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Family-friendly vacation rentals in Leeward Settlement

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Leeward Settlement

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

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Villa in Providenciales and West Caicos

4.84 out of 5 average rating, 125 reviews

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

Cottage in Long Bay Hills

4.94 out of 5 average rating, 101 reviews

Flame Tree Cottage|Ocean view&pool.Walk to beach

Built in 2013. 1 bedroom 2 bathroom cottage with PRIVATE POOL. Sunrise & ocean view from the front deck and only 1/4 mile to the beach. Perfect for 2, but can sleep up to 6. Full kitchen, 2 bathrooms + outdoor shower. No bathtub. Propane Grill. AC in master bedroom. WIFI throughout & local cell provided. This quaint clutter-free 1200 square foot home is surrounded by indigenous foliage, cactus', succulents and native stonework. A rental car is recommended to explore all the island has to offer!

Rental unit in Grace Bay

4.85 out of 5 average rating, 111 reviews

Elegant Penthouse in the Heart of Grace Bay

Nestled in the heart of Grace Bay is this charming one bedroom penthouse, one of the most desirable on Grace Bay road. This condo is surrounded by shops, restaurants, bars and only a two minute walk to Grace bay beach. Grace Bay Beach has been named Number 1 Beach in the World and is known for its turquoise, gin clear water and white powdery sand beaches. Snorkelling is one of the Top Three Things To Do while vacationing in this Paradise, don your mask and fins an get ready for adventure.

Rental unit in Leeward Settlement

4.95 out of 5 average rating, 219 reviews

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.

Condo in Providenciales

4.91 out of 5 average rating, 219 reviews

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

• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub • Highest Rated Spa on Island • Fully equipped kitchen • Private front patio + grill • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Condo in Turtle Cove

4.93 out of 5 average rating, 102 reviews

Allies Rest - Seaflowers townhome

Modern and spacious two story townhome in the quiet, prime Lower Bight location, near the Princess Alexandra National Park. Just a short walk away from the gorgeous turquoise waters via a beach front access, to one of the best snorkeling sites on Providenciales! Close to Graceway IGA grocery store, boating marina, restaurants, and within walking distance to the weekly Fish Fry event - every Thursday, local food, drinks, music and souvenirs!

Home in Grace Bay

4.82 out of 5 average rating, 130 reviews

Tropical Guest House

Guest house, stylish and cozy with cold AC. Nested in a Tropical Nursery Garden on back of a semi-detached Villa. Well equipped! Studio. 15 Minute walk to beach, less than a minute by car. Best way to see all island and beaches is to rent a car!! Coco Bistro and Coco Van is just down the road! Easy access to all kind of shops and grocery store. Grill on your deck for your private use. Great Value location & close to Grace Bay Beach!

Loft in Long Bay Hills

4.88 out of 5 average rating, 153 reviews

Best deal on island! On the water w/pool!

♥♥ The studio is a secluded get-away place apart from the tourist areas. It overlooks the lake of Juba Sound National Park. The studio is only a 10-minute drive to the world-famous Grace Bay Beach and Longbay Beach (kiteboarding beach)! Restaurants and nightlife are also close by. The studio is in a secure, quiet location where you can relax and enjoy your vacation. This studio is ideal for singles, couples, and kiteboarders.

Rental unit in Providenciales

4.89 out of 5 average rating, 158 reviews

Corona #2 (2 minutes walk Grace Bay Beach)

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 neighborhoods and quiet area. Place is good for couples, solo adventurers, families and business travelers. This is the same house where Coco and Crescent apartment are located (look review).

Home in Grace Bay

4.94 out of 5 average rating, 114 reviews

THE GECKO HOUSE awesome pool 🌞 - Grace Bay

One of very few affordable stand alone houses with a beautiful pool and beautiful gardens! This uniqueness lovely house is located in a quiet residential neighborhood in Grace Bay just a short 8 minute walk (less than a 3 minute ride) to the beach and walking distance to many of the islands attractions, shops, restaurants and activities.

Condo in Grace Bay

4.93 out of 5 average rating, 168 reviews

22 Middle of Gracebay, Heated Pool, Gated Condo.

Granvia is center of Gracebay, very close to Gracebay Gourmet, restaurant, there is beach access close by, 6min walking to World no.1 Gracebay Beach. Security gate, privacy, Full Kitchen with Air flyer, Washer and Dryer Wi-Fi (fastest speed on island 50MBPS) 70" Samsung 4K TV with Samsung sound bar, Live TV, Movie, TV show

Rental unit in Providenciales

4.96 out of 5 average rating, 223 reviews

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 2 potcakes Buster and Boxer.

Vacation rentals for every style

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Convenient locations with everyday essentials

Popular amenities for Leeward Settlement family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Condo in Leeward Settlement

4.6 out of 5 average rating, 25 reviews

Charming Studio at Gated Resort Amazing Rates!

Condo in Caicos Islands

4.61 out of 5 average rating, 46 reviews

*OCEAN VIEW* *FULL KITCHEN* 1 BDRM

Villa in Grace Bay

4.97 out of 5 average rating, 30 reviews

CoCo Gardens - Beautiful 3 Bedroom Island Hideaway

Rental unit in Providenciales

4.88 out of 5 average rating, 72 reviews

Serene Caribbean Deluxe Beach Front Studio Pool K2

Condo in The Bight Settlement

4.82 out of 5 average rating, 124 reviews

Modern Boutique Style Condo and La Vista Azul

Condo in Turtle Cove, Providenciales

4.73 out of 5 average rating, 15 reviews

Peaceful Paradise

Condo in Wheeland Settlement

4.93 out of 5 average rating, 76 reviews

Palmas Del Mar Oceanview at Northwest Point Resort

Condo in Providenciales

4.75 out of 5 average rating, 85 reviews

Contemporary 1400 SqF Green Corner Suite🌿🌴🌊

Family- and pet-friendly home rentals

Guesthouse in Venetian Road Settlement

4.85 out of 5 average rating, 100 reviews

Romantic Studio with Stunning Views

Cottage in Venetian Road Settlement

4.84 out of 5 average rating, 83 reviews

Sunrise Ridge Amazing 2 Bed Home

Home in Blue Hills, Providenciales

4.63 out of 5 average rating, 59 reviews

Enjoy a peaceful and affordable stay in Paradise ☺

Villa in Caicos Islands

4.63 out of 5 average rating, 8 reviews

Sweet Escape Villa Waterfront Kayak + SUV BOAT Opt

Cottage in Venetian Road Settlement

4.89 out of 5 average rating, 9 reviews

Secluded Privacy on Sunrise Ridge

Rental unit in Long Bay Hills

4.76 out of 5 average rating, 84 reviews

Casa Verde: Affordable, on the water, with pool!

Rental unit in Caicos Islands

4.61 out of 5 average rating, 70 reviews

Luko Kayo Lodge-Eclectic 2 BRM + Pool+tennis court

Family-friendly home rentals with a pool

Villa in Providenciales, Long Bay Beach

5 out of 5 average rating, 23 reviews

Private Villa w chef, gym, pickleball, bocci & mor

Cottage in Cooper Jack Bay Settlement

4.86 out of 5 average rating, 139 reviews

The Breeze House , canal front and private pool

Home in Grace Bay

4.86 out of 5 average rating, 91 reviews

Popular GraceBay Villa for Family, Couples, Groups

Condo in Grace Bay

4.97 out of 5 average rating, 35 reviews

Provo Villa 2-minute walk to Grace Bay Beach

Home in Providenciales

5 out of 5 average rating, 29 reviews

Sea Villa @ The Sun and Sea Villas

Villa in Providenciales

4.95 out of 5 average rating, 76 reviews

Blanca: Taylor Bay Beach-Ocean View

Villa in Providenciales

4.98 out of 5 average rating, 85 reviews

Villa Jayla

Rental unit in Grace Bay

4.97 out of 5 average rating, 29 reviews

Inn at Grace Bay

Quick stats about vacation rentals that are family-friendly in Leeward Settlement

Total rentals
250 properties
Nightly prices starting at
$160 before taxes and fees
Total number of reviews
3.5K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
220 properties have a pool
Rentals with dedicated workspaces
100 properties have a dedicated workspace

Destinations to explore