Boston Bay Vacation Rentals from $94: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Boston Bay vacation rentals

Ahh! (Pool/Ocean View Room w/ Private Bath)

Boston Bay

$157 nightly

Apr 13 - Apr 14

Total with taxes and fees

Boston Bay, Portland Cozy Corner

Boston Bay

$389 nightly

Apr 14 - Apr 15

Total with taxes and fees

Private Oasis - Portland’s Coastal Gated Hideaway

Fair Prospect

$94 nightly

May 12 - May 13

Total with taxes and fees

1 bedroom, iron/ironing board, free WiFi, bed sheets

Kai's Place @ Tim Pappies 3rd Floor luxury villa

Port Antonio

Shanice M.

$124 nightly

Apr 12 - Apr 13

Total with taxes and fees

Eco-Rustic Museum House & Art Stage between two beaches

Port Antonio

Andrew

$70 nightly

Apr 12 - Apr 13

Total with taxes and fees

House - Sleeps 4 - Patio - Parking

Port Morant

$156 nightly

Apr 20 - Apr 21

Total with taxes and fees

2 bedrooms, iron/ironing board, free WiFi

DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon

Fairy Hill

Suzette

$125 nightly

Apr 12 - Apr 13

Total with taxes and fees

Charming new 2 BR, 2 BR ocean view villa in Snow District, AC, private/secure

Snow District

$254 nightly

Apr 12 - Apr 13

Total with taxes and fees

Lovely 1 bedroom, 2 Guest +, holiday rentals in St Thomas Jamaica

Port Morant

Virginia

$59 nightly

Apr 23 - Apr 24

Total with taxes and fees

Views from every angle - 2nd floor cozy villa

Port Antonio

$155 nightly

Apr 13 - Apr 14

Total with taxes and fees

Romantic 2 bedroom, 4 Guest+, holiday rental in Port Morant, St Thomas, Jamaica

Port Morant

$101 nightly

Apr 18 - Apr 19

Total with taxes and fees

Entire Luxury Apartment with contemporary decor

Port Antonio

$260 nightly

Apr 12 - Apr 13

Total with taxes and fees

Hope Bay-Peaceful getaway w/ pool and steps to natural beach

Hope Bay

Fiona L.

$149 nightly

Apr 12 - Apr 13

Total with taxes and fees

Kingvilla

Port Morant

$85 nightly

Apr 12 - Apr 13

Total with taxes and fees

The villa with ocean view

Manchioneal

Anonymous traveler

$75 nightly

Apr 19 - Apr 20

Total with taxes and fees

Family Reunions Holiday 4 Bedrooms, 5 Beds Rentals in St Thomas,jamaica

Port Morant

Brenda

$153 nightly

Apr 20 - Apr 21

Total with taxes and fees

Port Antonio East Side Villa

Port Antonio

$145 nightly

Apr 12 - Apr 13

Total with taxes and fees

Mack's holiday room. 1 bedroom

Port Morant

"This listing has been changed since I booked it, but it's still inaccurate. It was originally listed as a 2brm 2ba entire home with fully loaded kitchen, linens, etc. It was all a lie! AND as if that wasn't enough, the host tried to make us feel guilty because he messed up the listing & wasn't making much money. He told us the 2nd ba wouldn't be available til 3wks into our 4wk stay. THEN, we found out the house was shared with other ppl. The kitchen isn't fully stocked, no dryer, no linens & the...

Ronika C.

$56 nightly

Apr 14 - Apr 15

Total with taxes and fees

Lovely 2 Bedroom House in St Thomas Jamaica

Port Morant

Arlene

$130 nightly

May 12 - May 13

Total with taxes and fees

Large home in Portland Parrish

Black Hill

$286 nightly

Apr 12 - Apr 13

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Villas

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Boston Bay Hotel Reviews

Jamaica Palace Hotel

8/10 Good

"Great hotel in a stunning property with really friendly staff at reception. Had an issue with bathroom shower which sprayed onto the wall and then the floor - apparently a result of bath/shower design so the staff couldn't help. Otherwise had a great stay with good food, although the restaurant was pricey. Would stay again though."

Golden Shore Resort

2/10 Terrible

"All 4 of us arrived Monday 16th March 2026 in the night and the heavy rain. Our room was pre booked via Expedia. Upon arrival we were told that we had no room and the room was occupied until the next day. This made no sense as we pre booked many weeks ago and received the booking confirmation. The hotel had already spoken to us weeks before our arrival and confirmed the booking. So we were so confused and disappointed that the hotel didn’t even understand what was happening to us was wrong and an unpleasant experience for us. We spent a number of hours trying to explain why this was unacceptable. They sent us to another local hotel where they said they had booked us one night. Upon arrival the hotel had no knowledge of this and this created a problem and panic as we were unable to sleep anywhere that night. This hotel didn’t follow any customer service policy or rules to ensure we were safe and had a bed for the night. It was a nightmare experience. I would not recommend having a vacation there as they don’t follow the rules or instructions to provide what they have agreed to do. We still wasn’t given a proper explanation for the mess. This place to be dragged into 2026 it really needs a refurbishment and staff require training and better customer service skills. "

Sea Cliff Resort

2/10 Terrible

"Absolutely Disappointing Stay – Would Not Recommend During Easter break, my family and I stayed at Sea Cliffs Resort, and unfortunately, our experience was extremely disappointing from start to finish. Check-in was smooth, but that was the only positive part of our stay. As soon as we entered the room, we noticed that the door had a deadbolt that could only be locked with a key. This created an immediate inconvenience, as we were only given one working key forcing all of us to leave and return together at all times. The very next day, the lock stopped working entirely. We reported it right away, but it was not fixed until day three. In the meantime, we had to block the door with our suitcases just to feel safe, which is completely unacceptable. We were told delays were due to the holiday, but basic security should never be compromised. The room itself was extremely underwhelming. There was no TV, no dresser, and barely any storage space, just a small hanging area for clothes. The beds were average at best, offering little comfort. The bathroom situation was just as frustrating. The showerhead sprayed water in multiple directions instead of flowing properly, and the hot water barely worked. We had to turn on the sink and let it run just to trigger hot water in the shower only to be left with low water pressure. The food was another major letdown The food was another major letdown. Breakfast options were extremely limited. One morning offered ackee and saltfish, cabbage, banana"

Find out more about Boston Bay

Everything you need to know about Boston Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Boston Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Boston Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Boston Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Boston Bay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Boston Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $94 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Boston Bay rentals

At Expedia, we put the best Boston Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Boston Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Boston Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Boston Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Boston Bay?

Yes, we offer vacation rentals close to well known local attractions in Boston Bay, or you can select a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Boston Bay?

RVGH 10 bedrooms, 1300.00 PER NIGHT PER ROOM, MAX 2 PER ROOM, amazing views.: This vacation home rental near Boston Bay is located in the mountains and has a balcony, a hot tub, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Boston Bay?

While you're exploring the area, Boston Bay Beach and Blue Lagoon are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find San San Beach and Frenchman's Cove Beach.

What are vacation rentals like in Boston Bay?

Vacation rentals are privately owned accommodations you can reserve for a couple days or more in Boston Bay. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family gatherings.

Boston Bay Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Boston Bay vacation rentals

Ahh! (Pool/Ocean View Room w/ Private Bath)

Boston Bay, Portland Cozy Corner

Private Oasis - Portland’s Coastal Gated Hideaway

Kai's Place @ Tim Pappies 3rd Floor luxury villa

Eco-Rustic Museum House & Art Stage between two beaches

House - Sleeps 4 - Patio - Parking

DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon

Charming new 2 BR, 2 BR ocean view villa in Snow District, AC, private/secure

Lovely 1 bedroom, 2 Guest +, holiday rentals in St Thomas Jamaica

Views from every angle - 2nd floor cozy villa

Romantic 2 bedroom, 4 Guest+, holiday rental in Port Morant, St Thomas, Jamaica

Entire Luxury Apartment with contemporary decor

Hope Bay-Peaceful getaway w/ pool and steps to natural beach

Kingvilla

The villa with ocean view

Family Reunions Holiday 4 Bedrooms, 5 Beds Rentals in St Thomas,jamaica

Port Antonio East Side Villa

Mack's holiday room. 1 bedroom

Lovely 2 Bedroom House in St Thomas Jamaica

Large home in Portland Parrish

Find vacation rentals that suit your style

Top Boston Bay Hotel Reviews

Jamaica Palace Hotel

Find out more about Boston Bay

Explore a world of travel with Expedia

Trending destinations on Expedia.com

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app