18 Sep Islamorada Resort Collection Review: 3 Resorts, 1 Perfect Family Vacation
When we returned to the Islamorada Resort Collection for our second stay, we knew we’d found something special. Here’s our honest review of why resort hopping in the Florida Keys works so well for families.
Why We Chose Islamorada Resort Collection (Again)
This was our second time staying at La Siesta, and returning to any resort with kids is high praise. The first time, we loved the intimate feel and waterfront location, but we didn’t fully explore the resort collection concept. This trip, we made it a priority to experience all three properties connected by the complimentary shuttle and water taxi.
We chose Islamorada over Key West because it’s less crowded, much more family-friendly, and saves us two hours of driving (not a bad bonus!). For homeschooling families like ours, avoiding the party atmosphere of Key West while still getting authentic Keys character made perfect sense.
The deal: For $59 per night in resort fees, we got access to not one, not two, but three different resorts. By the end of this review, you’ll know if this is worth it for your family.
Book your stay: Islamorada Resort Collection – Expedia Link
La Siesta Resort: Where We Actually Stayed
La Siesta served as our home base, and we were thrilled with our room upgrade to a full-size kitchen. This was perfect for storing snacks and boat food, saving us money and providing flexibility for different meal times.
What makes La Siesta special for families:
- Full kitchen options for meal flexibility and cost savings
- Small-scale property (kids loved the intimate pool area)
- Waterfront location perfect for early morning wildlife viewing
- Dog-friendly policy (important for families traveling with pets)
Three Waters Resort: The Bustling Heart of the Collection
Three Waters is the newest and most bustling of the three resorts. This property delivered classic beach resort vibes with the most amenities and activities.
Family highlights at Three Waters:
- Multiple pool areas including a swim-up bar (kids loved this new experience!)
- Private beach access with calm, shallow water
- On-site arcade (the boys are always down for arcade games)
- Live music offered nightly (I even got to dance with my dad)
- Historic significance: literally where the Rum Runner cocktail was invented in 1969
- Easy tarpon feeding access (bait available at their shop)
The boys were obsessed with feeding the tarpon, they absolutely lost their minds over this activity. Having bait readily available at the resort’s shop made this so easy to enjoy!
Dining experience: Resort restaurants are definitely pricier than local spots, but the food was good at both resort restaurants we tried. The convenience factor and quality made it worthwhile for some easy, convenient meals.
We spent most of our active time here, and it felt like the social hub of the resort collection.
Amara Cay Resort: Quieter Luxury
Amara Cay is the third resort in the collection, with a much quieter feel than the other two. We didn’t spend as much time here, but when we did visit, we enjoyed the more refined atmosphere.
What we experienced at Amara Cay:
- One morning exploring their beach games
- Shark tooth hunting on their beach area (set up by the very friendly resort staff)
- Friendly cannonball contest at their pool
- Beautiful sunset viewing opportunities
This property seemed designed for adults seeking tranquility, but still welcomed families with family-friendly amenities.
The Transportation: Shuttle Service and Water Taxi
The complimentary shuttle and limited water taxi service connecting all three properties worked well for our family.
Transportation benefits:
- No need to move your car between properties
- Easy way to explore different dining and activity options
- Access to amenities across all three locations
Note: The water taxi service is limited so check schedules and availability during your stay.
Family-Friendly Amenities Across All Properties
Each resort maintains high standards for family accommodations:
Room features we appreciated:
- Full-sized kitchen and kitchenette options for snacks and simple meals
- Spacious layouts accommodating pack-n-plays, if needed
- Reliable air conditioning (crucial in August!!)
- Balconies or patios for quiet outdoor space
Service consistency:
- Staff across all three properties clearly communicate with each other
- Towel service available at each property
- Pool and beach equipment available at all locations
- Consistent check-in/check-out policies
Honest Assessment: What Works and What Doesn’t
What exceeded expectations:
- Resort hopping eliminated the “we’re stuck here” feeling that can be common with resort vacations
- Each property matched different moods and energy levels
- Educational opportunities appeared naturally (marine life, local history, learning about the hospitality industry)
- Value improved significantly when using all three properties
What could be improved:
- Water taxi schedule seems to be inconsistent and unreliable
- Some dining reservations fill quickly during peak season
Cost Analysis: Is Resort Hopping Worth It?
Booking the Islamorada Resort Collection costs the same as staying at any single property, but provides access to amenities across three different resorts. For families, this translates to:
Dining flexibility: Six different restaurants and bars across the properties Activity variety: Multiple pools, beach access points, and recreational options Accommodation options: Different room types and locations available Weather backup: Indoor and covered areas at each property
Budget consideration: Resort-level pricing reflects the premium location and amenities. Factor in dining costs, as Keys restaurants generally command higher prices.
Best (Off-Peak) Time to Visit with Kids
August worked well despite heat concerns:
- Early morning and evening hours offered comfortable outdoor time
- Summer schedule aligned with our homeschool flexibility
- Lower tourist density is such a plus for us!
Weather management strategy: Plan outdoor activities for early morning, embrace afternoon pool time as a respite from the heat.
Booking Tips for Families
Direct booking vs. third-party sites: Use our Expedia affiliate link for booking convenience and potential package deals, but check the resort’s official website for any direct-booking benefits or special offers.
Room selection tips:
- Request water-view rooms at La Siesta for best sunrise experiences, there’s also a dock, sunrise viewing area, must do for early risers!
- Choose poolside access at Three Waters for easy access
- Amara Cay sunset-view rooms provide memorable evening experiences
Advance planning:
- Make dinner reservations immediately after booking
- Request pack-n-plays or additional bedding while booking
- Confirm water taxi schedules with front desk staff
Educational Opportunities for Homeschool Families
The resort collection offered unexpected learning moments:
Marine biology: Tarpon feeding, reef fish identification, water ecosystem observations Hospitality industry: Observing resort operations, service coordination, tourism economics Local history: Staff knowledge about Keys development and environmental conservation Geography: Understanding barrier island formation and hurricane impact
Why We’ll Return Again
This second stay confirmed the Islamorada Resort Collection as our Keys accommodation of choice. The boys are already asking about our next visit (and honestly, so am I!), which speaks to how comfortable and welcome we felt.
Return factors:
- Staff recognition and personalized service
- Familiarity breeding comfort rather than boredom
- Consistent quality across all three locations
Planning our next trip: We’re already discussing a yearly family tradition!
Final Verdict: Resort Hopping Success
For families wanting resort amenities with authentic Keys character, the Islamorada Resort Collection delivers. The ability to move between three distinct properties keeps vacation experiences fresh while maintaining consistent service standards.
Best fit for families who want:
- Resort-level amenities and service
- Variety in daily experiences and dining
- Educational opportunities alongside relaxation
- Dog-friendly accommodations
- Professional but not overly formal atmosphere
Consider alternatives if:
- Budget constraints make Keys resort pricing prohibitive
- Family prefers single-location familiarity
- Very young children who struggle with transition and travel
- Planning primarily adventure-based rather than resort-based vacation
Our rating: 4.5/5 stars
The Islamorada Resort Collection successfully balances luxury resort amenities with authentic Florida Keys character. Resort hopping adds variety without sacrificing service quality, making it ideal for families seeking both comfort and adventure.
Ready to book your own resort hopping adventure? Book through our Expedia partnership link
Questions about traveling to the Keys with kids? Drop them in the comments, we love helping other families plan educational adventures!
No Comments