Shettlewood Vacation Rentals

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Our top choices for Shettlewood vacation rentals

Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
The price is CA $86
CA $237 total
includes taxes & fees
May 5 - May 6
Serenitys Hideaway Montego Bay

Bev Rosevilla

Bev Rosevilla
2.5 star property
Rhyne Park Village
The price is CA $117
CA $177 total
includes taxes & fees
Apr 28 - Apr 29
Bev Rosevilla

Short and longTerm ,Vacational rental home.

Short and longTerm ,Vacational rental home.
Rhyne Park Village
8.8 out of 10, Excellent, (3 reviews)
"Kadean is the best!.. very helpful everyday of my stay.."
United States
Julia M.
The price is CA $123
CA $150 total
includes taxes & fees
Apr 28 - Apr 29
Short and longTerm ,Vacational rental home.

Hospitality Expert CB1: Pool, Beach & Chef

Hospitality Expert CB1: Pool, Beach & Chef
Montego Bay
8.8 out of 10, Excellent, (10 reviews)
"Had a good experience shower pressure, and bathroom flushing was a lil problem otherwise all was well for me"
United States
Kevin D.
The price is CA $156
CA $289 total
includes taxes & fees
May 1 - May 2
Hospitality Expert CB1: Pool, Beach & Chef

Half Hill 3BR

Half Hill 3BR
3.5 star property
Montego Bay
The price is CA $359
CA $551 total
includes taxes & fees
Apr 29 - Apr 30
Half Hill 3BR

Sunshine Lodge- Your Home Away From Home

Sunshine Lodge- Your Home Away From Home
4.0 star property
Montego Bay
7.4 out of 10, Good, (3 reviews)
"It was beautiful on the inside and had an amazing view of Montego Bay."
United States
AGNES
The price is CA $93
CA $116 total
includes taxes & fees
May 5 - May 6
Sunshine Lodge- Your Home Away From Home

Impeccable Spacious 3 Bedroom Home Near Beach!

Impeccable Spacious 3 Bedroom Home Near Beach!
Montego Bay
9.0 out of 10, Wonderful, (7 reviews)
"Our stay at this property was pleasant, relaxing and quiet. Host was very responsive and checked in during our stay to make sure all was well. There is a local grocery store and restaurant within walking distance which was a plus. Will definitely stay again!"
United States
Bridgette E.
The price is CA $123
CA $219 total
includes taxes & fees
Apr 29 - Apr 30
Impeccable Spacious 3 Bedroom Home Near Beach!

Nianna Chatham

Nianna Chatham
2.5 star property
Hip Strip
The price is CA $195
CA $308 total
includes taxes & fees
Apr 28 - Apr 29
Nianna Chatham

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Mount Salem
10.0 out of 10, Exceptional, (1 review)
"I stayed at Topaz Dream Guesthouse in Montego Bay during Sumfest 2025, and it was such a beautiful and unforgettable experience. The space is cozy, artistic, and full of character, but what truly makes it special is Cherri, the host.Cherri is warm, wise, and simply amazing. She carries the spirit of Jamaica in her heart and has the most incredible stories of life, love, triumph, and resilience. Connecting with her was the true highlight of my trip—our conversations left me feeling inspired and...
United States
English C.
The price is CA $68
CA $109 total
includes taxes & fees
May 4 - May 5
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Nianna Luxurious Villa

Nianna Luxurious Villa
3.5 star property
Montego Bay
8.4 out of 10, Very good, (6 reviews)
"The property was beautiful and offered great views and even had a small private pool. The space was welcoming and large, perfect for a small family! We do recommend the resort, especially during hot months, to have the AC units serviced appropriately as there aren’t many close dining options so most meals are prepared in the home, and no AC in the kitchen was miserably hot. We did have a difficult time after check in to get in touch with the resort to arrange transportation in a timely manner....
United States
William
The price is CA $245
CA $385 total
includes taxes & fees
Apr 29 - Apr 30
Nianna Luxurious Villa

Rose Hall

Rose Hall
3.5 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"Great house and wonderful caretaker! Wish we had more time there!"
United States
Deborah
The price is CA $310
CA $563 total
includes taxes & fees
Apr 28 - Apr 29
Rose Hall

Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is CA $194
CA $327 total
includes taxes & fees
May 12 - May 13
Sunshine Seashore Escape Jamaica

The Best 2 Bedrooms Townhouse in Montego Bay!

The Best 2 Bedrooms Townhouse in Montego Bay!
Ironshore
8.6 out of 10, Excellent, (7 reviews)
"Chester was the best host EVER!!!"
United States
Weslyn A.
The price is CA $342
CA $390 total
includes taxes & fees
Apr 28 - Apr 29
The Best 2 Bedrooms Townhouse in Montego Bay!

Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.

Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
Montego Bay
10.0 out of 10, Exceptional, (68 reviews)
"Such a nice stay at windfall Villas, Mel was great and always able to get us to anywhere at almost anytime we needed. It was beautiful and peaceful at the property. Would highly recommend to anyone checking out Montego Bay. Think twice begore trying drive here. In my opinion this is one dangerous place to drive unless you’ve driven here before. Mel made this part of our trip completely safe. "
United States
Jeff B.
The price is CA $416
CA $476 total
includes taxes & fees
Apr 30 - May 1
Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.

Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.4 out of 10, Exceptional, (26 reviews)
"Beautifully kept property! Will stay again! "
United States
cherise
The price is CA $94
CA $109 total
includes taxes & fees
May 17 - May 18
Montego Bay Ironshore Luxury Studios

The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.

The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.
Lucea
8.0 out of 10, Very good, (4 reviews)
"We enjoyed ourselves. And our stay was very pleasant."
United States
Cynthia N.
The price is CA $136
CA $237 total
includes taxes & fees
May 6 - May 7
The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.

Eden Luxe 1

Eden Luxe 1
2.5 star property
Montego Bay
10.0 out of 10, Exceptional, (2 reviews)
"The place was beautiful. Staff was friendly and helpful with the check in process. Will be planning another visit in the near future."
United States
Kelleia
The price is CA $396
CA $560 total
includes taxes & fees
Apr 30 - May 1
Eden Luxe 1

Hospitality Expert SF: Private Pool, Beach, Chef

Hospitality Expert SF: Private Pool, Beach, Chef
Montego Bay
9.8 out of 10, Exceptional, (9 reviews)
"Beautiful property. Well-decorated and landscaped. Nice pool with incredible view! Only thing I would wish for is to have stayed longer!"
United States
David G.
The price is CA $284
CA $501 total
includes taxes & fees
Apr 29 - Apr 30
Hospitality Expert SF: Private Pool, Beach, Chef

Hospitality Expert SWF104 - Pool, Beach, Chef

Hospitality Expert SWF104 - Pool, Beach, Chef
Montego Bay
10.0 out of 10, Exceptional, (2 reviews)
"Nice place and breakfast"
Spain
Xavier
The price is CA $185
CA $326 total
includes taxes & fees
May 8 - May 9
Hospitality Expert SWF104 - Pool, Beach, Chef

Serenity Suite; The Jamaican Retreat

Serenity Suite; The Jamaican Retreat
Montego Bay
The price is CA $96
CA $137 total
includes taxes & fees
Apr 28 - Apr 29
Serenity Suite; The Jamaican Retreat
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 Shettlewood Hotel Reviews

Find out more about Shettlewood

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Shettlewood. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Shettlewood?

Yes, we give you a choice of vacation rentals near popular points of interest in Shettlewood, or you can choose a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Shettlewood?

Sunshine Lodge- Your Home Away From Home: You might want to consider this vacation home rental near Shettlewood, which is located by the ocean and has a private balcony, a private yard, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Shettlewood?

Explore the area and family-friendly sights such as Montego Bay Marine Park, or get out into nature at a spot like Freeport Peninsula. Montego Bay Cruise Ship Terminal and Saint James Parish Church are a couple of places you'll find in the larger area.

What’s a vacation rental in Shettlewood like?

Vacation rentals are private properties you can stay in for several days or longer in Shettlewood. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a small group gathering.