Leeward Settlement Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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Leeward Settlement Flight + Hotel packages

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

Windsong on the Reef

Grace Bay
Save 100% on your flight
$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

Rooftop Villa Collection

Grace Bay
Save 100% on your flight
$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 Beach Club

Long Bay Hills
Save 100% on your flight
$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.
.

Reviewed on Aug 3, 2026

Dream Villas Provo

Dream Villas Provo

Blue Hills
Save 100% on your flight
$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

Beachfront at Windsong on the Reef

Grace Bay
Save 100% on your flight
$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

Bungalows at Windsong on the Reef

Grace Bay
Save 100% on your flight
$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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Top Hotel Deals

Blue Haven Resort - All-Inclusive

Blue Haven Resort - All-Inclusive

Leeward Marina Providenciales Providenciales
0.59 km from Leeward Settlement
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

The Atrium Resort

Governor's Road Providenciales Providenciales
0.98 km from Leeward Settlement
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

Checkers Vacation Homes

63 Grace Bay Road Providenciales Providenciales
1.81 km from Leeward Settlement
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

The Ritz-Carlton, Turks & Caicos

Grace Bay Road Providenciales
3.6 km from Leeward Settlement
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

Hotel Indigo Turks Caicos Grace Bay by IHG

Forbes Road Providenciales
6.33 km from Leeward Settlement
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

Royal West Indies Resort

Grace Bay Rd Providenciales Providenciales
2.63 km from Leeward Settlement
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

Windsong on the Reef

Stubbs Rd Providenciales Providenciales
6.45 km from Leeward Settlement
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

Wymara Resort and Villas

Lower Bight Road Providenciales Providenciales
7.22 km from Leeward Settlement
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

Alexandra Resort - All-Inclusive

Princess Dr, Grace Bay Providenciales Providenciales
5.17 km from Leeward Settlement
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

West Bay Club

Lower Bight Road Bldg A Providenciales Providenciales
7.11 km from Leeward Settlement
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

The Sands at Grace Bay

Grace Bay Beach Providenciales
4.5 km from Leeward Settlement
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

Zenza Boutique Hotel

Bridge Rd. Providenciales Caicos Islands
8.55 km from Leeward Settlement
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

Rock House

1 International Drive Providenciales
10.11 km from Leeward Settlement
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

Seven Stars Resort & Spa

Grace Bay Road Providenciales Providenciales
3.48 km from Leeward Settlement
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

Ports of Call Resort Turks, Tapestry Collection by Hilton

Grace Bay Road Providenciales
3.53 km from Leeward Settlement
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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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.

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.

JetBlue Airways
Delta
Sat, Nov 14 - Sat, Nov 21
JFK
John F. Kennedy Intl.
PLS
Providenciales Intl.
$411
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 14 from John F. Kennedy Intl. to Providenciales Intl., returning Sat, Nov 21, priced at $411 found 1 day ago
United
Sun, Jan 10 - Sat, Jan 16
EWR
Newark Liberty Intl. Airport
PLS
Providenciales Intl.
$411
Roundtrip
found 12 hours ago
Select United flight, departing Sun, Jan 10 from Newark Liberty Intl. Airport to Providenciales Intl., returning Sat, Jan 16, priced at $411 found 12 hours ago
American Airlines
BermudAir
Sat, Jan 9 - Thu, Jan 21
EWR
Newark Liberty Intl. Airport
PLS
Providenciales Intl.
$559
Roundtrip
found 4 days ago
Select BermudAir flight, departing Sat, Jan 9 from Newark Liberty Intl. Airport to Providenciales Intl., returning Thu, Jan 21, priced at $559 found 4 days ago