Greenwood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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
7.0 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 CA $79
CA $100 total
includes taxes & fees
Jun 14 - Jun 15
Sunshine Lodge- Your Home Away From Home

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, (10 reviews)
"Quick check in and great communications and house was very clean will definitely be staying again."
United States
Ava
The price is CA $155
CA $240 total
includes taxes & fees
Jun 7 - Jun 8
This is a three bedrooms three bathrooms house that is fully furnihsed

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Hopewell
10.0 out of 10, Exceptional, (4 reviews)
"Bonnie was amazing and goes over and beyond to make you feel at home. She is very friendly but gives you your space and privacy I really enjoyed her house with the amazing view and her pool. "
United States
Roberta M.
The price is CA $124
CA $186 total
includes taxes & fees
Jun 14 - Jun 15
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
6.0 out of 10, (2 reviews)
"Camille and the rest of the team were amazing! They definitely made it an unforgettable experience! Thank you so much"
United States
Adrian Ruiz
The price is CA $116
CA $218 total
includes taxes & fees
Jun 8 - Jun 9
Serenitys Hideaway Montego Bay

Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.4 out of 10, Exceptional, (28 reviews)
"Very close to the airport and safe."
United States
Chukwufumnaya
The price is CA $90
CA $105 total
includes taxes & fees
Jun 20 - Jun 21
Montego Bay Ironshore Luxury Studios

Vacation Home Rental

Vacation Home Rental
Florence Hall
10.0 out of 10, Exceptional, (1 review)
The price is CA $94
CA $189 total
includes taxes & fees
Jun 7 - Jun 8
Vacation Home Rental

Bev Rosevilla

Bev Rosevilla
2.5 star property
Rhyne Park Village
The price is CA $118
CA $178 total
includes taxes & fees
Jun 4 - Jun 5
Bev Rosevilla

Villa Jamaica

Villa Jamaica
3.0 star property
Hague
9.6 out of 10, Exceptional, (23 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 CA $155
CA $283 total
includes taxes & fees
Jun 23 - Jun 24
Villa Jamaica

Half Hill 3BR

Half Hill 3BR
3.5 star property
Montego Bay
The price is CA $521
CA $739 total
includes taxes & fees
Jun 4 - Jun 5
Half Hill 3BR

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (24 reviews)
"Room was clean and staff was very welcoming with great communication. "
United States
Kenneth
The price is CA $132
CA $153 total
includes taxes & fees
Jun 7 - Jun 8
Claudeville Condo

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, (5 reviews)
"We felt cared and safe at the lovely place"
United States
Maria
The price is CA $211
CA $240 total
includes taxes & fees
Jun 7 - Jun 8
Seaside Jamaica Cottage with Lush Garden, Hammock, 1 minute Walk to Beach!

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
The price is CA $276
CA $310 total
includes taxes & fees
Jun 30 - Jul 1
Steps To Beach - Spacious Clean Cottage w/ Cook

Hospitality Expert CB4

Hospitality Expert CB4
3.5 star property
Montego Bay
8.4 out of 10, Very good, (28 reviews)
"Felt like home away from home."
United States
paul
The price is CA $162
CA $256 total
includes taxes & fees
Jun 3 - Jun 4
Hospitality Expert CB4

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 CA $69
CA $110 total
includes taxes & fees
Jun 10 - Jun 11
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Splendid Sensation

Splendid Sensation
Florence Hall
The price is CA $97
CA $196 total
includes taxes & fees
Jun 10 - Jun 11
Splendid Sensation

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 CA $124
CA $152 total
includes taxes & fees
Jun 10 - Jun 11
Short and longTerm ,Vacational rental home.

Bayview Apartment Montego Bay Montego Freeport

Bayview Apartment Montego Bay Montego Freeport
Montego Bay
9.6 out of 10, Exceptional, (11 reviews)
"Host was amazing and quick to respond! Made the visit seamless! "
United States
Rebekah S.
The price is CA $242
CA $368 total
includes taxes & fees
Jun 4 - Jun 5
Bayview Apartment Montego Bay Montego Freeport

Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
2.0 out of 10, (1 review)
"The room was very clean, however the rooms are located in a very local shopping mall with lots of loitering outside, very noisy, no windows so felt claustrophobic. The outside was dirty , crowded and noisy I did not feel safe enough to stay there so I left."
United States
chevone
The price is CA $137
CA $152 total
includes taxes & fees
Jun 10 - Jun 11
Sky Beach Rooms
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Greenwood Hotel Reviews

Find out more about Greenwood

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

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

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.