
Vacation rentals with a pool in Cooper Jack Bay Settlement
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cooper Jack Bay Settlement
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

The Hideaway / Modern Zen Studio with Private Pool
A Modern & Stylish Zen Studio with private Pool in the gated, secure and idyllic neighbourhood of Harbour Gates, Sapodilla Bay. Elevated with partial views of the brilliant turquoise waters of Chalk Sound and beyond. Secluded amongst the tropical flora is the pathway that leads to Direct Beach Access on the beautiful and sheltered Sapodilla Bay Beach (300m). High end finishes and beach charm abound in this spacious & well equipped studio. Welcome to the Hideaway. You have found your Vacation☀️

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.

Blue-tiful Studio near Beaches w/ Gym & Pool
Welcome to your idyllic island retreat! Our centrally located unit offers the perfect blend of convenience and tranquility. Nestled at the heart of the island, you're just minutes away from pristine beaches, supermarkets, cultural hotspots and the airport. Unwind in our thoughtfully designed space, boasting island-inspired decor. Whether you seek adventure or relaxation, this rental is your gateway to a memorable island experience. Book now and make our home yours during your island getaway!

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.

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

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.

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.

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.

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

Amazing GraceBay Views, Pools,Location PH Studio
Perched above this Mediterranean hillside Villa resort with Panoramic views of Grace Bay, get inspired while taking in the views and relaxing at this unique and tranquil getaway. The studio is clean, comfortable and quiet; and situated overlooking parts of the resort hot tub, two almost Olympic size pools and the two 6,000 sq ft Terrazza decks!
Popular amenities for Cooper Jack Bay Settlement rentals with a pool
House rentals with a pool

Tropical Carabas Villa!

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

Ocean Seacret Views/Gated & Pool

The Sapphire Villa. Tropical Oasis. Make memories

NEW Water Access! Luxe Villa, Infinity Pool& Views

Sea More Getaway

Harbour House - 2 Bed Waterfront; 7 Min to Beach

Charming Gecko House with porch & pool - Grace Bay
Condo rentals with a pool

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

Amazing Ocean views -Modern Condo -Balcony - Pool

Spacious 3 Bedroom Condo on Grace Bay

★★★★★ Modern Condo | Amazing Pool | On Site Spa

Shore to Please - Large Studio Condo with Patio

Inn by the Beach, Grace Bay

Sea Dreams - Jr 1 bdrm with Panoramic Ocean views!

Grace Bay Luxury Studio walk to beach and town
Other vacation rentals with a pool

1 BR Starfish Stay in the Heart of Grace Bay

Sapodilla Bay - Walk to the Beach!

Private Pool Villa w/ Firepit & Outdoor Dining

"Soleil" - Updated Luxury Studio-TurtleCove

Frankie's Suite @ Yacht Club

Grace Bay Studio

Large Family Duplex, 5 Mins To Beach, Ocean Views

*Blue Oasis TCI* Sun, Sand & Poolside Perfection
Quick stats about vacation rentals with a pool in Cooper Jack Bay Settlement

Total vacation rentals
Explore 120 vacation rentals in Cooper Jack Bay Settlement

Nightly prices starting at
Cooper Jack Bay Settlement vacation rentals start at G$25,096 GYD per night before taxes and fees

Verified guest reviews
Over 5,100 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
120 of Cooper Jack Bay Settlement vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cooper Jack Bay Settlement rentals

4.9 Average rating
Cooper Jack Bay Settlement stays are highly rated by guests—averaging 4.9 out of 5!
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