Greenwood Vacation Rentals

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Our top choices for Greenwood vacation rentals

Sunshine Lodge- Your Home Away From Home

Sunshine Lodge- Your Home Away From Home
4.0 star property
Montego Bay
7.4 out of 10, Good, (3 reviews)
"It was beautiful on the inside and had an amazing view of Montego Bay."
United States
AGNES
$73 nightly
The price is $85
Jun 6 - Jun 7
Total with taxes and fees
Sunshine Lodge- Your Home Away From Home

Ocean View 2BR Palm Villa 1st Floor

Ocean View 2BR Palm Villa 1st Floor
St. James Parish
$203 nightly
The price is $203
May 8 - May 9
Total with taxes and fees
Ocean View 2BR Palm Villa 1st Floor

Ocean View 2BR Palm Villa 2nd Floor

Ocean View 2BR Palm Villa 2nd Floor
St James
$258 nightly
The price is $258
May 8 - May 9
Total with taxes and fees
Ocean View 2BR Palm Villa 2nd Floor

Modern Sea View Renovated Studio Hip Strip

Modern Sea View Renovated Studio Hip Strip
Hip Strip
9.6 out of 10, Exceptional, (4 reviews)
"Great location"
United States
Kemy S.
$232 nightly
The price is $249
May 28 - May 29
Total with taxes and fees
Modern Sea View Renovated Studio Hip Strip

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
9.2 out of 10, Wonderful, (9 reviews)
"Quick check in and great communications and house was very clean will definitely be staying again."
United States
Ava
$164 nightly
The price is $164
May 8 - May 9
Total with taxes and fees
This is a three bedrooms three bathrooms house that is fully furnihsed

Bev Rosevilla

Bev Rosevilla
2.5 star property
Rhyne Park Village
$113 nightly
The price is $126
May 12 - May 13
Total with taxes and fees
Bev Rosevilla

Vacation Home Rental

Vacation Home Rental
Florence Hall
10.0 out of 10, Exceptional, (1 review)
$133 nightly
The price is $137
May 8 - May 9
Total with taxes and fees
Vacation Home Rental

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

2 Bedroom 2 Bathroom Kitchen Living room and verandah Close to a beach
Coral Spring
$170 nightly
The price is $170
May 8 - May 9
Total with taxes and fees
2 Bedroom 2 Bathroom Kitchen Living room and verandah Close to a beach

Half Hill 3BR

Half Hill 3BR
3.5 star property
Montego Bay
$373 nightly
The price is $430
May 8 - May 9
Total with taxes and fees
Half Hill 3BR

Jhadano 3BR Pool & Gym Shuttle Gated

Jhadano 3BR Pool & Gym Shuttle Gated
Florence Hall
10.0 out of 10, Exceptional, (5 reviews)
"Clean, comfortable and Natoya very accommodating and hospitable."
United States
Gregory K.
$258 nightly
The price is $258
May 10 - May 11
Total with taxes and fees
Jhadano 3BR Pool & Gym Shuttle Gated

Steps To Beach - Spacious Clean Cottage w/ Cook

Steps To Beach - Spacious Clean Cottage w/ Cook
Duncan Bay
9.6 out of 10, Exceptional, (13 reviews)
"Comfortable, clean, cozy and excellent communication from the owner. Would absolutely stay again! This was the best part of our stay in Jamaica. Thank you for the hospitality!"
United States
Valerie
$215 nightly
The price is $215
May 10 - May 11
Total with taxes and fees
Steps To Beach - Spacious Clean Cottage w/ Cook

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.
$110 nightly
The price is $110
May 8 - May 9
Total with taxes and fees
Short and longTerm ,Vacational rental home.

Impeccable Spacious 3 Bedroom Home Near Beach!

Impeccable Spacious 3 Bedroom Home Near Beach!
Montego Bay
9.0 out of 10, Wonderful, (7 reviews)
"Our stay at this property was pleasant, relaxing and quiet. Host was very responsive and checked in during our stay to make sure all was well. There is a local grocery store and restaurant within walking distance which was a plus. Will definitely stay again!"
United States
Bridgette E.
$155 nightly
The price is $160
May 8 - May 9
Total with taxes and fees
Impeccable Spacious 3 Bedroom Home Near Beach!

Beautiful 3 Bedroom Villa with swimming pool, overlooking The Caribbean Sea

Beautiful 3 Bedroom Villa with swimming pool, overlooking The Caribbean Sea
Greenside, Falmouth
$382 nightly
The price is $382
May 8 - May 9
Total with taxes and fees
Beautiful 3 Bedroom Villa with swimming pool, overlooking The Caribbean Sea

Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.4 out of 10, Exceptional, (26 reviews)
"Very close to the airport and safe."
United States
Chukwufumnaya
$71 nightly
The price is $82
May 17 - May 18
Total with taxes and fees
Montego Bay Ironshore Luxury Studios

Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"Camille and the rest of the team were amazing! They definitely made it an unforgettable experience! Thank you so much"
United States
Adrian Ruiz
$148 nightly
The price is $171
May 23 - May 24
Total with taxes and fees
Serenitys Hideaway Montego Bay

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.
$80 nightly
The price is $80
May 14 - May 15
Total with taxes and fees
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

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

VILLA BY THE SEA - Steps to the BEACH - CHEF services included
duncans bay
9.8 out of 10, Exceptional, (209 reviews)
"We had an amazing time. Beautiful beach and the sunrises were spectacular. Annette cooked wonderful meals everyday. "
United States
Norma B.
$198 nightly
The price is $198
May 17 - May 18
Total with taxes and fees
VILLA BY THE SEA - Steps to the BEACH - CHEF services included

Seaside Jamaica Cottage with Lush Garden, Hammock, 1 minute Walk to Beach!

Seaside Jamaica Cottage with Lush Garden, Hammock, 1 minute Walk to Beach!
Duncans Bay
10.0 out of 10, Exceptional, (4 reviews)
"The entire experience was delightful. A total private getaway. Ms. Annette is a gem. Anything we needed, she was right there to assist. We will definitely be back. "
United States
Marcus S.
$173 nightly
The price is $173
May 8 - May 9
Total with taxes and fees
Seaside Jamaica Cottage with Lush Garden, Hammock, 1 minute Walk to Beach!

Rose Hall

Rose Hall
3.5 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"Great house and wonderful caretaker! Wish we had more time there!"
United States
Deborah
$345 nightly
The price is $398
May 9 - May 10
Total with taxes and fees
Rose Hall
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 $82 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.