Villa vacation rentals in Leeward Settlement
Find and book unique villas on Airbnb
Top-rated villa rentals in Leeward Settlement
Guests agree: these villas 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 villa rentals
Private villa rentals
Villa in Grace Bay
4.95 out of 5 average rating, 41 reviewsMermaid's Retreat - 3Bd Villa - Heart of Grace Bay
Aug 30 – Sep 6
Villa in Providenciales
5.0 out of 5 average rating, 22 reviewsVilla & Studio: ocean view & private pool
Apr 22 – 29
Villa in Grace Bay
4.86 out of 5 average rating, 7 reviewsHopeWell Villa West - 5 Minutes to Grace Bay Beach
Dec 6 – 13
Villa in Providenciales
4.81 out of 5 average rating, 42 reviewsCanal Front Luxury Villa!
Sep 2 – 9
Villa in Long Bay
4.9 out of 5 average rating, 48 reviewsHakuna Matata Villa + Golf Cart!
Oct 14 – 21
Villa in Leeward Settlement
4.86 out of 5 average rating, 35 reviewsSea Sun Relax - villa 5 min walk to Grace Bay
Sep 14 – 21
Villa in Providenciales
5.0 out of 5 average rating, 46 reviewsWALK TO BEACH IN 2! RECLINE … RELAX … RECHARGE …
May 8 – 15
Villa in Long Bay Hills
4.91 out of 5 average rating, 11 reviewsThe Haven
Dec 31 – Jan 7
Luxury villa rentals
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
Villa in Providenciales
5.0 out of 5 average rating, 25 reviewsModern 2 Bedroom Luxury Villa & stunning sea views
Nov 28 – Dec 5
Villa in The Bight Settlement
5.0 out of 5 average rating, 12 reviewsShades of Blue Grace Bay Beach
Aug 20 – 27
Villa in Venetian Road Settlement
5.0 out of 5 average rating, 5 reviewsHarpers Haven Ocean Front Villa in Turtle Tail
Oct 9 – 16
Villa in The Bight Settlement
5.0 out of 5 average rating, 12 reviewsWalk to Grace Bay Beach ~ 3 bedroom en-suite
Oct 8 – 15
Villa in Providenciales
4.96 out of 5 average rating, 28 reviewsStunning Villa - short walk to Sapodilla Beach
Jan 10 – 17
Villa in Providenciales
4.93 out of 5 average rating, 60 reviewsBlanca: Taylor Bay Beach-Ocean View
Jan 17 – 24
Villa in Providenciales
4.9 out of 5 average rating, 39 reviewsVista Cove - Entire Property
Oct 13 – 20
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
Nov 2 – 9
Villa in Grace Bay
4.88 out of 5 average rating, 16 reviewsYour own private oasis in Grace Bay w/pool !
Sep 3 – 10
Villa in Grace Bay
4.79 out of 5 average rating, 14 reviewsBeautiful Villa in the Heart of Grace Bay!
Apr 12 – 19
Villa in Cooper Jack Bay Settlement
4.94 out of 5 average rating, 36 reviewsT'PII Villa: Brand New Villa in Turtle Creek
Apr 8 – 15
Villa in TC
4.88 out of 5 average rating, 91 reviewsWaterfront Point Villa - A Taste of Island Living
Aug 20 – 27
Villa in Providenciales
4.95 out of 5 average rating, 61 reviewsSapodilla Bay - Walk to the Beach!
Jan 20 – 27
Villa in Providenciales
4.81 out of 5 average rating, 16 reviewsBeach Front 1 Bedroom Suite
Sep 21 – 28
Villa in Providenciales
4.93 out of 5 average rating, 42 reviews‘My Little Hideaway’ at Lucayan Cays
Aug 21 – 28
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
$170 before taxes and fees
Destinations to explore
- Grace Bay Vacation rentals
- Grand Turk Vacation rentals
- Taylor Bay Vacation rentals
- North Caicos Vacation rentals
- Long Bay Beach Vacation rentals
- Sapodilla Bay Vacation rentals
- Chalk Sound Vacation rentals
- Turtle Cove Vacation rentals
- Salt Cay Vacation rentals
- Santiago de los Caballeros Vacation rentals
- Santo Domingo Vacation rentals
- Las Terrenas Vacation 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 a fire pit Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- House rentals Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
- Beachfront rentals Leeward Settlement
- Monthly Rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Apartment rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Villa rentals Caicos Islands
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes