Leeward Settlement flight + hotel vacation packages

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

Dream Villas Provo

$2,337

per person

Feb 7 - Feb 13

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.

Point Grace

Grace Bay

$3,912

per person

Feb 7 - Feb 13

found 1 day ago

Roundtrip 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.

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.

West Bay Club

Grace Bay

Save 100% on your flight

$3,040

per person

Feb 7 - Feb 13

found 1 day 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.

Rock House

Save 100% on your flight

$2,865

per person

Feb 7 - Feb 13

found 1 day ago

Roundtrip 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

$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.

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.