Leeward Settlement Vacation Packages 2026 from $2,274

Leeward Settlement flight + hotel vacation packages

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

Windsong on the Reef

Grace Bay

Save 100% on your flight

$2,274

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Providenciales (PLS)

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.

Dream Villas Provo

Save 100% on your flight

$2,867

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Beachfront at Windsong on the Reef

Grace Bay

Save 100% on your flight

$3,039

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Providenciales (PLS)

A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury hotel. Enjoy the 3 hot tubs and free perks like continental breakfast and free self parking. Make the most of the 24-hour gym and a rooftop terrace, and relax with drinks at one of the 3 bars/lounges.

The Park at Grace Bay

Grace Bay

Save 100% on your flight

$3,179

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Providenciales (PLS)

This condo resort features an outdoor pool and a bar/lounge. Families will appreciate the free kid's club, barbecue grills, and in-room childcare. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free beach shuttle.

Rock House

Save 100% on your flight

$5,864

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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

$1,229 nightly

$1,229 total

Apr 10 - Apr 11

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

Get rates

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

Checkers Vacation Homes

63 Grace Bay Road Providenciales Providenciales

Get rates

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

Beach Enclave

47 Joe Wood Drive Providenciales

Get rates

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.

Pool

Breakfast included

Villa Kendara~BK 3/28-4/4 & ON~Beachfront~Private~Gated Guesthouse~Panorama View

Long Bay Providenciales

Get rates

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

Pool

Free WiFi

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

providenciales Caicos Islands

Get rates

An outdoor pool is featured at this cottage, along with laundry facilities and concierge services. Barbecue grills are provided for your convenience.

Pool

Kitchen

Don't see what you're looking for?

See all available properties in Leeward Settlement

View all properties

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

Beach vacation paradise woman tourist walking alone on remote island in the tuamotu islands, French Polynesia. Luxury travel destination. Panoramic banner.

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.

Provo Conch Farm

4/5(33 reviews)

You can learn about the history of Providenciales with a visit to Provo Conch Farm. Stroll along the seaside or discover the beautiful coral reefs in this romantic area.

Frequently asked questions

How much are vacation packages to Leeward Settlement?

$2,274 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.