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

Strawberry Hill vs Taylormade Golf Retreat III

Choosing between Strawberry Hill and Taylormade Golf Retreat III? This in-depth comparison breaks down location, vibe, rooms, food, nightlife, 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 • Spa & Infinity Pool

Best for travelers who want a quiet Blue Mountains hideaway with cottage-style stays, an infinity pool, spa, and a relaxed all-ages atmosphere.

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

Better for travelers who want a private villa-style golf retreat experience with more independence and a residential feel.

Quick Verdict: Strawberry Hill vs Taylormade Golf Retreat III

If you want a polished mountain resort with cool Blue Mountains air, individually styled cottages, strong wellness appeal, and restaurant-and-bar service on-site, Strawberry Hill is the easier fit.

If your priority is a more private villa retreat with a golf-focused setting and less of a traditional hotel rhythm, Taylormade Golf Retreat III is likely the better match.

Bottom line: choose Strawberry Hill for a serene Jamaican mountain resort with spa, dining, views, and atmosphere; choose Taylormade Golf Retreat III for a more independent villa-style golf escape.

Strawberry Hill vs Taylormade Golf Retreat III – At a Glance

Category Strawberry Hill Taylormade Golf Retreat III
Overall Vibe Quiet, sophisticated Blue Mountains resort with individually decorated cottages, a signature infinity pool, gardens, spa, and a relaxed all-ages atmosphere. Private villa-style golf retreat with a more residential, independent feel for travelers who prefer a self-contained stay.
Location Set high in Jamaica’s Blue Mountains above Kingston, reached by a winding mountain drive and surrounded by cooler air, gardens, and views. A golf-retreat setting better suited to travelers who want their stay centered around privacy, villa living, and time on or near the course.
Rooms & Suites Individually decorated Georgian-style cottages, studios, and villas spread across a mountaintop estate, with a more intimate resort layout. Villa-style accommodations designed for guests who want a more private base rather than a full-service cottage resort atmosphere.
Dining On-site New Jamaican cuisine at The Strawberry Hill Restaurant, plus The Strawberry Hill Bar as the resort’s social center. Best for travelers comfortable with a more independent dining style, depending on the villa setup and their own plans.
Pools & Setting Signature infinity-edge pool with views over Kingston and the Blue Mountains, plus gardens and a quiet mountain-resort setting. More private retreat-style setting, with the golf focus taking priority over a classic resort pool-and-spa scene.
Kids & Family Children are welcome, though the quiet hillside setting, steps, drops, and unfenced pool make it better suited to older children and careful supervision. Better considered for families or groups who want a private villa base, especially if golf and shared space matter more than children’s programming.
Price & Value Best value for travelers who will use the spa, restaurant, bar, pool, mountain setting, and full resort atmosphere. Best value for travelers who prioritize privacy, golf-retreat convenience, and the flexibility of a villa-style stay.

Rooms & Suites: Mountain Cottages vs Private Villa Retreat

Strawberry Hill – Room Style

Rooms at Strawberry Hill are part of the property’s intimate Blue Mountains identity, with individually decorated Georgian-style cottages, studios, and villas set across a gardened mountaintop estate.

  • Individually styled cottages, studios, and villas
  • Great for couples, solo travelers, and families who want a quiet mountain base
  • Continental breakfast and WiFi are included, though connectivity can be inconsistent in mountain areas

Strawberry Hill is the better pick if you want a characterful resort stay with space, views, gardens, and on-site service rather than a purely self-contained villa setup.

Taylormade Golf Retreat III – Room Style

Taylormade Golf Retreat III is better framed as a private villa-style retreat, appealing to travelers who want a more independent stay with a golf-centered focus.

  • Villa-style setup for a more private stay
  • Better for guests who want shared living space and independence
  • Best for travelers who prefer a golf-retreat feel over a traditional resort room experience

If you want a more residential base and a stay shaped around golf and privacy, Taylormade Golf Retreat III is the stronger fit.

Dining & Drinks: New Jamaican Restaurant vs Independent Villa Flexibility

Strawberry Hill – Restaurants & Bars

Dining at Strawberry Hill is a central part of the experience, with The Strawberry Hill Restaurant serving New Jamaican cuisine and a bar that acts as the social heart of the property.

Expect:

  • New Jamaican cuisine with traditional Jamaican flavors and international influence
  • The Strawberry Hill Bar, known for tropical mixed drinks and a relaxed mountain atmosphere
  • A full vegetarian menu and a setting suited to lingering meals with views

Taylormade Golf Retreat III – Dining Style

Taylormade Golf Retreat III is better for travelers who are comfortable with a more self-directed dining experience, using the villa as a private base rather than relying on a full resort restaurant scene.

  • More independent dining rhythm
  • Better for guests who like planning meals around golf days and group time
  • Ideal if privacy matters more than having restaurant-and-bar service built into the stay

If you want on-site dining, a defined bar scene, and a more classic resort food-and-drink setup, Strawberry Hill has the advantage.

Pool & Setting: Blue Mountains Infinity Pool vs Golf-Retreat Privacy

Strawberry Hill – Pool & Mountain Scene

Strawberry Hill’s setting is one of its biggest strengths, with a signature infinity-edge pool overlooking Kingston and the Blue Mountains, plus a cooler, quieter mountaintop atmosphere.

  • Infinity-edge pool with expansive mountain and city views
  • Cooler Blue Mountains setting above Kingston
  • Best for travelers who want scenery, quiet, and a restorative resort feel

Taylormade Golf Retreat III – Retreat Scene

Taylormade Golf Retreat III is less about a hotel-style pool scene and more about the privacy and pace of a villa-style golf retreat.

  • Golf-focused retreat atmosphere
  • More private and residential in feel
  • Better for travelers who want their days shaped around golf, group time, and independence

If the pool, mountain views, spa access, and resort setting matter most, Strawberry Hill is the more complete choice.

Kids & Family: Quiet All-Ages Resort vs Private Group Retreat

Strawberry Hill – Family Considerations

Strawberry Hill welcomes children, but it is a quiet hillside resort rather than a kids-club style property, and some sources caution that steps, steep drops, and an unfenced pool make it less ideal for very young children.

  • Children are welcome at the property
  • No dedicated children’s facilities were found in available sources
  • Better for older children, careful supervision, and families who want a calm mountain setting

Taylormade Golf Retreat III – Family & Group Fit

Taylormade Golf Retreat III may suit families or groups who prefer a private villa base, especially when shared space and a golf-focused itinerary are the priority.

  • Villa-style privacy for families or small groups
  • Better for travelers who want independence rather than resort programming
  • Strongest for groups who plan to spend much of the trip together

If you want a full resort atmosphere with dining, spa, and a scenic pool, choose Strawberry Hill; if your group wants privacy and flexibility, Taylormade Golf Retreat III may fit better.

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

Strawberry Hill – Value Snapshot

Strawberry Hill offers the most value when you will use its full setting: the Blue Mountains location, individually styled accommodations, on-site restaurant and bar, spa, gardens, and signature infinity pool.

  • Best for travelers who want a quiet, character-rich mountain resort
  • Great if on-site dining, spa treatments, and pool views matter
  • Strong value for couples, solo travelers, and families with older children who want atmosphere over activity overload

Taylormade Golf Retreat III – Value Snapshot

Taylormade Golf Retreat III is the better value if your priorities are privacy, villa-style independence, and a golf-centered retreat rather than a full-service resort experience.

  • Best for travelers who want a private retreat base
  • Stronger for golfers and groups who value shared space
  • Worth it if independence and a residential feel matter more than resort amenities

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, views, an infinity pool, spa, restaurant, bar, and an all-ages but peaceful atmosphere.

Best for Golf-Focused Privacy
Taylormade Golf Retreat III resort

Taylormade Golf Retreat III

Taylormade Golf Retreat III is the better pick for travelers who want a private villa-style golf retreat with more independence and less of a traditional hotel structure.

Best for Quiet Resort Atmosphere
Strawberry Hill resort

Strawberry Hill

For travelers who want cool mountain air, gardens, wellness, and a memorable pool-and-view setting above Kingston, Strawberry Hill is the stronger choice.

Best for Independent Group Stays
Taylormade Golf Retreat III resort

Taylormade Golf Retreat III

If you want privacy, a golf-centered stay, and a more residential group-retreat feel, Taylormade Golf Retreat III makes more sense.

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Strawberry Hill

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