Enterprise Vacations from $1,195

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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.

The Latest Enterprise vacation packages

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

South Point Hotel

4.5 out of 5
Green Garden
Save 100% on your flight
Price was $2,024, price is now $1,195 per person
$1,195
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
18.4/10 Exceptional! (93 reviews)
My stay was very pleasant. The a/c was working well in my bedroom but the coolness didnt extend to the living room. I did love that I had two balconies. The property itself was well maintained. The staff was friendly. The beach was a short walk from the property. It was not crowded and I was able to relax and even take a nap under the shade of a tree.

Reviewed on Nov 12, 2025

Concierge Collection at O2 Beach Club & Spa by Ocean Hotels

Concierge Collection at O2 Beach Club & Spa by Ocean Hotels

5 out of 5
Price was $8,615, price is now $3,925 per person
$3,925
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
18/10 Exceptional! (36 reviews)
The staff was exceptionally friendly and professional. Location is great if you want peace and quiet; it’s not near too many other resorts. There are clubs nearby, outdoor which allows you to enjoy the outdoor air and environment. You have to take a taxi to go from the resort to downtown or walk maybe quarter a mile to bus transportation, which was easy to use.

Reviewed on Sep 15, 2025

Luxury Collection at Sea Breeze Beach House by Ocean Hotels

Luxury Collection at Sea Breeze Beach House by Ocean Hotels

4.5 out of 5
Price was $6,421, price is now $3,470 per person
$3,470
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
17.2/10 Exceptional! (100 reviews)
Staff was absolutely amazing… great job team

Reviewed on Oct 28, 2025

The Crane Resort

The Crane Resort

4.5 out of 5
Save 100% on your flight
Price was $2,816, price is now $1,581 per person
$1,581
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
17.2/10 Exceptional! (1,002 reviews)
Great room, staff were great

Reviewed on Nov 16, 2025

Sea Breeze Beach House by Ocean Hotels - All Inclusive

Sea Breeze Beach House by Ocean Hotels - All Inclusive

4 out of 5
Save 100% on your flight
Price was $5,135, price is now $2,930 per person
$2,930
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
16.8/10 Exceptional! (367 reviews)
Maybe because it was all inclusive, the food service staff were not attentive. On our last nite, I called to the front desk TWICE to request some towels so that my wife & I could bathe and they never arrived so we had to improvise. The property was nicely maintained but I didn't remember seeing that our bldg DID NOT have an elevator & we were on the 3rd floor. This wasn't a big problem for us but for older and guests with challenges this would have been a major issue.

Reviewed on Nov 18, 2025

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Limited-time deals: Save up to 50% on select hotels.
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Discover the most popular places to visit in Enterprise

Miami Beach featuring a sandy beach and landscape views

Miami Beach

4.5/5(128 reviews)

A great beach with tide pools for toddlers and big waves for aspiring surfers. Plenty of sun and sand for everyone else.

Miami Beach

Oistin's Friday Night Fish Fry

4.5/5(186 reviews)

Enjoy a stop at Oistin's Friday Night Fish Fry, an entertaining place to visit in Scarborough. Discover the area's beautiful sunsets and seafood restaurants.

Oistin's Friday Night Fish Fry

Christ Church Parish Church

4.5/5(45 reviews)

After visiting Christ Church Parish Church, make a plan to see the other sights and activities in Scarborough. Discover the area's beautiful sunsets and seafood restaurants.

Christ Church Parish Church

What to do in Enterprise

Harrison’s Cave Tram and Nature Walk Experience

Harrison’s Cave Tram and Nature Walk Experience

$100
per traveler
80% of travellers recommend
Harrison’s Cave Tram and Nature Walk Experience
Barbados -Luxury Cruise with Lunch and Open Bar

Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx

$125
per adult
100% of travellers recommend
Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx
See all activities in Enterprise

Enterprise Hotel Deals

The Crane Resort

The Crane Resort

4.5 out of 5
Crane Diamond Valley St. Philip
Fully refundableReserve now, pay when you stay
$489 nightly
The price is $546 total per night from Nov 23 to Nov 24
$546 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Great room, staff were great

Reviewed on Nov 16, 2025

The Crane Resort
Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point Bridgetown
Fully refundableReserve now, pay when you stay
$365 nightly
The price is $407 total per night from Dec 15 to Dec 16
$407 total
Dec 15 - Dec 16
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Room was clean, staff very friendly..

Reviewed on Nov 12, 2025

Hilton Barbados Resort
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
$670 nightly
The price is $747 total per night from Nov 23 to Nov 24
$747 total
Nov 23 - Nov 24
Total with taxes and fees
7.6/10 Good! (538 reviews)
Amazing resort and staff!!!!

Reviewed on Nov 21, 2025

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
See all 3,621 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.

Find the Best Enterprise Vacation Packages

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 0.6 miles (0.9 km) 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!

Enterprise Essential Information

Language
English
Currency
Barbadian dollars
Closest Airport
Grantley Adams Intl. Airport (BGI)
Top Sights
Miami Beach, Oistins Friday Night Fish Fry and Christ Church Parish Church

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Frequently asked questions

How much does an Enterprise vacation package cost?
Offering excellent value package deals from $1,195 on Expedia, you'll be pleasantly surprised at how much a vacation to Enterprise costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Enterprise?
You're likely to find lower rates and greater availability in September, October and December. Check out our cheap Enterprise vacation packages and you could get some great off-season discounts.
How many days is enough for Enterprise?
Typically, a handful of days is enough to see the top attractions during your Enterprise vacation. But if you'd like to have time to chill out or go on day trips, consider extending your itinerary.
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 vacation package well in advance.
Is it cheaper to book an Enterprise vacation as a package?
An Expedia vacation 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 vacation package to Enterprise?
If you've got your Enterprise vacation 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. Pick your travel dates: The things you'd like to do in Enterprise and your preferred season will help you decide when to travel.
  2. Plan your budget wisely: On top of the cost of your accommodations, you'll need to factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Enterprise.
  3. Use our trip planning tool to discover Enterprise: Research every part of your trip to Enterprise with this comprehensive planner. Invite your family and friends to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide how long to go for: Now that you know more about Enterprise, you can work out the perfect length of your vacation. Create a draft plan and allocate enough time to cover everything you want to see.
  5. Combine your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the perfect Enterprise vacation package for you.
  6. Book any activities or excursions: Now to the fun part — organizing everything you want to see and do. Explore some of the top things to do in Enterprise and book your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Enterprise vacation packages?
Your Enterprise break is meant to be a relaxing escape from your busy life, not a source of money worries. So to give you that extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.