Leeward Settlement vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Leeward Settlement

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Villa in Long Bay Hills

4.97 out of 5 average rating, 79 reviews

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

Jan 23 – 30

ﺩ.ﺇ2,111 per night
Guest favorite

Guesthouse in Long bay

4.96 out of 5 average rating, 68 reviews

Villa Kendara~BK 6/22 & On~Gated~SeaFront GH~View

Private~Gated~Seafront~Unique Loc~Beautiful by Nature~Panoramic Water & Bay Views~A+ Sunrises/Sunsets~5 min to Grace Bay, Stores, Restaurants, Marina~Exclusive ”Johnson Guide to Provo & Car Travel Guide~LOFT FOR KIDS~Fully Equipped~Loaded with Supplies~Pool, CoralStone Deck, Pergola for Shade, BBQ, AC, Fans, TV, DVD, Phone, Wi-Fi, Snorkel Gear, Portable Beach Chairs & Umbrella~Island Partner Discounts for Car Rental, Water Sports/Eco-Tours, Cruise, Massages~Swim, Snorkel, KiteBoard, PaddleBoard

Oct 19 – 26

ﺩ.ﺇ1,314 per night
Superhost

Villa in Providenciales

4.9 out of 5 average rating, 110 reviews

Gardenia Villa

Gardenia Villa. This contemporary Oasis is perfect for a small family or couples, located steps away from the world’s #1 Grace Bay Beach. The villa entrance opens to a bright entryway leading to the living room area with a spectacular view through a wall of sliding doors to the covered deck and pool. The open plan is perfect for entertaining with the dining and kitchen area all part of the living space. The upstairs consist a master King and second queen sized bedrooms both ensuite baths.

Sep 27 – Oct 4

ﺩ.ﺇ2,626 per night

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 Resort7 locals recommend
Blue Haven Marina5 locals recommend
Pelican Beach7 locals recommend
Big Blue Collective17 locals recommend

Other great vacation rentals in Leeward Settlement

Guest favorite

Home in Leeward Settlement

4.95 out of 5 average rating, 59 reviews

PERIWINKLE | Charming Island Home|Near to Beach

Dec 3 – 10

ﺩ.ﺇ1,172 per night
Guest favorite

Home in Leeward Settlement

5.0 out of 5 average rating, 24 reviews

Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool

Feb 22 – Mar 1

ﺩ.ﺇ3,587 per night
Guest favorite

Home in Leeward Settlement

5.0 out of 5 average rating, 13 reviews

Ocean Pearl - 2bed home @leeward/sunset beach

Sep 29 – Oct 6

ﺩ.ﺇ2,754 per night
Guest favorite

Villa in Leeward Settlement

5.0 out of 5 average rating, 29 reviews

Perroquet | Family Villa near Leeward Beach

Oct 23 – 30

ﺩ.ﺇ2,230 per night
Guest favorite

Villa in Caicos Islands

5.0 out of 5 average rating, 44 reviews

NEW Luxe Private Pool Villa, Golf Course View, BBQ

Mar 16 – 23

ﺩ.ﺇ2,721 per night
Guest favorite

Home in Leeward Settlement

5.0 out of 5 average rating, 48 reviews

Cocodemer, a short walk to secluded Pelican Beach.

Aug 16 – 23

ﺩ.ﺇ1,394 per night
Guest favorite

Condo in Leeward Settlement

5.0 out of 5 average rating, 17 reviews

Grace’s Condo In Leeward Settlement

Jul 12 – 19

ﺩ.ﺇ1,125 per night
Guest favorite

Cottage in Leeward Settlement

4.96 out of 5 average rating, 68 reviews

Sandpiper Cottage, minutes from the beach

Jan 12 – 19

ﺩ.ﺇ1,470 per night
Guest favorite

Villa in Providenciales

5.0 out of 5 average rating, 14 reviews

Salt Life Villa

Aug 9 – 16

ﺩ.ﺇ3,041 per night
Guest favorite

Guest suite in Leeward Settlement

4.96 out of 5 average rating, 68 reviews

Erisa Studio near Grace Bay Beach

Sep 11 – 18

ﺩ.ﺇ506 per night
Guest favorite

Home in Providenciales

4.96 out of 5 average rating, 79 reviews

Sunny Paradise Long Bay

Nov 14 – 21

ﺩ.ﺇ1,791 per night
Guest favorite

Villa in Leeward Settlement

5.0 out of 5 average rating, 22 reviews

Caribbean Luxury Waterfront Villa w Housekeeping

Aug 18 – 25

ﺩ.ﺇ3,419 per night

Other great vacation rentals in Leeward Settlement

Guest favorite

Home in Grace Bay

4.91 out of 5 average rating, 11 reviews

Welcome to Hope's Cottage!

Aug 30 – Sep 6

ﺩ.ﺇ1,258 per night
Guest favorite

Condo in Grace Bay

5.0 out of 5 average rating, 14 reviews

Luxury Grace Bay Beachfront - Perfection!

Mar 4 – 11

ﺩ.ﺇ3,352 per night
Guest favorite

Guest suite in Long Bay Hills

4.93 out of 5 average rating, 58 reviews

Sea La Vie - Beachside 1 bedroom Unit #7

Nov 1 – 8

ﺩ.ﺇ1,149 per night
Guest favorite

Condo in The Bight Settlement

4.97 out of 5 average rating, 74 reviews

Coral Condo on Grace Bay Beach

Mar 25 – Apr 1

ﺩ.ﺇ2,525 per night
Superhost

Villa in Providenciales

4.87 out of 5 average rating, 39 reviews

Canal Front Luxury Villa!

Jun 18 – 25

ﺩ.ﺇ4,003 per night
Guest favorite

Condo in Grace Bay

4.93 out of 5 average rating, 40 reviews

BEACH FRONT on Grace Bay Gorgeous 1 bedroom 2 bath

Jan 19 – 26

ﺩ.ﺇ2,729 per night
Guest favorite

Condo in Caicos Islands

5.0 out of 5 average rating, 16 reviews

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

Sep 20 – 27

ﺩ.ﺇ822 per night
Superhost

Apartment in Caicos Islands

4.88 out of 5 average rating, 16 reviews

Spectacular view 2 bedroom condo Grandview 205

May 9 – 16

ﺩ.ﺇ3,457 per night
Guest favorite

Home in Leeward Settlement

4.96 out of 5 average rating, 24 reviews

Pelican Paradise Villa - Leeward Beach

May 21 – 28

ﺩ.ﺇ3,763 per night
Guest favorite

Vacation home in Providenciales

4.88 out of 5 average rating, 8 reviews

Sun Villa @ The Sun and Sea Villas

Nov 26 – Dec 3

ﺩ.ﺇ1,286 per night
Superhost

Villa in Leeward Settlement

4.88 out of 5 average rating, 32 reviews

Sea Sun Relax - villa 5 min walk to Grace Bay

Sep 14 – 21

ﺩ.ﺇ1,193 per night
Superhost

Cottage in Providenciales, Turks and Caicos Islands

4.86 out of 5 average rating, 88 reviews

Welcome to Artemis Retreat!

Jul 10 – 17

ﺩ.ﺇ945 per night

Quick stats about vacation rentals in Leeward Settlement

Total rentals

310 properties

Rentals with a pool

260 properties have a pool

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

240 properties are a good fit for families

Total number of reviews

4.8K reviews

Nightly prices starting at

ﺩ.ﺇ73 before taxes and fees

Frequently Asked Questions

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

    Yes! Dive into the perfect getaway at one of over 70 house 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 $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

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

  • 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 villa rentals in Leeward Settlement?

    Leeward Settlement has more than 130 family-friendly villa rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Leeward Settlement have wifi?

    Absolutely! We offer over 30 apartment 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 30 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 vacation rentals in Leeward Settlement?

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

  • 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 70 homes with a bbq area, over 140 homes with wifi, over 30 homes with a gym, over 140 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore