Boston Bay Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Boston Bay

Ahh! (Ocean View Studio with Private Bath)
10.0 out of 10, Exceptional, (2)
"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."
Ahh! (Ocean View Studio with Private Bath)
Cozy Cabin in the Sky-Wood Thorpe Villa-Ocean View
9.6 out of 10, Exceptional, (14)
"I spent 3 weeks at the Villa with my mom and brother and we had a great time. Portland is a beautiful parish so being in the hillside with the panoramic views overlooking Portlands beauty was just breath taking. Donna is a very gracious host, very accommodating and responsive. Communicating with Donna before we even left for JA and during our time there was easy and pleasant. Donna made sure to provide useful information in the villa such as local places to eat, nearby beaches etc. On our first...
Cozy Cabin in the Sky-Wood Thorpe Villa-Ocean View
Hope Bay-Peaceful getaway w/ pool and steps to natural beach
8.0 out of 10, Very good, (6)
"Great place. Down to earth and clean place. The host is always available and respond quickly."
The price is NZ$267
includes taxes & fees
24 Sept - 25 Sept
Hope Bay-Peaceful getaway w/ pool and steps to natural beach
"Little Paradise" on a peninsula right by the sea!
10.0 out of 10, Exceptional, (24)
"We stayed with our 19 year old adult kid and 10 year old. We snorkeled off the private beach and the dock. Saw plenty of sea life. The accommodations were perfect and the food prepared by Donna was some of the best we’d had here. Definitely wish we stayed here longer."
"Little Paradise" on a peninsula right by the sea!
Heaven Villa - We are not on the water, we are above!
9.2 out of 10, Wonderful, (9)
"Heaven Villa lived up to its name, with one of the best ocean views on the island from the infinity pool and the entire back of the place. We enjoyed ourselves to the fullest at Heaven, including spectacular authentic Jamaican meals prepared by the chef for breakfast and dinner, which we enjoyed as a group. The entire staff were topnotch, especially Marjorie who managed the operation and accommodated our every request. We all love her and will forever appreciate her lovely personality and...
Heaven Villa - We are not on the water, we are above!
Jungle, waterfall, sea view, 5 minutes from beach, lap pool & gym. Bird watching
10.0 out of 10, Exceptional, (2)
"Look no further, this is it. We had a great time and the hosts David and Olga were super nice and helpful. It was very easy to access local attractions, this jungle cottage is so cozy and relaxing you hardly want to leave. We will come back and stay longer next time. Thank you again for making our stay so great. Greetings J."
Jungle, waterfall, sea view, 5 minutes from beach, lap pool & gym. Bird watching
A place in paradise - family villa on a peninsula directly by the sea
10.0 out of 10, Exceptional, (49)
"Our stay was nothing less than exceptional. Joe was our chef and everything we ate was so delicious. The aesthetic of the house is vintage and definitely embodies the island vibe. The view and the grounds at the house were so beautiful. Definitely coming back here very soon! "
A place in paradise - family villa on a peninsula directly by the sea
Beautiful House, Sea and mountain View property less than 1 mile from shopping
9.6 out of 10, Exceptional, (5)
"First I must say this house is even more beautiful than the pictures. My Family and I loved , did I say loved this place. It deserves more than a 5 star ratings, it has everything I needed felt like I was at my own house. The property was CLEAN and exactly as described. The neighborhood was quiet and I felt safe. Everything I needed was in close proximity our host Mr. Anthony is amazing very understanding, readily available and accommodating. I am really looking forward to staying at this...
Beautiful House, Sea and mountain View property less than 1 mile from shopping
Huge villa on two acres of grounds; close to beaches
10.0 out of 10, Exceptional, (2)
"Beaches and hiking close by. Quiet non touristy location "
The price is NZ$454
includes taxes & fees
4 Oct - 5 Oct
Huge villa on two acres of grounds; close to beaches
RVGH 10 bedrooms, 2 guest per room max, 120.00 per nite per room, amazing views
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."
The price is NZ$226
includes taxes & fees
24 Sept - 25 Sept
RVGH 10 bedrooms, 2 guest per room max, 120.00 per nite per room, amazing views
Port Antonio East Side Villa
The price is NZ$232
includes taxes & fees
24 Sept - 25 Sept
Port Antonio East Side Villa
Charming 1-bedroom House in St Thomas Jamaica
3.5 star property
The price is NZ$79
includes taxes & fees
25 Sept - 26 Sept
Charming 1-bedroom House in St Thomas Jamaica
San San Portland private 5 acre estate 4 bedrooms staffed villa
8.6 out of 10, Excellent, (7)
"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...
San San Portland private 5 acre estate 4 bedrooms staffed villa
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
8.4 out of 10, Very good, (6)
"Well located in Port Antonio Denny,Keith and Karen went over and beyond to make our stay memorable. My grand kids loved them! Please consider putting a dishwasher in the kitchen as that will be of great help !"
The price is NZ$1,425
includes taxes & fees
30 Sept - 1 Oct
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
A Private Cottage with a Lovely Pool, Lush Gardens & Breathtaking Views
A Private Cottage with a Lovely Pool, Lush Gardens & Breathtaking Views
Jungle, waterfall, sea view, 5 minutes from beach, lap pool & gym. Bird watching
10.0 out of 10, Exceptional, (7)
"This was our second stay here. The main road from Port Antonio to the turn off is still under construction and the driveway up to the cottages is needing repair. Other than that this place is great value. Includes a well-equipped kitchen for preparing your own meals. We enjoy using the pool and the gym facility with the amazing views. And relaxing in the hammock on the porch surrounded by birds and lush greenery. Local music in the valley can be disturbing at times but not much control over...
Jungle, waterfall, sea view, 5 minutes from beach, lap pool & gym. Bird watching
Kai's Place @ Tim Pappies 3rd Floor luxury villa
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!!!!"
The price is NZ$213
includes taxes & fees
24 Sept - 25 Sept
Kai's Place @ Tim Pappies 3rd Floor luxury villa
Cozy Studio by the Beach
The price is NZ$243
includes taxes & fees
24 Sept - 25 Sept
Cozy Studio by the Beach
Serenity 2-Bed Apartment in Port Antonio
Serenity 2-Bed Apartment in Port Antonio
Blissful Tides
Blissful Tides
Don't see what you're looking for?
See all available properties in Boston Bay
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.
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Boston Bay you may be interested in

Mountainside Guesthouse with stunning coastline views
9.0 out of 10, Wonderful, (46)
"The property is very nice and taken care of. They view from our balcony is absolutely breathtaking. Amazing food and beach within walking distance. John was super helpful and gave us advice as of where to go. He really cares. I will be back."
Mountainside Guesthouse with stunning coastline views
Ahh! (Ocean View Studio with Private Bath)
10.0 out of 10, Exceptional, (2)
"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."
Ahh! (Ocean View Studio with Private Bath)
Jamaica Palace Hotel
3.5 star property
8.2 out of 10, Very good, (189)
"Jamaica Palace was very beautiful. I enjoyed my stay a will definitely stay again."
The price is NZ$327
includes taxes & fees
7 Oct - 8 Oct
Jamaica Palace Hotel
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.

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?

Hope Bay-Peaceful getaway w/ pool and steps to natural beach: This holiday home rental outside of Boston Bay offers an outdoor pool, 1 hot tub and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.