Middlesex Villas
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Villas in Middlesex
Gorgeous 2 Bedroom Beachfront Villa @ Paradise Point Negril
Negril Westmoreland Parish
When you stay at this villa in Negril, you'll be on the beach, within a 15-minute walk of Seven Mile Beach and Jamaica Beaches.
Pool
Kitchen
Villas Sur Mer
West End Road Negril Westmoreland
$430 nightly
The price is $474 total per night
$474 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
Located in Negril (West End), Villas Sur Mer is within a 5-minute drive of Negril Lighthouse and Negril Cliffs.
Pool
Hot Tub
Idle Awhile Cliffs
Negril Cliffs, West End Road Negril Westmoreland
With a stay at Idle Awhile Cliffs in Negril (West End), you'll be within a 15-minute drive of Seven Mile Beach and Jamaica Beaches.
Pool
Kitchen
Idle Awhile Villas
Norman Manley Boulevard Negril
When you stay at Idle Awhile Villas in Negril, you'll be on the beach, within a 5-minute drive of Seven Mile Beach and Jamaica Beaches.
Pool
Kitchen
Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica
Montego Bay St. James, Mobay
$177 nightly
The price is $177 total per night
$177 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at this villa in Montego Bay (Paradise Acres), you'll be within a 10-minute drive of Montego Bay Cruise Ship Terminal and Jamaica Beaches.
Kitchen
Free WiFi
EXCLUSIVE 4BR DESIGNER WATERFRONT VILLA CHEF POOL BEACH ACCESS PICKLEBALL GYM
Montego Bay St. James Parish
When you stay at this villa in Montego Bay, you'll be on the waterfront, within a 15-minute drive of Montego Bay Cruise Ship Terminal and Jamaica Beaches.
Pool
Kitchen
5 BDR LUX MODERN BEACHFRONT VILLA PRIVATE INFINITY POOL & OCEAN VIEWS STAFF
Montego Bay St. James Parish
When you stay at this villa in Montego Bay, you'll be on the beach, within a 15-minute drive of Montego Bay Cruise Ship Terminal and Jamaica Beaches.
Pool
Kitchen
YanceyLargoEstate 2BR Villa w/Mountain Views by RedAwning
Montego Bay St. James Parish
$243 nightly
The price is $264 total per night
$264 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Free Cancellation
With a stay at this villa in Montego Bay, you'll be within a 10-minute drive of Jamaica Beaches and Montego Bay Cruise Ship Terminal.
Pool
Washer
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
103 Hamilton Drive Montego Bay Saint James
$152 nightly
The price is $175 total per night
$175 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
With a stay at this villa in Montego Bay, you'll be within a 10-minute drive of Jamaica Beaches and Montego Bay Cruise Ship Terminal.
Washer
Free WiFi
Turquoise Sea Villa
Blairgowrie, Reading Montego Bay Saint James
$2,256 nightly
The price is $2,580 total per night
$2,580 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Located in Montego Bay, Turquoise Sea Villa is within a 15-minute drive of Montego Bay Cultural Centre and Tryall Golf Club.
Pool
Hot Tub
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.
Middlesex Villas essential information
Accommodation | 197 Villas |
|---|---|
Lowest Price | $175 |
Highest Price | $2,580 |
Popular accommodation | Gorgeous 2 Bedroom Beachfront Villa @ Paradise Point Negril, Villas Sur Mer, Idle Awhile Cliffs, Idle Awhile Villas, Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica, EXCLUSIVE 4BR DESIGNER WATERFRONT VILLA CHEF POOL BEACH ACCESS PICKLEBALL GYM , 5 BDR LUX MODERN BEACHFRONT VILLA PRIVATE INFINITY POOL & OCEAN VIEWS STAFF, YanceyLargoEstate 2BR Villa w/Mountain Views by RedAwning, YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning, Turquoise Sea Villa, Fully staffed. private, Beachfront villa with a pool in Negril, Jamaica , Little Waters on the Cliff |