Title: Pelican Key Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,114 Expedia.ca

[Pelican Key Travel Guide](https://expedia.ca/Simpson-Bay-Pelican-Key.dx553248635976196664)[Hotels in Pelican Key](https://expedia.ca/Pelican-Key-Simpson-Bay-Hotels.0-n553248635976196664-0.Travel-Guide-Filter-Hotels)[Flights to Simpson Bay](https://expedia.ca/Cheap-Flights-To-Simpson-Bay.d8941.Travel-Guide-Flights)[Things to do in Simpson Bay](https://expedia.ca/Things-To-Do-In-Simpson-Bay.d8941.Travel-Guide-Activities)[Pelican Key Car Rentals](https://expedia.ca/Car-Rentals-In-Pelican-Key.d553248635976196664.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635976196664/3a98ed37-7f56-481f-968d-fd4224533886.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Pelican Key Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 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 Holiday Package Deals in Pelican Key

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

![Princess Heights Luxury Boutique Condo Hotel](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/3eb207bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,114

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

9.2/10 Wonderful! (973 reviews)

Room was very clean and staff was friendly. The room was spacious and elegant and had a great view.

Reviewed on Feb 5, 2026

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,403

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

Clean spacious room. Great housekeeping. Great shuttle service and shuttle staff. Everything you need right on the property. Grounds well maintained. Excellent overall.

Reviewed on Feb 7, 2026

![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Villas at Simpson Bay Resort

Pelican Key

CA $2,251

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

It was our 2nd time there. It was great. We love being able to walk to restaurants and live music. Staff is always friendly and funny!

Reviewed on Feb 6, 2026

![Oceans at Divi Little Bay](https://images.trvl-media.com/lodging/75000000/74270000/74267800/74267774/fee04e6c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oceans at Divi Little Bay

CA $2,046

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

8.4/10 Very Good! (266 reviews)

First time ever at Sint Maarten. Our 4-night stay was very enjoyable. The resort staff were very friendly and helpful. Mousekeeping and maintenance staff were very attentive. All facilities were kept clean and in good repair. Very relaxing campus. The food served at all the resort's restaurants was excellent. We especially enjoyed the pizza at "Slice" and the fish & shrimp tacos at "The Shack" were delicious as well. Lovely dinner served on hot lava rocks at "Seabreeze". Great taxi service to rest of island & to/from airport. We will definitely be returning to this resort. Highly recommended!

Reviewed on Feb 7, 2026

![Divi Little Bay Beach Resort](https://images.trvl-media.com/lodging/1000000/480000/470900/470827/e8112429_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Divi Little Bay Beach Resort

CA $1,920

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

8.4/10 Very Good! (1,002 reviews)

Beautiful location and views. Pools and beach very nice. Quiet and relaxing. Rooms were clean and adequate. Rooftop restaurant bar and tapas was very nice and really liked the Shack for lunch! The little (not so little) grocery on site was great and so many options of wine and alcohol plus snacks and other drinks. If staying a short time this is fine as I hear prices are a bit higher than outside the resort although to me still reasonable. Need to take cabs or rent a car for anything off the resort recommend renting a car driving is pretty easy and definitely explore! Food on the island is very good.

Reviewed on Feb 5, 2026

## Pelican Key Hotel Deals

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay 

CA $419

CA $503 total

Feb 15 - Feb 16

includes taxes & fees

8.8/10 Excellent! (1,593 reviews)

Room was spacious and spotless. Staff was friendly and helpful. The pools were perfect!

Reviewed on Feb 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=1256868&PinnedHotelID=1256868&HadPinnedHotel=true&regionId=553248635976196664)

![Hilton Vacation Club Flamingo Beach St. Maarten](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/67b50717_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay 

CA $436

CA $494 total

Mar 8 - Mar 9

includes taxes & fees

9/10 Wonderful! (1,429 reviews)

Everything was great would definitely go back

Reviewed on Feb 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=796441&PinnedHotelID=796441&HadPinnedHotel=true&regionId=553248635976196664)

![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Villas at Simpson Bay Resort

Billy Folly Road No. 37A Simpson Bay 

CA $572

CA $687 total

Mar 1 - Mar 2

includes taxes & fees

9.2/10 Wonderful! (1,368 reviews)

Excellent location and amenities

Reviewed on Jan 26, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=4553784&PinnedHotelID=4553784&HadPinnedHotel=true&regionId=553248635976196664)

[See all 3,562 properties in Pelican Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&regionId=553248635976196664)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Pelican Key vacation package cost?

### How do I get a cheap travel package to Pelican Key?

### Where should I stay in Pelican Key?

### What are the top hotels in Pelican Key?

### How far in advance should I book my Pelican Key vacation?

### What does an Expedia Pelican Key travel package include?

### What should I know before booking a Pelican Key travel package?

### Can I choose my airline with a Pelican Key Expedia vacation package?

### If I'm not able to travel, can I cancel my Pelican Key vacation package?

### Discover the most popular places to visit in Pelican Key

![Hollywood Casino which includes a casino and interior views](https://images.trvl-media.com/place/6079643/303d2f30-0651-4bf4-89b8-08f40a94c2b8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Hollywood Casino

Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.

[](https://expedia.ca/Hollywood-Casino-Pelican-Key.d6079643.Vacation-Attraction)

![Kim Sha Beach showing a coastal town, a sandy beach and general coastal views](https://images.trvl-media.com/place/6079645/6be51115-068f-4fd6-823b-d7a21aa2a276.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Kim Sha Beach

Why not spend a carefree afternoon at Kim Sha Beach during your travels in Simpson Bay? Check out the shops and top-notch restaurants in this romantic area. 

[](https://expedia.ca/Kim-Sha-Beach-Simpson-Bay.d6079645.Vacation-Attraction)

### Things to do

![High-Speed Ferry to St. Barths](https://mediaim.expedia.com/localexpert/176989/803f204c-e59b-47d1-9a40-1a59056c3ffb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### High-Speed Ferry to St. Barths

CA $102

per adult

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/high-speed-ferry-to-st-barths.a176989.activity-details)

![Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line](https://mediaim.expedia.com/localexpert/466226/f1e62739-a072-49a6-976a-ce1a3facd837.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $184

per adult

**90%** of travellers recommend

[](https://expedia.ca/things-to-do/sky-explorer-flying-dutchman-schooner-sentry-hill-line.a466226.activity-details)

![Panoramic view of vibrant St. Martin ](https://mediaim.expedia.com/localexpert/413439/1889a377-cdfa-4a6e-bdf7-cb7a36cef979.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Edge Ferry Tickets to St. Barts

CA $136

per adult

**84%** of travellers recommend

[](https://expedia.ca/things-to-do/edge-ferry-tickets-to-st-barts.a413439.activity-details)

[See all activities in Simpson Bay](https://expedia.ca/things-to-do/search?rid=553248635976196664)

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