Trippy Mates - Vacation Rentals in Westmoreland

Windsor Luxury Palace From US $113
         

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9.3 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Idle Awhile Villas From US $2,749
         

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10.0 (15 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Betta A Yaad Ocean View Villa, New upgrades From US $171
         

9.0 (11 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Designated Smoking Area
beautiful private Villa in Negril From US $171
         

6.6 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Luxury Places to Stay in Westmoreland

Over 809+ Luxury Places to Stay in or Near Westmoreland
Royal Savanna Inn Hotel From US $5,000
         

New
Hotel
  • Parking
  • Designated Smoking Area
  • Balcony/Terrace
Luxury Villa on Jamaica's South Coast From US $3,564
         

10.0 (6 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Luxury Private Seaside Villa with Spectacular Ocean View and Memorable Sunsets From US $2,740
         

Big Family Beachfront Villa From US $2,015
         

Top-Rated Vacation Rentals with a Pool in Westmoreland

Over 324+ Top-Rated Vacation Rentals with a Pool in or Near Westmoreland
Heaven-Can-Wait @ Point Village From US $216
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Coral Cove Wellness Resort From US $232
         

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10.0 (10 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Luxury Modern 2 Bedrooms 2.5 Bathrooms, sleep 6 From US $263
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Beach Studio on Negril's Seven Mile Beach From US $115
         

10.0 (5 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Bak A Yaad Timberland Cottage From US $149
         

10.0 (3 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Little Waters on the Cliff From US $1,074
         

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10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Westmoreland

Over 83+ Pet-Friendly Vacation Rentals in or Near Westmoreland
The Artist cabin is a mountain cabin overlooking the sea and coastline From US $70
         

10.0 (1 Review)
House
  • Pet Friendly
  • Designated Smoking Area
  • Bedding/Linens
Whispering Clouds Beach House From US $454
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Eleven30 Luxury Apartments From US $122
         

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New
Apartment
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Kimoya's cottage is a mountain cottage overlooking the sea and coastline From US $80
         

9.0 (2 Reviews)
House
  • Pet Friendly
  • Designated Smoking Area
  • Bedding/Linens
Dre's Cozy Casa - Negril, Jamaica From US $57
         

8.4 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
NEW! Designer Villa on Top of Negril From US $617
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Westmoreland

Over 155+ Large Vacation Homes & Villas in or Near Westmoreland
Blue Lotus Villa From US $297
         

New
Villa
  • Air Conditioner
  • Parking
  • Child Friendly
Beachcliff Villa Negril From US $640
         

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10.0 (2 Reviews)
Villa
  • Parking
  • Designated Smoking Area
  • TV
Williams Manor [Across From Ricks Cafe Negril] From US $147
         

High Life Resort & Spa nEntire Villa From US $1,083
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Award-winning villa with private beachfront and pool From US $785
         

Wheelchair Accessible Vacation Homes in Westmoreland

Over 29+ Wheelchair Accessible Vacation Homes in or Near Westmoreland
Stoney Gate Cottages From US $65
         

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8.9 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Sandals South Coast - ALL INCLUSIVE Couples Only From US $618
         

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8.6 (142 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Perfect Home Away from Home From US $124
         

5.0 (1 Review)
Condo
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Bak A Yaad From US $59
         

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8.5 (350 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Beaches Negril Resort - ALL INCLUSIVE From US $1,121
         

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8.0 (71 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Cliff-side resort on the West End in Negril From US $100
         

3.0 (2 Reviews)
House
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Boutique B&B at Stone Village From US $270
         

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8.5 (2 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Pet Friendly
  • Pool

Westmoreland Vacation Rentals and Airbnb Places to Stay Under $200

Over 546+ Westmoreland Vacation Rentals and Airbnb Places to Stay Under $200
Windsor Luxury Palace From US $147
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Boutique B & B at Stonevillage From US $161
         

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10.0 (2 Reviews)
Bed & Breakfast
  • Parking
  • Pool
  • TV
Shades Cottage Room #2 From US $70
         

10.0 (2 Reviews)
House
  • Balcony/Terrace
  • Security/Safety
  • Kitchen
Firefly cottage with Ocean view From US $59
         

10.0 (27 Reviews)
House
  • Designated Smoking Area
  • Balcony/Terrace
  • Sports/Activities
Sea Beach Escape & Vacation Rental From US $95
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Dragon fly Cottage From US $67
         

10.0 (7 Reviews)
House
  • Balcony/Terrace
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Westmoreland

Over 363+ Instantly Bookable Vacation Homes in or Near Westmoreland
Shades Cottage Room #2 From US $70
         

10.0 (2 Reviews)
House
  • Balcony/Terrace
  • Security/Safety
  • Kitchen
Condo in a Picturesque, Relaxing Gated Property in Negril From US $151
         

Glamping by the Beach in Little Bay, Jamaica From US $124
         

10.0 (2 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • View
Bak a Yaad Caribbean Blue Cottage From US $108
         

10.0 (2 Reviews)
Cottage
  • Parking
  • Pool
  • TV
Cozy Escape Negril From US $82
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Westmoreland Vacation Rentals

With more than 818 Westmoreland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Trippymates and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Westmoreland.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Trippymates Westmoreland, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Westmoreland. Places to stay near Westmoreland are 573.23 ft² on average, with prices averaging $270 a night.

Trippymates makes it easy and safe to find and compare vacation rentals in Westmoreland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Westmoreland

Type Count
Holiday Apartments 229
Vacation Homes 195
Villas 116
Hotels with Suites 100
Resorts 43
B&B 30
Cottages 27
Cabin Rentals 18
Hostels 6
Others 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Westmoreland

Pro Tip: Trippymates makes it easy to compare the best listings on Trippymates homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Trippymates homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Westmoreland.

Weather in Westmoreland

View the weather forecast for Westmoreland before booking your Westmoreland Vacation Rentals to confirm your best time to go.

December - February
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Westmoreland Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Westmoreland?
How many vacation rentals are available in Westmoreland?

Currently, the total number of properties listed in 2026 is over 818 in the Westmoreland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Westmoreland.