Winter Park, Colorado · Kāʻanapali, Maui
Paradise, reimagined.
The family company behind Ramble On House and Mahana 418 — two properties we own, manage, and answer for personally.
These aren't standard rentals. They're homes we love — curated, finished, and equipped to a standard you'll feel the moment you walk in.
Four floors of considered detail in downtown Winter Park — designer finishes, a chef’s kitchen, a private theater, and a rooftop spa under the stars. Built new, and built to be loved.
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The destination
Downtown Winter Park, Colorado
Ramble On House sits in downtown Winter Park — a five-minute walk to Main Street's restaurants, breweries, and shops, and three minutes from the lifts at Winter Park Resort and Mary Jane. Winters are for skiing and snowboarding; summers bring the Fraser River Trail, Trestle Bike Park, and day trips to Rocky Mountain National Park, forty-five minutes away. Denver is 67 miles over the pass, and the Winter Park Express ski train runs straight from Union Station. It's a natural basecamp for ski weeks, mountain-biking trips, and family holidays in Grand County.
Read the hosts' Winter Park guides →
Mahana 418
Sleeps 4 · 1 BR · 1 BA · Kāʻanapali, Maui
The most finely appointed residence at the Mahana — a full designer renovation thirty feet from the Pacific, with sea turtles below the lanai and whales off the living room in season.
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The destination
Kāʻanapali & Kahekili Beach, Maui
Mahana 418 sits on Kahekili Beach at the quiet north end of Kāʻanapali, on five landscaped oceanfront acres thirty feet from the water. World-class snorkeling at Black Rock is steps away, the Kāʻanapali boardwalk connects you to Whalers Village, Duke's Beach House, and Merriman's, and whale watching runs December through April right off the lanai. Historic Lahaina town and the championship golf courses at Kapalua are minutes away, and the Mahana's low-density grounds keep the pool and beach uncrowded year-round.
Read the hosts' Maui guides →Curated by our family, for yours.
Guest experiences
“This place ranks as one of the top places I’ve stayed with Airbnb. Just awesome.”
“Arguably the best place in Maui to stay! This condo is as close as you can get to the water. We saw dozens of turtles and a couple of whales.”
“This was such a great place to stay. All first class! We loved the house!”
“Gorgeous! Comfortable! Exactly as described! The hosts were extremely friendly and helpful. We will be back!”
“Our family had a wonderful stay! It's a great location for all ages, with easy access to parks, fishing and shopping. If you are looking for a place to accommodate a large family or group, this is it!”
“We've visited Hawaii over a dozen times and Mahana was the most beautiful place we have stayed — both the condo and the view. Everything you see in the pictures is exactly what you'll get.”
“Within minutes of arriving, we saw green sea turtles, a breathtaking sunset, and more whales breaching than we could count — better than a whale-watching tour!”
“Squeaky clean and ultra comfy. This is the last unit on the road — quieter, with less traffic — and the beach access is the last on the beach, so it's less crowded.”
Common questions
Where is Ramble On House located?
In downtown Winter Park, Colorado — a five-minute walk to Main Street restaurants and shops, and about three minutes from the lifts at Winter Park Resort. Denver is 67 miles away.
How many guests does Ramble On House sleep?
Ten guests, comfortably, across four bedrooms and three and a half baths on four finished levels.
What amenities does Ramble On House have?
A rooftop hot tub and gas fire pit with an outdoor TV, a cedar barrel sauna and cold plunge, full-body red light therapy, an arcade, a private theater with a 100-inch screen and velvet couch, and a chef's kitchen.
Is Mahana 418 oceanfront?
Truly oceanfront — the Mahana sits about thirty feet from the Pacific on Kahekili Beach, Kāʻanapali, and every window of unit 418 faces the water.
How many guests does Mahana 418 sleep?
Four — a king bed in the bedroom and a queen sleeper sofa in the living room, with one bath and central air conditioning.
When can you see whales from Mahana 418?
Humpback whale season in Maui runs roughly December through April, and they're visible right from the lanai and living room. Sea turtles swim below the lanai year-round.
How do I book these homes?
Directly with our family — no platform fees. Check dates at rambleonwp.com for Winter Park and mahana418.com for Maui.
Who manages the properties?
We do — Gather Destinations is family owned, and we manage both homes ourselves, answering every inquiry personally, usually within a few hours.
Availability & rates
Availability and rates are maintained on each property’s dedicated site.
Both homes are booked directly with us — no platform fees, no intermediaries. Reservation requests come straight to the family, and peak ski weeks and whale season book earliest.
Where we are
About Gather
A family company for places worth returning to.
Gather Destinations is the parent company of Ramble On House and Mahana 418. We own, manage, and maintain both homes ourselves — answering every inquiry personally and holding each property to the standard we expect on our own vacations.
Contact
Ramble On email
103ramble@gmail.com
Mahana 418 email
mauimahanaoceanfrontstays@gmail.com