Villa holiday rentals in Leeward Settlement
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Top-rated villa rentals in Leeward Settlement
Guests agree: these villas 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 villa rentals in Leeward Settlement
Private villa rentals
Villa in Grace Bay
4.95 out of 5 average rating, 40 reviewsMermaid's Retreat - 3Bd Villa - Heart of Grace Bay
26 Aug – 2 Sep
Villa in Providenciales
5.0 out of 5 average rating, 22 reviewsVilla & Studio: ocean view & private pool
23 Feb – 2 Mar
Villa in Long Bay Hills
4.87 out of 5 average rating, 30 reviewsCheerful 2 Bedrooms Villa 4 Mins Walk To The Beach
9–16 Mar
Villa in Providenciales
4.83 out of 5 average rating, 41 reviewsCanal Front Luxury Villa!
27 Sep – 4 Oct
Villa in Providenciales
5.0 out of 5 average rating, 46 reviewsWALK TO BEACH IN 2! RECLINE … RELAX … RECHARGE …
8–15 May
Villa in Long Bay Hills
4.82 out of 5 average rating, 98 reviewsLong Bay Beach Private Pool Villa with VIP Extras!
25 Sep – 2 Oct
Villa in Grace Bay
4.86 out of 5 average rating, 7 reviewsHopeWell Villa West - 5 Minutes to Grace Bay Beach
25 May – 1 Jun
Villa in Long Bay
4.9 out of 5 average rating, 48 reviewsHakuna Matata Villa + Golf Cart!
24 Sep – 1 Oct
Luxury villa rentals
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 The Bight Settlement
5.0 out of 5 average rating, 12 reviewsShades of Blue Grace Bay Beach
11–18 Sep
Villa in Providenciales
5.0 out of 5 average rating, 25 reviewsModern 2 Bedroom Luxury Villa & stunning sea views
25 Nov – 2 Dec
Villa in Providenciales
4.82 out of 5 average rating, 68 reviewsBeachHaus Villa with ocean view and private pool
20–27 Feb
Villa in Providenciales
4.95 out of 5 average rating, 42 reviewsRockspray Villa | On Point in Ocean | Waterfront |
8–15 Apr
Villa in Providenciales
4.93 out of 5 average rating, 59 reviewsBlanca: Taylor Bay Beach-Ocean View
3–10 Nov
Villa in The Bight Settlement
5.0 out of 5 average rating, 12 reviewsWalk to Grace Bay Beach ~ 3 bedroom en-suite
9–16 Oct
Villa in Providenciales
4.96 out of 5 average rating, 28 reviewsStunning Villa - short walk to Sapodilla Beach
3–10 Mar
Villa rentals with a pool
Villa in Long Bay Hills
5.0 out of 5 average rating, 24 reviews2 BR Private Pool - Modern & Airy -Flame Tree #3
15–22 Aug
Villa in Providenciales
4.95 out of 5 average rating, 61 reviewsSapodilla Bay - Walk to the Beach!
19–26 Aug
Villa in Cooper Jack Bay Settlement
4.94 out of 5 average rating, 36 reviewsT'PII Villa: Brand New Villa in Turtle Creek
26 Dec – 2 Jan
Villa in Grace Bay
4.88 out of 5 average rating, 16 reviewsYour own private oasis in Grace Bay w/pool !
22–29 Jul
Villa in Grace Bay
4.77 out of 5 average rating, 13 reviewsBeautiful Villa in the Heart of Grace Bay!
14–21 Dec
Villa in Providenciales
4.93 out of 5 average rating, 42 reviews‘My Little Hideaway’ at Lucayan Cays
27 Jan – 3 Feb
Villa in Providenciales
4.81 out of 5 average rating, 16 reviewsBeach Front 1 Bedroom Suite
30 Sep – 7 Oct
Villa in TC
4.88 out of 5 average rating, 91 reviewsWaterfront Point Villa - A Taste of Island Living
25 Feb – 4 Mar
Quick stats about villa rentals in Leeward Settlement
Total rentals
120 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Rentals with a pool
110 properties have a pool
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
1.3K reviews
Nightly prices starting at
€ 159 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
- Villa rentals Turks and Caicos Islands
- Villa rentals Turks and Caicos Islands
- Villa rentals Providenciales
- Villa rentals Providenciales
- Villa 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
- Family-friendly rentals Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Luxury rentals Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Family-friendly rentals Leeward Settlement
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- House rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Rentals with a firepit Leeward Settlement
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