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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.

Guest favorite
Condo in Providenciales
★★★★★ 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
Jan 6 – 13
$564 per night
4.9 out of 5 average rating, 189 reviews
Guest favorite
Home in Grace Bay
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!
Nov 13 – 20
$188 per night
4.79 out of 5 average rating, 115 reviews
Superhost
Apartment in Providenciales
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).
Jul 17 – 24
$185 per night
4.89 out of 5 average rating, 135 reviews

Popular amenities for Leeward Settlement family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Apartment in The Bight Settlement
A Little Bit of Heaven...Beautiful Beach Suite
Oct 11 – 18
$188 per night
4.94 out of 5 average rating, 156 reviews
Superhost
Condo in The Bight Settlement
Modern Boutique Style Condo and La Vista Azul
Jun 7 – 14
$256 per night
4.86 out of 5 average rating, 117 reviews
Guest favorite
Condo in Providenciales and West Caicos
Providenciales Artist’s Studio. Grace Bay view
Aug 6 – 13
$307 per night
4.84 out of 5 average rating, 140 reviews
Guest favorite
Apartment in Providenciales
Serene Caribbean Deluxe Beach Front Studio Pool K2
May 1 – 8
$368 per night
4.87 out of 5 average rating, 60 reviews
Guest favorite
Condo in Grace Bay
Splendid condo walks out to Grace Bay Beach
Feb 24 – Mar 3
$978 per night
4.95 out of 5 average rating, 55 reviews
Superhost
Condo in Turtle Cove, Providenciales
Peaceful Paradise
Nov 13 – 20
$248 per night
4.77 out of 5 average rating, 13 reviews
Superhost
Condo in Wheeland Settlement
Palmas Del Mar Oceanview and Northwest Point Resort
Jul 28 – Aug 4
$275 per night
4.93 out of 5 average rating, 69 reviews
Superhost
Condo in Wheeland Settlement
Stunning one bdrm ocean front views-pool, hot tub
Apr 16 – 23
$600 per night
4.73 out of 5 average rating, 33 reviews
Superhost
Condo in Caicos Islands
*OCEAN VIEW* *FULL KITCHEN* 1 BDRM
Jan 22 – 29
$200 per night
4.63 out of 5 average rating, 43 reviews
Condo in Providenciales
Sea Dreams - Jr 1 bdrm with Panoramic Ocean views!
Dec 13 – 20
$282 per night
4.88 out of 5 average rating, 156 reviews
Condo in Providenciales
Modern Garden Corner Suite Condo In Lush Garden🌿🌴🌊
Jun 12 – 19
$336 per night
4.73 out of 5 average rating, 115 reviews
Condo in Leeward Settlement
Charming Studio at Gated Resort Amazing Rates!
Jun 29 – Jul 6
$172 per night
4.65 out of 5 average rating, 20 reviews

Family- and pet-friendly home rentals

Guest favorite
Loft in Long Bay Hills
Best deal on island! On the water w/pool!
Jul 17 – 24
$154 per night
4.88 out of 5 average rating, 136 reviews
Guest favorite
Villa in Cooper Jack Bay Settlement
Waterfront Villa, Pool, Kayaks, & Boat Charters
Aug 19 – 26
$342 per night
4.98 out of 5 average rating, 153 reviews
Superhost
Guesthouse in Venetian Road Settlement
Romantic Studio with Stunning Views
Aug 18 – 25
$399 per night
4.85 out of 5 average rating, 99 reviews
Superhost
Villa in Caicos Islands
Aventine Villa
Oct 19 – 26
$700 per night
4.56 out of 5 average rating, 16 reviews
Superhost
Villa in Caicos Islands
Sweet Escape Villa Waterfront Kayaks Boat SUV Opt
Feb 13 – 20
$323 per night
4.63 out of 5 average rating, 8 reviews
Home in Long Bay Hills
Long Bay Oasis -Car Included
Sep 4 – 11
$549 per night
4.52 out of 5 average rating, 139 reviews
Home in Blue Hills, Providenciales
Enjoy a peaceful and affordable stay in Paradise ☺
Jan 16 – 23
$302 per night
4.64 out of 5 average rating, 58 reviews
Guest favorite
Cottage in Venetian Road Settlement
Sunrise Ridge Amazing 2 Bed Home
Oct 21 – 28
$399 per night
4.85 out of 5 average rating, 80 reviews
Superhost
Apartment in Long Bay Hills
Casa Verde: Affordable, on the water, with pool!
Dec 20 – 27
$475 per night
4.77 out of 5 average rating, 78 reviews
Guest favorite
Cottage in Venetian Road Settlement
Secluded Privacy on Sunrise Ridge
Feb 22 – Mar 1
$783 per night
4.89 out of 5 average rating, 9 reviews

Family-friendly home rentals with a pool

Superhost
Cottage in Cooper Jack Bay Settlement
Canal front 3 bedroom villa with private pool
Jan 17 – 24
$537 per night
4.86 out of 5 average rating, 132 reviews
Superhost
Loft in Providenciales and West Caicos
Cozy Loft Condo Great Location w/Pool
Jan 15 – 22
$267 per night
4.83 out of 5 average rating, 40 reviews
Guest favorite
Vacation home in Providenciales
Sun Villa @ The Sun and Sea Villas
Oct 2 – 9
$298 per night
5.0 out of 5 average rating, 6 reviews
Guest favorite
Villa in Providenciales, Long Bay Beach
Private Villa w Pool and Hotel Amenities/Services
Nov 13 – 20
$720 per night
5.0 out of 5 average rating, 11 reviews
Guest favorite
Cottage in Long Bay Hills
Flame Tree Cottage|Ocean view&pool.Walk to beach
Feb 19 – 26
$225 per night
4.94 out of 5 average rating, 88 reviews
Guest favorite
Home in Grace Bay
THE GECKO HOUSE awesome pool 🌞 - Grace Bay
May 26 – Jun 2
$275 per night
4.93 out of 5 average rating, 99 reviews
Guest favorite
Villa in Providenciales
Villa Jayla
Oct 16 – 23
$600 per night
4.97 out of 5 average rating, 76 reviews
Guest favorite
Condo in Grace Bay
Provo Villa 2-minute walk to Grace Bay Beach
Oct 23 – 30
$375 per night
4.96 out of 5 average rating, 24 reviews
Superhost
Apartment in Providenciales Turks and Caicos Islands
Beach Front Deluxe Studio
Oct 24 – 31
$484 per night
4.84 out of 5 average rating, 98 reviews
Superhost
Apartment in The Bight Settlement
Private Apartment/150yards to Grace Bay beach/Pool
Jun 28 – Jul 5
$387 per night
4.9 out of 5 average rating, 67 reviews
Guest favorite
Condo in Turtle Cove
Allies Rest - Seaflowers townhome
Jun 13 – 20
$350 per night
4.93 out of 5 average rating, 83 reviews
Guest favorite
Apartment in Providenciales
Hibiscus Villa
Oct 13 – 20
$370 per night
5.0 out of 5 average rating, 8 reviews

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

Total rentals

240 properties

Rentals with dedicated workspaces

90 properties have a dedicated workspace

Rentals with a pool

210 properties have a pool

Pet-friendly rentals

10 properties allow pets

Total number of reviews

2.6K reviews

Nightly prices starting at

$20 before taxes and fees

Destinations to explore