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 $83
CA $234 total
includes taxes & fees
May 7 - May 8
Serenitys Hideaway Montego Bay

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 11 - May 12
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

One Bedroom Apartment minutes from Ys Falls, Safari and Zoo: Royale Flush Suites

One Bedroom Apartment minutes from Ys Falls, Safari and Zoo: Royale Flush Suites
Middle Quarters
The price is CA $109
CA $136 total
includes taxes & fees
May 4 - May 5
One Bedroom Apartment minutes from Ys Falls, Safari and Zoo: Royale Flush Suites

Bev Rosevilla

Bev Rosevilla
2.5 star property
Rhyne Park Village
The price is CA $116
CA $176 total
includes taxes & fees
Apr 30 - May 1
Bev Rosevilla

Hideaway by the Sea

Hideaway by the Sea
Montego Bay
9.8 out of 10, Exceptional, (37 reviews)
"Very clean space and Sherri thought of every convenience you could need that made my stay very comfortable "
United States
Renardo
The price is CA $95
CA $182 total
includes taxes & fees
Apr 30 - May 1
Hideaway by the Sea

Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Cave
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely gorgeous property and views, bird sounds, fantastic food prepared by the friendly hosts. Simple living with wi-fi if needed."
United States
David G.
The price is CA $82
CA $109 total
includes taxes & fees
May 4 - May 5
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (24 reviews)
"Staff was very friendly and welcoming. "
United Kingdom
Sophia
The price is CA $130
CA $151 total
includes taxes & fees
May 7 - May 8
Claudeville Condo

Angels Hideaway Blue Room

Angels Hideaway Blue Room
2.0 star property
Ironshore
9.0 out of 10, Wonderful, (2 reviews)
"Very convenient location, very affordable. And very clean. The host took good care of us. "
United States
DUSTIN
The price is CA $106
CA $123 total
includes taxes & fees
May 7 - May 8
Angels Hideaway Blue Room

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
May 2 - May 3
Short and longTerm ,Vacational rental home.

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 $93
CA $108 total
includes taxes & fees
May 20 - May 21
Montego Bay Ironshore Luxury Studios

Charming & Comfortable 1-Bedroom Suite in Montego Bay

Charming & Comfortable 1-Bedroom Suite in Montego Bay
Montego Bay
8.2 out of 10, Very good, (12 reviews)
"The kitchen was clean and tidy, had all i needed to cook, shops was walking distance, but can take a cab if you wanted to."
United Kingdom
Lynfus
The price is CA $80
CA $108 total
includes taxes & fees
May 4 - May 5
Charming & Comfortable 1-Bedroom Suite in Montego Bay

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 $94
CA $117 total
includes taxes & fees
May 30 - May 31
Sunshine Lodge- Your Home Away From Home

Lawrence Pool House

Lawrence Pool House
3.5 star property
Ironshore
6.8 out of 10, (69 reviews)
"Great property, great host. Clean, comfortable. I would recommend it to everyone"
United States
Demieco
The price is CA $86
CA $123 total
includes taxes & fees
May 1 - May 2
Lawrence Pool House

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
May 2 - May 3
Impeccable Spacious 3 Bedroom Home Near Beach!

Nianna Coral Bay Deluxe Townhouse 1

Nianna Coral Bay Deluxe Townhouse 1
3.5 star property
Montego Bay
8.6 out of 10, Excellent, (14 reviews)
"Great townhouse. Clean and up to date. The beach is far. And the pool advertised is not the properties pool. I would absolutely stay here again I’m a frequent visitor of the island. I will be back "
United States
Clayteea
The price is CA $163
CA $257 total
includes taxes & fees
May 1 - May 2
Nianna Coral Bay Deluxe Townhouse 1

The heart of Montego Bay

The heart of Montego Bay
Montego Bay
The price is CA $82
CA $134 total
includes taxes & fees
May 2 - May 3
The heart of Montego Bay

Hip Strip Beach Apartment walkable to clubs, beaches and restaurants

Hip Strip Beach Apartment walkable to clubs, beaches and restaurants
Hip Strip
8.6 out of 10, Excellent, (7 reviews)
"Such a great place great location!!"
United States
Matthew K.
The price is CA $102
CA $129 total
includes taxes & fees
May 30 - May 31
Hip Strip Beach Apartment walkable to clubs, beaches and restaurants

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
The price is CA $111
CA $350 total
includes taxes & fees
May 2 - May 3
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1 review)
"I LIKE HOW THEY COMMUNICATED AND ADDRESSED THE PROBLEMS ! Only thing I didn’t like was the no working ac and there wasn’t stuff close to go shop "
United States
Susan
The price is CA $129
CA $177 total
includes taxes & fees
Apr 30 - May 1
Unity Villa
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.