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

Greenwood Holiday Rentals

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Our top choices for Greenwood holiday 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 NZ$138
includes taxes & fees
21 Sept - 22 Sept
Sunshine Lodge- Your Home Away From Home

2. 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 NZ$187
includes taxes & fees
22 Aug - 23 Aug
Claudeville Condo

3. 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 NZ$293
includes taxes & fees
24 Aug - 25 Aug
Hospitality Expert CB4

4. Lawrence Pool House

Lawrence Pool House
3.5 star property
Ironshore
6.8 out of 10, (70 reviews)
"Very convenient and the apartment had everything you needed to feel at home"
United Kingdom
Vincent
The price is NZ$152
includes taxes & fees
24 Aug - 25 Aug
Lawrence Pool House

5. Montego Bay Club Apartments

Montego Bay Club Apartments
3.5 star property
Hip Strip
7.2 out of 10, Good, (87 reviews)
"Condo is Centrally located on the hip strip . The host was easy to reach when needed. Close to the beach and shopping ."
United States
Reina
The price is NZ$247
includes taxes & fees
24 Aug - 25 Aug
Montego Bay Club Apartments

6. Half Hill All

Half Hill All
3.5 star property
Montego Bay
The price is NZ$1,066
includes taxes & fees
23 Aug - 24 Aug
Half Hill All

7. 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 NZ$251
includes taxes & fees
28 Aug - 29 Aug
La Rose Apartment Jamaica

8. 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 NZ$164
includes taxes & fees
27 Aug - 28 Aug
Angels Hideaway Blue Room

9. 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 NZ$404
includes taxes & fees
22 Aug - 23 Aug
Comfy Villa With Ocean View

10. Summer Shades Villa at Legacy Townhouse

Summer Shades Villa at Legacy Townhouse
2.5 star property
Montego Bay
The price is NZ$1,549
includes taxes & fees
2 Sept - 3 Sept
Summer Shades Villa at Legacy Townhouse

11. Half Hill 1BR

Half Hill 1BR
3.5 star property
Montego Bay
The price is NZ$339
includes taxes & fees
29 Aug - 30 Aug
Half Hill 1BR

12. 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 NZ$921
includes taxes & fees
2 Sept - 3 Sept
Hospitality Expert Eden

13. 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 NZ$369
includes taxes & fees
7 Sept - 8 Sept
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

14. 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 NZ$268
includes taxes & fees
21 Sept - 22 Sept
Villa Jamaica

15. Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
7.4 out of 10, Good, (3 reviews)
"I recommend them and will book agin"
United States
Ainsley
The price is NZ$173
includes taxes & fees
22 Aug - 23 Aug
Sky Beach Rooms

16. Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.6 out of 10, Exceptional, (37 reviews)
"I love love love this place it was more than my expectations this place is like a hidden gem it had everything that I needed 😃 I brought items with me thinking that I needed and to my surprise it had everything I can’t say enough wonderful things about here.And Muhammad who is the caretaker was great he made sure that I was comfortable. It was nice and clean the grounds was well kept and I saw Muhammad always keeping the pool clean this place is great and I will be going back"
United States
Karen
The price is NZ$167
includes taxes & fees
22 Aug - 23 Aug
Montego Bay Ironshore Luxury Studios

17. 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 NZ$283
includes taxes & fees
1 Sept - 2 Sept
Hospitality Expert CB2

18. Blue Turquoise Sea Villa

Blue Turquoise Sea Villa
2.5 star property
Montego Bay
The price is NZ$378
includes taxes & fees
22 Aug - 23 Aug
Blue Turquoise Sea Villa

19. Hospitality Expert CB All

Hospitality Expert CB All
3.0 star property
Montego Bay
The price is NZ$3,135
includes taxes & fees
14 Sept - 15 Sept
Hospitality Expert CB All

20. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is NZ$320
includes taxes & fees
23 Aug - 24 Aug
Turquoise Sea Villa
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Greenwood holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Greenwood. 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 Greenwood. 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 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 holiday 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 Greenwood short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more 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 holiday rentals that Greenwood has to offer?

Sunshine Lodge- Your Home Away From Home: This highly rated holiday home rental in Greenwood is located by the ocean, and has a private balcony, a private garden and a BBQ 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 games in this rental home to help you unwind.

How many holiday rentals are there in Greenwood?

With 6 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.