
Vacation rentals with a kayak in Cooper Jack Bay Settlement
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Top-rated kayak rentals in Cooper Jack Bay Settlement
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Secluded 3 BR Villa on Taylor Bay -Place De La Sol
The luxury of privacy is what this villa is all about. A few steps through a private tropical path takes you to the pristine waters and powder sand beach that is Taylor Bay. This Villa is split between the main villa which hosts 2 bedrooms, living room, bathroom and kitchen/dining. The Master Suite is located across the patio with it's private bathroom and outdoor/indoor shower. Sunsets are 2nd to none and should be done at least once beachside since the villa faces west. **12% TCI Tax Included

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.

Sunset Paradise Waterfront Dock SUP + Pontoon Opt
Relax with the whole family at this peaceful oasis. This one level home otherwise known as a ranch bungalow is located on a 2 acre, fully fenced, gated, waterfront property. There is 75 feet of waterfront on the discovery bay canal system which runs north south thru south side marina, Cooper Jack bay beach the new home to The Strand Resort and next to the Wymara Villa's. Southside Marina is home to Bob's Bar, Flamingo Divers & Caicos Adventures. Enjoy snorkeling at Smiths Reef or Coral Gardens.

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.

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.

Couple’s Retreat - ocean view, pool and hot tub!
Free cancellation! Oceanside oasis with pool, ocean and garden views. Escape to the pristine blue waters at Northwest Point. Pool, ocean and hot tub within steps of condominium. Free access to kayaks and SUPs, snorkel gear, owners beach chairs, loungers and miles of secluded beach for walking, exploring or beachcombing. Airport is appoximately a 15 minute drive from Northwest Point Condominiums (formerly Northwest Point Resort). New refrigerator and new TV added October 2025!

3 Bed Beach Oasis on Flamingo Lake w/Private Pool
Márohu is a stunning 3-bedroom modern Caribbean villa set within the exclusive neighbourhood of Turtle Tail, just a 10-minute drive from the world-renowned Grace Bay Beach. This spacious, well-equipped, and family-oriented villa offers expansive floor-to-ceiling views over Flamingo Lake from every room. You’ll experience the best of outdoor living with our own pool and sandy beach, ideal for lounging, a friendly game of cornhole, or exploring the lake with our included kayaks.

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.

Breeze Luxury 3 Br Waterfront Villa
Welcome to your dream getaway in Turks and Caicos! This stunning 3-bedroom, 2 bath luxury villa sits directly on the peaceful canal in the prestigious Cooper Jack community, just minutes from the world famous Grace Bay Beach. Luxury 3BR canal-front villa in Turks & Caicos with private pool, dock, full kitchen, ensuite baths, and minutes from Grace Bay Beach. Ideal for families or couples seeking upscale comfort, water access, and serene island vibes.

NEW Water Access! Luxe Villa, Infinity Pool& Views
Welcome to Maresia Villa — a luxury waterfront retreat in Turks & Caicos. ** NEW: direct water access with a kayak for guest use** Enjoy an infinity pool, rooftop terrace for stargazing, and breathtaking sunset views and Chalk Sound’s turquoise lagoon from every room. Just 1 minute drive from Sapodilla Bay beach, this villa is ideal for couples, families, or group of friends. SPECIAL OFFER: Stay 7+ nights and enjoy 10% off your booking!

“The Lighthouse”, Private Pool, Ocean Views, Beach
The Lighthouse private cottage features a tower fashioned after a lighthouse affording stellar ocean views Private pool just outside living room doors! Deck & patio lounge w/ BBQ for fun & sun Nestled in the Thompson Cove Canal area and just a 3-minute walk to the beach WiFi, Smart TV with Netflix. Book now for a relaxing yet adventurous getaway! Kayaks, SUPs & snorkel gear included!

Sea La Vie - Beachside Studio Unit #3
Located in a secluded Beachside property, 500 ft from Long Bay Beach, and 5-minutes drive from Grace Bay Resorts and shops, this private Studio unit with it own private entry and patio, can accommodate up to 2 guests, with a queen size bed. It is located on the ground floor, roughly 15 yards from the pool. No pool view.
Popular amenities for Cooper Jack Bay Settlement kayak rentals
House rentals with a kayak

Casa de Isle, Taylor Bay, Chalk Sound area

Tropical Retreat: 360° Views, Pool, Beaches Nearby

Water Terrace Villa - with PrivateTropical Garden

Blue Chill Your Tropical Escape in Chalk Sound

Coastal Vibes Villa Near Sapodilla Beach

3bd ~ Private Pool ~ Kayak to the Mangroves

Guest House 2B&2B near Grace Bay Beach & Long Bay

Peaceful 1BR Private Cottage w/ HotTub Beach Front
Cottage rentals with a kayak

Swan cottages #6 Waterfront

Cute tropical getaway cottage at Dragon Cay Resort

Ridgetop Cottage for 2| Dragon Cay | Mudjin Harbor

Your waterfront Dream Getaway Starts Here

Caicos Cottage, 2 bdrm/2 bath beachfront w/pool

Cottage for 2 | Dragon Cay Resort | Mudjin Harbour

SunSeaSand 2Bdrm Seaside Cottage - Long Bay Hills

Swan Cottages
Other vacation rentals with a kayak

Pelican View #4 amazing beach views

Villa Serenity - (3-Bed Waterfront Villa)

Apt with private pool and direct beach access

“Sail Loft STBD”, Duplex with a Pool, Beach Access

Villa DelEvan 4B / 1-bedrm villa

Stunning Life. Style Resort w/Garden View

Northwest Paradise - Gorgeous, Modern & Peaceful

The Old Beach House 2 bedroom
Quick stats about vacation rentals with a kayak in Cooper Jack Bay Settlement

Total vacation rentals
Explore 20 vacation rentals in Cooper Jack Bay Settlement

Nightly prices starting at
Cooper Jack Bay Settlement vacation rentals start at G$18,829 GYD per night before taxes and fees

Verified guest reviews
Over 340 verified reviews to help you choose

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

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 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

4.8 Average rating
Cooper Jack Bay Settlement stays are highly rated by guests—averaging 4.8 out of 5!
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