Leeward Settlement vacation rentals

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Top-rated vacation rentals in Leeward Settlement

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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

Apr 12 – 19

G$78,144 GYD per night

Superhost

Guest suite in Leeward Settlement

4.91 out of 5 average rating, 89 reviews

Handfield's Hideaway Cozy One Bedrm

Spacious one bedroom, with a/c, situated in the residential area of Leeward Palms. Leeward Palms is located just 10mins (or less) from Grace Bay. Your safety is our priority; so, we have a fully enclosed yard. The community is mainly made up of working professionals and families--some of whom (our family included) have dogs as pets. Because of this, dogs may be heard barking; However, we provide earplugs to cancel any sound. The unit has a fully equipped kitchen, bathroom and bedroom.

Sep 22 – 29

G$28,653 GYD per night

Superhost

Villa in Providenciales

4.9 out of 5 average rating, 113 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.

Oct 12 – 19

G$161,692 GYD 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

Jan 10 – 17

G$134,426 GYD per night

Guest favorite

Condo in Grace Bay, Providenciales

4.99 out of 5 average rating, 111 reviews

1 Bedroom Luxury Grace Bay Condo

The perfect location, and only a 7 minute walk to world famous Grace Bay Beach! Located in the heart of Grace Bay near Seven Stars Resort and the Ritz Carlton Resort. 7 minute walk to the beach. 4 minute walk to the grocery store, and 10 minute walk to the best restaurants and shopping on the island. No rental car is needed. This 790 sq. ft. luxury one bedroom, newly built condo (Nov 2020), provides all necessary amenities for your home away from home.

Jun 23 – 30

G$77,744 GYD 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!

Dec 18 – 25

G$149,942 GYD 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.

Feb 20 – 27

G$59,690 GYD per night

Guest favorite

Guesthouse in Long Bay Hills

4.99 out of 5 average rating, 133 reviews

Juba Sunset

Waterfront Private apartment that is fully furnished. Private deck. fantastic views overlooking Juba Sound. within 7mins to Grace Bay, world famous Grace Bay Beach and shops. Very quiet and safe area. Infinity edge pool included. Glorious sunsets. BBQ on the waterfront. Only a couple of mins away from popular Kite Surfing spot. There is also a Kayak available for guests use down on the waterfront.

Aug 12 – 19

G$40,794 GYD 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.

Sep 24 – Oct 1

G$37,172 GYD per night

Guest favorite

Condo in Grace Bay

4.95 out of 5 average rating, 145 reviews

22 Middle of Gracebay, Heated Pool, Gated Condo.

Granvia is center of Gracebay, very close to Gracebay Gourmet, restaurant, there is beach access close by, 6min walking to World no.1 Gracebay Beach. Security gate, privacy, Full Kitchen with Air flyer, Washer and Dryer Wi-Fi (fastest speed on island 50MBPS) 70" Samsung 4K TV with Samsung sound bar, Cable TV, Netflix, Disney Plus, IPTV.

Dec 12 – 19

G$93,995 GYD 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.

Dec 9 – 16

G$71,966 GYD 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.

Sep 24 – Oct 1

G$37,756 GYD 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

Villa in Long Bay Hills

4.98 out of 5 average rating, 84 reviews

VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY

Nov 27 – Dec 4

G$120,304 GYD per night

Guest favorite

Condo in Leeward Settlement

5.0 out of 5 average rating, 21 reviews

Grace’s Condo In Leeward Settlement

Dec 1 – 8

G$66,296 GYD 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

Sep 3 – 10

G$97,963 GYD per night

Guest favorite

Home in Leeward Settlement

5.0 out of 5 average rating, 25 reviews

Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool

Oct 5 – 12

G$158,453 GYD per night

Guest favorite

Villa in Caicos Islands

5.0 out of 5 average rating, 46 reviews

NEW Luxe Private Pool Villa, Golf Course View, BBQ

Aug 12 – 19

G$91,553 GYD per night

Superhost

Home in Leeward Settlement

4.95 out of 5 average rating, 60 reviews

PERIWINKLE | Charming Island Home|Near to Beach

Oct 4 – 11

G$62,203 GYD per night

Guest favorite

Villa in Leeward Settlement

5.0 out of 5 average rating, 30 reviews

Perroquet | Family Villa near Leeward Beach

Sep 17 – 24

G$126,573 GYD per night

Guest favorite

Home in Leeward Settlement

4.98 out of 5 average rating, 50 reviews

Cocodemer, a short walk to secluded Pelican Beach.

Oct 24 – 31

G$79,144 GYD per night

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Other great vacation rentals in Leeward Settlement

Guest favorite

Condo in Caicos Islands

5.0 out of 5 average rating, 20 reviews

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

Oct 16 – 23

G$46,647 GYD per night

Guest favorite

Villa in The Bight Settlement

4.97 out of 5 average rating, 77 reviews

Idyllic getaway villa | 250 yds to the beach

Feb 8 – 15

G$118,710 GYD per night

Guest favorite

Condo in Providenciales

5.0 out of 5 average rating, 42 reviews

Beachy Chic / Grace Bay / Grandview on Grace Bay

Sep 7 – 14

G$151,078 GYD per night

Superhost

Guest suite in Grace Bay

4.88 out of 5 average rating, 65 reviews

55 Oasis Cottage Nearby World's #1 Grace Bay Beach

Sep 13 – 20

G$27,282 GYD per night

Guest favorite

Guesthouse in Providenciales

5.0 out of 5 average rating, 11 reviews

CoCo Lingo Guest Cottage

Mar 15 – 22

G$79,423 GYD per night

Guest favorite

Home in Grace Bay

5.0 out of 5 average rating, 14 reviews

Villa in Providenciales

Jul 27 – Aug 3

G$180,414 GYD per night

Guest favorite

Villa in Long Bay Hills

5.0 out of 5 average rating, 24 reviews

Hang Five Surf Villa in Long Bay

Jul 5 – 12

G$107,995 GYD per night

Guest favorite

Condo in Grace Bay

5.0 out of 5 average rating, 20 reviews

Luxury 2 Bedroom - Central Grace Bay

Oct 23 – 30

G$107,589 GYD 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
G$22,933 GYD before taxes and fees

Frequently Asked Questions

Are there Leeward Settlement apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 apartment 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 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 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 villa rentals in Leeward Settlement have wifi?
Absolutely! We offer over 120 villa 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 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 120 homes with air conditioning, over 120 homes with wifi, over 20 homes with a gym, 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

Houses

Apartments

Villas

Popular amenities for Leeward Settlement vacation rentals

Stay near Leeward Settlement's top sights

Other great vacation rentals in Leeward Settlement

Villa in Long Bay Hills

Condo in Leeward Settlement

Villa in Leeward Settlement

Home in Leeward Settlement

Villa in Caicos Islands

Home in Leeward Settlement

Villa in Leeward Settlement

Home in Leeward Settlement

Other great vacation rentals in Leeward Settlement

Condo in Caicos Islands

Villa in The Bight Settlement

Condo in Providenciales

Guest suite in Grace Bay

Guesthouse in Providenciales

Home in Grace Bay

Villa in Long Bay Hills

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 apartment rentals on Airbnb with pools?

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

Are there house 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 villa 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 Villa Rentals in Leeward Settlement?

Destinations to explore