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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 $138 total
includes taxes & fees
Aug 30 - Aug 31
Private Oasis - Portland’s Coastal Gated Hideaway

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

Ahh! (Pool/Ocean View Room w/ Private Bath)
Boston Bay
The price is CA $117
CA $263 total
includes taxes & fees
Aug 26 - Aug 27
Ahh! (Pool/Ocean View Room w/ Private Bath)

3. Downstairs Bedroom at Robin Hood guesthouse

Downstairs Bedroom at Robin Hood guesthouse
Port Antonio
The price is CA $63
CA $100 total
includes taxes & fees
Jul 31 - Aug 1
Downstairs Bedroom at Robin Hood guesthouse

4. Bright Country Apartment at Robin Hood guesthouse

Bright Country Apartment at Robin Hood guesthouse
Port Antonio
The price is CA $135
CA $163 total
includes taxes & fees
Jul 31 - Aug 1
Bright Country Apartment at Robin Hood guesthouse

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
The price is CA $140
CA $185 total
includes taxes & fees
Aug 5 - Aug 6
DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon

6. Port Antonio East Side Villa

Port Antonio East Side Villa
Port Antonio
The price is CA $140
CA $204 total
includes taxes & fees
Jul 31 - Aug 1
Port Antonio East Side Villa

7. 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 $414
CA $465 total
includes taxes & fees
Jul 31 - Aug 1
Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC

8. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
The price is CA $760
CA $915 total
includes taxes & fees
Aug 13 - Aug 14
The Grand Sinopia Inn Portland

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

Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland
Port Antonio
The price is CA $114
CA $198 total
includes taxes & fees
Jul 31 - Aug 1
Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland

10. 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 $48
CA $166 total
includes taxes & fees
Aug 28 - Aug 29
Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

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

Views from every angle - 2nd floor cozy villa
Port Antonio
The price is CA $162
CA $218 total
includes taxes & fees
Jul 31 - Aug 1
Views from every angle - 2nd floor cozy villa

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

Horse Shoe Villa Port Antonio air conditioned close to it all family friendly
Port Antonio
The price is CA $140
CA $190 total
includes taxes & fees
Jul 31 - Aug 1
Horse Shoe Villa Port Antonio air conditioned close to it all family friendly

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, (13 reviews)
"The staff made the visit memorable. "
United States
Eric
The price is CA $1,264
CA $1,443 total
includes taxes & fees
Jul 31 - Aug 1
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.

14. Ridge Bay Chateau

Ridge Bay Chateau
3.0 star property
Port Antonio
The price is CA $458
CA $646 total
includes taxes & fees
Jul 31 - Aug 1
Ridge Bay Chateau

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

Horse Shoe Villas A family friendly 2 bedroom villa near to it all
Port Antonio
The price is CA $140
CA $205 total
includes taxes & fees
Jul 31 - Aug 1
Horse Shoe Villas A family friendly 2 bedroom villa near to it all

16. 2 Bedroom Sea View Villa, Frenchman's Cove Resort

2 Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
The price is CA $632
CA $814 total
includes taxes & fees
Aug 11 - Aug 12
2 Bedroom Sea View Villa, Frenchman's Cove Resort

17. 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 $913
CA $1,180 total
includes taxes & fees
Aug 11 - Aug 12
Luxury Three Bedroom Sea View Villa, Frenchman's Cove Resort

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

Charming new 2 BR, 2 BR ocean view villa in Snow District, AC, private/secure
Snow District
10.0 out of 10, Exceptional, (1 review)
"As someone who will only stay at a property that has white sheets & presents as very updated/clean, this property was 10/10. Coming from someone who spent several hours looking for the perfect airbnb for our stay in Portland, to get a 10/10 from me is pretty wild. My husband and I booked last minute and the owner Randy and his team were responsive and helpful from the beginning. The property was exactly as pictured but better. At the time of booking, they didn't have any many photos that really...
United States
Matthew N.
The price is CA $316
CA $407 total
includes taxes & fees
Aug 4 - Aug 5
Charming new 2 BR, 2 BR ocean view villa in Snow District, AC, private/secure

19. Charming 1-bedroom jacuzzi suite in fabulous Amity Hal with AC, WiFi

Charming 1-bedroom jacuzzi suite in fabulous Amity Hal with AC, WiFi
Amity Hal
The price is CA $211
CA $284 total
includes taxes & fees
Jul 31 - Aug 1
Charming 1-bedroom jacuzzi suite in fabulous Amity Hal with AC, WiFi

20. Teejay's rustic retreat

Teejay's rustic retreat
Port Antonio
9.0 out of 10, Wonderful, (2 reviews)
"Best ever home the host Brenon was amazing. Brennon made sure me and my family was comfortable and felt at home. Beautiful home, parking was safe and good. Hot water, air conditioner comfort all around"
United States
Andrea W.
The price is CA $161
CA $344 total
includes taxes & fees
Jul 31 - Aug 1
Teejay's rustic retreat
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: 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.