A beach with clear turquoise waters, a sandy shore, and a rocky outcrop with a gazebo.

Greenwood Vacation Rentals

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Our top choices for Greenwood vacation rentals

1. Sunshine Lodge- Your Home Away From Home

Sunshine Lodge- Your Home Away From Home
4.0 star property
Montego Bay
7.0 out of 10, Good, (4 reviews)
"The host was very easy to communicate with. She greeted us when we arrived. She was great. The house is very beautiful inside and out, the view was amazing. It is very clean inside. The only issue is the way to the house is very difficult to get to. We drove up on a hill that had a lot of bumpy roads and a lot of garbage. Keep in mind if you stay here that once you go out, try to do all of your outings because it’s hard to go back and forth to the house."
United States
Ana Cristina
The price is CA $77
CA $97 total
includes taxes & fees
Sep 11 - Sep 12
Sunshine Lodge- Your Home Away From Home

2. Half Hill 3BR

Half Hill 3BR
3.5 star property
Montego Bay
7.4 out of 10, Good, (3 reviews)
"We loved this property with its’s scenic views and comfortable accommodation. Very pleasant staff."
United States
Canute
The price is CA $280
CA $462 total
includes taxes & fees
Sep 3 - Sep 4
Half Hill 3BR

3. Hospitality Expert Eden

Hospitality Expert Eden
4.0 star property
Montego Bay
8.8 out of 10, Excellent, (6 reviews)
"Yes fabulous view Beautiful and tranquil Lorna was so welcoming and made us feel welcome! Would return again. "
United Kingdom
Jonnette
The price is CA $481
CA $763 total
includes taxes & fees
Sep 8 - Sep 9
Hospitality Expert Eden

4. Hospitality Expert CB4

Hospitality Expert CB4
3.5 star property
Montego Bay
8.2 out of 10, Very good, (32 reviews)
"Felt like home away from home."
United States
paul
The price is CA $123
CA $212 total
includes taxes & fees
Sep 14 - Sep 15
Hospitality Expert CB4

5. BTS6

BTS6
2.0 star property
Montego Bay
The price is CA $163
CA $418 total
includes taxes & fees
Sep 3 - Sep 4
BTS6

6. 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 $1,326
CA $1,734 total
includes taxes & fees
Sep 12 - Sep 13
Villa Nilaja

7. Comfy Villa With Ocean View

Comfy Villa With Ocean View
3.0 star property
Ironshore
10.0 out of 10, Exceptional, (1 review)
The price is CA $216
CA $250 total
includes taxes & fees
Sep 13 - Sep 14
Comfy Villa With Ocean View

8. This is a three bedrooms three bathrooms house that is fully furnihsed

This is a three bedrooms three bathrooms house that is fully furnihsed
Florence Hall
9.0 out of 10, Wonderful, (13 reviews)
"Quick check in and great communications and house was very clean will definitely be staying again."
United States
Ava
The price is CA $162
CA $248 total
includes taxes & fees
Sep 10 - Sep 11
This is a three bedrooms three bathrooms house that is fully furnihsed

9. Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.6 out of 10, Exceptional, (38 reviews)
"Great location . The studio is very convenient. Host is very responsive and always willing to help and go the extra mile. Muhammad was super helpful. Will definitely return anytime I visit. Highly recommended"
United Kingdom
Dapea
The price is CA $131
CA $152 total
includes taxes & fees
Sep 4 - Sep 5
Montego Bay Ironshore Luxury Studios

10. 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 $125
CA $152 total
includes taxes & fees
Sep 4 - Sep 5
Short and longTerm ,Vacational rental home.

11. Eden Luxe 1

Eden Luxe 1
2.5 star property
Montego Bay
10.0 out of 10, Exceptional, (3 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 $243
CA $385 total
includes taxes & fees
Sep 3 - Sep 4
Eden Luxe 1

12. Hospitality Expert SF

Hospitality Expert SF
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 $193
CA $328 total
includes taxes & fees
Sep 9 - Sep 10
Hospitality Expert SF

13. Hospitality Expert CB2

Hospitality Expert CB2
3.5 star property
Montego Bay
8.2 out of 10, Very good, (14 reviews)
"This Place was clean and comfortable. If you need a nice place to relax this place will fit your needs"
United States
Robert
The price is CA $141
CA $233 total
includes taxes & fees
Sep 9 - Sep 10
Hospitality Expert CB2

14. 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
The price is CA $133
CA $154 total
includes taxes & fees
Sep 3 - Sep 4
Claudeville Condo

15. Half Hill 1BR

Half Hill 1BR
3.5 star property
Montego Bay
The price is CA $182
CA $279 total
includes taxes & fees
Sep 3 - Sep 4
Half Hill 1BR

16. Villa Jamaica

Villa Jamaica
3.0 star property
Hague
9.6 out of 10, Exceptional, (24 reviews)
"The environment was exceptionally welcoming, I felt as though I was at home, the environment was impeccably clean, and the host was exemplary."
United States
Oretta
The price is CA $99
CA $219 total
includes taxes & fees
Sep 10 - Sep 11
Villa Jamaica

17. Villa Solstice Luxury 4 Bedroom

Villa Solstice Luxury 4 Bedroom
3.5 star property
Montego Bay
The price is CA $1,552
CA $1,924 total
includes taxes & fees
Sep 3 - Sep 4
Villa Solstice Luxury 4 Bedroom

18. Lawrence Pool House

Lawrence Pool House
3.5 star property
Ironshore
6.8 out of 10, (71 reviews)
"Very convenient and the apartment had everything you needed to feel at home"
United Kingdom
Vincent
The price is CA $87
CA $125 total
includes taxes & fees
Sep 3 - Sep 4
Lawrence Pool House

19. BTS4

BTS4
3.0 star property
Montego Bay
The price is CA $154
CA $407 total
includes taxes & fees
Sep 4 - Sep 5
BTS4

20. Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
8.4 out of 10, Very good, (5 reviews)
"Clean room and the staff were efficient and family friendly, the location was absolutely ideal."
United States
Clayton
The price is CA $109
CA $122 total
includes taxes & fees
Sep 9 - Sep 10
Sky Beach Rooms
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 Greenwood Hotel Reviews

Find out more about Greenwood

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 Greenwood. 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 Greenwood?

Yes, we offer vacation rentals close to the most popular points of interest in Greenwood, or you can choose a secluded option if you're looking for a relaxing stay. Greenwood is known for its local tours and seaside.

What are some of the best vacation home rentals that Greenwood has to offer?

Sunshine Lodge- Your Home Away From Home: This highly rated vacation home rental in Greenwood 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.

How many vacation rentals are there in Greenwood?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

Explore the area and family-friendly sights such as Montego Bay Marine Park, or get out into nature at a spot like Martha Brae River. Greenwood Great House and Rose Hall Great House are a couple of places you'll find in the larger area.

What’s a vacation rental in Greenwood like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Greenwood. Vacation rentals provide amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you a great travel experience. 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 family trips or small group gatherings.