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

Strawberry Hill vs Oaklands Guest Oasis

Choosing between Strawberry Hill and Oaklands Guest Oasis? 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 • Infinity Pool

Best for couples, wellness travelers, and scenery seekers who want a quiet Blue Mountains retreat with a signature infinity pool, spa, and refined Jamaican dining.

Oaklands Guest Oasis resort
Oaklands Guest Oasis
Kingston Guesthouse • Simple Stay • City Base

Better for travelers who want a simpler Kingston guesthouse stay with an easier city base and a more residential, low-key feel.

Quick Verdict: Strawberry Hill vs Oaklands Guest Oasis

If you want a polished mountain escape above Kingston, Strawberry Hill is the stronger choice: it offers cottage-style accommodations, dramatic views, a destination restaurant and bar, and a spa-focused atmosphere.

If your priority is a straightforward Kingston stay over a full resort experience, Oaklands Guest Oasis is better suited to travelers who want a practical guesthouse base rather than a destination retreat.

Bottom line: choose Strawberry Hill for the Blue Mountains setting, infinity-pool views, wellness, and dining; choose Oaklands Guest Oasis for a simpler guesthouse-style Kingston stay.

Strawberry Hill vs Oaklands Guest Oasis – At a Glance

Category Strawberry Hill Oaklands Guest Oasis
Overall Vibe Relaxed yet sophisticated all-ages mountaintop retreat with individually styled cottages, lush gardens, spa time, and sweeping Kingston and Blue Mountains views. Low-key Kingston guesthouse option with a more practical, residential feel—better for travelers who value simplicity over resort-style facilities.
Location Set high in the Blue Mountains above Kingston, reached by a winding road through Irish Town, with cooler mountain air and a tucked-away retreat feel. In Kingston, better suited to travelers who want to stay closer to the city rather than retreating into the mountains.
Rooms & Suites Individually decorated Georgian-style cottages, studios, and villas across a 26-acre estate—best for travelers who want character and privacy. Guesthouse-style accommodations with a simpler setup, best for travelers who do not need a full resort room experience.
Dining The Strawberry Hill Restaurant & Bar serves New Jamaican cuisine, with mountain-view verandas, Sunday brunch, and a social bar scene. Dining is less of the main draw here; Oaklands Guest Oasis is better approached as a base for a Kingston stay rather than a dining destination.
Pools & Setting Signature infinity-edge pool with dramatic views over Kingston and the Blue Mountains, plus gardens, lawns, and a quiet mountain-resort setting. More about guesthouse convenience than a destination pool-and-spa setting; choose it for a simple place to stay in Kingston.
Kids & Family Children are welcome, but the quiet hillside layout, steps, steep drops, and unfenced pool make it better for older children than toddlers. A more straightforward lodging option for travelers who want a simple Kingston base; family-specific facilities should be checked directly before booking.
Price & Value Best value when the setting, views, spa, restaurant, and boutique resort atmosphere are central to the trip. Best value for travelers who mainly need a simpler Kingston guesthouse stay and do not plan to use resort-style amenities.

Rooms & Suites: Mountain Cottages vs Guesthouse Simplicity

Strawberry Hill – Room Style

Rooms at Strawberry Hill are part of the experience: individually decorated Georgian-style cottages, studios, and villas spread across a 26-acre Blue Mountains estate.

  • Cottage, studio, and villa-style accommodations with a historic mountain-retreat feel
  • Best for travelers who want privacy, character, gardens, and views instead of a standard city hotel room
  • Continental breakfast and free WiFi are included, though service can be sporadic in some areas

Strawberry Hill is the better pick if your room should feel like part of a destination stay, not just a place to sleep.

Oaklands Guest Oasis – Room Style

Oaklands Guest Oasis is better framed as a simpler guesthouse stay, with the appeal centered on practicality and a Kingston base rather than a resort-style room experience.

  • Guesthouse-style setup for travelers who want a straightforward place to stay
  • Better for city-focused trips where the room is secondary to the location and itinerary
  • Best for travelers who prefer simplicity over a boutique mountain-resort atmosphere

If you want distinctive lodging, gardens, and a retreat-style setting, Strawberry Hill has the edge; if you want a simpler Kingston base, Oaklands Guest Oasis is the more practical fit.

Dining & Drinks: Destination Restaurant vs Simple Stay

Strawberry Hill – Restaurants & Bars

Dining is one of Strawberry Hill’s major strengths, led by The Strawberry Hill Restaurant & Bar and its New Jamaican cuisine in a mountain-view setting.

Expect:

  • New Jamaican dishes with traditional Jamaican flavors and international influences
  • A wraparound veranda atmosphere, Sunday brunch, and a bar that serves as the social center of the property
  • A relaxed yet sophisticated dress mood—breezy island casual works, though dressing up also fits

Oaklands Guest Oasis – Restaurants & Bars

Oaklands Guest Oasis is not the stronger choice if your hotel dining is meant to anchor the trip; it is better for travelers who plan to keep meals flexible around Kingston.

  • Better for guests who are comfortable using the property as a lodging base
  • Less of a destination restaurant-and-bar experience than Strawberry Hill
  • Ideal if dining variety at the hotel itself is not a top priority

If food, drinks, views, and a memorable on-property restaurant matter, Strawberry Hill is the clear winner.

Pools & Setting: Blue Mountains Infinity Pool vs Kingston Guesthouse Base

Strawberry Hill – Pool & Mountain Scene

Strawberry Hill’s signature infinity-edge pool is one of its defining features, with views over Kingston and the surrounding Blue Mountains.

  • Infinity-edge pool set high above Kingston
  • Cooler mountain atmosphere with gardens, lawns, and a quiet retreat feel
  • Best for travelers who want slow mornings, views, and a strong sense of place

Oaklands Guest Oasis – Setting

Oaklands Guest Oasis is better suited to travelers who want a Kingston guesthouse base rather than a pool-centered mountain resort.

  • More practical and city-oriented than resort-like
  • Better for itineraries focused on Kingston rather than on-site relaxation
  • A fit for travelers who do not need a destination pool or spa setting

If the trip is about scenery, quiet, and poolside views, Strawberry Hill is the stronger choice.

Kids & Family: All-Ages Mountain Retreat vs Simple Kingston Base

Strawberry Hill – Family Considerations

Strawberry Hill welcomes children, but the property is quiet and hillside-based, with lots of steps, steep drops, and an unfenced pool noted by specialist reviews.

  • Children of all ages are welcome, with no official adults-only policy found
  • No dedicated children’s facilities were found in the available property information
  • Better for families with older children who can manage a hillside resort setting

Oaklands Guest Oasis – Family Considerations

Oaklands Guest Oasis may suit families or small groups who want a simpler Kingston stay, but family-specific facilities should be confirmed directly before booking.

  • Straightforward guesthouse-style lodging
  • Better for travelers who want practicality over curated resort programming
  • A fit for guests who will spend more time out in Kingston than on property

If you are traveling with young children, Strawberry Hill’s scenery is beautiful but its hillside layout deserves extra caution.

Price & Value: Which Kingston-Area Stay Feels More Worth It?

Strawberry Hill – Value Snapshot

Strawberry Hill offers the most value when you will use the resort-style strengths: the Blue Mountains setting, infinity pool, spa, restaurant, bar, and cottage atmosphere.

  • Best for couples, solo travelers, and families with older children who want a quiet retreat
  • Great if views, wellness, gardens, and dining are part of the reason you are booking
  • Strong “destination stay” value for travelers who want to slow down above Kingston

Oaklands Guest Oasis – Value Snapshot

Oaklands Guest Oasis is the better value if you mainly need a practical Kingston guesthouse stay and do not plan to pay for a resort-style experience.

  • Best for travelers who want simpler lodging
  • Stronger for city-focused itineraries where the hotel is mostly a base
  • Worth considering if resort amenities, spa time, and destination dining are not priorities

Who Wins? Best Kingston-Area Stay by Travel Style

Best for Mountain Views & Wellness
Strawberry Hill resort

Strawberry Hill

Choose Strawberry Hill if you want a quiet all-ages Blue Mountains retreat with cottage-style rooms, a signature infinity pool, spa treatments, and destination dining.

Best for Simple Kingston Stays
Oaklands Guest Oasis resort

Oaklands Guest Oasis

Oaklands Guest Oasis is the better pick for travelers who want a simpler Kingston guesthouse base rather than a polished mountain resort.

Best for Quiet Retreat Atmosphere
Strawberry Hill resort

Strawberry Hill

For scenery, wellness, cooler mountain air, and a stay that feels removed from the city while still connected to Kingston, Strawberry Hill wins.

Best for Practical City-Base Travel
Oaklands Guest Oasis resort

Oaklands Guest Oasis

If you want practicality, a low-key lodging style, and less emphasis on on-property dining or spa amenities, Oaklands Guest Oasis makes more sense.

BOOK YOUR STAY NOW

Questions? Contact Us!

Strawberry Hill

BOOK YOUR STAY NOW

Questions? Contact Us!

Close