Cay Bay Hill Holidays from NZ$3,203

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The Latest Cay Bay Hill Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
per person
1 Oct - 3 Oct
found 24 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9/10 Wonderful! (1,270 reviews)
Cleanliness and good environment and good view

Reviewed on 14 Aug. 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
per person
1 Oct - 3 Oct
found 24 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,220 reviews)
The property is within walking distance to restaurants, bars and lounges. There are several restaurants on site as well.

Reviewed on 17 Aug. 2025

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
per person
1 Oct - 3 Oct
found 24 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
8.4/10 Very Good! (1,005 reviews)
Amazing place to stay, resort was beautiful and the staff very helpful, I would definitely recommend.

Reviewed on 13 Aug. 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
1 Oct - 3 Oct
found 24 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9.2/10 Wonderful! (949 reviews)
This property was very nice and astonishing. The area was quiet and lovely place to have a vacation at. The beds were so comfortable after a day of activities and excursions. The place is very peaceful and beautiful. The staff were amazing as well. The views were amazing. I would definitely recommend.

Reviewed on 15 Aug. 2025

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
per person
1 Oct - 3 Oct
found 24 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
8.6/10 Excellent! (909 reviews)
It was so relaxed and beautiful. The views from the lighthouse were spectacular

Reviewed on 12 Aug. 2025

Cay Bay Hill Holiday

Our pick of the best Cay Bay Hill Hotel Deals

condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-

4 out of 5
38 Marina Terrace, Cole Bay
The price is NZ$666 per night from 18 Aug to 19 Aug
NZ$666
18 Aug - 19 Aug
includes taxes & fees
9.4/10 Exceptional! (22 reviews)
"Good location easy access to a private beach"

Reviewed on 11 Aug. 2025

condostmaarten by the sea -Adults Only-
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road, Maho Bay, Lowlands
The price is NZ$478 per night from 18 Aug to 19 Aug
NZ$478
18 Aug - 19 Aug
includes taxes & fees
7.8/10 Good! (2,498 reviews)
"Planes. Did not like attitude of the pool bar tender"

Reviewed on 16 Aug. 2025

Sonesta Maho Beach All Inclusive Resort Casino & Spa
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is NZ$201 per night from 31 Aug to 1 Sept
NZ$201
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,290 reviews)
"Love the place"

Reviewed on 15 Aug. 2025

Simpson Bay Resort, Marina & Spa
See all 3,585 properties in Cay Bay Hill
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.

Discover the most popular places to visit in Cay Bay Hill

Guana Bay Beach featuring cuddly or friendly animals, a coastal town and a sandy beach

Guana Bay Beach

Enjoy this peaceful paradise without the crowds and surf or swim in the warm Caribbean ocean.

Guana Bay Beach

Little Bay Beach

If a restful holiday is part of your travel plans, Little Bay Beach might be the perfect place to visit during your trip to Philipsburg. Amble around this romantic area's seaside and enjoy its top-notch restaurants.

Little Bay Beach

What to do in Cay Bay Hill

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

NZ$125
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Sky Explorer and Flying Dutchman

Sky Explorer and Flying Dutchman

NZ$154
per adult
74% of travellers recommend
Sky Explorer and Flying Dutchman
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

NZ$248
per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
See all activities in Cay Bay Hill

Frequently asked questions

How much does a Cay Bay Hill holiday package cost?
You can pick up a holiday package to this popular destination from NZ$3,203 on Expedia. But how much your holiday to Cay Bay Hill costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Cay Bay Hill?
Plan your getaway for the low or shoulder season and you're likely to score cheap Cay Bay Hill holiday packages. Bear in mind that school holiday periods and major events and festivals can have an impact on prices, so do some research before you go.
How many days is enough for Cay Bay Hill?
With a well-organised itinerary, you can easily visit the main Cay Bay Hill sights in a handful of days. But if you prefer to discover hidden gems or take day trips, consider booking your Cay Bay Hill holiday for longer.
How to find the best Cay Bay Hill package deals?
Landing a cheap Cay Bay Hill package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalise your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most affordable Cay Bay Hill package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Cay Bay Hill holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging flights and hotels separately. Better still, you can customise your Cay Bay Hill escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Cay Bay Hill?
If you're planning an impromptu Cay Bay Hill holiday, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Cay Bay Hill?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Cay Bay Hill.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will probably be the largest expense during your trip to Cay Bay Hill.
  3. Work out your trip length: Consider how much time you'd like to spend exploring Cay Bay Hill. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Cay Bay Hill holiday package.

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