Enterprise Vacations from $1,368

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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.
Oceanfront 2-bed Apt With Pool Near Surfing - Rosalie #2 2 Bedroom Apts by Bluescape

Oceanfront 2-bed Apt With Pool Near Surfing - Rosalie #2 2 Bedroom Apts by Bluescape

3.5 out of 5
Green Garden
Price was $3,146, price is now $1,368 per person
$1,368
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Bridgetown (BGI)
No reviews
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 $6,260, price is now $3,226 per person
$3,226
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
9/10 Wonderful! (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

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 $2,920, price is now $1,553 per person
$1,553
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.4/10 Very Good! (367 reviews)
Staff willingness to make your stay comfortable.

Reviewed on Dec 30, 2025

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

5 out of 5
Price was $4,402, price is now $2,359 per person
$2,359
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.8/10 Excellent! (192 reviews)
Hotel was wonderful, our room was everything we could have asked for and more with beautiful views of the beach and stunning sunset every day. The staff were fantastic, super friendly and helpful they all made us feel right at home and like we could ask anything anytime. Great food, great entertainment ( New Year’s Eve was brilliant) and great location. Will be back very soon

Reviewed on Jan 4, 2026

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
Save 100% on your flight
Price was $3,851, price is now $2,229 per person
$2,229
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.6/10 Excellent! (100 reviews)
Clean and amazing Staff

Reviewed on Dec 31, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Enterprise

Miami Beach featuring a sandy beach and landscape views

Miami Beach

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

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

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

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
A Guided Walking Tour of The History of a City – Bridgetown

Bridgetown: A Guided Walking Tour of The History of a City

$25
per adult
98% of travellers recommend
Bridgetown: A Guided Walking Tour of The History of a City
Bathsheba, Barbados

Barbados Small-Group Monkey Feeding Experience

$75
per adult
100% of travellers recommend
Barbados Small-Group Monkey Feeding Experience
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
$623 nightly
The price is $693 total per night from Jan 21 to Jan 22
$693 total
Jan 21 - Jan 22
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Fabulous. Best resort we’ve ever experienced

Reviewed on Jan 10, 2026

The Crane Resort
Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point Bridgetown
Fully refundableReserve now, pay when you stay
$538 nightly
The price is $596 total per night from Jan 20 to Jan 21
$596 total
Jan 20 - Jan 21
Total with taxes and fees
8.2/10 Very Good! (1,015 reviews)
Amazing! Clean, and everyone is friendly.

Reviewed on Jan 10, 2026

Hilton Barbados Resort
South Point Hotel

South Point Hotel

4.5 out of 5
100 Ocean Way, Silver Sands Oistins Christ Church
Fully refundableReserve now, pay when you stay
$332 nightly
The price is $369 total per night from Jan 20 to Jan 21
$369 total
Jan 20 - Jan 21
Total with taxes and fees
9/10 Wonderful! (112 reviews)
The staff was wonderful. We arrived at 11:00 pm. Our flight came in late and we still were served with a rum punch (the bar was already closed). Our reception girl was awesome! We came with friends and the hotel managed to get our rooms together. The property is landscaped nicely. The onsite restaurant ...

Reviewed on Jan 12, 2026

South Point Hotel
See all 3,566 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 $1,368 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.