
Leeward Settlement Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Leeward Settlement Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Windsong on the Reef
Grace Bay
$1,306
per person
Oct 22 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Providenciales (PLS)
Book a stay at this luxury resort in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grace Bay Beach and Long Bay Beach are located nearby.

Rooftop Villa Collection
Grace Bay
$3,267
per person
Oct 22 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Providenciales (PLS)
Book a stay at this luxury resort in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Grace Bay Beach and Long Bay Beach are located nearby.

Long Bay Beach Club
Long Bay Hills
$3,863
per person
Oct 22 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Providenciales (PLS)
Book a stay at this luxury villa in Providenciales. Enjoy free WiFi, 3 outdoor pools, and a private beach. Popular attractions Grace Bay Beach and Long Bay Beach are located nearby.
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Reviewed on Aug 3, 2026

Dream Villas Provo
Blue Hills
$1,797
per person
Oct 22 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Providenciales (PLS)
Book a stay at this beach villa in Providenciales. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Grace Bay Beach and Thompson's Cove are located nearby.

Beachfront at Windsong on the Reef
Grace Bay
$1,602
per person
Oct 22 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Providenciales (PLS)
Book a stay at this luxury hotel in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Grace Bay Beach and Long Bay Beach are located nearby.
This was our first time in this hotel and it was absolutely amazing experience. The room was spotless and the staff went above and beyond to meet our needs. The views and the beach were great. Overall this was the most enjoyable and wonderful experience…we will definitely be back to this hotel very soon.
Reviewed on Aug 30, 2026

Bungalows at Windsong on the Reef
Grace Bay
$1,661
per person
Oct 22 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Providenciales (PLS)
Book a stay at this beach hotel in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Grace Bay Beach and Long Bay Beach are located nearby.
We had an AMAZING stay. The property is well maintained. Amenities convenient. Food GOOD. Staff EXCEPTIONAL! Shout Out to Raheem!
Reviewed on Aug 6, 2026
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See all available trips from Columbus to Leeward Settlement
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Blue Haven Resort - All-Inclusive
Leeward Marina Providenciales Providenciales
Book a stay at this luxury property in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

The Atrium Resort
Governor's Road Providenciales Providenciales
Book a stay at this spa aparthotel in Providenciales. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Grace Bay Beach and Long Bay ...

Checkers Vacation Homes
63 Grace Bay Road Providenciales Providenciales
Stay at this aparthotel in Providenciales. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Grace Bay Beach and Long Bay Beach are located ...

The Ritz-Carlton, Turks & Caicos
Grace Bay Road Providenciales
Book a stay at this luxury hotel in Providenciales. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...

Hotel Indigo Turks Caicos Grace Bay by IHG
Forbes Road Providenciales
Stay at this hotel in Providenciales. Enjoy free WiFi, free parking, and a free beach shuttle. Popular attractions Grace Bay Beach and Long Bay Beach are located ...

Royal West Indies Resort
Grace Bay Rd Providenciales Providenciales
Book a stay at this beach hotel in Providenciales. Enjoy free parking, 2 outdoor pools, and a beach locale. Our guests praise the pool and the restaurant in ...

Windsong on the Reef
Stubbs Rd Providenciales Providenciales
Book a stay at this luxury resort in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...

Wymara Resort and Villas
Lower Bight Road Providenciales Providenciales
Book a stay at this luxury resort in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...

Alexandra Resort - All-Inclusive
Princess Dr, Grace Bay Providenciales Providenciales
Book a stay at this beach property in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...

West Bay Club
Lower Bight Road Bldg A Providenciales Providenciales
Book a stay at this luxury resort in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

The Sands at Grace Bay
Grace Bay Beach Providenciales
Book a stay at this beach hotel in Providenciales. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms ...

Zenza Boutique Hotel
Bridge Rd. Providenciales Caicos Islands
Stay at this hotel in Providenciales. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...

Rock House
1 International Drive Providenciales
Book a stay at this luxury hotel in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...

Seven Stars Resort & Spa
Grace Bay Road Providenciales Providenciales
Book a stay at this luxury resort in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in ...

Ports of Call Resort Turks, Tapestry Collection by Hilton
Grace Bay Road Providenciales
Book a stay at this beach hotel in Providenciales. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
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See all available properties in Leeward Settlement
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Nov 13 - Sat, Nov 21
JFK
John F. Kennedy Intl.
PLS
Providenciales Intl.
$401
Roundtrip
found 1 day ago

Sat, Nov 14 - Sat, Nov 21
JFK
John F. Kennedy Intl.
PLS
Providenciales Intl.
$411
Roundtrip
found 1 day ago

Sun, Jan 10 - Sat, Jan 16
EWR
Newark Liberty Intl. Airport
PLS
Providenciales Intl.
$411
Roundtrip
found 12 hours ago

Sat, Nov 14 - Sat, Nov 21
JFK
John F. Kennedy Intl.
PLS
Providenciales Intl.
$430
Roundtrip
found 1 day ago
Sat, Jan 9 - Thu, Jan 21
EWR
Newark Liberty Intl. Airport
PLS
Providenciales Intl.
$559
Roundtrip
found 4 days ago
Best points of interest in Providenciales
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