Enterprise Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Enterprise Beach Holiday

Get ready to live out your beach fantasies on your upcoming Enterprise holiday. Go on a romantic walk, soak up the sparkling ocean views and pick up pretty seashells during your trip to Enterprise. Only 0.97 kilometres from the city centre, Miami Beach is the place to be for many travellers. Look through our Enterprise holiday packages and watch your travel budget stretch further!

Top hotels in Enterprise

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

5 out of 5
End of Belair Road Long Bay St. Philip
Fully refundableReserve now, pay when you stay
The price is S$666 per night from 28 Jul to 29 Jul
S$666
28 Jul - 29 Jul
includes taxes & fees
7.8/10 Good! (727 reviews)
"Everything was lovely"

Reviewed on 15 Jul, 2026

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
Hilton Grand Vacations Club The Crane Barbados

Hilton Grand Vacations Club The Crane Barbados

4.5 out of 5
The Crane Resort Diamond Valley
Fully refundable
The price is S$248 per night from 27 Jul to 28 Jul
S$248
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (603 reviews)
"Great staff and customer service was next level."

Reviewed on 15 Jul, 2026

Hilton Grand Vacations Club The Crane Barbados
Divi Southwinds Beach Resort

Divi Southwinds Beach Resort

3 out of 5
St Lawrence Main Road St. Lawrence Gap Christ Church
Fully refundableReserve now, pay when you stay
The price is S$202 per night from 5 Aug to 6 Aug
S$202
5 Aug - 6 Aug
includes taxes & fees
8/10 Very good! (868 reviews)
"Amazing staff from the moment we checked in. Stayed 8 days and would stay here again."

Reviewed on 15 Jul, 2026

Divi Southwinds Beach Resort
See all 3,526 properties in Enterprise
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.

What to do in Enterprise

Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx

Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx

S$136
per adult
100% of travellers recommend
Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

S$110
per adult
96% of travellers recommend
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise
Cave & Monkey Zipline Experience at Harrison's Cave by Chukka

Harrison's Cave Tour & Monkey Zipline, Barbados

S$174
per adult
90% of travellers recommend
Harrison's Cave Tour & Monkey Zipline, Barbados
See all activities in Enterprise

Frequently asked questions

How much does an Enterprise holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Enterprise costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Enterprise?
The off-season is the best time to head to Enterprise if you're hoping to keep costs down. Another tip for scoring cheap Enterprise holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Enterprise?
With a well-organised itinerary, you can easily visit the most popular Enterprise sights in a handful of days. But if you'd like to explore off the beaten track or go on day trips, consider booking your Enterprise holiday for longer.
How to find the best Enterprise package deals?
Use Expedia's filters to find some of the best Enterprise package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Enterprise package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book an Enterprise holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Enterprise trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Enterprise?
If you've got your Enterprise holiday dates finalized, book as soon as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Enterprise?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to visit Enterprise.
  2. Budget wisely: Besides the price of your accommodation, you'll need to factor in other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that could arise during your trip to Enterprise.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you'd like to get to in Enterprise. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the ideal Enterprise holiday package for you.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.