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Vacation rentals in Leeward Settlement

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Leeward Settlement vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Stay near Leeward Settlement's top sights

Grace Bay Beach70 locals recommend
Coco Bistro104 locals recommend
Graceway Gourmet86 locals recommend
Le Bouchon Du Village39 locals recommend
Cocovan Airstream Lounge37 locals recommend
Turks Kebab33 locals recommend

Other great vacation rentals in Leeward Settlement

Guest favorite

Condo in Caicos Islands

4.97 out of 5 average rating, 34 reviews

Lil Chill -A cozy 1-Bedroom Unit near the beach

Guest favorite

Home in Grace Bay

5 out of 5 average rating, 37 reviews

Grace Bay/ New Luxurious home 3+ Bedrooms & Pool

Guest favorite

Villa in Grace Bay

5 out of 5 average rating, 17 reviews

November DEAL! Majestic Palm Villa

Guest favorite

Home in Providenciales

5 out of 5 average rating, 29 reviews

Sea Villa @ The Sun and Sea Villas

Guest favorite

Condo in Providenciales

5 out of 5 average rating, 8 reviews

NEW! Romantic Getaway, 3 Mins to the Beach !

Guest favorite

Home in Long Bay Hills

4.94 out of 5 average rating, 35 reviews

LUXURy Villa: Ocean View. Private Pool! Chef avail

Superhost

Villa in Caicos Islands

4.9 out of 5 average rating, 49 reviews

Private Pool Luxury Villa, 5min to Grace Bay beach

Guest favorite

Condo in Grace Bay

4.91 out of 5 average rating, 32 reviews

Luxe Studio - Grace Bay - (5-Min walk to Beach)

Show all

Quick stats about vacation rentals in Leeward Settlement

  • Total rentals

    320 properties

  • Nightly prices starting at

    $110 before taxes and fees

  • Total number of reviews

    6K reviews

  • Family-friendly rentals

    250 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    270 properties have a pool

Frequently Asked Questions

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

    Absolutely! We offer over 120 house rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

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

    Leeward Settlement has more than 250 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Yes! Dive into the perfect getaway at one of over 270 vacation homes with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Leeward Settlement have wifi?

    Absolutely! We offer over 80 house rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • 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 vacation rentals with a dedicated workspace in Leeward Settlement?

    Yes! Work meets play with ease at over 120 vacation 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 gym?

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

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

    Enhance your stay in our Villa Rentals with the most popular amenities: over 30 homes with a gym, over 80 homes with a bbq area, over 140 homes with air conditioning, over 140 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do condo rentals in Leeward Settlement have air conditioning?

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

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

    Four-legged friends are welcome in Leeward Settlement. Choose from more than 20 vacation rentals for guests traveling with pets.

Destinations to explore