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Boston Bay Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Boston Bay holiday 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
The price is NZ$165
includes taxes & fees
16 Sept - 17 Sept
Private Oasis - Portland’s Coastal Gated Hideaway
A wooden deck with a swimming pool, a covered seating area, and a view of the ocean.

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

Ahh! (Pool/Ocean View Room w/ Private Bath)
Boston Bay
The price is NZ$321
includes taxes & fees
17 Sept - 18 Sept
Ahh! (Pool/Ocean View Room w/ Private Bath)
A bedroom with a bed, white curtains, a wooden wardrobe, and an air conditioning unit.

3. 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$227
includes taxes & fees
23 Sept - 24 Sept
DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon
A group of people standing near a small structure by the beach, surrounded by palm trees and ocean views.

4. 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
The price is NZ$450
includes taxes & fees
16 Sept - 17 Sept
Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland
A two-story house with a balcony, surrounded by lush greenery.

5. Bright Country Apartment at Robin Hood guesthouse

Bright Country Apartment at Robin Hood guesthouse
Port Antonio
The price is NZ$201
includes taxes & fees
16 Sept - 17 Sept
Bright Country Apartment at Robin Hood guesthouse
A cozy living room with wicker furniture, a coffee table, and a patterned rug.

6. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
The price is NZ$971
includes taxes & fees
23 Sept - 24 Sept
The Grand Sinopia Inn Portland
A two-story house with a balcony, surrounded by lush greenery.

7. Downstairs Bedroom at Robin Hood guesthouse

Downstairs Bedroom at Robin Hood guesthouse
Port Antonio
The price is NZ$123
includes taxes & fees
16 Sept - 17 Sept
Downstairs Bedroom at Robin Hood guesthouse
A covered outdoor area with white columns, potted plants, and a tiled floor.

8. 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$616
includes taxes & fees
16 Sept - 17 Sept
Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC
A deck with outdoor seating and a view of the ocean at dusk.

9. Ridge Bay Chateau

Ridge Bay Chateau
3.0 star property
Port Antonio
The price is NZ$791
includes taxes & fees
30 Sept - 1 Oct
Ridge Bay Chateau
A spacious living area with a large flat-screen TV, a wooden coffee table, and comfortable seating. A staircase with a railing leads to an upper level.

10. Da Villa Juanita

Da Villa Juanita
Hordley
The price is NZ$450
includes taxes & fees
16 Sept - 17 Sept
Da Villa Juanita
A sunlit room with wicker furniture, large windows, and a view of the sea.

11. 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$664
includes taxes & fees
16 Sept - 17 Sept
One Bedroom Sea View Villa, Frenchman's Cove Resort
A balcony with a view of the ocean, a lounge chair, and two drinks on a table.

12. 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, (2 reviews)
"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 NZ$500
includes taxes & fees
18 Sept - 19 Sept
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
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
The price is NZ$251
includes taxes & fees
16 Sept - 17 Sept
Port Antonio East Side Villa
A garden with various plants and a metal fence.

14. 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$181
includes taxes & fees
16 Sept - 17 Sept
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.

15. 2 Bedroom Sea View Villa, Frenchman's Cove Resort

2 Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
The price is NZ$968
includes taxes & fees
29 Sept - 30 Sept
2 Bedroom Sea View Villa, Frenchman's Cove Resort
A bedroom with a bed, a ceiling fan, a window with a view, and a door.

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

Views from every angle - 2nd floor cozy villa
Port Antonio
The price is NZ$269
includes taxes & fees
16 Sept - 17 Sept
Views from every angle - 2nd floor cozy villa
A wooden staircase leading to an outdoor patio area with white railings, surrounded by lush greenery and a sign that reads "Spicy Portland."

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$1,766
includes taxes & fees
16 Sept - 17 Sept
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
A beach with pebbles, waves, and dense green foliage.

18. 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 NZ$244
includes taxes & fees
16 Sept - 17 Sept
Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland
A balcony with a view of a lush green landscape.

19. 3-bedroom in lovely Amity Hall with WiFi, AC, Private Bathrooms, Best View

3-bedroom in lovely Amity Hall with WiFi, AC, Private Bathrooms, Best View
Amity Hal
10.0 out of 10, Exceptional, (1 review)
"Thank you Michelle for a beautiful stay at YAP. The views were amazing and the cleanliness. Top notch! Michelle was an amazing host and made my mother and I feel like one of the family! Will be returning!"
United States
Karen G.
The price is NZ$555
includes taxes & fees
16 Sept - 17 Sept
3-bedroom in lovely Amity Hall with WiFi, AC, Private Bathrooms, Best View
A covered outdoor area with yellow walls, a white railing, and two chairs.

20. RVGH 10 bedrooms, 260.00 US PER NIGHT PER ROOM, MAX 2 PER ROOM, amazing views.

RVGH 10 bedrooms, 260.00 US PER NIGHT PER ROOM, MAX 2 PER ROOM, amazing views.
Port Antonio
10.0 out of 10, Exceptional, (1 review)
"Everything from the check-in to the stay and check-out was superb. Will be back for sure! Lovely home, with comfortable rooms and beds."
United States
tifevers@msn.com
The price is NZ$500
includes taxes & fees
16 Sept - 17 Sept
RVGH 10 bedrooms, 260.00 US PER NIGHT PER ROOM, MAX 2 PER ROOM, amazing views.
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

Geejam

Geejam

10/10 Excellent
"Great team. Jordan - thanks again. Norman - one in a million. You were all so friendly. Be ready for the steps to water. The room's beautiful but the bed is too soft IMO."
Angela 3-night trip
Posted 18 hours ago
Geejam

Find out more about Boston Bay

Everything you need to know about Boston Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Boston Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Boston Bay holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Boston Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Boston Bay holiday rentals we have selected for you start as low as NZ$121 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Boston Bay rentals

At Expedia, we put the best Boston Bay holiday 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 holiday.

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. 

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.