Kid-friendly holiday rentals in Leeward Settlement

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Top-rated family-friendly rentals in Leeward Settlement

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Home in Providenciales

4.86 out of 5 average rating, 7 reviews

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.

Guest favourite

Flat in Long Bay Hills

4.91 out of 5 average rating, 43 reviews

Sky Blue Vacation Rental

Luxurious, private, comfort, less than 5-minute walk to Long Bay Beach (a kite boarder's dream) and the Shore Club Resort with their two amazing restaurants, Sui-Ren, and The Almond Tree. During the day, lounge on the pool deck, take a dip in the refreshing water, and in the evening, soothe your muscles in the rejuvenating hot tub. Brand new, full kitchen installed in August 2023. Queen bed in main bedroom and two single beds in the second bedroom. Peaceful neighborhood with only 3 houses.

Superhost

Home in Providenciales

5 out of 5 average rating, 20 reviews

Central Hideaway/Kg+Qn Bd/4K 55”TV Ntflx/BchNearby

Welcome to Hibiscus Suites, a central paradise located in Frangipani Gardens, just off Millenium Highway, about 5 minutes driving from the airport and the hospital, 3 minutes driving to Blue Hills Beach, and 10 minutes to the famous Grace Bay Beach. If you’re looking for a comfortable place for you or your group to relax while in Providenciales, or the opportunity to experience our beautiful by nature island in a clean and safe space, then this is the perfect hideaway for you.

Guest favourite

Apartment in Providenciales

4.91 out of 5 average rating, 125 reviews

Romantic Escape with Stunning Pools & Sunset Views

Welcome to our private island paradise. This is a light, charming, one bedroom unit in a quiet setting with a view over the terraced pools & into Turtle Cove & the marina. Its 1091 square feet bring a spacious open plan living/dining/kitchen/balcony where you will particularly appreciate the new Bosch appliances. The patio door opening spans 16 feet. The large bedroom has a king size bed, walk-in closet, another TV, & a beautiful ensuite bath w/ a roomy walk-in shower.

Guest favourite

Apartment in Providenciales

4.95 out of 5 average rating, 44 reviews

The Cottonwood House - Beach Villa

Completely renovated condo at La Vista Azul in a prime area (Turtle Cove) of Providenciales. See what Turks and Caicos has to offer staying in a beautiful 1 bed 1 bath condo with an expansive balcony/patio. Enjoy your home away from home with a full kitchen, washer and dryer, gym, ocean view pools, all beach/snorkel gear, and restaurant on site. This condo is on the first floor and does require one flight of stairs. Family friendly and 3 minutes from Grace Bay Beach!

Superhost

Flat in Caicos Islands

4.84 out of 5 average rating, 139 reviews

Palm Point Loft - Waterfront Canal

Palm Point Loft is the perfect spot for you to come and experience the peace and beauty of Providenciales. Located canal side, this private and spacious 2 bedroom second floor apartment is centrally located, 5 mins to Grace Bay Beach, restaurants and grocery stores. The unit is airy and bright offering a private sanctuary for guests to relax on their own balcony - the perfect place to unwind and enjoy the gentle breeze off the water while watching the sunset.

Top guest favourite

Apartment in Grace Bay

4.99 out of 5 average rating, 140 reviews

1 Bedroom Luxury Grace Bay Condo in Best Location

The perfect location, and only a 5 minute walk to world famous Grace Bay Beach! Located in the heart of Grace Bay near Seven Stars Resort and the Ritz Carlton Resort. 5 minute walk to the beach. 2 minute walk to the best grocery store, and 10 minute walk to the best restaurants and shopping on the island. No rental car is needed. This 790 sq. ft. luxury one bedroom, newly built condo (Nov 2020), provides all necessary amenities for your home away from home.

Top guest favourite

Guest house in Leeward Settlement

4.97 out of 5 average rating, 114 reviews

"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.

Superhost

Cottage in Providenciales

4.8 out of 5 average rating, 5 reviews

Swan Cottages

This charming pair of newly renovated waterfront cottages with a brand new 28-foot pool is a 2-minute walk from the scenic Sopadilla Bay Beach and Las Brisas Restaurant and walking distance to the exclusive Taylor Bay Beach. Located directly on the Chalk Sound National Park with views of its breathtaking blue waters, this beautiful, idyllic location is perfect for kayaking and paddle boarding. Rare sightings of dolphins have been made in this area.

Superhost

Flat in Caicos Islands

4.85 out of 5 average rating, 299 reviews

Coco apartment (Grace Bay beach 2 min walk)

My place is close to the main attractions, bars, groceries, restaurants and about 2 minutes walking distance to the nicest beach in the world Grace Bay beach #1. You’ll love my place because of the neighbourhoods and quiet area. Place is good for couples, solo adventurers, families and business travelers. This is the same house where Corona apartment is located (look review). The couch is not a sofa bed and is not made to sleep on

Superhost

Holiday home in Long Bay Hills

5 out of 5 average rating, 3 reviews

Sea Castle w/ Pickleball #1

A unique castle vibe in Long Bay with a professional pickleball court in the front yard. A 1st floor unit with 2 bedrooms, en suite bathrooms, living room, kitchen, dining, and patio areas on each floor. The third floor provides 360-degree views of the island and amazing turquoise waters. A quick two-minute drive to Long Bay Beach or a 6-minute drive to Grace Bay will ensure the ultimate vacation getaway for your family or group.

Superhost

Villa in Chalk Sound

4.69 out of 5 average rating, 61 reviews

The Babbington Villa

Welcome to The Babbington Villa, a world of artful, immersive experiences, where you live life luxuriously. This is your time! Nestled on the Southside of Providenciales, secluded yet not far away from shopping, restaurants, beaches and other island activities. The Villa is the epitome of privacy, comfort, and tranquility. It’s an oasis of luxury in the lap of paradise, offering a perfect blend of bliss and play, chill and thrill.