Grace Bay Beach!

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.

“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.

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.

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views
Located in a secluded Beachside property, 500 ft from Long Bay Beach, and 5-minutes drive from Grace Bay Resorts and shops, this spacious, private, 2-Bedroom\2-Bathroom unit can accommodate up to 6 guests, with a king size bed, 2 full size beds, and a queen sofa bed. It occupies 2nd and 3rd floor of our middle building, roughly 15 yards from the pool, no pool view. With beautiful scenic views of the ocean and Long Bay Beach area, from its 3rd floor Livingroom and wrap-around balcony.

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.

Tropical Guest House
This stylish studio sits within a lush tropical garden behind a semi-detached villa. Enjoy cold AC, a well-equipped space, and your own private grill. Grace Bay Beach is just a 15-minute walk—or less than a minute by car—making it easy to enjoy one of the world’s most beautiful shorelines. Coco Bistro, a renowned island restaurant, and Coco Van are close by, with shops and a grocery store also within easy reach. A fantastic location, great value, and close to everything! 🏠🌴

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.

Modern Villa with Private Pool Near Long Bay Beach
- Immerse yourself in tranquil luxury at a gated two-story villa just minutes from Long Bay Beach. - Enjoy bright, spacious interiors, a modern kitchen, and a private, secure setting throughout. - Relax by the private pool, fire up the BBQ, and unwind in peaceful outdoor lounge areas. - Stay connected with fast WiFi and explore Grace Bay’s beaches, shops, and dining nearby. - Reserve your stay for a refined tropical retreat designed for comfort and relaxation.

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.

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
Popular amenities for Leeward rentals with a pool
House rentals with a pool

Sea Shell Villa 2.

Secluded Escape, Ocean Views, Pool and Hot Tub

Calme at Oceanside PrivatePool OceanView SunSet

2 BR Ocean View- Private Pool- Flame Tree Villa #2

Luxury 4 BR Ocean View Villa

Hopewell Villa East/Pool & walk to Gracebay Beach

NEW Water Access! Luxe Villa, Infinity Pool& Views

#10 The Enclave
Apartment rentals with a pool

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝

Amazing Ocean views -Modern Condo -Balcony - Pool

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞

Amazing GraceBay Views, Pools,Location PH Studio

Shore to Please - Large Studio Condo with Patio

Sea You Soon-King studio steps to beach/snorkeling

Sea Dreams - Jr 1 bdrm with Panoramic Ocean views!
Other holiday rentals with a pool

Sea Sun Relax - villa 5 min walk to Grace Bay

Lil Chill -A cozy 1-Bedroom Unit near the beach

Delightful Family Villa with Pool in Leeward

NEW *2 BR Villa Maya- BBQ- Golf- Pool in Grace Bay

Spacious 3 Bedroom Condo on Grace Bay

Luxe 1 BR with View, La Vista Azul

Grace Bay Studio

Large Family Duplex, 5 Mins To Beach, Ocean Views
Quick stats about holiday rentals with a pool in Leeward

Total holiday rentals
Explore 270 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at £104 per night before taxes and fees

Verified guest reviews
Over 5,420 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
270 of Leeward holiday rentals include wifi access

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

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