A 3-bedroom base for diving Islamorada's reefs
If you want three bedrooms, room for eight, and a dive-and-snorkel trip built around Alligator Reef and Cheeca Rocks, the home we'd point you at is The Oasis. It's 2.75 acres of private oceanfront in the heart of Islamorada, two houses rather than one, with 200 feet of sandy beachfront and the Alligator Reef Light sitting out on the horizon from the porch. That lighthouse is roughly four miles offshore, and it is one of the most reliably good snorkel spots in the Upper Keys. Looking at the thing you're going to snorkel over, from the house you booked to snorkel it, is a particular kind of pleasure.
We're Doli and Mark, and we've been hosting here for over twelve years. This is our house. Below is what we've learned about how dive weeks actually run from it.
Two houses, three bedrooms, eight people
The layout is the reason this works for a group. The main house holds a king bedroom with a Tempurpedic adjustable bed, a full kitchen and the wrap-around porch. The guest house holds the other two bedrooms, a queen and a queen/full, with its own full kitchen and an ocean-view living room. Three bedrooms, four beds, eight guests, three and a half baths across the two buildings.
Two kitchens matters more than it sounds on a dive trip. Charters leave early, and not everyone in a group of eight is diving. The people on the boat can be up and caffeinated in one house without waking the people who want to sleep until nine and then swim. The same split works for families travelling with grandparents, or for two couples who like each other but not at six in the morning.
- Sleeps: 8 across 3 bedrooms, 4 beds, 3.5 baths
- Setting: beachfront and waterfront, gated entrance, Islamorada
- Kitchens: full in both the main house and the guest house
- Dogs: welcome, with a fee, and there's a fenced grassy yard for them
What's in the water, and what's waiting on the beach
Four kayaks, two paddleboards and a private sandy beach to launch them from, plus a heated saltwater infinity pool looking straight out at the Atlantic. On days when the wind kicks up and the reef boats are bouncing, the pool is what saves the afternoon. Heated matters in January and February more than people expect.
The beach is your own, which changes the rhythm of a dive week. You come back salt-crusted from a morning on Cheeca Rocks or Hens and Chickens, rinse off, and the rest of the day happens on 200 feet of sand instead of in a parking lot. Dolphins pass offshore often enough that guests stop photographing them by day three. At night, more than a hundred palms stand over the property, sixty-odd of them lit.
Getting out to the reef
Charters go from the marinas near the house, and you book them directly with the operator. The ones worth knowing by name:
- Florida Keys Dive Center, a PADI 5-Star shop running daily scuba and snorkel charters out of Three Waters Marina at MM 84.5. Morning trips head for the Eagle wreck, the Duane and Crocker Wall. They also run certification courses, spearfishing and lobster diving.
- Islamorada Dive Center, based at the Postcard Inn Beach Resort and Marina. Divers report most sites sitting twenty to twenty-five minutes from the dock.
- Key Dives, in Upper Matecumbe right next door to Bud N' Mary's Marina.
For snorkelers, the three names that come up again and again are Alligator Reef Lighthouse, Cheeca Rocks and Hens and Chickens. Cheeca Rocks sits about a mile off Upper Matecumbe, straight out from Cheeca Lodge, which makes it a short, calm run and a good first stop for kids or anyone who hasn't had a mask on in a decade. Donut Hole and Conch Reef turn up on charter itineraries too.
If you'd rather snorkel without booking a boat at all, Founders Park at 87000 Overseas Highway has a white sand beach, an Olympic-size pool, kayaking and paddleboarding, and a marina that dive tours run from. Entry is three dollars. Further south at MM 73.5, Anne's Beach on Lower Matecumbe is shallow, wide Atlantic water with a sandbar, two parking lots joined by a 1,300-foot boardwalk through the mangroves, and six picnic pavilions. It's a good non-diving afternoon, especially with small children.
The bikes are not decoration
Six high-end bikes come with the house, and in this part of Islamorada you'll actually use them. Italian Food Company and Bayside Gourmet are walkable or a short ride, along with local breweries and the art galleries along the highway. Publix is less than a mile out, which is the detail that decides whether a group of eight cooks or eats out every night. With two kitchens and a BBQ area, most of our guests cook at least half the week.
Worth putting on the list while you're down here: Theater of the Sea at MM 84.5 runs dolphin and sea lion encounters, open daily from half nine to half three. Robbie's is bayside at MM 77.5, at the entrance to Lower Matecumbe. Lazy Days sits oceanside at MM 79.8, and Islamorada Fish Company at Bass Pro Shops is bayside at MM 81.5 with dockage if you've got a boat. Morada Bay and Pierre's are at MM 81.6. Mangrove Mike's, bayside at MM 82.2, does breakfast and lunch and is the one to know on a morning when the boat trip got cancelled.
Dogs, cars and the practical stuff
Dogs are welcome for a $350 fee, and the fenced grassy yard inside the gated entrance is the reason they tend to settle in fast. The whole estate is behind a gate, which also means gear can stay out: wetsuits on the line, kayaks on the sand, nothing to haul inside at night.
There's a Tesla charger and a NEMA 14-50 on site, which is rare enough in the Keys that EV drivers plan their Overseas Highway run around it. Enterprise-grade Wi-Fi covers the property, so the one person in the group who has to take a call can take it from the porch and not from a coffee shop.
Nightly rates run from around $1,155 in the quieter stretches up into the low four thousands at peak, before taxes and fees. Message us with your dates and who's coming: after twelve years and 126 five-star reviews, we have opinions about which weeks the water is clearest, and we're happy to share them before you book anything.