Leeward Settlement Vacation Packages 2025/2026 from $2,205

Leeward Settlement flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Callaloo Cottage

Turtle Cove

Save 100% on your flight

$2,205

per person

Jan 5 - Jan 9

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

An outdoor pool, free self parking, and laundry facilities are featured at this cottage. WiFi in public areas is free. A terrace, a garden, and barbecue grills are also on offer.

Dream Villas Provo

$2,649

per person

Jan 21 - Jan 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

This condo resort doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and a virtual front desk are also provided.

Long Bay Beach Club

Long Bay

Save 100% on your flight

$8,414

per person

Dec 21 - Dec 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

This smoke-free 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. A terrace, a garden, and barbecue grills are also on offer.

Point Grace

Grace Bay

$4,123

per person

Jan 21 - Jan 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this luxury resort. Business travelers can take advantage of the free WiFi in public areas. Enjoy the 24-hour gym and free perks like continental breakfast and free self parking.

West Bay Club

Grace Bay

$3,120

per person

Jan 21 - Jan 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

This luxury resort includes 2 restaurants, an outdoor pool, and a gym. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like full breakfast and free self parking.

Top Leeward Settlement hotels deals

Blue Haven Resort - All-Inclusive

Leeward Marina Providenciales Providenciales

$841 nightly

$841 total

Dec 18 - Dec 19

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

Checkers Vacation Homes

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.

Pool

Free airport shuttle

The Atrium Resort

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.

Pool

Hot Tub

Beach Enclave

47 Joe Wood Drive Providenciales

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This aparthotel features an outdoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and dry cleaning are also on offer.

Pool

Breakfast included

Villa Kendara~BOOK Jan 10-17~BeachFront~Private~Gated~GuestHouse~Panoramic View

Long Bay Providenciales

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A hot tub is featured at this guesthouse, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Pool

Hot Tub

Villa Tropica - Near Grace Bay Beach - Newly Remodelled

Providenciales Caicos Islands

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An outdoor pool is featured at this villa, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Pool

Kitchen

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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.

Popular places to visit

Beautiful small remote beach!! Breathtakingly beautiful!!

Leeward Beach

4.5/5(164 reviews)

Why not spend a carefree afternoon at Leeward Beach during your travels in Grace Bay? Amble around this relaxing area's seaside, or seek out the snorkeling spots.

Grace Bay Beach

5/5(1,015 reviews)

Nothing says vacation like spending a lazy day at Grace Bay Beach, a popular beach in Grace Bay. Amble around this relaxing area's seaside, or seek out the snorkeling spots.

Chalk Sound National Park

4.5/5(179 reviews)

Explore the great outdoors at Chalk Sound National Park, a lovely green space in Providenciales. Stroll along the beautiful beaches in this relaxing area, or seek out the snorkeling spots.

Frequently asked questions

How much are vacation packages to Leeward Settlement?

$2,205 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.