Greenwood Vacation Rentals

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Our top choices for Greenwood vacation rentals

Ocean View 2BR Palm Villa 1st Floor

St. James Parish
$201 nightly
The price is $201
Dec 11 - Dec 12
Total with taxes and fees
Ocean View 2BR Palm Villa 1st Floor

Ocean View 2BR Palm Villa 2nd Floor

St James
$258 nightly
The price is $258
Dec 11 - Dec 12
Total with taxes and fees
Ocean View 2BR Palm Villa 2nd Floor

Turquoise Sea Villa

3.5 star property
Montego Bay
$2,256 nightly
The price is $2,580
Dec 11 - Dec 12
Total with taxes and fees
Turquoise Sea Villa

Short and longTerm ,Vacational rental home.

Rhyne Park Village
8.8 out of 10, Excellent, (3)
"Kadean is the best!.. very helpful everyday of my stay.."
United States
Julia M.
$110 nightly
The price is $110
Dec 11 - Dec 12
Total with taxes and fees
Short and longTerm ,Vacational rental home.

Serenitys Hideaway Montego Bay

3.5 star property
Montego Bay
$187 nightly
The price is $216
Dec 11 - Dec 12
Total with taxes and fees
Serenitys Hideaway Montego Bay

Villa Solstice Luxury 4 Bedroom

3.5 star property
Montego Bay
$1,151 nightly
The price is $1,325
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Solstice Luxury 4 Bedroom

Lawrence Pool House

3.5 star property
Ironshore
7.0 out of 10, Good, (59)
"The property is nice. The owner was very friendly as well. I would definitely recommend and the pool is clean."
United States
Devine
$79 nightly
The price is $86
Dec 11 - Dec 12
Total with taxes and fees
Lawrence Pool House

Nianna Luxurious Villa

3.5 star property
Montego Bay
8.8 out of 10, Excellent, (5)
"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
$202 nightly
The price is $223
Dec 11 - Dec 12
Total with taxes and fees
Nianna Luxurious Villa

Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

4.0 star property
Falmouth
9.8 out of 10, Exceptional, (18)
"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
$169 nightly
The price is $195
Dec 15 - Dec 16
Total with taxes and fees
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

Villa Jamaica

3.0 star property
Falmouth
9.8 out of 10, Exceptional, (16)
"Clean and well kept "
United States
Kareema
$138 nightly
The price is $160
Jan 8 - Jan 9, 2026
Total with taxes and fees
Villa Jamaica

Bev Rosevilla

2.5 star property
Rhyne Park Village
$93 nightly
The price is $103
Dec 11 - Dec 12
Total with taxes and fees
Bev Rosevilla

Blue Turquoise Sea Villa

2.5 star property
Montego Bay
$154 nightly
The price is $163
Dec 11 - Dec 12
Total with taxes and fees
Blue Turquoise Sea Villa

VILLA BY THE SEA - Steps to the BEACH - CHEF services included

duncans bay
9.8 out of 10, Exceptional, (201)
"Lovely place steps from the beach!"
Canada
Steve N.
$155 nightly
The price is $155
Dec 13 - Dec 14
Total with taxes and fees
VILLA BY THE SEA - Steps to the BEACH - CHEF services included

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

Trelawny Jamaica West Indies
8.4 out of 10, Very Good, (5)
"It was a great experience waking up to an ocean view"
United States
Donnett M.
$178 nightly
The price is $178
Dec 11 - Dec 12
Total with taxes and fees
This is a three bedrooms three bathrooms house that is fully furnihsed

2 Bedroom 2 Bathroom Kitchen Living room and verandah Close to a beach

Coral Spring
$172 nightly
The price is $172
Dec 11 - Dec 12
Total with taxes and fees
2 Bedroom 2 Bathroom Kitchen Living room and verandah Close to a beach

Ultra

3.5 star property
Montego Bay
$3,260 nightly
The price is $3,750
Dec 11 - Dec 12
Total with taxes and fees
Ultra

Exclusive Mountain & Farm Villa Escape

Spring Garden
$188 nightly
The price is $194
Dec 11 - Dec 12
Total with taxes and fees
Exclusive Mountain & Farm Villa Escape

Villa Nilaja

5.0 star property
Ironshore
10.0 out of 10, Exceptional, (1)
"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
Villa Nilaja

Serenity Suite; The Jamaican Retreat

Montego Bay
$90 nightly
The price is $90
Dec 11 - Dec 12
Total with taxes and fees
Serenity Suite; The Jamaican Retreat

Quiet Vacation Home In Jamaica Martha Brae Trelawny. Jamaica Rental Getaway

Martha Brae
8.0 out of 10, Very Good, (6)
"Was a great stay, the host was very responsive!"
United States
Anna-Kay
$130 nightly
The price is $130
Dec 11 - Dec 12
Total with taxes and fees
Quiet Vacation Home In Jamaica Martha Brae Trelawny. Jamaica Rental Getaway
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

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 $86 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 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.