
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

Sea Sun Relax - villa 5 min walk to Grace Bay

Grace Bay/ Luxurious Coconat Villa 3 Bed + Pool

Modern two-bedroom Villa with pool!

WOW! Waterfront Chalk Sound Oasis w/ Infinity Pool

Peaceful island getaway in Long Bay (New 2BR)

4bd/3ba, 400 Steps to Grace Bay

Nirvana's Nest

The Haven
Luxury villa rentals

Villa Blu - A contemporary 3 BDR/BTH Villa minutes

Luxury Modern villa with pool

Designer Artist’s Estate - Stunning Interior/View

Blanca: Taylor Bay Beach-Ocean View

Luxury 3B Ocean View Villa/Pvt Pool, Walk to Beach

Live style villa

Hakuna Matata Villa + Golf Cart!

100 Steps to Beautiful Grace Bay Beach!
Villa rentals with a pool

Unique, Modern Cozy & Private | 2 minutes to Beach

Pelican Beach Villas 2

Villa Affiniti

‘My Little Hideaway’ at Lucayan Cays

Canal Front Luxury Villa!

NEW *2 BR Villa Maya- BBQ- Golf- Pool in Grace Bay

Modern 4BR oasis on 1 acre, 1 min from the Beach

New Luxury Caribbean Villa with Private Pool
Quick stats about villa rentals in Leeward Settlement
Total rentals
140 properties
Nightly prices starting at
₹15,700 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
140 properties are a good fit for families
Rentals with a pool
140 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
- Grace Bay Holiday rentals
- Grand Turk Holiday rentals
- North Caicos Holiday rentals
- Long Bay Hills Holiday rentals
- Long Bay Beach Holiday rentals
- Chalk Sound Holiday rentals
- The Bight Settlement Holiday rentals
- Turtle Cove Holiday rentals
- Sapodilla Bay Holiday rentals
- Cooper Jack Bay Settlement Holiday rentals
- Salt Cay Holiday rentals
- Santo Domingo Holiday rentals
- Villa rentals Turks and Caicos Islands
- Villa rentals Providenciales
- Villa rentals Grace Bay
- Villa rentals Caicos Islands
- Rentals with a patio Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Flat rentals Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Family-friendly rentals Leeward Settlement
- House rentals Leeward Settlement
- Rentals with a fireplace Leeward Settlement
- Beachfront rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Rentals with a firepit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Rentals with pools Leeward Settlement
- Monthly Rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Pet-friendly rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with a hot tub Leeward Settlement
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