Leeward Settlement Vacation Packages 2025/2026 from $1,577

Leeward Settlement flight + hotel vacation packages

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

Bungalows at Windsong on the Reef

Grace Bay

$1,577

per person

Dec 7 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

A full-service spa, 2 restaurants, and 2 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 24-hour gym and free perks like continental breakfast and free self parking.

Villa private Pool Long bay Hill

Long Bay

$2,108

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

An outdoor pool is available at this villa.

Long Bay Beach Club

Long Bay

$7,708

per person

Nov 7 - Nov 13

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

Save 100% on your flight

$1,983

per person

Dec 7 - Dec 13

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. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.

Rock House

$4,103

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

2 outdoor tennis courts, an outdoor pool, and a 24-hour gym are all featured at this smoke-free hotel. Enjoy a meal from the restaurant and perks like free continental breakfast and free self parking. A bar/lounge, a 24-hour front desk, and a beach bar are also provided.

Top Leeward Settlement hotels deals

Blue Haven Resort - All Inclusive

Leeward Marina, Providenciales, Providenciales

$679 nightly

$679 total

Oct 25 - Oct 26

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

Governor's Road, Leeward, 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

Villa Tropica - Near Grace Bay Beach - Newly Remodelled

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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.

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

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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.

Popular ocean front villa now offering 20% off for Sept and Oct.

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This villa featured laundry facilities and barbecue grills.

Pool

Kitchen

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.

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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

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.

Grace Bay Beach

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

Turtle Cove showing general coastal views and a bay or harbor

Turtle Cove Marina

Explore the waterfront in Providenciales with a trip to Turtle Cove Marina. Stroll along the seaside in this romantic area, or check out its top-notch restaurants.

Frequently asked questions

How much are vacation packages to Leeward Settlement?

$1,577 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.