Leeward Settlement Vacation Packages 2026 from $1,336

Leeward Settlement flight + hotel vacation packages

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

Kokomo Botanical Resort - Caribbean Family Cottages

The Bight

Save 100% on your flight

$1,336

per person

Feb 27 - Mar 5

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Providenciales (PLS)

This hotel features an outdoor pool, a hot tub, and a restaurant. Enjoy the a rooftop terrace and perks like free self parking and a free beach shuttle. A bar/lounge, a terrace, and a garden are also provided.

Bungalows at Windsong on the Reef

Grace Bay

$2,351

per person

Feb 27 - Mar 5

found 22 hours ago

Roundtrip flight included

Boston (BOS) 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.

The Strand Turks and Caicos

Save 100% on your flight

$2,866

per person

Feb 27 - Mar 5

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Providenciales (PLS)

This smoke-free hotel features a private beach, a marina, and a restaurant. Families will appreciate babysitting, along with kayaking. Enjoy the outdoor pool and perks like free WiFi.

Zenza Boutique Hotel

Turtle Cove

Save 100% on your flight

$1,441

per person

Feb 27 - Mar 5

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Providenciales (PLS)

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and outdoor pool are some of the featured amenities. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free beach shuttle. A coffee shop, a terrace, and luggage storage are also on offer.

West Bay Club

Grace Bay

Save 100% on your flight

$3,324

per person

Feb 27 - Mar 5

found 21 hours ago

Roundtrip 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

$1,130 nightly

$1,130 total

Jan 16 - Jan 17

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

Long Bay Providenciales

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This guesthouse features a garden, laundry facilities, and barbecue grills.

Pool

Free WiFi

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 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

Windsong on the Reef

Stubbs Rd Providenciales Providenciales

$611 nightly

$738 total

Jan 18 - Jan 19

Total with taxes and fees

A full-service spa, 2 outdoor pools, and a 24-hour gym are all featured at this smoke-free resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate barbecue grills, kid-friendly dining, and in-room childcare.

Pool

Hot Tub

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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?

$1,336 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.