We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.

Popular vacation rentals:

Explore the world! TripAdvisor has reviews and information on over 400,000 locations, including:
Vacation Rentals

Explore other Montego Bay resources:

Montego Bay Vacation Rentals

Hotels (61)

B&Bs / Inns (14)

Specialty Lodging (8)

Vacation Rentals (285)

The safest rental experience online

Rent from verified owners and managers, and read reviews before you book.

Find out what to expect »

In partnership with:

Get listed!

Add your property »

Featured listings
Tranquillty
Tranquillty
Ladywood Villa
Ladywood Villa
Caribbean Fairways
Caribbean Fairways
Sunrise, Tryall
Sunrise, Tryall
Mirador, Tryall, 1 br
Mirador, Tryall, 1 br
Mahogany Mews,Tryall 1br
Mahogany Mews,Tryall 1br
Ma Mer Bleu
Ma Mer Bleu
Linga Longer, Tryall
Linga Longer, Tryall
Karma Bay, Tryall
Karma Bay, Tryall
Island House, Tryall
Island House, Tryall

Search Montego Bay Vacation Rentals

Clear dates

Advanced Search

Vacation rentals you can trust

[ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
Ackee 8 at Tryall
Ackee 8 at Tryall
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Ackee 8 is named after Jamaica’s national fruit. This villa is located on a gentle sloping hillside, has spectacular views of the Caribbean Sea and is also ...
  • Nightly
    --
  • Weekly
    $4,400 - $10,725
  • Monthly
    --
Montego Bay Beach Villa
Montego Bay Beach Villa
Contact Owner
Nightly rate from
$800
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 5
Min stay:5
The Afimi Beach House is new waterfront villa in the Lagoons, an upscale gated community in Montego Bay. This spectacular villa with it's own private white ...
  • Nightly
    $800 - $1,271
  • Weekly
    $5,600 - $8,900
  • Monthly
    --
Villa Rococo
Villa Rococo
Contact Manager
Nightly rate from
$429
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 5
This very private and gated community features endless luxuries...Vila Rococo captures the allures of Western Jamaica sharing an ideal spanning of hundreds of ...
  • Nightly
    $429 - $1,000
  • Weekly
    $3,003 - $7,000
  • Monthly
    $10,210 - $23,800
Calypso at Tryall
Calypso at Tryall
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
Calypso is such a charming and tranquil home. It is set on four acres within the famous Tryall Resort and has beautiful gardens and orchards. From the pool ...
  • Nightly
    --
  • Weekly
    $4,950 - $14,750
  • Monthly
    --
Highland House
Highland House
Contact Manager
Nightly rate from
$929
Management: Professional
Property: Rental Home
Bedrooms: 6, sleeps 12
Bathrooms: 6
Highland House Estate is one of Jamaica's most elegant private homes, previously Oscar Hammerstein Estate in the 1960's. This large 7000sq ft home set on 17+ ...
  • Nightly
    $929 - $1,357
  • Weekly
    $6,500 - $9,500
  • Monthly
    $22,100 - $32,300
Fairwinds, Tryall
Fairwinds, Tryall
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
Fairwinds is located conveniently near to the Great House and world class facilities of the World famous Tryall Club Resort. This villa is special as it has a ...
  • Nightly
    --
  • Weekly
    $4,950 - $13,370
  • Monthly
    --
Following Seas, Tryall
Following Seas, Tryall
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 6, sleeps 14
Following Seas is one of Tryalls large Premier rated (the highest rating in the Tryall Club) villa set on 7 acres of manicured lawns and gardens. The villa is ...
  • Nightly
    --
  • Weekly
    $15,000 - $30,000
  • Monthly
    --
Ma'Moura, Tryall
Ma'Moura, Tryall
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
Ma' Moura is a wonderful villa which is open and spacious with a sparkling circular swimming pool as the focal point for entertaining and relaxing. This villa ...
  • Nightly
    --
  • Weekly
    $4,950 - $12,155
  • Monthly
    --
Seaspray, Tryall
Seaspray, Tryall
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
This is a wonderful 4 bedroom waterfront villa located within the famous Tryall Club estate. It has the most wonderful views of the Caribbean sea. There is a ...
  • Nightly
    --
  • Weekly
    $6,050 - $17,500
  • Monthly
    --
silent_waters_2br
silent_waters_2br
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 3
Silent Waters Villa is a premier Caribbean luxury villa located in Montego Bay, Jamaica. The exclusive 18-acre property is situated on one of the highest ...
  • Nightly
    --
  • Weekly
    $14,000 - $19,000
  • Monthly
    --
Folly at Tryall
Folly at Tryall
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
This lovely villa has a lovely garden courtyard as you enter through the front gates. The Moorish fountain is a wonderful feature at the entrance of this ...
  • Nightly
    --
  • Weekly
    $4,950 - $12,155
  • Monthly
    --
sea_island_4br
sea_island_4br
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 4
Sea Island's spectacular renovation has produced a stunning private villa located on the western hillside of Montego Bay. There are 4 air-conditioned ...
  • Nightly
    --
  • Weekly
    $4,500 - $7,000
  • Monthly
    --
pinnacle
pinnacle
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 4
Located at the Tryal Club about 20 minutes west of Montego Bay proper. The open air casual style of Pinnacle makes this lovely three bedroom, three and a half ...
  • Nightly
    --
  • Weekly
    $4,400 - $8,250
  • Monthly
    --
eureka_at_tryall
eureka_at_tryall
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 3
Eureka is among the private villas at Tryall Club. Located at the end of a cul de sac, it overlooks the 8th fairway of the famous Tryall golf course and the ...
  • Nightly
    --
  • Weekly
    $5,500 - $11,000
  • Monthly
    --
Elysian Plain, Tryall
Elysian Plain, Tryall
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 12
Elysian Plain is a waterfront villa which has a wonderful majestic, tall palm tree which guards the entrance of this villa. The unique feature of this villa ...
  • Nightly
    --
  • Weekly
    $7,700 - $19,250
  • Monthly
    --
Montego Bay Vacation Rental Advice
Bartering in Jamaica
Posted by easton714, Nov 6, 2009
... off the price of a rental home in ... ... with them once we leave--and it is good business sense for any vacation rental to have access to a crib. I never thought about that until I had my own children--and, sometimes, it is difficult to find places that do ... more
First trip to Jamaica...help
Posted by jammon13, Oct 18, 2009
... with a cart), and club rental at Negril ... ... I don't play on vacation unless that is the purpose of the trip. My take on a casual round during vacation is that it's time-consuming, expensive and frustrating. I've quit doing it. I can play golf most anywhere ... more
Posted by debdun, Oct 20, 2009
Thanks for all you help...We are looking forward to our vacation.... more
Calling all of my Mocha Sistahs
Posted by NewYorkSigma, Jan 1, 2009
... to do the family style vacation. If my information is incorrect, someone please let me know. Big Daddy and his boyz vote for an adult only all inclusive for that week. I really wanna have all of us in the same resort, but I don't play well with kids ... more
Posted by BLACKIEMANGO, Jan 2, 2009
... Our girls trip is planned for July 19-26, 2009. We want to attend Reggae Sumfest. We have not made a final decision on accommodations yet. We are looking at Sunset Resort or Royal Decameron. We have even considered a villa vacation this time. Looking forward to final decision. Blackiemango ... more
Posted by BLACKIEMANGO, Jan 3, 2009
... us to www.vrbo.com (Vacation Rental by Owners). We have tried for the past two years to get Calypso Shores #96468 during Sumfest, and it is booked by someone elso at least a year in advance. Destiny #209734 and AFIMI #196434 also looks interesting. I hope that this helps ... more
Villas by Linda Smith
Posted by BBMOchie, Jul 8, 2009
Linda Smith is one of the quality villa rental agencies representing some of the more exclusive villas on the island. Very good reputation. Round Hill and Tryall are both high end properties so you'll have a great vacation whichever you choose ! ... more
Hearing negative comments about Jamaica...what is true?
Posted by SilverQ, Jun 19, 2009
... never choose Jamaica as a vacation destination because of the danger. I have researched a little and found that Kingston is where there is a high amount of violence, etc. How cautious do we need to be? Can I have our shuttle driver (from the resort) stop at a grocery ... more
Posted by Bgiants, Jun 19, 2009
... out in Jersey City...otherwise tell your friends to hang out in Jersey City and they will find where not to vacation. Jamaica is a wonderful place for young-old, with kids-without kids, adventursome fun-or just chilling. You will have a great time AND get off the resort ... more
Posted by prolls, Jun 20, 2009
... not safe to walk around there.I will tell you they are terribly wrong about this one.Use your head & you will be fine. I spent 10 yrs of my life in Toronto & there are places there that i would not venture to go.Go on vacation & enjoy. One Love ... more
Go to Montego Bay Forums »
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns