Family-friendly holiday 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.
Holiday 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
4.55 out of 5 average rating, 22 reviewsCharming Studio at Gated Resort Amazing Rates!
12–19 Dec
Flat in Providenciales
4.94 out of 5 average rating, 31 reviewsRelaxing Modern 1BR Garden Villa BeachFront + Pool
24 Sep – 1 Oct
Apartment in Grace Bay
4.84 out of 5 average rating, 99 reviewsBeachfront 1BR Walkout Royal West Indies Resort
Apartment in Caicos Islands
4.8 out of 5 average rating, 56 reviewsMODERN CONDO IN PARADISE
9–16 Dec
Apartment in Providenciales
4.75 out of 5 average rating, 84 reviewsContemporary 1400 SqF Green Corner Suite🌿🌴🌊
9–16 Sep
Apartment in Wheeland Settlement
4.73 out of 5 average rating, 33 reviewsStunning one bdrm ocean front views-pool, hot tub
30 Nov – 7 Dec
Apartment in Wheeland Settlement
4.93 out of 5 average rating, 70 reviewsPalmas Del Mar Oceanview and Northwest Point Resort
4–11 Jan
Apartment in The Bight Settlement
4.86 out of 5 average rating, 120 reviewsModern Boutique Style Condo and La Vista Azul
22–29 Jun
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
9–16 Apr
Villa in Caicos Islands
4.56 out of 5 average rating, 18 reviewsAventine Villa
2–9 Nov
Cottage in Venetian Road Settlement
4.89 out of 5 average rating, 9 reviewsSecluded Privacy on Sunrise Ridge
10–17 Apr
Home in Blue Hills, Providenciales
4.64 out of 5 average rating, 58 reviewsEnjoy a peaceful and affordable stay in Paradise ☺
28 Aug – 4 Sep
Apartment in Grace Bay
4.84 out of 5 average rating, 56 reviewsPrincess Villas Grace Bay
28 May – 4 Jun
Home in Long Bay Hills
4.52 out of 5 average rating, 141 reviewsLong Bay Oasis -Car Included
14–21 Jan
Flat in Long Bay Hills
4.78 out of 5 average rating, 81 reviewsCasa Verde: Affordable, on the water, with pool!
12–19 Oct
Guest house in Venetian Road Settlement
4.85 out of 5 average rating, 99 reviewsRomantic Studio with Stunning Views
16–23 Nov
Family-friendly home rentals with a pool
Cottage in Cooper Jack Bay Settlement
4.86 out of 5 average rating, 136 reviewsCanal front 3 bedroom villa with private pool
11–18 Nov
Home in Providenciales
5.0 out of 5 average rating, 20 reviewsSea Villa @ The Sun and Sea Villas
4–11 Nov
Cottage in Leeward Settlement
4.77 out of 5 average rating, 61 reviewsSilver Palms Cottage
7–14 Sep
Cottage in Long Bay Hills
4.94 out of 5 average rating, 90 reviewsFlame Tree Cottage|Ocean view&pool.Walk to beach
3–10 Oct
Villa in Providenciales, Long Bay Beach
5.0 out of 5 average rating, 21 reviewsFamily Beachside Vacation Villa,ResortAmenities v8
31 Aug – 7 Sep
Villa in Providenciales
4.97 out of 5 average rating, 79 reviewsVilla Jayla
17–24 Aug
Flat in Grace Bay
5.0 out of 5 average rating, 12 reviewsInn at Grace Bay
24 Feb – 3 Mar
Apartment in Turtle Cove
4.93 out of 5 average rating, 88 reviewsAllies Rest - Seaflowers townhome
17–24 Sep
Quick stats about holiday 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
€ 168 before taxes and fees
Destinations to explore
- Grace Bay Holiday rentals
- Grand Turk Holiday rentals
- Taylor Bay Holiday rentals
- North Caicos Holiday rentals
- Long Bay Beach Holiday rentals
- Sapodilla Bay Holiday rentals
- Chalk Sound Holiday rentals
- Turtle Cove Holiday rentals
- Salt Cay Holiday rentals
- Santiago de los Caballeros Holiday rentals
- Santo Domingo Holiday rentals
- Las Terrenas Holiday rentals
- Family-friendly rentals Turks and Caicos Islands
- Family-friendly rentals Turks and Caicos Islands
- Family-friendly rentals Providenciales
- Family-friendly rentals Providenciales
- Family-friendly rentals Grace Bay
- Rentals with beach access Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Monthly Rentals Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
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- Rentals with a washing machine and dryer Leeward Settlement
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