Leeward Settlement Vacations from $1,551

Book a Hotel + Flight or Car together to unlock savings

Your Leeward Settlement Vacation

Say farewell to planning hassles and hello to a Leeward Settlement vacation package. With your travel details organized before you leave, you can focus on discovering this city, starting with Grace Bay Hills, which is great for families, watersports and coastal beaches. If your trip to Leeward Settlement includes some sightseeing, drop by much-loved attractions like Grace Bay Beach, Turtle Cove and Providenciales Beaches. Whoever you're taking time off with and whatever your bank balance, your dream Leeward Settlement vacation is just clicks away with Expedia.

The Latest Leeward Settlement Vacation Packages

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

Windsong on the Reef

4.5 out of 5
Grace Bay
Save 100% on your flight
Price was $2,618, price is now $1,551 per person
$1,551
per person
Jun 4 - Jun 9
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
9.2/10 Wonderful! (1,026 reviews)
Everything was great

Reviewed on Mar 12, 2026

Dream Villas Provo

Dream Villas Provo

4 out of 5
Save 100% on your flight
Price was $3,598, price is now $1,968 per person
$1,968
per person
Jun 4 - Jun 9
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
9/10 Wonderful! (58 reviews)
Excellent location. Walking distance to 2 restaurants, small store across street. Very clean and modern. Comfortable beds. Everything you need for a relaxing beach vacation!

Reviewed on Feb 26, 2026

Beachfront at Windsong on the Reef

Beachfront at Windsong on the Reef

5 out of 5
Grace Bay
Save 100% on your flight
Price was $3,687, price is now $2,102 per person
$2,102
per person
Jun 4 - Jun 9
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
9.2/10 Wonderful! (118 reviews)
-The free bikes need upgrading -Wish there was a place to hose off sand on your feet after coming from the beach -Rooftop restaurant had excellent food. We had prime rib and it was the best ! -Loved our room at the Beachfront at Windsong -Liked using phone number to get into room

Reviewed on Mar 13, 2026

The Park at Grace Bay

The Park at Grace Bay

4 out of 5
Grace Bay
Save 100% on your flight
Price was $3,585, price is now $2,191 per person
$2,191
per person
Jun 4 - Jun 9
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
No reviews
The Strand Turks and Caicos

The Strand Turks and Caicos

4.5 out of 5
Save 100% on your flight
Price was $3,494, price is now $2,157 per person
$2,157
per person
Jun 4 - Jun 9
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
8.8/10 Excellent! (6 reviews)
Staff was fantastic and service was excellent.

Reviewed on Feb 20, 2026

Where to stay in Leeward Settlement

Find the best Leeward Settlement areas and neighborhoods for the activities you enjoy most. Learn more about Leeward Settlement
Grace Bay which includes a sandy beach, tropical scenes and a house

Grace Bay

3 out of top 10 points of interest in this area

This picturesque stretch of white sand and warm, turquoise water is home to luxury resorts, restaurants and one of the world’s largest barrier reefs.

Find hotels in Grace Bay

Leeward Settlement Hotel Deals

Blue Haven Resort - All-Inclusive

Blue Haven Resort - All-Inclusive

4.5 out of 5
Leeward Marina Providenciales Providenciales
$1,365 nightly
The price is $1,365 total per night from Mar 16 to Mar 17
$1,365 total
Mar 16 - Mar 17
Total with taxes and fees
9/10 Wonderful! (711 reviews)
Nice room with view of mostly the pool area but waterways and mangroves in the background

Reviewed on Mar 12, 2026

Blue Haven Resort - All-Inclusive
The Atrium Resort

The Atrium Resort

3.5 out of 5
Governor's Road Providenciales Providenciales
Get rates
The Atrium Resort
Checkers Vacation Homes

Checkers Vacation Homes

3 out of 5
63 Grace Bay Road Providenciales Providenciales
7.6/10 Good! (47 reviews)
We enjoyed our stay at Checkers. The pool area was very clean and the pool was perfect for a lap or 2! The room was perfect for 2 people and clean! The office staff were a pleasure to deal with. I would recommend this property to friends and

Reviewed on Mar 9, 2026

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Checkers Vacation Homes
See all 1,690 properties in Leeward Settlement
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Leeward Settlement

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

Leeward Beach

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.

Leeward Beach

Provo Conch Farm

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.

Provo Conch Farm

Things to do

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)

$122
per adult
96% of travellers recommend
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)
VIP Arrival Fast Track Service

Airport Fast Track Arrival Service - SkyPass Caribbean

$76
per adult
100% of travellers recommend
Airport Fast Track Arrival Service - SkyPass Caribbean
Half-Day Snorkeling & Conch Cruise with Beach Picnic

Half-Day Snorkeling Cruise

$148
per adult
94% of travellers recommend
Half-Day Snorkeling Cruise
See all activities in Providenciales
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.