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

Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Greenwood vacation rentals

Traditional Cottage | Terrace/patio

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 ￥8,551
￥10,888 total
includes taxes & fees
Sep 7 - Sep 8
Sunshine Lodge- Your Home Away From Home
Villa, 3 Bedrooms | Property grounds

2. Yanceylargo Estate - Newly Renovated 3 Br Villa W Gorgeous Mountain Views 3 Bedroom Villa by RedAwning

Yanceylargo Estate - Newly Renovated 3 Br Villa W Gorgeous Mountain Views 3 Bedroom Villa by RedAwning
3.0 star property
Montego Bay
The price is ￥25,813
￥63,277 total
includes taxes & fees
Sep 8 - Sep 9
Yanceylargo Estate - Newly Renovated 3 Br Villa W Gorgeous Mountain Views 3 Bedroom Villa by RedAwning
Room

3. BTS4

BTS4
3.0 star property
Montego Bay
The price is ￥18,218
￥46,889 total
includes taxes & fees
Oct 7 - Oct 8
BTS4
Beach

4. Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
4.0 star property
Falmouth Historic Town Centre
10.0 out of 10, Exceptional, (21 reviews)
"This is my first time staying here, and it is a must-do! It has a great location, 24/7 security, and amazing amenities! The peace of the surrounding areas was also a great benefit to staying here! "
United States
Marcia
The price is ￥10,314
￥34,300 total
includes taxes & fees
Sep 7 - Sep 8
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
Exterior

5. Lawrence Pool House

Lawrence Pool House
3.5 star property
Ironshore
6.8 out of 10, (72 reviews)
"Very convenient and the apartment had everything you needed to feel at home"
United Kingdom
Vincent
The price is ￥9,844
￥14,110 total
includes taxes & fees
Sep 7 - Sep 8
Lawrence Pool House
Pool

6. 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 ￥19,298
￥29,353 total
includes taxes & fees
Sep 7 - Sep 8
This is a three bedrooms three bathrooms house that is fully furnihsed
Rooftop pool

7. 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 ￥11,356
￥24,935 total
includes taxes & fees
Sep 10 - Sep 11
Villa Jamaica
Living area

8. 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 ￥7,813
￥12,501 total
includes taxes & fees
Sep 13 - Sep 14
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Beach

9. 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 ￥14,063
￥17,188 total
includes taxes & fees
Sep 7 - Sep 8
Short and longTerm ,Vacational rental home.
Exterior

10. Ultra

Ultra
3.5 star property
Montego Bay
The price is ￥468,624
￥585,951 total
includes taxes & fees
Sep 7 - Sep 8
Ultra
Exterior

11. Angels Hideaway Blue Room

Angels Hideaway Blue Room
2.0 star property
Ironshore
9.6 out of 10, Exceptional, (5 reviews)
"Very convenient location, very affordable. And very clean. The host took good care of us. "
United States
DUSTIN
The price is ￥11,499
￥13,380 total
includes taxes & fees
Sep 7 - Sep 8
Angels Hideaway Blue Room
Beach

12. 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 ￥15,939
￥26,299 total
includes taxes & fees
Sep 8 - Sep 9
Hospitality Expert CB2
Restaurant

13. 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 ￥13,895
￥15,441 total
includes taxes & fees
Sep 9 - Sep 10
Sky Beach Rooms
Beach

14. 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 ￥13,947
￥24,008 total
includes taxes & fees
Sep 14 - Sep 15
Hospitality Expert CB4
Front of property

15. Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.6 out of 10, Exceptional, (39 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 ￥14,766
￥17,137 total
includes taxes & fees
Sep 7 - Sep 8
Montego Bay Ironshore Luxury Studios
Basic Loft | View from room

16. 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 ￥14,943
￥17,340 total
includes taxes & fees
Sep 7 - Sep 8
Claudeville Condo
Property grounds

17. La Rose Apartment Jamaica

La Rose Apartment Jamaica
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and relaxing. The resident host was very courteous, kind and accommodating."
United States
Earl
The price is ￥12,826
￥22,719 total
includes taxes & fees
Oct 7 - Oct 8
La Rose Apartment Jamaica
Pool

18. Montego Bay Ironshore Luxury GOLD ROOM

Montego Bay Ironshore Luxury GOLD ROOM
2.0 star property
Ironshore
The price is ￥11,805
￥13,732 total
includes taxes & fees
Sep 10 - Sep 11
Montego Bay Ironshore Luxury GOLD ROOM
Bar (on property)

19. BTS7

BTS7
3.0 star property
Montego Bay
The price is ￥16,720
￥27,197 total
includes taxes & fees
Sep 13 - Sep 14
BTS7
Beach

20. Charming 3-bedroom in gated community of StoneBrook Manor Trelawny.

Charming 3-bedroom in gated community of StoneBrook Manor Trelawny.
Florence Hall
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay in this beautiful home. I even left my cell phone and property person told me and made it easy for me to have someone come and retrieve it."
United States
Janet
The price is ￥27,346
￥39,534 total
includes taxes & fees
Sep 7 - Sep 8
Charming 3-bedroom in gated community of StoneBrook Manor Trelawny.
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

Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

8/10 Good
"We enjoyed our stay, but had a bad experience with management and how they dealt with a dangerous situation."
Alexi Shantal 7-night trip
Posted less than an hour ago
Ocean Coral Spring - All Inclusive

Find out more about Greenwood

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

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

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.