Prickly Pear Cays Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Prickly Pear Cays Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Coralito Bay Suites & Villas

Coralito Bay Suites & Villas

3.5 out of 5
Price was CA $2,036, price is now CA $1,784 per person
CA $1,784
per person
Jul 13 - Jul 17
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
9.8/10 Exceptional! (20 reviews)
We loved our stay at Coralito Bay. Our apartment was clean, comfortable and decorated well. The location was fabulous. Quiet, peaceful, lovely landscaping, beautiful view of the bay/Saint Martin, and at maximum, a 20 minute drive to anywhere we wanted to go. Ivor and the other staff we interacted with were warm, friendly and helpful. We would definitely stay there again!

Reviewed on Apr 26, 2026

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was CA $6,097, price is now CA $4,265 per person
CA $4,265
per person
Jul 13 - Jul 17
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
9.6/10 Exceptional! (196 reviews)
Beautiful oceanfront hotel with two golf courses, amazing restaurants, quiet pool area an the a waterpark for kids.

Reviewed on Mar 16, 2026

Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Price was CA $4,745, price is now CA $3,676 per person
CA $3,676
per person
Jul 13 - Jul 17
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
9.4/10 Exceptional! (98 reviews)
Great location on Meads Bay with easy access to beach. Great food, drinks, and sunsets.

Reviewed on May 17, 2026

Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Price was CA $3,954, price is now CA $3,276 per person
CA $3,276
per person
Jul 13 - Jul 17
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
9.8/10 Exceptional! (41 reviews)
Property well maintained. Only complaints no tea available in room and we were charged US $9 for tea by F&B personnel named P (female). Very disappointed. Special thanks to Simone, Arlan and Shawn along with the room staff and grounds keepers.

Reviewed on May 14, 2026

Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was CA $2,824, price is now CA $2,417 per person
CA $2,417
per person
Jul 13 - Jul 17
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
9/10 Wonderful! (34 reviews)
Title: Incredible Paradise – Best with a bit of Pre-Planning! Our vacation was truly amazing. The Rendezvous Bay Hotel has an incredible beachfront location and our rooms were perfect. The amenities and staff were excellent. Anguilla is absolute paradise. The people, the food and the scenery are second to none. A few tips for future guests: getting to and from the hotel can become expensive, so a car rental is almost a must if you want to explore. Time can be limited, so I highly recommend arranging payments for your activities and transportation before you arrive. It can be a bit costly and challenging to coordinate once you're there. Planning ahead ensures you can just relax and enjoy the island!

Reviewed on Apr 18, 2026

Ready to book your vacation to Prickly Pear Cays?

 

Choose your dates

Prickly Pear Cays Hotel Deals

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
The price is CA $1,138 per night from Jun 30 to Jul 1
CA $1,138
CA $1,448 total
Jun 30 - Jul 1
includes taxes & fees
9.6/10 Exceptional! (251 reviews)
"Amazing location, great separation between the pools, very quiet."

Reviewed on Jun 1, 2026

Four Seasons Resort and Residences Anguilla
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Maundays Bay Maunday's Bay
The price is CA $1,875 per night from Jun 16 to Jun 17
CA $1,875
CA $2,307 total
Jun 16 - Jun 17
includes taxes & fees
9.6/10 Exceptional! (143 reviews)
"Beautiful scenery of miles of coastline and mountains and nearby islands!"

Reviewed on May 22, 2026

Cap Juluca, A Belmond Hotel, Anguilla
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay Rendezvous Bay
Fully refundableReserve now, pay when you stay
The price is CA $1,105 per night from Jul 1 to Jul 2
CA $1,105
CA $1,398 total
Jul 1 - Jul 2
includes taxes & fees
9.6/10 Exceptional! (196 reviews)
"Beautiful oceanfront hotel with two golf courses, amazing restaurants, quiet pool area an the a waterpark for kids."

Reviewed on Mar 16, 2026

Aurora Anguilla Resort & Golf Club
See all 358 properties in Prickly Pear Cays
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
Family Vacations
Family Vacations

Frequently asked questions

Can I cancel my flight booking to Prickly Pear Cays due to COVID-19?
Our Customer Service Portal has useful information about changing or canceling your flight due to COVID-19. Before booking your tickets, it's smart to read the terms and conditions of your preferred airline too.
What's the best way to find cheap flights to Prickly Pear Cays that have flexible change policies?
We know that travel schedules can change from one day to the next, so locking in a flexible fare with Expedia is a sensible idea. Simply tick the "No change fee" box directly under the "Flexible change policies" filter. Your low-priced, flexible flight to Prickly Pear Cays is just a few clicks away.
What are some of the general tips for travelers to Prickly Pear Cays during the COVID-19 outbreak?
The COVID-19 pandemic has changed the way we travel, but it hasn't shut down our desire to explore. Here are some tips on how to handle the new challenges of traveling:
  • Understand if any restrictions apply to both your destination and origin. You may not be able to travel depending on local circumstances, so remember to check before you book your flight.
  • Keep your face mask on even during airport screening. A TSA officer will ask you to temporarily lower your mask for ID purposes.
  • To reduce the possibility of cross-contamination, position your boarding pass on the scanner yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA agent.
  • One liquid hand sanitizer container is now permitted in your carry-on bag. It must be no bigger than 12 oz (350 ml), and you'll need to remove it from your bag for X-ray scanning.
  • Put any personal items (e.g, keys, phone and coins) in your carry-on rather than a bin to minimize handling during screening.
  • If you're bringing food on board, place it in a clear plastic bag and then into a scanning bin. This reduces the likelihood that a TSA employee will need to touch your carry-on bag or food container for inspection.

Which airlines fly to Prickly Pear Cays?
St Barth Commuter operates flights into or near Prickly Pear Cays, including 486 that land at Princess Juliana Intl. Airport (SXM) each month. Pick your vacation dates and then book your airfare early to bag a bargain.
How can I find cheap tickets to Prickly Pear Cays?
One of the best ways to get a hold of cheap tickets to Prickly Pear Cays is to be flexible with your travel dates. Search for your flights, then click "flexible dates" at the top of your results. It'll reveal the cheapest prices for nearby days. The lowest price for a flight to Prickly Pear Cays in the last seven days was . Booking well in advance will generally help you get an even bigger bargain.
How much is a flight to Prickly Pear Cays?
In the last seven days, round-trip airfares to Prickly Pear Cays sold for as low as and peaked at . For one-way fares taking off from (), the cheapest seat during this time was only .
What are the most popular airports to fly into in Prickly Pear Cays?
Prickly Pear Cays's primary airport is Princess Juliana Intl. Airport (SXM). Get your next awesome journey underway by locking in an airfare on one of the 1632 flights per month to this destination.
When is the cheapest time to fly to Prickly Pear Cays?
Fly out on a Tuesday to raise your chances of picking up the cheapest airfare to Prickly Pear Cays. Mondays are usually the next most affordable day to take off. Saturday is typically the priciest day to fly anywhere.
How much is a plane ticket to Prickly Pear Cays?
In the last seven days, plane fares to Prickly Pear Cays varied from to .
Which airlines with flights to Prickly Pear Cays employ COVID-19 cleanliness policies?
In order to limit contact between travelers and flight crew during the COVID-19 pandemic, airlines have taken physical distancing and other protective measures to the skies. These carriers include:
  • Winair - this airline is known for cleaning with disinfectant and providing passenger masks.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.