A pool with a curved edge, surrounded by a stone walkway. There are two colorful Adirondack chairs near the pool.

Vacation Rentals in Saint Mary

Dates

November 2026

December 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Top cities in Saint Mary

An aerial view of a small island with clear turquoise waters, a few palm trees, and a structure with a tower.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Saint Mary vacation rentals

A two-story building with a swimming pool in the foreground.

1. Wave Crest Resort Race Course

Oracabessa

Beverly

￥24,607 total

includes taxes & fees

Nov 9 - Nov 10

A person overlooking a coastal area with a cruise ship, lush greenery, and a swimming pool.

2. Spring Palm Estate

Tower Isle

Shagufta

￥15,828 total

includes taxes & fees

Nov 8 - Nov 9

A swimming pool with a clear view of the surrounding landscape, including hills and a body of water.

3. Braata@Little Bay: Studio with Ocean View

Port Maria

Anneka

￥27,246 total

includes taxes & fees

Nov 18 - Nov 19

A lush, green outdoor area with dense foliage and a variety of trees, including palm trees.

4. Xpress Vacations Lifestyle

Ocho Rios

￥24,332 total

includes taxes & fees

Dec 1 - Dec 2

A beach with boats, a clear sky, and a mountain in the background.

5. Charming 3-bedrooms house in lovely Port Maria with AC, and WiFi and hot water

Port Maria

Shanna

￥53,074 total

includes taxes & fees

Nov 14 - Nov 15

A balcony with a view of a swimming pool and a mountainous landscape.

6. Braata @ Little Bay (Ocean View Villa)

Port Maria

Anneka

￥88,037 total

includes taxes & fees

Nov 16 - Nov 17

A swimming pool with a view of a building and trees in the background.

7. Cozy 1-bedroom apartment with WIFI and AC in enchanting Tower Isle

Tower Isle

Lisa H.

￥12,521 total

includes taxes & fees

Nov 8 - Nov 9

A bedroom with a sloped ceiling, a bed with striped bedding, two bedside tables with lamps, a hanging chair, and a wall-mounted shelf.

8. Leisure Duplex At Csompo Silver Manor

Tower Isle

Cedric

￥25,965 total

includes taxes & fees

Nov 15 - Nov 16

A clear swimming pool with a tiled edge, surrounded by palm trees and a view of the ocean.

9. Chrisanns Hidden Cove 2 bdr apt, sleeps 5, pool, beach

Ocho Rios

Shawn

￥35,751 total

includes taxes & fees

Nov 18 - Nov 19

A beach with a small island in the distance and waves approaching the shore.

10. Glen Sea Inn of St. Mary - Charming 2 Bedroom Beachside Home

Port Maria

Brenda Lee T.

￥17,324 total

includes taxes & fees

Nov 16 - Nov 17

A beach with clear turquoise water, a rocky breakwater, and a yellow building with a balcony.

11. Ocho Rios · Beach Front · 3BR Condo · Pool · Chef · JamaicaTime - Driftwood

Ocho Rios

Anneka

￥62,917 total

includes taxes & fees

Nov 13 - Nov 14

A covered outdoor area with a table and chairs, potted plants, and a view of buildings and trees.

12. one bedroom cozy and quiet neighborhood 10min from ocho rios town

St. Mary Parish

￥20,789 total

includes taxes & fees

Nov 8 - Nov 9

A room with large windows offering a view of a coastal landscape and dense greenery.

13. Dreaming in the Sun Getaway

St. Mary Parish

"This property was an unexpected great find in Robins Bay. Just 3 minutes from the fork in the town. The view of the ocean, the comfortable mattress, the lovely fruit trees and the spacious living room and verandah helped to make our stay a very pleasant one. Aleisha was extremely responsive and her husband Wray and Miss Chunny took care of every detail. The Jamaican breakfast that Chunny made was extremely delicious and it came with a very generous serving of local fruits for a reasonable...

Marva

￥25,040 total

includes taxes & fees

Nov 8 - Nov 9

A multi-story building with a gated entrance, palm trees, and a well-lit facade.

14. 1BR Island Hideaway Near Beaches & Ocho Rios

Tower Isle

Nichola G.

￥17,858 total

includes taxes & fees

Nov 10 - Nov 11

15. The Dream Nest At Csompo Silver Manor

Tower Isle

Fabian

￥22,017 total

includes taxes & fees

Nov 14 - Nov 15

A coastal view with a wooden fence, a gazebo, and a palm tree.

16. Boscobel Hilltop Home 2 Bedrooms & Ocean Views

Salt Gut

￥21,104 total

includes taxes & fees

Nov 10 - Nov 11

A bedroom with a wooden bed, a nightstand, a bedside table, a window with curtains, and a ceiling fan.

17. The Sandpiper Villa - Authentic Jamaican Experience!

Tower Isle

￥66,775 total

includes taxes & fees

Nov 8 - Nov 9

A clear view of the ocean with a rocky shoreline, a lounge chair, and a stone pathway leading to a white railing overlooking the water.

18. Chrisanns Hidden Cove Double Bed room max 3 guests, pool, beach

Tower Isle

Alfred

￥28,033 total

includes taxes & fees

Nov 20 - Nov 21

A large, yellow building with a swimming pool and multiple balconies, surrounded by lush greenery and a view of the ocean.

19. The Palms at Oracabessa Luxury Vacation Rental Fully Staffed

Oracabessa

"We really enjoyed our stay. The villa is modern and beautiful. The views from the balconies were amazing. The staff were attentive but discreet, Chef Shavon was very accommodating, one of our party was lactose intolerant with other intolerances and he at no point forgot that.We ate the mangoes which had fallen from the trees and they were so sweet and juicy.Our stay was short but memorable - it was very relaxing."

M. S.

￥257,023 total

includes taxes & fees

Nov 8 - Nov 9

A poolside area with lounge chairs, palm trees, and a view of the ocean.

20. Charming 1-bedroom in Tower Isle St Mary: AC, WiFi, pool, and a serene retreat.

Tower Isle

AZ SHUTTLE S.

￥45,782 total

includes taxes & fees

Nov 18 - Nov 19

View all properties

Find vacation rentals that suit your style

Top Saint Mary Hotel Reviews

A swimming pool with a white deck, surrounded by lush greenery and a white fence.

Millsborough B&B

Jack's Hill

10/10 Excellent

Boris

A resort with a pool, lounge chairs, and a stone wall.

GoldenEye

Oracabessa

10/10 Excellent

My wife and I just had the most incredible 4 night stay at GoldenEye for our anniversary. We stayed in one of the Lagoon Cottages which was very roomy and comfortable. We loved being directly on the lagoon where we could swim, kayak or just sit and watch the turtles go by. We enjoyed the beaches and pools on the property as well. All of the staff (front desk, restaurants, grounds, water sports, spa, etc.) were wonderful. And, every meal we had at Bizot Bar and Bamboo Bar was delicious and...

Nicholas

A white building with a blue door, black railings, and potted plants.

Sky's Villa Resort

Buff Bay

10/10 Excellent

Tannecia

A pool area with multiple white umbrellas and lounge chairs.

S Hotel Kingston

New Kingston

10/10 Excellent

Carla

A clear blue swimming pool with a stone border, surrounded by trees and a building in the background.

Sea Shell Palms

Tower Isle

10/10 Excellent

Anonymous traveler

Wave Crest Resort Race Course

Oracabessa

10/10 Excellent

Beverly

A wooden deck with a table and chairs, surrounded by lush greenery and a view of distant mountains.

Reggae Legends Estate

Jack's Hill

10/10 Excellent

After a handful of stays here, this definitely feels like a home away from home. If you're looking for a traditional hotel experience with typical hotel amenities, this may not be the spt for you (although it still may be - they have god wifi, TVs, a proper full kitchen, a pool and an onsite restaurant), but I will stay here every time I visit the Kingston area due to the good energy, friendly communication, beautiful property and location, the yummy breakfast - and the proximity to the things I...

Kathleen

A modern two-story building with a paved courtyard and a car parked in front.

Sago Palm Hotel

Ocho Rios

10/10 Excellent

I had the absolute pleasure of staying at this beautiful boutique hotel in Jamaica, and I can confidently say it exceeded all expectations. From the moment I arrived, the staff made me feel incredibly welcomed every single person I interacted with was warm, friendly, and genuinely helpful. Their hospitality truly made the experience feel like a home away from home. The food was another highlight of my stay every meal was fresh, flavorful, and clearly made with love. Knowing that the hotel...

Anonymous traveler

A yellow building with a black gate, a balcony, and a poster advertising Jamaica.

A taste of Jamaica Lavern place

Ocho Rios

10/10 Excellent

Melissa

A person seated at a wooden bar with a stone-tiled floor, holding a drink.

The Courtleigh Hotel and Suites

New Kingston

10/10 Excellent

Millicent

A spacious living area with modern furniture, a large window, and a unique chandelier.

AC Hotel by Marriott Kingston, Jamaica

New Kingston

10/10 Excellent

LENA

A bedroom with a bed, a desk, a chair, a table, and a view of the sea.

Inn The Town

Port Antonio

10/10 Excellent

Camile Ming Wilson

A covered garden pathway with a pond, surrounded by various plants and rocks.

Terra Nova, BW Premier Collection

Half Way Tree

10/10 Excellent

kala

A coastal view with a tree-lined walkway leading to a beach area with a thatched-roof structure.

Hibiscus Lodge

Ocho Rios

10/10 Excellent

Hibiscus was a beautiful hotel in a beautiful location. The view of the ocean is incredible. It's a 5 minute walk to the little beach though. It's on a cliff side with a beautiful garden and walkways that go down to the water. It has the feel of a Caribbean hotel, which is what I prefer over a big gated resort. Restaurants and shopping are a very short walk. Every part of the hotel is placed perfectly to view the ocean (rooms, bar, restaurants.)

Anonymous traveler

Find out more about Saint Mary

Vacation Apartments in Saint Mary

Search for Vacation rentals in Saint Mary on Expedia! You can easily find your home rentals, villas, Vacation apartments in Saint Mary using one of the methods below:

View our selection of featured Vacation rentals in Saint Mary
Use the map to find apartments and other Vacation homes in the Saint Mary neighbourhood you prefer
Enter your travel dates to view the best deals on Vacation rentals in Saint Mary while they last

Look no further and take a look at our great range of rental properties in Saint Mary!

Explore a world of travel with Expedia

Visit Castleton
Standard Link for Visit Castleton

Vacation Rentals in Saint Mary

Change your mind

Treat yourself

Be picky

Top cities in Saint Mary

Tower Isle

Check prices for these dates

Our top choices for Saint Mary vacation rentals

1. Wave Crest Resort Race Course

2. Spring Palm Estate

3. Braata@Little Bay: Studio with Ocean View

4. Xpress Vacations Lifestyle

5. Charming 3-bedrooms house in lovely Port Maria with AC, and WiFi and hot water

6. Braata @ Little Bay (Ocean View Villa)

7. Cozy 1-bedroom apartment with WIFI and AC in enchanting Tower Isle

8. Leisure Duplex At Csompo Silver Manor

9. Chrisanns Hidden Cove 2 bdr apt, sleeps 5, pool, beach

10. Glen Sea Inn of St. Mary - Charming 2 Bedroom Beachside Home

11. Ocho Rios · Beach Front · 3BR Condo · Pool · Chef · JamaicaTime - Driftwood

12. one bedroom cozy and quiet neighborhood 10min from ocho rios town

13. Dreaming in the Sun Getaway

14. 1BR Island Hideaway Near Beaches & Ocho Rios

15. The Dream Nest At Csompo Silver Manor

16. Boscobel Hilltop Home 2 Bedrooms & Ocean Views

17. The Sandpiper Villa - Authentic Jamaican Experience!

18. Chrisanns Hidden Cove Double Bed room max 3 guests, pool, beach

19. The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed

20. Charming 1-bedroom in Tower Isle St Mary: AC, WiFi, pool, and a serene retreat.

Find vacation rentals that suit your style

Top Saint Mary Hotel Reviews

Millsborough B&B

10/10 Excellent

Find out more about Saint Mary

Vacation Apartments in Saint Mary

Explore a world of travel with Expedia

19. The Palms at Oracabessa Luxury Vacation Rental Fully Staffed