Saint Leonards Vacation Rentals

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Our top choices for Saint Leonards vacation rentals

Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
The price is CA $85
CA $235 total
includes taxes & fees
May 16 - May 17
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 25 - Apr 26
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.

Cozy house in charming Montego Bay with AC, WiFi and all other amenities.

Cozy house in charming Montego Bay with AC, WiFi and all other amenities.
Montego Bay
The price is CA $123
CA $183 total
includes taxes & fees
Apr 28 - Apr 29
Cozy house in charming Montego Bay with AC, WiFi and all other amenities.

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 $185
CA $328 total
includes taxes & fees
Apr 27 - Apr 28
Hospitality Expert CB1: Pool, Beach & Chef

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 $137 total
includes taxes & fees
Apr 26 - Apr 27
One Bedroom Apartment minutes from Ys Falls, Safari and Zoo: Royale Flush Suites

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 27 - Apr 28
Impeccable Spacious 3 Bedroom Home Near Beach!

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
Apr 30 - May 1
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

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 $391 total
includes taxes & fees
Apr 30 - May 1
The Best 2 Bedrooms Townhouse in Montego Bay!

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 25 - Apr 26
Unity Villa

Nianna Chatham

Nianna Chatham
2.5 star property
Hip Strip
The price is CA $256
CA $377 total
includes taxes & fees
Apr 27 - Apr 28
Nianna Chatham

1 Bedroom Ocean view Apartment, The Lagoons

1 Bedroom Ocean view Apartment, The Lagoons
montego bay
7.6 out of 10, Good, (7 reviews)
"Places is nice view is good"
United States
Thomas G.
The price is CA $247
CA $279 total
includes taxes & fees
Apr 25 - Apr 26
1 Bedroom Ocean view Apartment, The Lagoons

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is CA $554
CA $706 total
includes taxes & fees
Apr 27 - Apr 28
Casia Villa

Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.4 out of 10, Exceptional, (25 reviews)
"Beautifully kept property! Will stay again! "
United States
cherise
The price is CA $94
CA $109 total
includes taxes & fees
May 19 - May 20
Montego Bay Ironshore Luxury Studios

Newly Furnished 1 Bedroom Apartment - Montego Bay

Newly Furnished 1 Bedroom Apartment - Montego Bay
Ironshore
8.0 out of 10, Very good, (5 reviews)
"Our stay was upgraded to a townhouse due to over booking. Really beautiful property. Yes, we would stay again."
United States
Lisa
The price is CA $164
CA $191 total
includes taxes & fees
Apr 30 - May 1
Newly Furnished 1 Bedroom Apartment - 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.

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 $547
CA $733 total
includes taxes & fees
May 5 - May 6
Eden Luxe 1

Villa Nilaja

Villa Nilaja
5.0 star property
Ironshore
10.0 out of 10, Exceptional, (1 review)
"I booked a destination for my 21 year old daughter birthday and she had aworry free amazing time. The host setup everything my daughter wanted to do flawlessly! The private chef was exceptional with Jamaican and American cuisine! The driver was always out front and on time! Can't wait for the next visit!"
United States
Nakish
The price is CA $1,308
CA $1,711 total
includes taxes & fees
May 8 - May 9
Villa Nilaja

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 $131
CA $152 total
includes taxes & fees
May 5 - May 6
Claudeville Condo

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
Apr 27 - Apr 28
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
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 Saint Leonards Hotel Reviews

Find out more about Saint Leonards

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 Saint Leonards. 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 Saint Leonards?

Yes, there are vacation rentals close to the most popular attractions in Saint Leonards, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Saint Leonards?

Bev Rosevilla: This vacation home near Saint Leonards offers a terrace, a private yard, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Saint Leonards?

Expedia has 373 vacation rentals for your stay in Saint Leonards.

What’s there to see and do in Saint Leonards?

While exploring the area, visit family-friendly sights like Montego Bay Marine Park, or get outside and enjoy nature at YS Falls. In the larger area, you’ll find Bluefields Beach and Appleton Estate.

What’s a vacation rental in Saint Leonards like?

Vacation rentals are private properties where you can stay for a couple of days or more in Saint Leonards. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment 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 family trip.