Leeward Settlement vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Leeward Settlement vacation rentals

Stay near Leeward Settlement's top sights

Caicos Conch Farm12 locals recommend
Provo Golf Club14 locals recommend
Blue Haven Marina5 locals recommend
Blue Haven Resort7 locals recommend
Pelican Beach7 locals recommend
Big Blue Collective17 locals recommend

Other great vacation rentals in Leeward Settlement

Guest favorite

Apartment in Leeward Settlement

5.0 out of 5 average rating, 36 reviews

Large Luxury Modern Condo + pool + close to beach

Jun 26 – Jul 3

$284 per night
Guest favorite

Home in Leeward Settlement

5.0 out of 5 average rating, 24 reviews

Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool

Jul 16 – 23

$736 per night
Guest favorite

Villa in Leeward Settlement

5.0 out of 5 average rating, 22 reviews

Caribbean Luxury Waterfront Villa w Housekeeping

Jul 29 – Aug 5

$810 per night
Guest favorite

Villa in Leeward Settlement

4.93 out of 5 average rating, 15 reviews

Ocean Pearl-Brand new villa/pool in governors road

Dec 13 – 20

$856 per night
Guest favorite

Villa in Caicos Islands

4.94 out of 5 average rating, 87 reviews

Cheers 🥂 Villa 🌴

Jun 28 – Jul 5

$495 per night
Guest favorite

Home in Leeward Settlement

4.95 out of 5 average rating, 60 reviews

PERIWINKLE | Charming Island Home|Near to Beach

May 19 – 26

$230 per night
Guest favorite

Villa in Caicos Islands

5.0 out of 5 average rating, 45 reviews

NEW Luxe Private Pool Villa, Golf Course View, BBQ

Jan 13 – 20

$676 per night
Guest favorite

Villa in Leeward Settlement

5.0 out of 5 average rating, 29 reviews

Perroquet | Family Villa near Leeward Beach

Aug 29 – Sep 5

$532 per night

Quick stats about vacation rentals in Leeward Settlement

  • Total rentals

    290 properties

  • Rentals with a pool

    240 properties have a pool

  • Pet-friendly rentals

    10 properties allow pets

  • Family-friendly rentals

    220 properties are a good fit for families

  • Total number of reviews

    5.2K reviews

  • Nightly prices starting at

    $110 before taxes and fees

Frequently Asked Questions

  • Are there Leeward Settlement villa rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 110 villa rentals with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in apartment rentals in Leeward Settlement?

    Experience the best of Leeward Settlement with our apartment rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there villa rentals with a dedicated workspace in Leeward Settlement?

    Yes! Work meets play with ease at over 40 villa rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do villa rentals in Leeward Settlement have a bbq area?

    Absolutely! We offer over 70 villa rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Leeward Settlement?

    Leeward Settlement has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do condo rentals in Leeward Settlement have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Leeward Settlement have a gym?

    Absolutely! We offer over 20 villa rentals with a gym in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Leeward Settlement have air conditioning?

    Absolutely! We offer over 30 apartment rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Leeward Settlement?

    Four-legged friends are welcome in Leeward Settlement. Choose from more than 10 house rentals for guests traveling with pets.

  • What are the most popular amenities for Condo Rentals in Leeward Settlement?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. Turks and Caicos Islands
  3. Caicos Islands
  4. Providenciales
  5. Leeward Settlement