Search Holiday Rentals in Greenwood

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Greenwood holiday rentals

Outdoor pool, pool loungers
Turquoise Sea Villa

Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is ฿67,055
฿80,255 total
includes taxes & fees
2 Jan - 3 Jan 2026
Turquoise Sea Villa
Beach nearby, white sand, beach shuttle, sun-loungers
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

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
The price is ฿2,032
฿6,804 total
includes taxes & fees
15 Jan - 16 Jan 2026
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
Luxury Studio, Hill View | In-room safe, desk, laptop workspace, blackout curtains
Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
The price is ฿2,660
฿6,200 total
includes taxes & fees
22 Jan - 23 Jan 2026
Serenitys Hideaway Montego Bay
Seasonal outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas
Villa Jamaica

Villa Jamaica

Villa Jamaica
3.0 star property
Falmouth
9.8 out of 10, Exceptional, (16)
"The property was very nice with all the amenities. "
United States
Tiara
The price is ฿2,262
฿4,967 total
includes taxes & fees
8 Jan - 9 Jan 2026
Villa Jamaica
Aerial view
Villa Nilaja

Villa Nilaja

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
Comfort Suite, 1 Bedroom, Non Smoking (2 Queen Beds) | Individually decorated, individually furnished, iron/ironing board
Bev Rosevilla

Bev Rosevilla

Bev Rosevilla
2.5 star property
Rhyne Park Village
The price is ฿1,960
฿3,218 total
includes taxes & fees
26 Dec - 27 Dec
Bev Rosevilla
Private beach nearby, white sand, beach shuttle, beach cabanas
Nianna Luxurious Villa

Nianna Luxurious Villa

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
The price is ฿7,065
฿10,490 total
includes taxes & fees
28 Dec - 29 Dec
Nianna Luxurious Villa
Exterior
Villa Solstice Luxury 4 Bedroom

Villa Solstice Luxury 4 Bedroom

Villa Solstice Luxury 4 Bedroom
3.5 star property
Montego Bay
The price is ฿34,831
฿43,198 total
includes taxes & fees
4 Jan - 5 Jan 2026
Villa Solstice Luxury 4 Bedroom
Exterior
Lawrence Pool House

Lawrence Pool House

Lawrence Pool House
3.5 star property
Ironshore
7.0 out of 10, Good, (61)
"If the pool was able to use then the stay would be much better "
United States
Rayon
The price is ฿1,960
฿2,809 total
includes taxes & fees
31 Dec - 1 Jan 2026
Lawrence Pool House
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greenwood Hotel Reviews

Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

10/10 Excellent
"Love everything about Ocean Eden Bay this was my 3rd time staying there and I never was disappointed "
Lizzah 5-night trip
Posted 3 days ago
Ocean Eden Bay - Adults Only - All inclusive

Find out more about Greenwood

Search for holiday rentals in Greenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenwood using one of the methods below:

  • View our selection of featured holiday rentals in Greenwood
  • Use the map to find apartments and other holiday homes in the Greenwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Greenwood while they last

Look no further and take a look at our great range of rental properties in Greenwood!

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.