Boston Bay Vacations from $577

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Your Boston Bay Vacation

Take the worry out of planning your next big adventure with a Boston Bay vacation package. Whether you're lured here by its art, food, architecture or other highlights, this city offers endless possibilities for fun. Any trip to Boston Bay needs a well-crafted itinerary. Fill yours with leading attractions like Boston Bay Beach, Blue Lagoon and Frenchmans Cove Beach. Expedia will help you escape the everyday. Tailor your vacation to Boston Bay to match your travel style, whatever that may look like.

The Latest Boston Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
AKA Hotel by Palermo Home 32 floor

AKA Hotel by Palermo Home 32 floor

3 out of 5
Brickell
Price was $1,394, price is now $577 per person
$577
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
10/10 Exceptional! (3 reviews)
This was an absolutely stunning place to stay! High end accommodations connected to the AKA hotel. Close to the water, great restaurant, the pool was fabulous. Easy to get around to everything in Miami from here. Parking included with this reservation, which was a huge plus. Highly recommend this for anyone staying in Miami whether for a couple or a family of four.

Reviewed on Jul 5, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $12,713, price is now $5,696 per person
$5,696
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Price was $2,092, price is now $943 per person
$943
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (829 reviews)
Rooms were clean and the staff were good as well.

Reviewed on Nov 19, 2025

The Club at Brickell Bay by Palermo Home

The Club at Brickell Bay by Palermo Home

2.5 out of 5
Brickell
Price was $2,119, price is now $956 per person
$956
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (1 review)
Iberostar Waves Berkeley Shore

Iberostar Waves Berkeley Shore

4 out of 5
South Beach
Price was $1,367, price is now $619 per person
$619
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,449 reviews)
Room very small and bed super small and low to the ground.

Reviewed on Nov 24, 2025

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Boston Bay Hotel Deals

Rasta Villa B&B

Rasta Villa B&B

Fair Prospect Portland Parish
6/10 (1 review)
Nice property and place to stay with few little exceptions
The property is beautiful. You are on a hill top so you have a nice view to see the Ocean from a distance. bigga owner was great, very friendly and accommodating. There is area for cooking. The rooms are nice and big. The only thing i have to say that isnt good is that my room and a few of the other ...

Reviewed on May 12, 2025

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Rasta Villa B&B
Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Fully refundable
$122 nightly
The price is $134 total per night from Nov 28 to Nov 29
$134 total
Nov 28 - Nov 29
Total with taxes and fees
8.2/10 Very Good! (165 reviews)
The best hotel that l've ever stayed at in my whole life,the staff were exceptional shout out to Monoque and the owner Errol went above and beyond to make it a personal interest in our well being,can't praise everyone enough loved it so much l've already reserved my room for next year

Reviewed on Nov 24, 2025

Sea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield Port Antonio Portland
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $164 total per night from Nov 30 to Dec 1
$164 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (258 reviews)
The room was clean. Breakfast and lunch was great. Thr staff was very friendly and accommodating.

Reviewed on Nov 22, 2025

Jamaica Palace Hotel
See all 272 properties in Boston Bay
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 Boston Bay Vacation Packages

Boston Bay Essential Information

Language
English
Currency
Jamaican dollars
Max Temp Winter
80ºF
Max Temp Summer
85ºF
Top Sights
Frenchmans Cove Beach, Trident Castle and Boston Bay Beach

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Frequently asked questions

How much does a Boston Bay vacation package cost?
Offering excellent value package deals from $577 on Expedia, you'll be surprised at how little a vacation to Boston Bay costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Boston Bay?
If you're looking to book a cheap Boston Bay vacation package, consider planning a trip in September, November and December. You'll generally find better rates on hotels and flights during these months — perfect for a budget-friendly break.
How many days is enough for Boston Bay?
The ideal length of your Boston Bay vacation depends on what you'd like to do and see. Generally, a few days to a week will give you time to hit all the major sights and discover some hidden spots along the way.
How to find the best Boston Bay package deals?
Begin your search for a Boston Bay package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Boston Bay package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Boston Bay adventure underway.
Is it cheaper to book a Boston Bay vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations separately. Better still, you can personalize your Boston Bay getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Boston Bay?
Enjoy amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Boston Bay escape.
How to plan a trip to Boston Bay?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the activities available will also help you decide when to vacation in Boston Bay.
  2. Set a budget: Factor in expenses like transportation, flights and meals when working out how much to set aside for your trip to Boston Bay. Then, select a property that fits your budget, whether that's an economical option or a swankier getaway.
  3. Organize your Boston Bay getaway with Expedia's trip planning tool: Search for and book hotels and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Boston Bay together.
  4. Decide your trip length: Consider how much time you'd like to spend exploring Boston Bay. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  5. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Boston Bay vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Have a look at our dedicated travel guide to find some fun things to do in Boston Bay. Book tickets or make reservations in advance to save time and avoid the stress of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Boston Bay vacation packages?
Your Boston Bay trip is meant to be an escape from your daily routine, not a source of money worries. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.