Enterprise Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Your Enterprise Vacation

Lock in a Enterprise vacation package and get ready to experience the best of this lively city. Consider staying in the neighborhood of Foul Bay, which is great for coastal beaches, watersports and nature. Fill your days with tours of Miami Beach, Oistins Friday Night Fish Fry and Christ Church Parish Church, some of the top attractions you shouldn't miss during a trip to Enterprise. Don't delay your visit to this destination any longer. The perfect Enterprise vacation is just a few clicks away with Expedia.

Top Enterprise Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sea Symphony Villa
O2 Beach Club & Spa by Ocean Hotels - All Inclusive
The Club, Barbados Resort & Spa Adults Only - All Inclusive
Luxury Collection at Sea Breeze Beach House by Ocean Hotels
Sea Breeze Beach House by Ocean Hotels - All Inclusive

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Enterprise Beach Vacation

Get ready to live out your beach fantasies on your upcoming Enterprise vacation. 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 center, Miami Beach is the place to be for many travelers. Look through our Enterprise vacation packages and watch your travel budget stretch further!

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Enterprise Hotel Deals

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
The price is CA $1,017 per night from Feb 15 to Feb 16
CA $1,017
CA $1,132 total
Feb 15 - Feb 16
includes taxes & fees
7.6/10 Good! (578 reviews)
Wonderful

Reviewed on Feb 7, 2026

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point Bridgetown
Fully refundableReserve now, pay when you stay
The price is CA $611 per night from Mar 3 to Mar 4
CA $611
CA $746 total
Mar 3 - Mar 4
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
The grounds were beautiful with very colorful plants and flowers. The staff were welcoming. The view from our balcony was awesome! Our room was clean. When we checked in, our safe needed a battery and someone came up immediately to fix it. The hotel was in a great location. I would definitely stay ...

Reviewed on Feb 1, 2026

Hilton Barbados Resort
The Crane Resort

The Crane Resort

4.5 out of 5
Crane Diamond Valley St. Philip
Fully refundableReserve now, pay when you stay
The price is CA $457 per night from Feb 25 to Feb 26
CA $457
CA $570 total
Feb 25 - Feb 26
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
Everything was first class

Reviewed on Feb 6, 2026

The Crane Resort
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.

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