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Boston Bay Vacation Rentals

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Our top choices for Boston Bay vacation rentals

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
The price is CA $70
CA $158 total
includes taxes & fees
Nov 2 - Nov 3
Private Oasis - Portland’s Coastal Gated Hideaway

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.
The price is CA $104
CA $248 total
includes taxes & fees
Nov 4 - Nov 5
Ahh! (Ocean View Studio with Private Bath)

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

Ahh! (Pool/Ocean View Room w/ Private Bath)
Boston Bay
The price is CA $115
CA $260 total
includes taxes & fees
Oct 30 - Oct 31
Ahh! (Pool/Ocean View Room w/ Private Bath)

4. Downstairs Bedroom at Robin Hood guesthouse

Downstairs Bedroom at Robin Hood guesthouse
Port Antonio
The price is CA $63
CA $99 total
includes taxes & fees
Oct 30 - Oct 31
Downstairs Bedroom at Robin Hood guesthouse

5. Bright Country Apartment at Robin Hood guesthouse

Bright Country Apartment at Robin Hood guesthouse
Port Antonio
The price is CA $134
CA $162 total
includes taxes & fees
Oct 31 - Nov 1
Bright Country Apartment at Robin Hood guesthouse

6. 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
The price is CA $140
CA $185 total
includes taxes & fees
Oct 30 - Oct 31
DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon

7. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
The price is CA $657
CA $790 total
includes taxes & fees
Nov 5 - Nov 6
The Grand Sinopia Inn Portland

8. Norse Hill Estate & Botanic Gardens

Norse Hill Estate & Botanic Gardens
3.5 star property
Port Antonio
The price is CA $1,931
CA $2,922 total
includes taxes & fees
Nov 5 - Nov 6
Norse Hill Estate & Botanic Gardens

9. Port Antonio East Side Villa

Port Antonio East Side Villa
Port Antonio
The price is CA $140
CA $203 total
includes taxes & fees
Oct 30 - Oct 31
Port Antonio East Side Villa

10. 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.
The price is CA $441
CA $498 total
includes taxes & fees
Oct 30 - Oct 31
Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC

11. 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
The price is CA $56
CA $151 total
includes taxes & fees
Nov 17 - Nov 18
Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

12. 2 Bedroom Sea View Villa, Frenchman's Cove Resort

2 Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
The price is CA $630
CA $814 total
includes taxes & fees
Oct 31 - Nov 1
2 Bedroom Sea View Villa, Frenchman's Cove Resort

13. 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
The price is CA $1,259
CA $1,438 total
includes taxes & fees
Oct 30 - Oct 31
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.

14. 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
The price is CA $420
CA $537 total
includes taxes & fees
Oct 31 - Nov 1
One Bedroom Sea View Villa, Frenchman's Cove Resort

15. 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
The price is CA $50
CA $145 total
includes taxes & fees
Nov 17 - Nov 18
Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.

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

Views from every angle - 2nd floor cozy villa
Port Antonio
The price is CA $161
CA $217 total
includes taxes & fees
Oct 30 - Oct 31
Views from every angle - 2nd floor cozy villa

17. Kingvilla

Kingvilla
2.0 star property
Port Morant
The price is CA $91
CA $133 total
includes taxes & fees
Nov 1 - Nov 2
Kingvilla

18. Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio

Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
Snow District
10.0 out of 10, Exceptional, (3 reviews)
"Randy's place is clean and is exactly as seen online. Must come back here"
Canada
Max L.
The price is CA $315
CA $403 total
includes taxes & fees
Oct 30 - Oct 31
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio

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

Luxury Three Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
The price is CA $909
CA $1,176 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Three Bedroom Sea View Villa, Frenchman's Cove Resort

20. Pearl Ocean Villa

Pearl Ocean Villa
3.5 star property
Saint Margarets Bay
10.0 out of 10, Exceptional, (1 review)
"Cleanest the hoast was superb"
United States
Michael
The price is CA $350
CA $414 total
includes taxes & fees
Nov 17 - Nov 18
Pearl Ocean Villa
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

Find out more about Boston Bay

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Boston Bay. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.