Leeward Settlement Vacation Packages 2026 from $1,655

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

$1,655

per person

Feb 27 - Mar 6

found 1 day 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.

Dream Villas Provo

$3,173

per person

Feb 27 - Mar 6

found 1 day ago

Roundtrip 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.

Zenza Boutique Hotel

Turtle Cove

$2,743

per person

Feb 27 - Mar 6

found 1 day 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.

Checkers Vacation Homes

Grace Bay

Save 100% on your flight

$4,568

per person

Feb 27 - Mar 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Providenciales (PLS)

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.

Top Leeward Settlement hotels deals

Blue Haven Resort - All-Inclusive

Leeward Marina Providenciales Providenciales

$1,106 nightly

$1,106 total

Feb 21 - Feb 22

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

Beach Enclave

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.

Pool

Breakfast included

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

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

Silver Palms # 2 – Exclusive Long Bay Beachfront Retreat with Pool

Providenciales Caicos Islands

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

Pool

Kitchen

Windsong on the Reef

Stubbs Rd Providenciales Providenciales

$602 nightly

$728 total

Jan 29 - Jan 30

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

4.5/5(164 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.

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 romantic area's seaside, or seek out the snorkeling spots.

I've visited and lived by a few beaches, but this place has the finest powered sand and clearest bright see though water I've ever experienced, other than St. Marteen. Now I've not been to the Fiji Islands yet, or Aruba, ...so I'm still experimenting. However, this is a great place to relax and unwind from the world.

Providenciales Beaches

5/5(229 reviews)

Why not spend a lazy afternoon at Providenciales Beaches during your trip to Grace Bay? Amble around this romantic area's beautiful beaches, or seek out the snorkeling spots.

Frequently asked questions

How much are vacation packages to Leeward Settlement?

$1,655 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.