Boston Bay Vacation Rentals from $62: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Boston Bay?

Perfect View - Entire House : This vacation home rental near Boston Bay has free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

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In two weeks

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In four months

Our top choices for Boston Bay vacation 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

Fair Prospect

"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...

Janet

$103 nightly

Nov 5 - Nov 6

Total with taxes and fees

A beach with clear turquoise water, a rocky cliff with vegetation, and a person standing in the water.

2. Ahh! (Ocean View Studio with Private Bath)

Boston Bay

Jerry B.

$163 nightly

Nov 5 - Nov 6

Total with taxes and fees

A wooden deck with a swimming pool, a covered seating area, and a view of the ocean.

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

Boston Bay

$180 nightly

Nov 19 - Nov 20

Total with taxes and fees

A large house with a swimming pool surrounded by lush greenery.

4. Norse Hill Estate & Botanic Gardens

Port Antonio

$1,815 nightly

Nov 5 - Nov 6

Total with taxes and fees

A cozy living room with wicker furniture, a coffee table, and a patterned rug.

5. The Grand Sinopia Inn Portland

Port Antonio

$510 nightly

Nov 5 - Nov 6

Total with taxes and fees

A bedroom with a bed, white curtains, a wooden wardrobe, and an air conditioning unit.

6. DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon

Fairy Hill

Suzette

$117 nightly

Nov 5 - Nov 6

Total with taxes and fees

A wooden sign with the text "Spicy Hill Portland VILLA".

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

Port Antonio

Eric

$977 nightly

Nov 5 - Nov 6

Total with taxes and fees

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

Fairy Hill

Sheneker R.

$342 nightly

Nov 5 - Nov 6

Total with taxes and fees

A kitchen with wooden cabinets, a black countertop, a stove, and a window with a view of greenery.

9. Bright Country Apartment at Robin Hood guesthouse

Port Antonio

$108 nightly

Nov 5 - Nov 6

Total with taxes and fees

A two-story house with a balcony, surrounded by lush greenery.

10. Downstairs Bedroom at Robin Hood guesthouse

Port Antonio

$63 nightly

Nov 5 - Nov 6

Total with taxes and fees

A bright, sunlit room with a glass door leading outside, a small round table, and a chair.

11. Port Antonio East Side Villa

Port Antonio

$137 nightly

Nov 5 - Nov 6

Total with taxes and fees

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.

12. 2 Bedroom Sea View Villa, Frenchman's Cove Resort

Drapers

$489 nightly

Nov 5 - Nov 6

Total with taxes and fees

A spacious room with a stone wall, wooden ceiling, and large windows. There is a dining table with chairs, a sofa, and a blue chair.

13. Luxury Three Bedroom Sea View Villa, Frenchman's Cove Resort

Drapers

$706 nightly

Nov 5 - Nov 6

Total with taxes and fees

A spacious living area with a wooden ceiling, large windows, a white entertainment unit, and a stone wall.

14. Two Bedroom Garden View Villa, Frenchman's Cove Resort

Drapers

$473 nightly

Nov 5 - Nov 6

Total with taxes and fees

A bedroom with a bed, a ceiling fan, a window with a view, and a door.

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

Port Antonio

$147 nightly

Nov 5 - Nov 6

Total with taxes and fees

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.

16. Da Villa Juanita

Hordley

$766 nightly

Nov 5 - Nov 6

Total with taxes and fees

A room with a table and chairs, a window with a decorative metal grill, and a view of greenery outside.

17. Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.

Port Antonio

$101 nightly

Nov 16 - Nov 17

Total with taxes and fees

18. Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

Port Antonio

$107 nightly

Nov 16 - Nov 17

Total with taxes and fees

A balcony with a view of the ocean, a lounge chair, and two drinks on a table.

19. Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio

Snow District

Max L.

$243 nightly

Nov 5 - Nov 6

Total with taxes and fees

20. Rockery Villa Cozy Hideaway for Couple.

Port Antonio

$82 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Top Boston Bay Hotel Reviews

Match Resort Hotel

10/10 Excellent

"Very peaceful, staff was very polite and helpful. Very good place to relaxAAAAA+++++"

Goblin Hill Villas at San San

10/10 Excellent

"Goblin Hill Villas is a spectacular property, with a perfect balance between lush greenery and amazing ocean views. Our villa was spacious, clean, and comfortable with a great retro vibe. We loved watching the waves roll into San San beach, sunrise and sunset, and floating in the pool surrounded by palms and flowers. The bird life is active and varied: one evening we even had a visit from a Jamaican Owl. The staff are professional and friendly, exceptionally helpful, and the food is fantastic. We love Jamaican food in general and theirs is so fresh and flavourful. Blue Lagoon, San San Beach and Frenchman’s Cove are all an easy walk from the villas and wonderful places to enjoy swimming and nature."

Jamaica Colors Eco-Retreat Hotel and Spa

10/10 Excellent

"I loved the ambience. Very mellow. Extraordinary scenery. The staff and property manager were extremely helpful. Breakfast was great, offering us simple but tasty Jamaican cuisine. There's room for improvement as it relates to room decor, but I'd definitely revisit. It was lovely."

All Nations Guesthouse

8/10 Good

"The location was spot on. Wasn’t crowed wasn’t noisy. We had a rental car more than enough parking when we came back from exploring most of what beautiful Portland had to offer. I am an amateur photographer, so Frenchman Cove , Blue Lagoon, Winnifred Beach Reach Falls .. you get me !!!! They got explored. We didn’t have to worry about about driving back home late. 10 - 15min from most local spots."

Moon San Villa at the Blue Lagoon

8/10 Good

"The property is perfectly located next to blue lagoon and the resort is beautiful. It could use some maintenance was a bit dusty, needed some refurbishing. There wasn’t any toiletries as the bookings saiid or the free boat ride so that should be updated. It is hard to get in contact with someone on site when needed. There is someone that pops in from time to time but no number to call. That would be nice to have. TVs don’t connect to wifi or have channels either. All in all it was a nice spot a/c works great, bed is comfy, the view is great, very welcoming and private. I would definitely go back"

Private Oasis - Portland’s Coastal Gated Hideaway

10/10 Excellent

"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 space is adequate to share two beds, a cute kitchen, and washroom is super cute. Loved it. Great choice and price."

Find out more about Boston Bay

Everything you need to know about Boston Bay vacation rentals

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

Boston Bay vacation 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 low season months. For more hustle and bustle, you may prefer to visit Boston Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $62 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Boston Bay rentals

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

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.

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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?

Perfect View - Entire House: This vacation home rental near Boston Bay has free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. 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, Boston Bay Beach and Blue Lagoon 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.

Room 1

Check prices for these dates

Our top choices for Boston Bay vacation rentals

1. Private Oasis - Portland’s Coastal Gated Hideaway

2. Ahh! (Ocean View Studio with Private Bath)

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

4. Norse Hill Estate & Botanic Gardens

5. The Grand Sinopia Inn Portland

6. DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon

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

8. Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC

9. Bright Country Apartment at Robin Hood guesthouse

10. Downstairs Bedroom at Robin Hood guesthouse

11. Port Antonio East Side Villa

12. 2 Bedroom Sea View Villa, Frenchman's Cove Resort

13. Luxury Three Bedroom Sea View Villa, Frenchman's Cove Resort

14. Two Bedroom Garden View Villa, Frenchman's Cove Resort

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

16. Da Villa Juanita

17. Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.

18. Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

19. Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio

20. Rockery Villa Cozy Hideaway for Couple.

Find vacation rentals that suit your style

Top Boston Bay Hotel Reviews

Match Resort Hotel

Great Huts

Sea Cliff Resort

Goblin Hill Villas at San San

Jamaica Colors Eco-Retreat Hotel and Spa

Inn The Town

All Nations Guesthouse

Moon San Villa at the Blue Lagoon

Private Oasis - Portland’s Coastal Gated Hideaway

Find out more about Boston Bay

Explore a world of travel with Expedia

Frequently asked questions

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