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Boston Bay Holiday Rentals

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Our top choices for Boston Bay holiday 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 NZ$184
includes taxes & fees
2 Nov - 3 Nov
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 NZ$300
includes taxes & fees
2 Nov - 3 Nov
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 NZ$315
includes taxes & fees
2 Nov - 3 Nov
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 NZ$126
includes taxes & fees
2 Nov - 3 Nov
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 NZ$206
includes taxes & fees
2 Nov - 3 Nov
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 NZ$234
includes taxes & fees
2 Nov - 3 Nov
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 NZ$1,003
includes taxes & fees
2 Nov - 3 Nov
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 NZ$3,708
includes taxes & fees
11 Nov - 12 Nov
Norse Hill Estate & Botanic Gardens

9. Port Antonio East Side Villa

Port Antonio East Side Villa
Port Antonio
The price is NZ$243
includes taxes & fees
2 Nov - 3 Nov
Port Antonio East Side Villa

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 NZ$190
includes taxes & fees
16 Nov - 17 Nov
Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

11. 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 NZ$581
includes taxes & fees
2 Nov - 3 Nov
Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC

12. 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 NZ$178
includes taxes & fees
16 Nov - 17 Nov
Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.

13. Kingvilla

Kingvilla
2.0 star property
Port Morant
The price is NZ$168
includes taxes & fees
3 Nov - 4 Nov
Kingvilla

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

Views from every angle - 2nd floor cozy villa
Port Antonio
The price is NZ$261
includes taxes & fees
2 Nov - 3 Nov
Views from every angle - 2nd floor cozy villa

15. 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 NZ$645
includes taxes & fees
2 Nov - 3 Nov
One Bedroom Sea View Villa, Frenchman's Cove Resort

16. 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 NZ$474
includes taxes & fees
2 Nov - 3 Nov
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio

17. 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 NZ$1,655
includes taxes & fees
2 Nov - 3 Nov
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.

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

2 Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
The price is NZ$979
includes taxes & fees
14 Nov - 15 Nov
2 Bedroom Sea View Villa, Frenchman's Cove Resort

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

Lovely 1 bedroom, 2 Guest +, holiday rentals in St Thomas Jamaica
Port Morant
8.0 out of 10, Very good, (2 reviews)
"The house was perfect and thanks to lulu "
United States
Virginia
The price is NZ$109
includes taxes & fees
2 Nov - 3 Nov
Lovely 1 bedroom, 2 Guest +, holiday rentals in St Thomas Jamaica

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 NZ$526
includes taxes & fees
16 Nov - 17 Nov
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Boston Bay holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Boston Bay. 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 Boston Bay. 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 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 holiday 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 Boston Bay short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Boston Bay?

Yes, there are holiday rentals close to the most popular sights in Boston Bay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Boston Bay has to offer?

Perfect View - Entire House: This holiday home rental outside of Boston Bay has free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. This holiday 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 wider area, you’ll find Frenchman's Cove Beach and Trident Castle.

What are holiday rentals like in Boston Bay?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Boston Bay. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for families.