Boston Bay Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Boston Bay

Property grounds
Rasta Villa B&B

Rasta Villa B&B

Fair Prospect
6.0 out of 10, (1)
"The property is beautiful. You are on a hill top so you have a nice view to see the Ocean from a distance. bigga owner was great, very friendly and accommodating. There is area for cooking. The rooms are nice and big. The only thing i have to say that isnt good is that my room and a few of the other rooms where dusty and needed a good clean. I could feel sand on the floor. Owner explained that house keeper isnt available on the day we came so he did the cleaning. They advertised 8 rooms but we...
United States
IOLANIN M.
Rasta Villa B&B
Beach
Private Oasis - Portland’s Coastal Gated Hideaway

Private Oasis - Portland’s Coastal Gated Hideaway

Fair Prospect
The price is ￥6,943
￥13,886 total
includes taxes & fees
Nov 18 - Nov 19
Private Oasis - Portland’s Coastal Gated Hideaway
Exterior detail
Boston Bay, Portland Cozy Corner

Boston Bay, Portland Cozy Corner

Boston Bay
The price is ￥29,365
￥60,120 total
includes taxes & fees
Nov 19 - Nov 20
Boston Bay, Portland Cozy Corner
Terrace/patio
RVGH 10 bedrooms, 2 guest per room max, 120.00 per nite per room, amazing views

RVGH 10 bedrooms, 2 guest per room max, 120.00 per nite per room, amazing views

Port Antonio
10.0 out of 10, Exceptional, (1)
"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 ￥200,915
￥226,879 total
includes taxes & fees
Nov 18 - Nov 19
RVGH 10 bedrooms, 2 guest per room max, 120.00 per nite per room, amazing views
Outdoor pool
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.

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

Port Antonio
9.0 out of 10, Wonderful, (10)
"The home is so beautiful and well kept. There were 10 of us that stayed in Spicy Hill and it still felt like plenty of space. The pool and garden is beautiful and there’s a great games room. The property is also perfectly located as you can walk to Frenchman’s Cove and the Blue Lagoon. We rented a car from Kingston which i’d recommend so we could drive the 10minutes from the house into town. What made the stay so special was the 3 wonderful caretakers who were incredibly helpful, welcoming and...
United States
Nathan A.
The price is ￥135,231
￥150,995 total
includes taxes & fees
Nov 24 - Nov 25
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
Outdoor dining
Rose Hill Villa with sea view

Rose Hill Villa with sea view

Port Antonio
Rose Hill Villa with sea view
Garden
Kingvilla

Kingvilla

2.0 star property
Port Morant
The price is ￥9,745
￥14,305 total
includes taxes & fees
Nov 18 - Nov 19
Kingvilla
Outdoor pool
Gather,relax, and indulge at Chateau, in your stunning private villa sleeps 12

Gather,relax, and indulge at Chateau, in your stunning private villa sleeps 12

San San
8.4 out of 10, Very Good, (8)
"This is a property built in the 70s that have not been upgraded since the 90s other than the clim units in the bedrooms. The main living area of the house is open do not have clim. During dinner, we were sweating a lot and we ended up with multiple bugs bites. The house has no real windows, it’s only ventilation shutters that separate you from outside. On the positive side, we ate extremely well and the staff was great. So pictures of the house on the website are deceiving and were probably...
United States
Anonymous traveler
Gather,relax, and indulge at Chateau, in your stunning private villa sleeps 12
TV
Charming 2-bedroom cottage in delightful Portland ,Jamaica West Indies with AC

Charming 2-bedroom cottage in delightful Portland ,Jamaica West Indies with AC

2.0 star property
Portland Parish
10.0 out of 10, Exceptional, (1)
"Yes we had a blast at the beach and the Boston jerk center up the street. Our host had great hospitality and was very informative about the area. We will definitely return."
United States
Kaydian S.
Charming 2-bedroom cottage in delightful Portland ,Jamaica West Indies with AC
Interior
Port Antonio East Side Villa

Port Antonio East Side Villa

Port Antonio
The price is ￥15,455
￥22,410 total
includes taxes & fees
Nov 18 - Nov 19
Port Antonio East Side Villa
Outdoor pool
A place in paradise - family villa on a peninsula directly by the sea

A place in paradise - family villa on a peninsula directly by the sea

Port Antonio,
10.0 out of 10, Exceptional, (53)
"This is a truly lovely place and couldn’t recommend it more. Hope I can come back some time soon. "
United States
Fernando G.
A place in paradise - family villa on a peninsula directly by the sea
Property grounds
Heaven Villa - We are not on the water, we are above!

Heaven Villa - We are not on the water, we are above!

Port Antonio
9.4 out of 10, Exceptional, (12)
"The villa itself is very nice and comfortable. Felt like a home away from home. The views are spectacular! The property manager Marjorie was such a pleasure, she made us feel so welcome and at home. She saw to our every need. Brenda our chef was good, anything we wanted she served and even accommodated special diets. We will definitely go to Heaven Villa again!"
United States
Arlene F.
Heaven Villa - We are not on the water, we are above!
Living area
Cozy Cabin in the Sky-Wood Thorpe Villa-Ocean View

Cozy Cabin in the Sky-Wood Thorpe Villa-Ocean View

Port Antonio
9.4 out of 10, Exceptional, (18)
"What an anazing view and such a great host. Couldnt ask for a better time :)"
United States
King
Cozy Cabin in the Sky-Wood Thorpe Villa-Ocean View
Private kitchen
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)
"The host was very welcoming, and miss Mariana was very kimd and friendly. Great place to stay "
United States
Suzette
The price is ￥15,453
￥20,399 total
includes taxes & fees
Nov 18 - Nov 19
DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon
Exterior detail
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)
"We loved our stay, the kids loved the house and we thought Edward was very responsive. It is a lovely house and convenient for our family. We would definitely return and would recommend to others. The house was very spacious and close to Winifred and Frenchman's cove beaches. The only recommendation I have is getting a dryer. It’s more convenient for guest and given it rains sometimes overnight or early morning there is less opportunity to have dry clothes for the next day. But otherwise your...
United States
Keri-Ann
The price is ￥45,592
￥52,083 total
includes taxes & fees
Nov 18 - Nov 19
Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC
Apartment | Property grounds
Serenity 2-bed Apartment in Port Antonio, Portland

Serenity 2-bed Apartment in Port Antonio, Portland

3.0 star property
Port Antonio
Serenity 2-bed Apartment in Port Antonio, Portland
Exterior detail
The Nest Guest House - Home Away From Home House

The Nest Guest House - Home Away From Home House

Port Antonio P.O.
The price is ￥12,364
￥15,455 total
includes taxes & fees
Nov 18 - Nov 19
The Nest Guest House - Home Away From Home House
1 bedroom, in-room safe, desk, iron/ironing board
Relaxing Cottage with Panoramic Mountain, Waterfall & Coast Views, sleeps 4

Relaxing Cottage with Panoramic Mountain, Waterfall & Coast Views, sleeps 4

Port Antonio
10.0 out of 10, Exceptional, (1)
Relaxing Cottage with Panoramic Mountain, Waterfall & Coast Views, sleeps 4
Outdoor pool
The Anton Villas

The Anton Villas

Port Antonio, Jamaica
The Anton Villas
Property grounds
Relax & recharge • Pool • Bird Sanctuary • Ocean, Mountain & Waterfall Views

Relax & recharge • Pool • Bird Sanctuary • Ocean, Mountain & Waterfall Views

Port Antonio
10.0 out of 10, Exceptional, (8)
"The view is phenomenal and peaceful."
United States
Amanda
Relax & recharge • Pool • Bird Sanctuary • Ocean, Mountain & Waterfall 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Boston Bay Hotel Reviews

Jamaica Palace Hotel

Jamaica Palace Hotel

10/10 Excellent
"Yes the room was very clean the staff was amazing and it show that the owner is on top of is biz it was a hurricane and they where prepared we had light hot water they told us the ac will not work so they gave us fan which did a great job it my go to spot whenever am in Portland love the pool the property clean lots of beautiful fords beautiful sea views amazing staff thank you to all the staff we appreciate you awesome service and I have to also big up the chef’s because the food was really good "
Gerry 5-night trip
Posted 7 days ago
Jamaica Palace Hotel

Find out more about Boston Bay

Search for holiday rentals in Boston Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Boston Bay using one of the methods below:

  • View our selection of featured holiday rentals in Boston Bay
  • Use the map to find apartments and other holiday homes in the Boston Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Boston Bay while they last

Look no further and take a look at our great range of rental properties in Boston Bay!

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?

Kingvilla: This vacation home near Boston Bay is equipped with a garden, laundry facilities, and free WiFi to help you feel comfortable during your stay. 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, Blue Lagoon and San San Beach 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.