Villa vacation 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.

Guest favorite
Villa in Long Bay Hills
VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY
Take it easy at this dreamy, unique and tranquil getaway. Villa infini brings privacy and relaxation all in one , Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway . Bali like dip pool that can create amazing instagramable moments . Located in long bay , 5 minute walk to long bay beach . 5 minute drive to IGA gourmet and 6 minute drive to grace bay beach KING SIZE BED QUEEN SIZE SOFA BED Famous Tiki bar pick up 2min away
Nov 1 – 8
$501 per night
4.97 out of 5 average rating, 76 reviews
Guest favorite
Villa in Grace Bay
Calico Villa
"CALICO VILLA is a luxurious Villa located in Grace Bay, just behind Coco Bistro & Coco Van. Grace Bay beach is a 2 minute ride by car, or approx a 12 minute walk. This Newly built 3 bed/3 bath Villa can accommodate up to 6 guests. You can relax by your own "Private Pool & Outdoor Shower" after a day at the beach! Each bedroom has its own bathroom & AC, Main floor AC! 2 Adjoining Upper outdoor balconies. Also a Rooftop Terrace! Fast Internet! Highly desired vacation Villa & Super Host Service!
Nov 14 – 21
$899 per night
4.96 out of 5 average rating, 85 reviews
Guest favorite
Villa in Caicos Islands
NEW Luxe Private Pool Villa, Golf Course View, BBQ
- Tranquil property located along the Royal Turks & Caicos Golf Club, beach 5 mins - Private pool, sun loungers, gas BBQ, shaded outdoor dining table & sitting area - Well-equipped spacious kitchen, dishwasher, washer/dryer, beach essentials - Good WiFi, laptop-friendly workspaces, Sonos Move BT sound system, Smart TV - Family-friendly! Travel crib, high chair, children’s books & toys, board games. - Don’t wait to reserve this luxe villa with great views in Grace Bay of Turks & Caicos!
Oct 26 – Nov 2
$465 per night
5.0 out of 5 average rating, 43 reviews

Popular amenities for Leeward Settlement villa rentals

Private villa rentals

Superhost
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
Nov 1 – 8
$336 per night
4.87 out of 5 average rating, 31 reviews
Guest favorite
Villa in Caicos Islands
Cheers 🥂 Villa 🌴
Jun 11 – 18
$495 per night
4.95 out of 5 average rating, 80 reviews
Guest favorite
Villa in Grace Bay
Sunny ☀️ Place
Jul 10 – 17
$495 per night
4.82 out of 5 average rating, 22 reviews
Guest favorite
Villa in Providenciales
1 Bedroom Cottage - near beach
Jan 3 – 10
$490 per night
4.84 out of 5 average rating, 32 reviews
Guest favorite
Villa in Discovery Bay Settlement
Newly built modern two-bedroom villa with pool!
May 29 – Jun 5
$450 per night
4.98 out of 5 average rating, 41 reviews
Guest favorite
Villa in Providenciales
Sapodilla Bay - Stunning view & walk to the Beach!
Nov 26 – Dec 3
$456 per night
4.95 out of 5 average rating, 58 reviews
Guest favorite
Villa in Grace Bay
The White House TCI Guests house
May 2 – 9
$645 per night
4.88 out of 5 average rating, 16 reviews
Superhost
Villa in Providenciales
Blanca: Taylor Bay Beach-Ocean View
Sep 23 – 30
$659 per night
4.93 out of 5 average rating, 54 reviews
Guest favorite
Villa in Cooper Jack Bay Settlement
T'PII Villa: Brand New Villa in Turtle Creek
Jul 22 – 29
$400 per night
4.93 out of 5 average rating, 28 reviews
Guest favorite
Villa in Providenciales
‘My Little Hideaway’ at Lucayan Cays
Jan 24 – 31
$300 per night
4.92 out of 5 average rating, 37 reviews
Guest favorite
Villa in TC
Waterfront Point Villa - A Taste of Island Living
Jan 13 – 20
$399 per night
4.88 out of 5 average rating, 83 reviews
Superhost
Villa in Providenciales
Waters Edge - Condo near Beach; Dining, Sleeps 6
Aug 20 – 27
$520 per night
4.9 out of 5 average rating, 10 reviews

Luxury villa rentals

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
Villa in The Bight Settlement
Idyllic getaway villa | 250 yds to the beach
Sep 30 – Oct 7
$512 per night
4.97 out of 5 average rating, 67 reviews
Guest favorite
Villa in Providenciales
Villa DelEvan 4B / 1-bedrm villa
Aug 28 – Sep 4
$895 per night
5.0 out of 5 average rating, 80 reviews
Guest favorite
Villa in Leeward Settlement
Perroquet | Family Villa near Leeward Beach
Feb 9 – 16
$592 per night
5.0 out of 5 average rating, 27 reviews
Guest favorite
Villa in Grace Bay
Grace Bay/ Luxurious Coconat Villa 3 Bed + Pool
Feb 18 – 25
$999 per night
4.95 out of 5 average rating, 38 reviews
Guest favorite
Villa in Leeward Settlement
Caribbean Style Waterfront Villa with Housekeeping
Aug 18 – 25
$813 per night
5.0 out of 5 average rating, 22 reviews
Superhost
Villa in Providenciales
Canal Front Luxury Villa!
Jul 8 – 15
$970 per night
4.86 out of 5 average rating, 36 reviews
Superhost
Villa in Long Bay Hills
C-House Villa. 4 Bedroom home in new development
Jul 26 – Aug 2
$901 per night
4.9 out of 5 average rating, 10 reviews
Guest favorite
Villa in Providenciales
Beach Front 1 Bedroom Suite
Apr 16 – 23
$666 per night
5.0 out of 5 average rating, 10 reviews
Guest favorite
Villa in Providenciales
Villa with ocean view and private pool
Dec 13 – 20
$717 per night
4.93 out of 5 average rating, 30 reviews
Guest favorite
Villa in Grace Bay
Modern Clean Villa Grace Bay Grace Shore Villas
Apr 28 – May 5
$771 per night
4.96 out of 5 average rating, 28 reviews
Guest favorite
Villa in Grace Bay
Mermaid's Retreat - 3Bd Villa - Heart of Grace Bay
Nov 4 – 11
$800 per night
4.94 out of 5 average rating, 36 reviews

Villa rentals with a pool

Superhost
Villa in Lower Bight Road
100 Steps to Beautiful Grace Bay Beach!
Apr 27 – May 4
$600 per night
4.75 out of 5 average rating, 12 reviews
Superhost
Villa in Providenciales
Cheerful 3bedroom Villa with Large Pool
Feb 10 – 17
$522 per night
4.8 out of 5 average rating, 15 reviews
Guest favorite
Villa in The Bight Settlement
SURFside: Charming Ocean View Retreat & Villa
Jun 12 – 19
$850 per night
4.95 out of 5 average rating, 20 reviews
Superhost
Villa in Providenciales
Best views on island!
Feb 4 – 11
$850 per night
4.87 out of 5 average rating, 15 reviews
Villa in Providenciales and West Caicos
Secluded 3 BR Villa on Taylor Bay -Place De La Sol
Feb 13 – 20
$873 per night
4.84 out of 5 average rating, 111 reviews
Guest favorite
Villa in Leeward Settlement
Unique, Modern Cozy & Private | 2 minutes to Beach
Feb 11 – 18
$375 per night
4.98 out of 5 average rating, 52 reviews
Villa in Caicos Islands
Swan Boat House
Apr 26 – May 3
$520 per night
5.0 out of 5 average rating, 4 reviews
Guest favorite
Villa in Long Bay Hills
Hang Five Surf Villa in Long Bay
Jun 29 – Jul 6
$518 per night
5.0 out of 5 average rating, 18 reviews
Guest favorite
Villa in Providenciales
Stunning Panoramic View - Calming Charm
Oct 9 – 16
$995 per night
5.0 out of 5 average rating, 11 reviews
Villa in Leeward Settlement
Our Home on the Water - I Land Time Villa
Nov 16 – 23
$630 per night
4.71 out of 5 average rating, 14 reviews
Villa in Grace Bay
Beautiful Villa in the Heart of Grace Bay!
Feb 25 – Mar 4
$334 per night
4.75 out of 5 average rating, 8 reviews
Guest favorite
Villa in Long Bay
Hakuna Matata Villa + Golf Cart!
Apr 17 – 24
$754 per night
4.89 out of 5 average rating, 47 reviews

Quick stats about villa rentals in Leeward Settlement

Total rentals

140 properties

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Rentals with a pool

130 properties have a pool

Family-friendly rentals

130 properties are a good fit for families

Total number of reviews

1.2K reviews

Nightly prices starting at

$20 before taxes and fees

Destinations to explore