Leeward Settlement vacation rentals

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Top-rated vacation rentals in Leeward Settlement

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

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Guest favorite

Villa in Long Bay Hills

4.98 out of 5 average rating, 84 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

Oct 4 – 11

R10,860 ZAR per night

Guest favorite

Guesthouse in Long bay

4.96 out of 5 average rating, 68 reviews

Villa Kendara~BK 7/13 & 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

Mar 1 – 8

R7,125 ZAR per night

Superhost

Villa in Providenciales

4.9 out of 5 average rating, 112 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.

Jul 6 – 13

R11,958 ZAR per night

Guest favorite

Condo in Leeward Settlement

4.95 out of 5 average rating, 40 reviews

New! Luxury 1Bed Large Condo

The perfect large condo, and only 3 minutes from the famous Grace Bay Beach! Located in the exclusive Leeward area, a gated, secure residential area where all the major luxury villas are. The beach is a short stroll away & the main Grace Bay shopping / resort area is 5 minutes by car. The condo boasts a large pool, stunning modern finish and appliances. This 925 sq. ft. luxury one bedroom, freshly renovated in Feb 2023, provides all necessary amenities for your home away from home.

Jun 22 – 29

R6,088 ZAR per night

Guest favorite

Condo in Leeward Settlement

5.0 out of 5 average rating, 21 reviews

Grace’s Condo In Leeward Settlement

Caribbean Diamond Residences is a quiet condominium located inside the exclusive and secured Leeward Settlement. Our ground floor Condo is a short 5-7 minute walk from the beautiful and picturesque Sunset Beach. The complex offers a walk-in pool, plenty of chaise loungers, outdoor furniture and BBQ grills to enjoy. We are a short 5-minute drive down Grace Bay Road to all the shopping and activities that Grace Bay has to offer, or a 15-20 minute bike ride along the sidewalk.

Jun 6 – 13

R5,825 ZAR per night

Guest favorite

Condo in Providenciales

4.9 out of 5 average rating, 195 reviews

★★★★★ Modern Condo | Amazing Pool | On Site Spa

• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub • Highest Rated Spa on Island • Fully equipped kitchen • Private front patio + grill • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Nov 6 – 13

R8,590 ZAR per night

Guest favorite

Home in Grace Bay

4.98 out of 5 average rating, 111 reviews

Follow Your Dreams Villa!

This a New Super Cool Upper Floor Loft Bedroom for one couple. Private Pool! Downstairs full Kitchen and 65" Giant TV entertainment area! Full Kitchen, Dishwasher, Laundry, all you need & more. Just behind Coco Bistro/Coco Van and 2 minutes by car to Beach! Grace Bay Beach that is! This is a Totally Private Villa for 2 Guests Only! Just landscaped with Palms around the Private pool! Great Location & New! Thanks for checking out "Follow Your Dreams!

Mar 8 – 15

R8,713 ZAR per night

Guest favorite

Home in Grace Bay

4.8 out of 5 average rating, 122 reviews

Tropical Guest House

Guest house, stylish and cozy with cold AC. Nested in a Tropical Nursery Garden on back of a semi-detached Villa. Well equipped! Studio. 15 Minute walk to beach, less than a minute by car. Best way to see all island and beaches is to rent a car!! Coco Bistro and Coco Van is just down the road! Easy access to all kind of shops and grocery store. Grill on your deck for your private use. Great Value location & close to Grace Bay Beach!

Jan 15 – 22

R4,132 ZAR per night

Guest favorite

Cottage in Leeward Settlement

4.96 out of 5 average rating, 68 reviews

Sandpiper Cottage, minutes from the beach

Kick back and relax in this delightful modern one bedroom cottage in the high end residential gated community of Leeward. Grace Bay Beach, most recently voted “The best in the world” is only a 4 minute walk away! This cozy cottage is perfect for a couple, wanting to relax and have some downtime. Complete with full kitchen, washer/dryer/ BBQ, high speed internet with cable TV and all amenities needed for the perfect getaway.

Aug 24 – 31

R4,357 ZAR per night

Guest favorite

Apartment in Grace Bay

4.86 out of 5 average rating, 112 reviews

Crescent #1 Grace bay (beach 2 min walk)

Our small studio apartment is setup in a new house (built 2020) with its own private access, nice and quiet neighbourhood. Studio is close to the main attractions, bars, groceries, restaurants and about 2 minutes walking distance to the nicest beach in the world Grace Bay beach. No car needed. Place is good for couples and solo adventurers. Apartment is a open concept only door for the bathroom.

Aug 21 – 28

R3,389 ZAR per night

Guest favorite

Apartment in Leeward Settlement

4.95 out of 5 average rating, 231 reviews

Leisure in Paradise

Wake up on a Mocking bird singing in the garden, sun rays sparkling through the lush green while you drink your cup of tea or coffee on your private screened patio. Take a walk in the topical garden and have a refreshing swim in crystal clear pool or take a short walk (3 minute) to the turquoise ocean and white sandy beach.

Mar 7 – 14

R7,305 ZAR per night

Superhost

Loft in Providenciales and West Caicos

4.84 out of 5 average rating, 44 reviews

Cozy Loft Condo Great Location w/Pool

Located in the perfect spot, Just minutes away from Grace Bay Beach, Restaurants, Supermarkets and attractions, this loft style apartment is the perfect couple's getaway to come enjoy and relax in the beautiful Turks and Caicos Islands. Apartment was newly renovated in September 2022.

Oct 10 – 17

R3,442 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Leeward Settlement vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

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

Home in Leeward Settlement

5.0 out of 5 average rating, 24 reviews

Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool

Oct 21 – 28

R16,507 ZAR 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

Jan 18 – 25

R16,085 ZAR 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

R17,685 ZAR 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

Aug 1 – 8

R9,738 ZAR per night

Guest favorite

Home in Leeward Settlement

4.95 out of 5 average rating, 60 reviews

PERIWINKLE | Charming Island Home|Near to Beach

Mar 18 – 25

R6,152 ZAR per night

Superhost

Guest suite in Leeward Settlement

4.91 out of 5 average rating, 89 reviews

Handfield's Hideaway Cozy One Bedrm

Jun 7 – 14

R2,633 ZAR per night

Guest favorite

Home in Leeward Settlement

4.98 out of 5 average rating, 49 reviews

Cocodemer, a short walk to secluded Pelican Beach.

Mar 9 – 16

R7,216 ZAR per night

Superhost

Home in Grace Bay

5.0 out of 5 average rating, 4 reviews

3 King Bedroom Villa, Grace Bay - Sanmar Villa

Oct 1 – 8

R17,735 ZAR per night

Show all

Other great vacation rentals in Leeward Settlement

Guest favorite

Guesthouse in Providenciales

5.0 out of 5 average rating, 11 reviews

CoCo Lingo Guest Cottage

Mar 22 – 29

R7,241 ZAR per night

Superhost

Villa in Providenciales

4.83 out of 5 average rating, 41 reviews

Canal Front Luxury Villa!

Sep 17 – 24

R21,398 ZAR per night

Guest favorite

Villa in Long Bay Hills

5.0 out of 5 average rating, 23 reviews

Hang Five Surf Villa in Long Bay

Dec 1 – 8

R13,273 ZAR per night

Guest favorite

Home in Providenciales

5.0 out of 5 average rating, 16 reviews

Villa Rae House in Long Bay Hills~walk to beach

Sep 9 – 16

R4,129 ZAR per night

Guest favorite

Home in Long Bay Hills

4.82 out of 5 average rating, 17 reviews

Vision Kite- Longbay beach house

Nov 19 – 26

R14,541 ZAR per night

Guest favorite

Home in Grace Bay

5.0 out of 5 average rating, 14 reviews

Villa in Providenciales

Sep 26 – Oct 3

R13,130 ZAR per night

Superhost

Cottage in Providenciales, Turks and Caicos Islands

4.87 out of 5 average rating, 90 reviews

Welcome to Artemis Retreat!

Jul 25 – Aug 1

R4,891 ZAR per night

Guest favorite

Condo in Grace Bay

5.0 out of 5 average rating, 14 reviews

Luxury Grace Bay Beachfront - Perfection!

Mar 2 – 9

R16,886 ZAR per night

Show all

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
R2,091 ZAR 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.

Leeward Settlement vacation rentals

Top-rated vacation rentals in Leeward Settlement

Vacation rentals for every style

Apartments

Houses

Villas

Popular amenities for Leeward Settlement vacation rentals

Stay near Leeward Settlement's top sights

Other great vacation rentals in Leeward Settlement

Home in Leeward Settlement

Villa in Leeward Settlement

Villa in Leeward Settlement

Villa in Caicos Islands

Home in Leeward Settlement

Guest suite in Leeward Settlement

Home in Leeward Settlement

Home in Grace Bay

Other great vacation rentals in Leeward Settlement

Guesthouse in Providenciales

Villa in Providenciales

Villa in Long Bay Hills

Home in Providenciales

Home in Long Bay Hills

Home in Grace Bay

Cottage in Providenciales, Turks and Caicos Islands

Condo in Grace Bay

Quick stats about vacation rentals in Leeward Settlement

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there Leeward Settlement villa rentals on Airbnb with pools?

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

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

Do villa rentals in Leeward Settlement have a bbq area?

Are there family-friendly house rentals in Leeward Settlement?

Do condo rentals in Leeward Settlement have wifi?

Do villa rentals in Leeward Settlement have a gym?

Do apartment rentals in Leeward Settlement have air conditioning?

Are there pet-friendly house rentals in Leeward Settlement?

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

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