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Boston Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Boston Bay vacation rentals

A beach scene with clear turquoise water, a person on a swing, and lush greenery in the background.

1. Private Oasis - Portland’s Coastal Gated Hideaway

Private Oasis - Portland’s Coastal Gated Hideaway
Fair Prospect
10.0 out of 10, Exceptional, (1 review)
"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...
Canada
Janet
$107 nightly
The price is $107
Oct 12 - Oct 13
Total with taxes and fees
Private Oasis - Portland’s Coastal Gated Hideaway
A beach with clear turquoise water, a rocky cliff with vegetation, and a person standing in the water.

2. Ahh! (Ocean View Studio with Private Bath)

Ahh! (Ocean View Studio with Private Bath)
Boston Bay
10.0 out of 10, Exceptional, (2 reviews)
"Not the easiest drive up to the place, but the view is magnificent. The place is clean, and the hosts are friendly and helpful. If you're looking for an inexpensive decent studio in Portland with air conditioning, hot water, and a terrific view, consider this place."
United States
Jerry B.
$179 nightly
The price is $179
Oct 18 - Oct 19
Total with taxes and fees
Ahh! (Ocean View Studio with Private Bath)
A wooden deck with a swimming pool, a covered seating area, and a view of the ocean.

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

Ahh! (Pool/Ocean View Room w/ Private Bath)
Boston Bay
$188 nightly
The price is $188
Oct 12 - Oct 13
Total with taxes and fees
Ahh! (Pool/Ocean View Room w/ Private Bath)
A bedroom with two beds, a chair, a staircase, and a large painting on the wall.

4. Norse Hill Estate & Botanic Gardens

Norse Hill Estate & Botanic Gardens
3.5 star property
Port Antonio
$1,815 nightly
The price is $2,088
Oct 12 - Oct 13
Total with taxes and fees
Norse Hill Estate & Botanic Gardens
A bedroom with a bed, white curtains, a wooden wardrobe, and an air conditioning unit.

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

DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon
Fairy Hill
8.0 out of 10, Very good, (1 review)
"The host was very welcoming, and miss Mariana was very kimd and friendly. Great place to stay "
United States
Suzette
$125 nightly
The price is $132
Oct 12 - Oct 13
Total with taxes and fees
DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon
A two-story house with a balcony, surrounded by lush greenery.

6. Downstairs Bedroom at Robin Hood guesthouse

Downstairs Bedroom at Robin Hood guesthouse
Port Antonio
$71 nightly
The price is $71
Oct 12 - Oct 13
Total with taxes and fees
Downstairs Bedroom at Robin Hood guesthouse
A two-story house with a balcony, surrounded by lush greenery.

7. Bright Country Apartment at Robin Hood guesthouse

Bright Country Apartment at Robin Hood guesthouse
Port Antonio
$116 nightly
The price is $116
Oct 12 - Oct 13
Total with taxes and fees
Bright Country Apartment at Robin Hood guesthouse
A cozy living room with wicker furniture, a coffee table, and a patterned rug.

8. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
$522 nightly
The price is $571
Oct 13 - Oct 14
Total with taxes and fees
The Grand Sinopia Inn Portland
A group of people standing near a small structure by the beach, surrounded by palm trees and ocean views.

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

Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland
Long Bay
$248 nightly
The price is $248
Oct 23 - Oct 24
Total with taxes and fees
Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland
Beach

10. 3-bedroom ocean front bungalow in delightful Long Bay, Portland w AC ,Ocean View

3-bedroom ocean front bungalow in delightful Long Bay, Portland w AC ,Ocean View
Long Bay
$353 nightly
The price is $353
Oct 12 - Oct 13
Total with taxes and fees
3-bedroom ocean front bungalow in delightful Long Bay, Portland w AC ,Ocean View
A white porch with columns and a railing, overlooking a lush green landscape and hills.

11. The Retreat

The Retreat
Lyssons
$87 nightly
The price is $87
Oct 12 - Oct 13
Total with taxes and fees
The Retreat
A covered outdoor area with white columns, potted plants, and a tiled floor.

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

Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC
Fairy Hill
10.0 out of 10, Exceptional, (2 reviews)
"I spent the weekend with my family for my brothers birthday and it was a lovely experience , the ambiance was great and the rooms were spacious and beautiful! I would definitely come back ! Big up !"
United States
Sheneker R.
$360 nightly
The price is $360
Oct 12 - Oct 13
Total with taxes and fees
Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC
A bright, sunlit room with a glass door leading outside, a small round table, and a chair.

13. Port Antonio East Side Villa

Port Antonio East Side Villa
Port Antonio
$145 nightly
The price is $145
Oct 12 - Oct 13
Total with taxes and fees
Port Antonio East Side Villa
A dining area with a table and chairs, a decorative partition, and a view through a window with a metal grill.

14. Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.

Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.
Port Antonio
$103 nightly
The price is $103
Oct 13 - Oct 14
Total with taxes and fees
Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.
A wooden staircase leading to an outdoor patio area with white railings, surrounded by lush greenery and a sign that reads "Spicy Portland."

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

Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
Port Antonio
9.4 out of 10, Exceptional, (15 reviews)
"The staff made the visit memorable. "
United States
Eric
$1,028 nightly
The price is $1,028
Oct 12 - Oct 13
Total with taxes and fees
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
A deck with outdoor seating and a view of the ocean at dusk.

16. Ridge Bay Chateau

Ridge Bay Chateau
3.0 star property
Port Antonio
$417 nightly
The price is $460
Oct 12 - Oct 13
Total with taxes and fees
Ridge Bay Chateau
A garden with various plants and a metal fence.

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

Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.
Port Antonio
$103 nightly
The price is $103
Oct 13 - Oct 14
Total with taxes and fees
Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.
A bedroom with a view of the ocean, a bed with white bedding, a nightstand with a lamp, and a window with a view of trees and the sea.

18. 2 Bedroom Sea View Villa, Frenchman's Cove Resort

2 Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
$514 nightly
The price is $582
Oct 12 - Oct 13
Total with taxes and fees
2 Bedroom Sea View Villa, Frenchman's Cove Resort
A sunlit room with wicker furniture, large windows, and a view of the sea.

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

One Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
6.0 out of 10, (1 review)
"The property has a unique cove and the beach area was very clean and well maintained. The staff there were very polite and helpful. The Villa itself was tidy but showed signs of massive wear and tear. It was more a lack of maintenance rather than true heritage status."
Canada
David
$343 nightly
The price is $388
Oct 12 - Oct 13
Total with taxes and fees
One Bedroom Sea View Villa, Frenchman's Cove Resort
A tropical beach scene with palm trees, a stone structure, and the ocean.

20. Oceanfront 5BDR on beautiful Long Bay Beach in Portland,JA

Oceanfront 5BDR on beautiful Long Bay Beach in Portland,JA
Long Bay
$522 nightly
The price is $522
Nov 1 - Nov 2
Total with taxes and fees
Oceanfront 5BDR on beautiful Long Bay Beach in Portland,JA
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.
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Top Boston Bay Hotel Reviews

Match Resort Hotel

Match Resort Hotel

8/10 Good
"It was close enough to Port Antonio without being in town"
Laurene 5-night trip
Posted 1 day ago
Match Resort Hotel

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 $69 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?

Perfect View - Entire House: This vacation home rental near Boston Bay 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.

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 Frenchman's Cove Beach and Trident Castle.

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.