
Vacation rentals with a kayak in Cooper Jack Bay Settlement
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Top-rated accommodations with a kayak in Cooper Jack Bay Settlement
Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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.

Vista Cove 1 Bedroom Villa
Vista Cove 1 Bedroom is a beautifully appointed Villa. This listing is an offering of the main "1 Bedroom Unit". Nestled at the bottom of the hill in the quiet area of Chalk Sound, Vista Cove provides a feeling of privacy and tranquility that can match any super high end Villa property for a fraction of the cost. It is a few minutes walk away from the beautiful and peaceful Taylor Bay beach and is filled with all the amenities one needs for a great vacation of relaxation and adventure!

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.

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!

Water Terrace Villa - with PrivateTropical Garden
WATER TERRACE is a 2 bedroom+2 bathroom villa, completely gated property on the clear sea water canal, surrounded by tropical plants and fruit trees. Located quiet neighborhood of Discovery Bay area in Providenciales, the property is very private and peaceful. The villa is only 2 miles from Grace Bay beach, 5 minutes to Smith leaf and Turtle Cove Marina by car. Centrally located, 10 mins drive from the airport, close to lots of good local restaurants/bars and grocery stores.

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 Old Beach House 2 bedroom
We have two Garden apartments downstairs that we renovated. One two bedroom two bathroom, and one 1 bed 1 bathroom. Just a 3 minute walk from a white sandy beach. You can walk to Da Conch shack restaurant along the beach in 5-10 minutes. Off the beaten trail. We live upstairs with our our potcake Boxer. We are so sad to say we just lost our legend Buster who you would have read about in all of our reviews.
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

Blue Chill Your Tropical Escape in Chalk Sound

Coastal Vibes Villa Near Sapodilla Beach

Perfect 3BR Family Getaway with Stunning Views!

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

The Old Beach House

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

"Dive Shop" Guesthouse, Easy Walk to Beach, Kayaks
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 $126 CAD 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 and kid-friendly amenities

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Cooper Jack Bay Settlement vacation rentals include wifi 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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