Deals on vacations and trips to Leeward Settlement

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Leeward Settlement flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Bungalows at Windsong on the Reef

Bungalows at Windsong on the Reef

4 out of 5
Grace Bay
Price was $2,049, price is now $1,480 per person
$1,480
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Providenciales (PLS)
A full-service spa, 2 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. Enjoy the 3 hot tubs and free perks like continental breakfast and free self parking.
Rooftop Villa Collection

Rooftop Villa Collection

4.5 out of 5
Grace Bay
Save 100% on your flight
Price was $5,748, price is now $3,261 per person
$3,261
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Providenciales (PLS)
A full-service spa, 5 restaurants, and 3 outdoor pools are all featured at this luxury resort. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like continental breakfast and free self parking. A beach bar, a 24-hour front desk, and a coffee shop are also provided.
Long Bay Beach Club

Long Bay Beach Club

5 out of 5
Long Bay Hills
Price was $11,948, price is now $7,388 per person
$7,388
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Providenciales (PLS)
This luxury villa's private beach and 3 outdoor pools are some of the highlights. Enjoy a day at the beach scuba diving, or relax with sun loungers. Enjoy the gym and conveniences like a terrace and barbecue grills.
Beach Enclave

Beach Enclave

5 out of 5
Leeward Settlement
Save 100% on your flight
Price was $7,765, price is now $4,990 per person
$4,990
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Providenciales (PLS)
This aparthotel features an outdoor pool and a 24-hour gym. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Families will appreciate the onsite laundry facilities and in-room childcare.
Dream Villas Provo

Dream Villas Provo

3.5 out of 5
Blue Hills
Save 100% on your flight
Price was $3,219, price is now $2,242 per person
$2,242
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Providenciales (PLS)
This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and a virtual front desk are also provided.

Top Leeward Settlement hotels deals

Blue Haven Resort - All-Inclusive

Blue Haven Resort - All-Inclusive

4.5 out of 5
Leeward Marina Providenciales Providenciales
$900 nightly
The price is $900 total per night
$900 total
Sep 17 - Sep 18
Total with taxes and fees
This all-inclusive property features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a playground, and babysitting is an added bonus.
On private beach
Pool
The Atrium Resort

The Atrium Resort

3.5 out of 5
Governor's Road Providenciales Providenciales
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A full-service spa and an outdoor pool are featured at this Art Deco aparthotel. There's fun for all ages with a children's pool and an arcade/game room, and babysitting is an added bonus. Enjoy the 24-hour gym and perks like free self parking and free WiFi.
Villa Kendara~50% OFF 8/21-9/26~Beach~Private~Gated~GuestHouse~Panoramic View

Villa Kendara~50% OFF 8/21-9/26~Beach~Private~Gated~GuestHouse~Panoramic View

Long Bay Providenciales
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This guesthouse features a garden, laundry facilities, and barbecue grills.
Checkers Vacation Homes

Checkers Vacation Homes

3 out of 5
63 Grace Bay Road Providenciales Providenciales
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An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. Guests will appreciate perks like free WiFi and a free airport shuttle. A garden and barbecue grills are also provided.
Beach Enclave

Beach Enclave

5 out of 5
47 Joe Wood Drive Providenciales
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This aparthotel features an outdoor pool and a 24-hour gym. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Families will appreciate the onsite laundry facilities and in-room childcare.
Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay

Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay

providenciales Caicos Islands
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An outdoor pool is featured at this cottage, along with laundry facilities and concierge services. Barbecue grills are provided for your convenience.
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See all available properties in Leeward Settlement
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Leeward Settlement attractions

A beach with clear turquoise water, white sand, and palm trees under a bright blue sky.

Leeward Beach

9.2/10 (962 reviews)
Why not spend a carefree afternoon at Leeward Beach during your travels in Grace Bay? Amble around this romantic area's seaside, or seek out the snorkeling spots.
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Frequently asked questions

How much are vacation packages to Leeward Settlement?
$1,480 is all you need to spend for a wonderful escape in Leeward Settlement. Bundle your hotel and flights into a Travelocity vacation package and see the savings start to add up. With prices this good, there's never been a better time to travel.
How long should my Leeward Settlement vacation be?
Typically, 5 nights is what many tourists book for their Leeward Settlement trip. That's a great guide, but there's plenty more to explore if you give yourself a few extra days.
Where can I get the best vacation package deals for Leeward Settlement?
For an excellent package deal to Leeward Settlement, you can't go past Travelocity. Select from 400 partner airlines and 1,000,000 worldwide properties to create your dream trip — it couldn't be simpler.
Why should I book my Leeward Settlement vacation package with Travelocity?
With top-notch service, 24/7 customer support and some of the most idyllic getaways around, you'll never roam alone. And if you happen to find a better price, we'll match it. That's our Price Match Guarantee.
Will I save money on my Leeward Settlement car rental if I combine it with hotels and flights?
Bundling your bookings into a Leeward Settlement vacation package will certainly save you money. You can book a car and flight; a flight, car and hotel; or a car and hotel. You won't find a better way to explore the greater Leeward Settlement area than with your own ride. You can also add tours and experiences to your Travelocity package.
Which airport is best for Leeward Settlement?
You have two options for flying into Leeward Settlement, starting with Providenciales Intl. Airport (PLS). It's situated 8 mi from the center of the city, while South Caicos Airport (XSC) is 45 mi away from central Leeward Settlement.
Where should I stay when visiting Leeward Settlement?
If you're after a place to lay your head, take a look at the The Atrium Resort. It's the top choice for many visitors.

Photos of local treasures

Browse Leeward Settlement vacation photos for more inspiration

A beach with thatched umbrellas and a clear blue sea.
A beach with people walking, clear blue water, and green vegetation in the foreground.
An outdoor restaurant with tables and chairs, palm trees, and the ocean in the background.
A beach with turquoise water, white sand, and rocky outcrops.
A beach with pink umbrellas, sun loungers, and palm trees.