Family-friendly vacation rentals in Leeward Settlement
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Top-rated family-friendly rentals in Leeward Settlement
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Leeward Settlement family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Leeward Settlement
4.89 out of 5 average rating, 18 reviewsSpacious 1 BDRM/1.5 Bath Condo in Gated Resort
Jul 10 – 17
Condo in Grace Bay
4.93 out of 5 average rating, 72 reviewsBeachfront Studio, Royal West Indies Resort Bldg 1
May 11 – 18
Apartment in Providenciales
4.94 out of 5 average rating, 31 reviewsRelaxing Modern 1BR Garden Villa BeachFront + Pool
Sep 24 – Oct 1
Condo in Caicos Islands
4.8 out of 5 average rating, 56 reviewsMODERN CONDO IN PARADISE
Jul 14 – 21
Condo in Providenciales
4.75 out of 5 average rating, 84 reviewsContemporary 1400 SqF Green Corner Suite🌿🌴🌊
Jul 6 – 13
Condo in Wheeland Settlement
4.73 out of 5 average rating, 33 reviewsStunning one bdrm ocean front views-pool, hot tub
May 15 – 22
Condo in Wheeland Settlement
4.93 out of 5 average rating, 71 reviewsPalmas Del Mar Oceanview and Northwest Point Resort
Nov 7 – 14
Condo in The Bight Settlement
4.85 out of 5 average rating, 121 reviewsModern Boutique Style Condo and La Vista Azul
Jun 27 – Jul 4
Family- and pet-friendly home rentals
Villa in Caicos Islands
4.63 out of 5 average rating, 8 reviewsSweet Escape Villa Waterfront Kayaks Boat SUV Opt
Nov 4 – 11
Villa in Caicos Islands
4.56 out of 5 average rating, 18 reviewsAventine Villa
Nov 2 – 9
Cottage in Venetian Road Settlement
4.89 out of 5 average rating, 9 reviewsSecluded Privacy on Sunrise Ridge
Feb 7 – 14
Home in Blue Hills, Providenciales
4.64 out of 5 average rating, 58 reviewsEnjoy a peaceful and affordable stay in Paradise ☺
Sep 1 – 8
Condo in Grace Bay
4.84 out of 5 average rating, 56 reviewsPrincess Villas Grace Bay
May 28 – Jun 4
Home in Long Bay Hills
4.53 out of 5 average rating, 142 reviewsLong Bay Oasis -Car Included
Jan 16 – 23
Apartment in Long Bay Hills
4.78 out of 5 average rating, 81 reviewsCasa Verde: Affordable, on the water, with pool!
Sep 8 – 15
Guesthouse in Venetian Road Settlement
4.85 out of 5 average rating, 99 reviewsRomantic Studio with Stunning Views
Aug 5 – 12
Family-friendly home rentals with a pool
Cottage in Cooper Jack Bay Settlement
4.86 out of 5 average rating, 137 reviewsCanal front 3 bedroom villa with private pool
Nov 17 – 24
Home in Providenciales
5.0 out of 5 average rating, 20 reviewsSea Villa @ The Sun and Sea Villas
Apr 15 – 22
Cottage in Long Bay Hills
4.95 out of 5 average rating, 91 reviewsFlame Tree Cottage|Ocean view&pool.Walk to beach
Oct 8 – 15
Cottage in Leeward Settlement
4.77 out of 5 average rating, 61 reviewsSilver Palms Cottage
Apr 7 – 14
Home in Long Bay Hills
4.75 out of 5 average rating, 79 reviewsValhead Villa
Oct 26 – Nov 2
Apartment in Grace Bay
5.0 out of 5 average rating, 13 reviewsInn at Grace Bay
Sep 14 – 21
Villa in Providenciales
4.97 out of 5 average rating, 79 reviewsVilla Jayla
Dec 20 – 27
Villa in Providenciales, Long Bay Beach
5.0 out of 5 average rating, 12 reviewsPrivate Villa w Pool and Hotel Amenities/Services
Apr 23 – 30
Quick stats about vacation rentals that are family-friendly in Leeward Settlement
Total rentals
220 properties
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Rentals with a pool
200 properties have a pool
Pet-friendly rentals
10 properties allow pets
Total number of reviews
2.9K reviews
Nightly prices starting at
$180 before taxes and fees
Destinations to explore
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