Island Outpost, Irish Town, Saint Andrew, Jamaica
resort comparison guide

Strawberry Hill vs Taylormade Golf Retreat

Choosing between Strawberry Hill and Taylormade Golf Retreat? This in-depth comparison breaks down location, vibe, rooms, dining, amenities, price & more so you can decide which stay is the best fit for your next getaway.

Strawberry Hill resort
Strawberry Hill
All-Ages • Blue Mountains • Boutique Mountain Resort

Best for travelers who want a quiet Blue Mountains hideaway with individually styled cottages, spa time, mountain views, and easy access to Kingston by road.

Taylormade Golf Retreat resort
Taylormade Golf Retreat
Golf Retreat • Villa-Style Stay • Private Escape

Better for travelers who want a private villa-style golf retreat experience in Jamaica with a more self-contained, golf-focused stay.

Quick Verdict: Strawberry Hill vs Taylormade Golf Retreat

If you want a relaxed yet sophisticated mountain resort with a signature infinity pool, New Jamaican dining, spa treatments, and a cooler Blue Mountains setting, Strawberry Hill is the stronger choice.

If your priority is a golf-centered retreat with more of a villa-stay feel, Taylormade Golf Retreat is the better fit.

Bottom line: choose Strawberry Hill for boutique mountain atmosphere, wellness, dining, and views; choose Taylormade Golf Retreat for a more golf-focused Jamaican villa escape.

Strawberry Hill vs Taylormade Golf Retreat – At a Glance

Category Strawberry Hill Taylormade Golf Retreat
Overall Vibe Quiet, all-ages Blue Mountains resort with Georgian-style cottages, tropical gardens, a relaxed yet sophisticated mood, and sweeping Kingston and mountain views. Private, villa-style golf retreat suited to travelers who want a more self-contained stay built around golf and downtime.
Location Set high in the Blue Mountains near Irish Town, roughly a 50-minute road transfer from Kingston’s Norman Manley International Airport. A Jamaica golf retreat setting, better suited to guests who want their stay oriented around the course rather than a mountain resort base.
Rooms & Suites Individually decorated cottages, studios, and villas across a 26-acre mountaintop estate, with a romantic, heritage-inspired feel. Villa-style accommodation, best for travelers who prefer a private retreat format over a traditional boutique resort stay.
Dining The Strawberry Hill Restaurant & Bar serves New Jamaican cuisine, with a known Sunday Brunch and a bar that acts as the social center of the resort. Dining details are less central to the stay; the appeal is more about the private retreat and golf-focused experience.
Pools & Grounds Signature infinity-edge pool with views over Kingston and the Blue Mountains, plus lawns, gardens, a yoga pavilion, and a quiet mountaintop setting. More about villa-style downtime and golf than a resort-style pool-and-spa scene.
Kids & Family All-ages and welcoming to children, though the quiet atmosphere, steps, unfenced pool, and hillside drops mean it is not ideal for inquisitive toddlers. Best considered for travelers whose group is centered on golf and a private retreat-style stay.
Price & Value Best value for guests who will use the mountain setting, restaurant, spa, infinity pool, and Kingston/Blue Mountains access. Best value for travelers who mainly want a golf retreat and villa-style privacy rather than a full boutique resort experience.

Rooms & Suites: Mountain Cottages vs Villa-Style Retreat

Strawberry Hill – Room Style

Rooms at Strawberry Hill are spread across a small collection of individually decorated Georgian-style cottages, studios, and villas on a 26-acre mountaintop estate.

  • Individually styled cottages, studios, and villas
  • Best for travelers who want character, quiet, and a strong sense of place
  • Continental breakfast and property-wide WiFi are included, though connectivity can be sporadic in some areas

Strawberry Hill is the better pick if you want a boutique mountain resort feel with heritage style, gardens, and cooler Blue Mountains air.

Taylormade Golf Retreat – Room Style

Taylormade Golf Retreat is better framed as a villa-style golf stay, with the accommodation experience tied closely to privacy and time on or around the course.

  • Villa-style stay suited to private groups or golf-focused travelers
  • Better for guests who want a retreat format rather than a classic resort room
  • Best for travelers prioritizing golf, space, and self-contained downtime

If you want your accommodation to feel more private and golf-oriented, Taylormade Golf Retreat is the more natural match.

Dining & Drinks: New Jamaican Restaurant vs Retreat-Style Simplicity

Strawberry Hill – Restaurants & Bars

Dining is a clear strength at Strawberry Hill, where The Strawberry Hill Restaurant & Bar serves New Jamaican cuisine in a mountain-view setting.

Expect:

  • New Jamaican dishes with both local and international influences
  • A relaxed bar known as the social center of the property
  • Sunday Brunch and a refined but island-casual atmosphere

Taylormade Golf Retreat – Restaurants & Bars

Taylormade Golf Retreat is less about a named restaurant scene and more about the ease of a private, golf-centered retreat.

  • Better for travelers who do not need a destination restaurant on property
  • Suited to guests whose days revolve around golf and villa-style relaxation
  • Ideal if dining is secondary to privacy and the retreat setting

If food, cocktails, and a memorable restaurant setting matter most, Strawberry Hill has the clearer advantage.

Pools & Grounds: Iconic Infinity Pool vs Golf Retreat Setting

Strawberry Hill – Pool & Grounds Scene

Strawberry Hill’s infinity-edge pool is one of its defining features, set high above Kingston with broad Blue Mountains views.

  • Signature infinity pool with a dramatic mountaintop outlook
  • Gardens, lawns, and a yoga pavilion for quiet relaxation
  • Best for travelers who want scenery and calm rather than a beach-resort scene

Taylormade Golf Retreat – Golf & Outdoor Scene

Taylormade Golf Retreat is better suited to guests who want their outdoor time focused on golf and a private retreat atmosphere.

  • Golf-oriented setting rather than a classic resort pool scene
  • Appeals to travelers who want privacy and time outdoors
  • Better for guests who would choose fairways over mountain spa-and-pool lounging

If you want the stronger pool-and-view experience, Strawberry Hill wins; if golf is the point of the trip, Taylormade Golf Retreat fits better.

Kids & Family: All-Ages Mountain Resort vs Golf-Focused Retreat

Strawberry Hill – Family Considerations

Strawberry Hill is an all-ages resort and children are welcome, but the atmosphere is quiet and some hillside features make it better suited to older children than toddlers.

  • Children are welcome, but there are no major kids’ facilities to build a trip around
  • Steps, steep drops, and an unfenced pool require extra caution with young children
  • Best for families who want calm, scenery, and a slower mountain stay

Taylormade Golf Retreat – Family Considerations

Taylormade Golf Retreat is most appealing when the group’s travel style centers on golf, privacy, and a retreat-like base.

  • Works best for groups aligned around golf and villa-style downtime
  • Less suited to travelers seeking extensive resort programming
  • Better for golf-focused families, couples, or small groups

If you need structured children’s programming, neither property is defined by that; if you want an all-ages mountain stay, Strawberry Hill is the clearer resort choice.

Price & Value: Which Jamaica Stay Feels More Worth It?

Strawberry Hill – Value Snapshot

Strawberry Hill offers the most value when you will use the full setting: the cottages, restaurant, bar, spa, infinity pool, and Blue Mountains location.

  • Best for travelers who want a boutique mountain resort rather than a beach stay
  • Great if dining, wellness, views, and atmosphere matter
  • Strong value for couples, families with older children, and quiet-getaway travelers

Taylormade Golf Retreat – Value Snapshot

Taylormade Golf Retreat is the better value if your trip is built around golf and you prefer a private villa-style base.

  • Best for golf-focused travelers
  • Stronger for groups who value privacy and a self-contained retreat feel
  • Worth it if you do not need a full resort dining, spa, and pool scene

Who Wins? Best Jamaica Stay by Travel Style

Best for Mountain Views & Wellness
Strawberry Hill resort

Strawberry Hill

Choose Strawberry Hill if you want a quiet Blue Mountains resort with character, New Jamaican dining, a spa, an infinity pool, and cooler mountain air.

Best for Golf-Focused Travelers
Taylormade Golf Retreat resort

Taylormade Golf Retreat

Taylormade Golf Retreat is the better pick for travelers who want a golf-centered escape with a more private villa-style rhythm.

Best for Quiet Atmosphere & Dining
Strawberry Hill resort

Strawberry Hill

For couples, families with older children, and scenery-focused travelers, Strawberry Hill offers the stronger sense of place and the more complete boutique resort experience.

Best for Villa-Style Privacy
Taylormade Golf Retreat resort

Taylormade Golf Retreat

If your main goal is a Jamaica golf retreat and you prefer privacy over resort amenities, Taylormade Golf Retreat is the simpler, more targeted choice.

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Strawberry Hill

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