Boston Bay Vacation Rentals from $88: Search Short-Term Rentals

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

Perfect View - Entire House : Located near Boston Bay, this vacation home rental has free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Boston Bay is Welcoming 2-bedroom house with AC in Long Bay .

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In two weeks

In two months

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In four months

Our top choices for Boston Bay vacation rentals

1. Private Oasis - Portland’s Coastal Gated Hideaway

Fair Prospect

"The listing didn’t really represent this quant hideaway. I grew up in this community so it was great visiting and have this place to decompress and chill. Very cute spot, the host was super, asked if I needed anything at the store and he was very available to assist as needed, I had my ex to assist so didn’t need him, but he checked if I needed anything and was available if I did. And the view from the gazebo was my favourite. You will not be disappointed perfect for couples or just friends...

Janet

$90 nightly

Sep 3 - Sep 4

Total with taxes and fees

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

Boston Bay

$189 nightly

Aug 31 - Sep 1

Total with taxes and fees

2 bedrooms, iron/ironing board, WiFi (free)

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

Fairy Hill

Suzette

$125 nightly

Aug 6 - Aug 7

Total with taxes and fees

4. Downstairs Bedroom at Robin Hood guesthouse

Port Antonio

$71 nightly

Aug 6 - Aug 7

Total with taxes and fees

5. Bright Country Apartment at Robin Hood guesthouse

Port Antonio

$116 nightly

Aug 6 - Aug 7

Total with taxes and fees

6. Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland

Long Bay

$262 nightly

Sep 1 - Sep 2

Total with taxes and fees

7. Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

Port Antonio

$108 nightly

Aug 14 - Aug 15

Total with taxes and fees

8. Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC

Fairy Hill

Sheneker R.

$336 nightly

Aug 6 - Aug 7

Total with taxes and fees

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Top Boston Bay Hotel Reviews

Sea Cliff Resort

10/10 Excellent

"WiFi wasn’t working at first but besides that no complaints"

Great Huts

10/10 Excellent

"More Than a Hotel—A True Jamaican Experience Great Huts is not just a hotel—it is an experience. The property stretches from the cliffs down to the beach, with winding paths through sea grape trees, coral rock, African-inspired art, treehouses, hidden sitting areas, and incredible views of the Caribbean. Everywhere you look feels like a postcard. We stayed in a treehouse and absolutely loved it. The room was unique, peaceful, and surrounded by nature. At night, the property became even more magical with warm lighting, ocean sounds, and a relaxed atmosphere. The staff was one of the best parts of our stay. Everyone was kind, attentive, welcoming, and genuinely cared about making sure we were comfortable. The food was also delicious, especially breakfast, and the dining area has so much character. Great Huts also helped arrange transportation and local experiences, including our Rio Grande rafting trip. They connected us with trusted people who took excellent care of us from beginning to end. This is not a typical polished resort with identical rooms and concrete hallways. It is rustic, artistic, cultural, and built into the natural landscape. That is exactly what makes it special. We had a tremendous stay and would absolutely return. Great Huts became one of the highlights of our entire Jamaica trip."

Moon San Villa at the Blue Lagoon

8/10 Good

"The property is perfectly located next to blue lagoon and the resort is beautiful. It could use some maintenance was a bit dusty, needed some refurbishing. There wasn’t any toiletries as the bookings saiid or the free boat ride so that should be updated. It is hard to get in contact with someone on site when needed. There is someone that pops in from time to time but no number to call. That would be nice to have. TVs don’t connect to wifi or have channels either. All in all it was a nice spot a/c works great, bed is comfy, the view is great, very welcoming and private. I would definitely go back"

Private Oasis - Portland’s Coastal Gated Hideaway

10/10 Excellent

"The listing didn’t really represent this quant hideaway. I grew up in this community so it was great visiting and have this place to decompress and chill. Very cute spot, the host was super, asked if I needed anything at the store and he was very available to assist as needed, I had my ex to assist so didn’t need him, but he checked if I needed anything and was available if I did. And the view from the gazebo was my favourite. You will not be disappointed perfect for couples or just friends space is adequate to share two beds, a cute kitchen, and washroom is super cute. Loved it. Great choice and price."

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 $88 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.

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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?

Perfect View - Entire House: Located near Boston Bay, this vacation home rental has free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Boston Bay is Welcoming 2-bedroom house with AC in Long Bay.

What can I see and do in Boston Bay?

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

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Check prices for these dates

Our top choices for Boston Bay vacation rentals

1. Private Oasis - Portland’s Coastal Gated Hideaway

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

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

4. Downstairs Bedroom at Robin Hood guesthouse

5. Bright Country Apartment at Robin Hood guesthouse

6. Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland

7. Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

8. Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC

9. Port Antonio East Side Villa

10. The Grand Sinopia Inn Portland

11. Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland

12. Views from every angle - 2nd floor cozy villa

13. Ridge Bay Chateau

14. Horse Shoe Villa Port Antonio air conditioned close to it all family friendly

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

16. Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.

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

18. Pearl Ocean Villa

19. Horse Shoe Villas A family friendly 2 bedroom villa near to it all

20. One Bedroom Sea View Villa, Frenchman's Cove Resort

Find vacation rentals that suit your style

Top Boston Bay Hotel Reviews

Sea Cliff Resort

Find out more about Boston Bay

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