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
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Boston Bay

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 18 - Nov 19
Boston Bay, Portland Cozy Corner
Pool
Ahh! (Pool/Ocean View Room w/ Private Bath)

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

Boston Bay
The price is ￥11,591
￥23,646 total
includes taxes & fees
Nov 18 - Nov 19
Ahh! (Pool/Ocean View Room w/ Private Bath)
Property entrance
Cocosan Villa

Cocosan Villa

4.0 star property
Port Antonio
Cocosan Villa
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
House | Property grounds
Lovely 2 Bedroom House in St Thomas Jamaica

Lovely 2 Bedroom House in St Thomas Jamaica

2.0 star property
Port Morant
The price is ￥12,252
￥14,245 total
includes taxes & fees
Nov 20 - Nov 21
Lovely 2 Bedroom House in St Thomas Jamaica
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
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
1 bedroom, iron/ironing board, free WiFi, bed sheets
Kai's Place @ Tim Pappies 3rd Floor luxury villa

Kai's Place @ Tim Pappies 3rd Floor luxury villa

Port Antonio
10.0 out of 10, Exceptional, (1)
"Totally recommend to stay at this accomodation!!!! The place was spectacular, looked exactly as the images provided!!! It is explained truthfully from the information provided.The ambiance of the place is so peaceful and relaxing!!! Double thumbs up to the hosts for being fantastic and welcoming!!!!"
United Kingdom
Shanice M.
The price is ￥12,936
￥19,118 total
includes taxes & fees
Nov 18 - Nov 19
Kai's Place @ Tim Pappies 3rd Floor luxury villa
Outdoor dining
Eco-Rustic Museum House & Art Stage between two beaches

Eco-Rustic Museum House & Art Stage between two beaches

Port Antonio
7.0 out of 10, Good, (2)
"Host was extremely Helpful and Kind. If you need a ride somewhere just ask. Walking distance to Beach and great places to eat. Its I nice Town with Friendly People. "
United States
Andrew
The price is ￥7,728
￥11,978 total
includes taxes & fees
Nov 18 - Nov 19
Eco-Rustic Museum House & Art Stage between two beaches
Pool
Cosy and quiet retreat, overlooking the blue lagoon. Enjoy the clean crisp air.

Cosy and quiet retreat, overlooking the blue lagoon. Enjoy the clean crisp air.

Port Antonio
8.0 out of 10, Very Good, (1)
"Stay was wonderful! Love the privacy! "
Canada
Vinola C.
The price is ￥23,183
￥35,392 total
includes taxes & fees
Dec 3 - Dec 4
Cosy and quiet retreat, overlooking the blue lagoon. Enjoy the clean crisp air.
Property grounds
House - Sleeps 4 - Patio - Parking

House - Sleeps 4 - Patio - Parking

Port Morant
The price is ￥14,657
￥14,657 total
includes taxes & fees
Dec 15 - Dec 16
House - Sleeps 4 - Patio - Parking
Terrace/patio
Teejay's rustic retreat

Teejay's rustic retreat

Port Antonio
9.0 out of 10, Wonderful, (2)
"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 ￥17,773
￥38,019 total
includes taxes & fees
Nov 18 - Nov 19
Teejay's rustic retreat
Interior
Charming 1-bedroom in wonderful Amity Hal with AC, WiFi

Charming 1-bedroom in wonderful Amity Hal with AC, WiFi

Amity Hal
The price is ￥11,591
￥18,121 total
includes taxes & fees
Nov 18 - Nov 19
Charming 1-bedroom in wonderful Amity Hal with AC, WiFi
Sun loungers
Romantic 2 bedroom, 4 Guest+, holiday rental in Port Morant, St Thomas, Jamaica

Romantic 2 bedroom, 4 Guest+, holiday rental in Port Morant, St Thomas, Jamaica

Port Morant
The price is ￥12,011
￥15,268 total
includes taxes & fees
Nov 18 - Nov 19
Romantic 2 bedroom, 4 Guest+, holiday rental in Port Morant, St Thomas, Jamaica
Microwave, oven, stovetop
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)
"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 ￥34,774
￥46,868 total
includes taxes & fees
Nov 18 - Nov 19
3-bedroom in lovely Amity Hall with WiFi, AC, Private Bathrooms, Best View
Terrace/patio
Bright Country Apartment at Robin Hood guesthouse

Bright Country Apartment at Robin Hood guesthouse

Port Antonio
The price is ￥14,837
￥17,928 total
includes taxes & fees
Nov 29 - Nov 30
Bright Country Apartment at Robin Hood guesthouse
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
House | Beach
House - Sleeps 6 - Patio - Parking

House - Sleeps 6 - Patio - Parking

2.0 star property
Port Morant
The price is ￥16,506
￥19,137 total
includes taxes & fees
Nov 20 - Nov 21
House - Sleeps 6 - Patio - Parking
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
￥152,541 total
includes taxes & fees
Nov 24 - Nov 25
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
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.