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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Greenwood vacation rentals

A covered outdoor area with a wooden deck, a green railing with pineapple decorations, and palm trees in the background.

1. Sunshine Lodge- Your Home Away From Home

Sunshine Lodge- Your Home Away From Home
4.0 star property
Montego Bay
7.6 out of 10, Good, (5 reviews)
"Very cool place to stay. Very few minor issues, communication was great. Any real issue we had was not reflective on the property, if you ever drove in Jamaica roads are a little bit rough and the one going up to the property is a little rough but not impossible by any means. The view is amazing the place is clean and the AC in the bedroom works amazing. We had an issue with the gas for the stove, but that might have been more of a user issue than anything else. Everything else worked out fine."
United States
DUSTIN
$72 nightly
The price is $83
Nov 8 - Nov 9
Total with taxes and fees
Sunshine Lodge- Your Home Away From Home
A beach resort with a clear blue sea, palm trees, and a small hut on a pier.

2. 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
$152 nightly
The price is $168
Oct 13 - Oct 14
Total with taxes and fees
Hospitality Expert CB2
A swimming pool with a tiled deck, surrounded by greenery and a few lounge chairs.

3. Angels Hideaway Blue Room

Angels Hideaway Blue Room
2.0 star property
Ironshore
9.8 out of 10, Exceptional, (6 reviews)
"Very convenient location, very affordable. And very clean. The host took good care of us. "
United States
DUSTIN
$74 nightly
The price is $86
Oct 12 - Oct 13
Total with taxes and fees
Angels Hideaway Blue Room
A yellow villa with a swimming pool, surrounded by lush greenery and a clear view of the sea.

4. Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.6 out of 10, Exceptional, (40 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
$95 nightly
The price is $110
Oct 17 - Oct 18
Total with taxes and fees
Montego Bay Ironshore Luxury Studios
A spacious kitchen with wooden cabinets, a refrigerator, and a dining area with a table and chairs.

5. Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.8 out of 10, Excellent, (29 reviews)
"Property was clean and host was accommodating. We had an additional request and host was able to assist."
United States
Sabrina
$96 nightly
The price is $111
Oct 11 - Oct 12
Total with taxes and fees
Claudeville Condo
A beach resort with a clear blue sea, palm trees, and a small hut on a pier.

6. 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
$403 nightly
The price is $442
Oct 14 - Oct 15
Total with taxes and fees
Hospitality Expert Eden
A swimming pool with clear blue water, white lounge chairs, and a large beige umbrella providing shade.

7. Villa Jamaica

Villa Jamaica
3.0 star property
Hague
9.2 out of 10, Wonderful, (25 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
$184 nightly
The price is $212
Nov 3 - Nov 4
Total with taxes and fees
Villa Jamaica
A beach view from a balcony with a clear ocean, a pier, and a few umbrellas on the sand.

8. Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.6 out of 10, (99 reviews)
"Overall great location w/great Ocean Views, various activities and very close to airport. However, property really needs repairs and renovations."
United States
JAMIE
$143 nightly
The price is $163
Nov 10 - Nov 11
Total with taxes and fees
Montego Bay Club Beach Resort
A spacious room with a large bed, a sofa, a wooden coffee table, and a balcony with a view of the ocean.

9. BTS4

BTS4
3.0 star property
Montego Bay
$200 nightly
The price is $231
Oct 19 - Oct 20
Total with taxes and fees
BTS4
A beach resort with a clear blue sea, palm trees, and a small hut on a pier.

10. 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
$215 nightly
The price is $236
Oct 12 - Oct 13
Total with taxes and fees
Hospitality Expert SF
A river with boats docked on both sides, surrounded by lush greenery.

11. Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
6.0 out of 10, (4 reviews)
"Very comfortable setting"
United States
dawn Marie
$188 nightly
The price is $217
Oct 16 - Oct 17
Total with taxes and fees
Serenitys Hideaway Montego Bay
A beach scene with two people running.

12. 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
$179 nightly
The price is $207
Oct 17 - Oct 18
Total with taxes and fees
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
A spacious living area with a pool, blue chairs, and a view of the ocean.

13. 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
$280 nightly
The price is $323
Oct 12 - Oct 13
Total with taxes and fees
Eden Luxe 1
A beach resort with a clear blue sea, palm trees, and a small hut on a pier.

14. Hospitality Expert CB1

Hospitality Expert CB1
3.5 star property
Montego Bay
8.0 out of 10, Very good, (16 reviews)
"Great townhouse. Clean and up to date. The beach is far. And the pool advertised is not the properties pool. I would absolutely stay here again I’m a frequent visitor of the island. I will be back "
United States
Clayteea
$131 nightly
The price is $145
Oct 16 - Oct 17
Total with taxes and fees
Hospitality Expert CB1
A bedroom with a wooden headboard, a bed with plaid bedding, a bedside lamp, and a mirror.

15. Bev Rosevilla

Bev Rosevilla
2.5 star property
Rhyne Park Village
2.0 out of 10, (1 review)
"I was unable to use the accommodation because there was no one there to welcome me and they didn't answer the phone; consequently, I couldn't get in and had to look for somewhere else to stay."
United States
AURELIAN MARIUS
$116 nightly
The price is $129
Oct 11 - Oct 12
Total with taxes and fees
Bev Rosevilla
A swimming pool with a tiled deck, surrounded by a fence and chairs, with a view of greenery and a distant building.

16. Montego Bay Ironshore Luxury GOLD ROOM

Montego Bay Ironshore Luxury GOLD ROOM
2.0 star property
Ironshore
$76 nightly
The price is $88
Oct 11 - Oct 12
Total with taxes and fees
Montego Bay Ironshore Luxury GOLD ROOM
An outdoor dining area with a view of the sea, featuring a thatched-roof structure and wicker furniture.

17. Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
8.4 out of 10, Very good, (6 reviews)
"Clean room and the staff were efficient and family friendly, the location was absolutely ideal."
United States
Clayton
$97 nightly
The price is $108
Oct 11 - Oct 12
Total with taxes and fees
Sky Beach Rooms
A large house with a swimming pool, outdoor seating, and a well-lit patio area.

18. Half Hill 1BR

Half Hill 1BR
3.5 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"The property was convenient to the airport about 10 minutes without traffic. Villas was clean and exactly as shown. On-site staff was attentive and very responsive, so was the entire hospitality expert team. Would stay again."
United States
Nye
$174 nightly
The price is $202
Oct 12 - Oct 13
Total with taxes and fees
Half Hill 1BR
A beach resort with a clear blue sea, palm trees, and a small hut on a pier.

19. Hospitality Expert CB4

Hospitality Expert CB4
3.5 star property
Montego Bay
8.0 out of 10, Very good, (35 reviews)
"Felt like home away from home."
United States
paul
$145 nightly
The price is $160
Nov 10 - Nov 11
Total with taxes and fees
Hospitality Expert CB4
A large house with a swimming pool, outdoor seating, and a well-lit patio area.

20. Half Hill 3BR

Half Hill 3BR
3.5 star property
Montego Bay
8.0 out of 10, Very good, (4 reviews)
"Beautiful and peaceful property. I would definitely visit again. Perfect for large groups and families."
Canada
Kervin
$303 nightly
The price is $349
Oct 12 - Oct 13
Total with taxes and fees
Half Hill 3BR
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

10/10 Excellent
"Sooo beautiful"
Jasmine 7-night trip
Posted 1 hour ago
Ocean Coral Spring - All Inclusive

Find out more about Greenwood

Everything you need to know about Greenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $83 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Cinnamon Hill Golf Course 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.