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Shettlewood Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Shettlewood vacation rentals

Rafting

Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
6.0 out of 10, (4 reviews)
"Very comfortable setting"
United States
dawn Marie
$166 nightly
The price is $192
Jul 27 - Jul 28
Total with taxes and fees
Serenitys Hideaway Montego Bay
Living area

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.
$80 nightly
The price is $80
Aug 2 - Aug 3
Total with taxes and fees
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Front of property

Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very Good, (1 review)
"I like that the property was quiet. The place was clean. The neighbor I met was really nice. I like that. It was outside of the tourist area."
United States
Fashira
$83 nightly
The price is $93
Aug 10 - Aug 11
Total with taxes and fees
Unity Villa
Restaurant

Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
2.0 out of 10, (1 review)
"The room was very clean, however the rooms are located in a very local shopping mall with lots of loitering outside, very noisy, no windows so felt claustrophobic. The outside was dirty , crowded and noisy I did not feel safe enough to stay there so I left."
United States
chevone
$98 nightly
The price is $109
Aug 21 - Aug 22
Total with taxes and fees
Sky Beach Rooms
Property grounds

The Artist cabin is a mountain cabin overlooking the sea and coastline

The Artist cabin is a mountain cabin overlooking the sea and coastline
Cave
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay in the mountains of Jamaica! The food was excellent, and we loved watching the sunset every evening. Terry was wonderful company — he even picked us up in Negril to bring us to the beautiful cabins in the woods. A truly magnificent stay!"
United States
Ana G.
$70 nightly
The price is $70
Jul 27 - Jul 28
Total with taxes and fees
The Artist cabin is a mountain cabin overlooking the sea and coastline
Terrace/patio

Seaside Escape

Seaside Escape
Montego Bay
$134 nightly
The price is $134
Aug 4 - Aug 5
Total with taxes and fees
Seaside Escape
Basic Loft | View from room

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.8 out of 10, Excellent, (27 reviews)
"The property was very close to the airport. Bed is comfortable. Only thing is I would av appreciated a kitchen curtain. Apart from that it was great and I love the host she is sweet"
United States
Devine
$96 nightly
The price is $111
Jul 27 - Jul 28
Total with taxes and fees
Claudeville Condo
Outdoor pool

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Hopewell
8.8 out of 10, Excellent, (6 reviews)
"Bonnie was amazing and goes over and beyond to make you feel at home. She is very friendly but gives you your space and privacy I really enjoyed her house with the amazing view and her pool. "
United States
Roberta M.
$155 nightly
The price is $155
Aug 4 - Aug 5
Total with taxes and fees
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Exterior

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
$112 nightly
The price is $130
Jul 27 - Jul 28
Total with taxes and fees
Unity Villa
Outdoor pool, sun loungers

Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
$300 nightly
The price is $332
Jul 29 - Jul 30
Total with taxes and fees
Turquoise Sea Villa
Front of property

Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.4 out of 10, Exceptional, (33 reviews)
"Clean room, serene space and setting, and ideal location."
United States
Remone
$86 nightly
The price is $99
Aug 2 - Aug 3
Total with taxes and fees
Montego Bay Ironshore Luxury Studios
1 bedroom, WiFi, bed sheets

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.
$80 nightly
The price is $80
Jul 27 - Jul 28
Total with taxes and fees
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Terrace/patio

Serene 1-bedroom apartment in Montego Bay perfect for relaxing stays

Serene 1-bedroom apartment in Montego Bay perfect for relaxing stays
Montego Bay
$2,895 nightly
The price is $2,895
Jul 27 - Jul 28
Total with taxes and fees
Serene 1-bedroom apartment in Montego Bay perfect for relaxing stays
Outdoor dining

Come on Home to Paradise, Your Montego Bay Escape.

Come on Home to Paradise, Your Montego Bay Escape.
Paradise Acres
10.0 out of 10, Exceptional, (1 review)
"Beautiful property in a great location! Everything was spotless, comfortable, and exactly as described. The host was incredibly welcoming, responsive, and made our stay effortless. We had a fantastic experience and would happily stay here again. Highly recommend!"
United States
Dionna
$145 nightly
The price is $164
Aug 10 - Aug 11
Total with taxes and fees
Come on Home to Paradise, Your Montego Bay Escape.
Beach nearby

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
$186 nightly
The price is $211
Aug 9 - Aug 10
Total with taxes and fees
Hospitality Expert SWF104 - Pool, Beach, Chef
Outdoor dining

Firefly cottage with Ocean view

Firefly cottage with Ocean view
Cave District
10.0 out of 10, Exceptional, (27 reviews)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
$79 nightly
The price is $79
Jul 30 - Jul 31
Total with taxes and fees
Firefly cottage with Ocean view
Property grounds

Comfy Villa With Ocean View

Comfy Villa With Ocean View
3.0 star property
Ironshore
$187 nightly
The price is $216
Jul 29 - Jul 30
Total with taxes and fees
Comfy Villa With Ocean View
Property grounds

Dragon fly Cottage

Dragon fly Cottage
Cave
10.0 out of 10, Exceptional, (7 reviews)
"We had a lot of fun relaxing here. Geneva made excellent breakfast and suppers and we spent the majority of our time relaxing on the deck/hammock reading and hiking around the property and the town of Kentucky. If you want an escape from the tourism scene, this is a nice place to go! "
Canada
Kaili
$99 nightly
The price is $99
Aug 14 - Aug 15
Total with taxes and fees
Dragon fly Cottage
View from property

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.4 out of 10, (91 reviews)
"The view is amazing just imagine waking to a beautiful blue ocean. Walking distance to the beach and the best restaurants, I recommend this place any day and the price is right.."
United States
Natalie
$148 nightly
The price is $169
Jul 27 - Jul 28
Total with taxes and fees
Montego Bay Club Beach Resort
Property grounds

La Rose Apartment Jamaica

La Rose Apartment Jamaica
3.0 star property
Montego Bay
$129 nightly
The price is $149
Jul 27 - Jul 28
Total with taxes and fees
La Rose Apartment Jamaica
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

Toby's Resort

Toby's Resort

10/10 Excellent
"Old but clean friendly staff"
angella 3-night trip
Posted 3 hours ago
Toby's Resort

Find out more about Shettlewood

Everything you need to know about Shettlewood 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 Shettlewood 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 Shettlewood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shettlewood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shettlewood. 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 Shettlewood 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 $90 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 Shettlewood rentals

At Expedia, we put the best Shettlewood 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 Shettlewood 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 Shettlewood 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 Shettlewood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Shettlewood vacation home rental for your stay. It 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 Rastafari Indigenous Village 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.