Title:  Dawn Beach Estates Vacation Packages & Trips 2025 from $753 | Expedia.ca

  

[Dawn Beach Estates Travel Guide](https://expedia.ca/Oyster-Pond-Dawn-Beach-Estates.dx553248635976659260)[Hotels in Dawn Beach Estates](https://expedia.ca/Dawn-Beach-Estates-Oyster-Pond-Hotels.0-n553248635976659260-0.Travel-Guide-Filter-Hotels)[Flights to Oyster Pond](https://expedia.ca/Cheap-Flights-To-Oyster-Pond.d6025558.Travel-Guide-Flights)[Things to do in Oyster Pond](https://expedia.ca/Things-To-Do-In-Oyster-Pond.d6025558.Travel-Guide-Activities)[Dawn Beach Estates Car Rentals](https://expedia.ca/Car-Rentals-In-Dawn-Beach-Estates.d553248635976659260.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6079641/be29b483-1d6f-4757-be4a-3e89758c8624.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Dawn Beach Estates 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 Dawn Beach Estates

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

![Holland House Beach Hotel](https://images.trvl-media.com/lodging/2000000/1170000/1160500/1160500/ef6e99b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holland House Beach Hotel

Downtown Philipsburg

CA $1,699

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Philipsburg (SXM)

9.2/10 Wonderful! (1,004 reviews)

The breakfast options were amazing, dinner was amazing .. the view amazing.. definitely consider booking at this resort Check in process was easy

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-11/2025-12-17/?FromAirport=YTO&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1160500&paandie=true&dealMarker=2Etb03gh1ZBYFHcq-1Hrdp-4eiED9QewCYlVpYIk3POdXPEWw9UYNa70In1voL0d)

![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

CA $1,890

per person

Dec 14 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,241 reviews)

Central location, lots of options in walking distance. Clean resort, friendly staff. Budget friendly compared to other islands

Reviewed on Oct 3, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-14/2025-12-21/?FromAirport=YMQ&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4553784&paandie=true&dealMarker=snyYlfDcl_3Va8lTUe7YH-JE60ZobyRXgdGsX8Ae21o8SnBDe4EEjz6Hpo-4MtXa)

![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 $1,986

per person

Dec 16 - Dec 23

found 11 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9/10 Wonderful! (1,345 reviews)

They need some shuttles on property to move around.

Reviewed on Oct 1, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-16/2025-12-23/?FromAirport=YMQ&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1256868&paandie=true&dealMarker=XjXMC19lKyqVN3TDWNLxm8FLfJQMdclqDfb6qFXQKttXnHyw9336jNxIp6YdSDY1)

![Hilton Vacation Club Royal Palm St. Maarten](https://images.trvl-media.com/lodging/1000000/810000/807900/807815/ddd10394_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Vacation Club Royal Palm St. Maarten

CA $2,054

per person

Dec 14 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9/10 Wonderful! (1,116 reviews)

Clean room Breath taking view Staff wonderful

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-14/2025-12-21/?FromAirport=YMQ&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=807815&paandie=true&dealMarker=YWiWtCm_b0sHuiTPqDk47_azYWtdPnNFp_i9XqjnBfGijh_hjJiRi1gpNwgkPexs)

![La Playa Orient Bay](https://images.trvl-media.com/lodging/1000000/910000/908100/908054/42567e6f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Playa Orient Bay

CA $1,727

per person

Dec 14 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9.4/10 Exceptional! (592 reviews)

It was okay, could be better

Reviewed on Sep 15, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-14/2025-12-21/?FromAirport=YMQ&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=908054&paandie=true&dealMarker=YWiWtCm_b0sHuiTPqDk47wF2GgKxKnvD_d2nAUkRvX3m4IlugqCffUzgaji1FKDx)

## Where to stay in Dawn Beach Estates

Find the best Dawn Beach Estates areas and neighborhoods for the activities you enjoy most. [Learn more about Dawn Beach Estates](https://expedia.ca/Oyster-Pond-Dawn-Beach-Estates.dx553248635976659260)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Oyster Pond

2 out of top 10 points of interest in this area

4/5(13 area reviews)

Oyster Pond is a destination visitors seek out for is beaches, abundant dining options, and seaside views. You might want to check out attractions like Dawn Beach or Oyster Bay Marina while you're exploring the neighborhood.

[Find hotel + flight trips in Oyster Pond](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Oyster%20Pond&DestID=6131289&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Tamarind Hill Estates

Tamarind Hill Estates might not have many top sights, but Dawn Beach and Oyster Bay Marina are two attractions nearby that you can check out.

[Find hotel + flight trips in Tamarind Hill Estates](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Tamarind%20Hill%20Estates&DestID=553248635976659229&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Red Pond Estates

While visiting Red Pond Estates, you might make a stop by sights like Guana Bay Beach and Gibb's Bay Beach.

[Find hotel + flight trips in Red Pond Estates](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Red%20Pond%20Estates&DestID=553248635976659228&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Dawn Beach Estates Hotel Deals

![Luxury Villa, Walk to beach, BRAND NEW 55KW BACKUP GENERATOR](https://images.trvl-media.com/lodging/39000000/38360000/38358600/38358580/6e794716_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Luxury Villa, Walk to beach, BRAND NEW 55KW BACKUP GENERATOR

Upper Prince's Quarter

10/10 Exceptional! (104 reviews)

"The villa was spectacular. Not only did it have a ton of space, but the layout enabled our group to spend time together, but areas where you could just relax. The villa is well equipped with everything we needed. We have a large family, so we always stay in a vacation home when traveling and hands ..."

Reviewed on Aug 6, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=18%2F10%2F2025&endDate=19%2F10%2F2025&selected=38358580&PinnedHotelID=38358580&HadPinnedHotel=true&regionId=553248635976659260)

[](https://expedia.ca/Hotel-Search?startDate=18%2F10%2F2025&endDate=19%2F10%2F2025&selected=38358580&PinnedHotelID=38358580&HadPinnedHotel=true&regionId=553248635976659260)

![Sonesta Maho Beach All Inclusive Resort Casino & Spa](https://images.trvl-media.com/lodging/1000000/570000/565700/565666/9a0f47b8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road, Maho Bay, Lowlands

CA $266

CA $322 total

Oct 6 - Oct 7

includes taxes & fees

7.8/10 Good! (2,631 reviews)

"Great stay"

Reviewed on Sep 30, 2025

[](https://expedia.ca/Hotel-Search?startDate=06%2F10%2F2025&endDate=07%2F10%2F2025&selected=565666&PinnedHotelID=565666&HadPinnedHotel=true&regionId=553248635976659260)

![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

Fully refundableReserve now, pay when you stay

CA $144

CA $173 total

Oct 22 - Oct 23

includes taxes & fees

8.8/10 Excellent! (1,365 reviews)

"Met every need we had."

Reviewed on Sep 30, 2025

[](https://expedia.ca/Hotel-Search?startDate=22%2F10%2F2025&endDate=23%2F10%2F2025&selected=1256868&PinnedHotelID=1256868&HadPinnedHotel=true&regionId=553248635976659260)

[See all 3,572 properties in Dawn Beach Estates](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025&regionId=553248635976659260)

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 Dawn Beach Estates vacation package cost?

> Maybe less than you imagined — from a tempting CA $1,699, actually! By bundling hotels, flights and car rentals into your own tailor-made package, your Dawn Beach Estates escape is just clicks away.

### How do I get a cheap travel package to Dawn Beach Estates?

> If you love landing a bargain, combine your bookings into a Dawn Beach Estates vacation package. Whether you're looking for flights, hotels, activities or rental cars, you can browse and book them all in one place. You'll have a wealth of choice at your fingertips as well. Expedia has over 550 partner airlines and 1,000,000 hotels across the globe to take your pick of. Fly with who you prefer, stay where you like and save precious money — now that's the perfect vacation!

### Where should I stay in Dawn Beach Estates?

> There's loads to do in Dawn Beach Estates, so spend your nights close to its top attractions and spend more time sightseeing. Guana Bay Beach is one spot to add to your to-do list.

### What are the top hotels in Dawn Beach Estates?

> Get your vacation off to an excellent start by reserving a room at [Prana By Island Properties Online](https://www.expedia.ca/Oyster-Pond-Hotels-Prana-By-Island-Properties-Online.h36883188.Hotel-Information). It's one of most sought-after properties in Dawn Beach Estates. Another cozy option is [Stunning And Secluded Waterfront W](https://www.expedia.ca/Oyster-Pond-Hotels-Stunning-Secluded-Waterfront-WBeach-And-Dawn-Beach-Club-Access.h45498999.Hotel-Information).

### How far in advance should I book my Dawn Beach Estates vacation?

> Earlier is always better. Air carriers generally release flights around a year ahead of departure, and this is your chance to score some of the lowest prices. Just been told you should take some vacation time in a few weeks? That's alright! Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at an affordable price.

### What does an Expedia Dawn Beach Estates travel package include?

> Expedia has everything you need to plan your Dawn Beach Estates getaway, but how your package is structured is your call. Select from a combination of rental cars, flights and hotels. After some activities or tours to keep you busy? Once you've made your booking, you can add them on too. Whatever your style or budget, there's a package deal to suit your needs.

### What should I know before booking a Dawn Beach Estates travel package?

> A travel package can be easier on the wallet than individually booking all you need for your getaway. For example, bundle your hotels, flights and rental cars and save a tidy sum. Whatever sort of vacation you're planning, you're bound to find a package that fits your budget.

### Can I choose my airline with a Dawn Beach Estates Expedia vacation package?

> Yes, the choice is all yours. Expedia has access to more than 550 partner airlines all over the world, so you can tailor your Dawn Beach Estates trip according to your needs and budget.

### If I'm not able to travel, can I cancel my Dawn Beach Estates vacation package?

> Yes you can, and we'll help you every step of the way. You may be able to cancel or amend your Dawn Beach Estates vacation package at no cost if you booked in the last 24 hours. But you may be charged a fee by your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, look up our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) for further information.

### Things to do

![Sand Dollar Snorkeling Adventure](https://mediaim.expedia.com/localexpert/253868/cee07738-52cd-498c-b693-2512d348c7bb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Half Day Snorkeling Adventure

CA $90

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/half-day-snorkeling-adventure.a253868.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 $138

per adult

**84%** of travellers recommend

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

![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 $103

per adult

**76%** of travellers recommend

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

[See all activities in Oyster Pond](https://expedia.ca/things-to-do/search?rid=553248635976659260)

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