Cheeca Lodge & Spa
27-Acre Oceanfront Estate · Islamorada
The grande dame of Islamorada — over 70 years old and recently renovated, with a 525-ft fishing pier, 9-hole golf course, and three pools.
From $600 / night
The Upper and Middle Florida Keys — from Key Largo through Marathon — offer the best diving, fishing, and natural beauty in the Florida Keys chain, with a quieter pace and stronger connection to the water than Key West.
Quick Picks: Best Hotels in Upper & Middle Florida Keys
Best Overall
Baker’s Cay Resort Key Largo
Best All-Inclusive
Best for Families
Best Value
Best Luxury
Best Boutique / Unique Stay
Where to Base Yourself
Best Areas to Stay
4 areas
Key Largo
Diving Capital of North AmericaThe first key you hit from Miami, Key Largo is defined by what lies offshore. John Pennekamp Coral Reef State Park — anchors the town, offering snorkel tours, glass-bottom boat rides, and access to the famous Christ of the Abyss submerged statue. Above water, it's low-key and local: tiki bars, fishing marinas, and mangrove kayak trails.
Islamorada
Sportfishing Capital of the WorldIslamorada is actually six keys strung together, and it's the most refined stretch of the Upper Keys. Top restaurants, premier resorts, and the finest fishing guides are all here. Tarpon, bonefish, and permit swarm the backcountry flats. Robbie's Marina, the Islamorada Sandbar, and Alligator Reef Lighthouse make it essential.
Marathon
Family-Friendly Middle Keys HubAt the center of the island chain, Marathon is the most practical and unpretentious base in the Keys. Sombrero Beach is one of the best sandy beaches in the Keys. The Turtle Hospital lets you meet recovering sea turtles up close. The iconic Seven Mile Bridge looms to the south. Best base if you plan to explore both north and south.
Tavernier
Quiet Gateway VillageA quiet hamlet between Key Largo and Islamorada that most drivers pass through without stopping. Worth stopping for the Florida Keys Wild Bird Center — a roadside rescue sanctuary — and the Blonde Giraffe, which many claim serves the finest key lime pie in the Keys.
Curated Stays
Where to Stay
8 hotels
Getaway Unpacked may earn a commission when you book through selected links, at no additional cost to you. Recommendations remain independently curated.
Luxury
Baker's Cay Resort Key Largo
Curio Collection by Hilton · Key Largo
14 acres on the bay in Key Largo, with a private marina, five pools, and the leading sustainability commitment in the Upper Keys. No single-use plastics, beehives on property.
From $450 / night
Playa Largo Resort & Spa, Autograph Collection
Key Largo · Autograph Collection · Beachfront · 3 Restaurants · Kids Club · Best Full-Service Key Largo Resort
Key Largo's premier full-service resort — a Marriott Autograph Collection beachfront property on the Atlantic with a watersports center, Ocean Spa, kids club, three restaurants including La Marea and Las Olas, private bungalows, and a three-bedroom beach house for groups. Marriott Bonvoy redeemable.
From $350 / night
Mid-Range
Isla Bella Beach Resort
Marathon · Full-Service Beach Resort
Marathon's best full-service resort — a handsome beachfront, impeccable service, multiple pools, and a spa. The Middle Keys' hidden gem.
From $350 / night
Three Waters Resort & Marina
Islamorada · Tribute Portfolio (Marriott)
The rebranded Postcard Inn — now a Marriott Tribute Portfolio property on a famous beach, still home to the Tiki Bar where the Rum Runner was invented.
From $280 / night
Kona Kai Resort & Gallery
Key Largo · 13 Rooms · Boutique · Art Gallery · Florida Bay · Adults-Preferred (14+)
The premier boutique on Key Largo — 13 rooms set within a working art gallery and lush tropical botanical gardens on Florida Bay, with a beachfront pool, hot tub, complimentary kayaks and paddleboards, and sweeping Everglades sunset views. Adults-preferred (14+). The most romantic and intimate retreat in the Upper Keys.
From $280 / night
Budget
Bungalows Key Largo
Adults-Only All-Inclusive — Key Largo
The only true all-inclusive in the Upper Keys — adults-only, with all meals, drinks, water sports, and yoga included. Two pools, two beaches, and direct reef access.
From $550 / night (all-inclusive)
Drop Anchor Resort
Islamorada · Classic Keys Motel
A cheerfully retro waterfront motel in Islamorada with direct bay access, a dock, kayaks, and hammocks. Unpretentious and booked by repeat guests.
From $175 / night
Where to Eat
Restaurants
7 picks
01
Morada Bay Beach Café
Bare feet in the sand, a cold Kalik in hand, and the finest sunset table in Islamorada. Consistently among the best-loved restaurants in the Upper Keys.
Learn MoreCasual
02
Robbie's Marina Fish Stand
The original open-air fish stand at the world-famous tarpon feeding dock. Grilled hogfish sandwich. Ice-cold beer. That's the whole agenda.
Learn MoreStreet Food
03
Marker 88
The granddaddy of fine dining in the Upper Keys. Waterfront tables, impeccable seafood, and a serious wine list in a polished setting.
Learn MoreBest Fine Dining
04
The Fish House
Key Largo's beloved no-frills seafood institution. The matecumbe-style preparation — oven-baked with olive oil, capers, tomatoes — is the dish to order.
Learn MoreBest Seafood
05
Keys Fisheries
Marathon's working waterfront fish house. Pull up to the outdoor counter and order the lobster Reuben — the legendary sandwich of the Keys.
Learn MoreBest Local
06
Islamorada Fish Company
A working fish market and restaurant at Snake Creek in Islamorada with live lobster tanks, a waterfront deck, and the freshest mahi-mahi and Florida lobster in the Keys.
Learn MoreFine Dining
07
Lazy Days Restaurant
An Islamorada institution on the ocean side of US-1 with a sunset deck and the best stone crab claws in the Upper Keys.
Learn MoreFine Dining
Worth Your Time
Things to Do
6 experiences
John Pennekamp Coral Reef State Park
America's first underwater state park — snorkel tours, glass-bottom boats, and the famous submerged Christ of the Abyss statue.
Learn MoreTarpon Feeding at Robbie's
Lean over a rickety dock and hand-feed 100-lb tarpon from a bucket of fish. The quintessential Keys experience in the Upper Keys.
Learn MoreSnorkeling Alligator Reef Lighthouse
A gorgeous reef surrounding a 19th-century iron lighthouse five miles offshore. Rated one of the best snorkel sites in the entire Keys.
Learn MoreThe Turtle Hospital, Marathon
The world's only state-certified veterinary hospital for sea turtles. Educational tours let you meet patients recovering from boat strikes and fishing line entanglement.
Learn MoreSeven Mile Bridge Walk & Bike
among the most dramatic road structures in America, stretching 6.79 miles across open water from Marathon to the Lower Keys. Walk or bike the old bridge.
Backcountry Flats Fishing Charter
Pole a skiff across the glassy backcountry flats of Florida Bay hunting bonefish, permit, and tarpon — the holy trinity of saltwater fly fishing.
Learn MoreKnow Before You Go
Travel Facts
Best Time
November–April for dry weather, clearest water, and peak season. December–April for the most reliable conditions and full restaurant openings. Summer is hot and humid but offers better fishing and water sports rates.
Getting Around
A car is essential — there is no meaningful public transit in the Keys. The Overseas Highway (US-1) is the only road. Kayak and boat rentals widely available for water access.
Currency
US Dollar (USD).
Language
English.
Visa
Not applicable — domestic US destination.
Time Zone
Eastern Time (ET) — EST (UTC−5) in winter, EDT (UTC−4) in summer.
Getting There
Miami International Airport (MIA) is the main gateway — 1.5 to 2.5 hours south on the Overseas Highway depending on your Keys destination (Islamorada, Marathon, or Key Largo). The Overseas Highway drive through 42 bridges is one of the most scenic drives in the US.
Practical Notes
The Overseas Highway (US-1) is the only road. It's one lane each way most of the way. Allow extra time — 60mph often means 35mph behind an RV.
Florida spiny lobster season: Aug 6 – Mar 31. The mini-season (last Wed–Thu of July) lets divers and snorkelers harvest them directly.
A Florida saltwater fishing license is required for anyone 16 and older not fishing from a licensed boat. Buy online at myfwc.com — takes 2 minutes.
Gas is significantly more expensive in the Keys than on the mainland. Fill up in Florida City before crossing.
Mosquitoes and no-see-ums can be fierce at dawn and dusk, especially near mangroves. Pack DEET and reef-safe sunscreen.
Hurricane season June–November. September–October are highest risk. Most Keys properties are built to strict storm codes but evacuations do happen.
FAQ
Frequently Asked Questions About Upper & Middle Florida Keys
When is the best time to visit the Upper & Middle Florida Keys?
December through April offers the most reliable weather — dry, sunny, and 70s — and the clearest water for snorkeling and diving. Summer is hotter and rainier but cheaper, with excellent fishing. Hurricane season peaks September.
How long does it take to drive from Miami to the Keys?
Key Largo is about 1 to 1.5 hours from Miami International Airport, Islamorada is roughly 2 hours, and Marathon is 2 to 2.5 hours. The Overseas Highway (US-1) is the only road and can slow significantly behind RVs, so allow extra time.
Which Key should I stay on — Key Largo, Islamorada, or Marathon?
Key Largo is best for divers and first-timers closest to Miami. Islamorada is the sportfishing capital with the best restaurants and upscale lodges. Marathon is the most family-friendly and central, closest to the Seven Mile Bridge and the Lower Keys.
Is it better to snorkel or dive the Keys?
Both are world-class. Snorkelers get plenty at John Pennekamp and Alligator Reef — the coral sits in 10 feet of water. Certified divers can explore deeper wrecks like the Spiegel Grove. If you’re new, start with a half-day snorkel tour.
Do I need a car in the Florida Keys?
Yes. There is no meaningful public transit and everything is spread along the Overseas Highway. Rent at Miami International Airport and drive down.
When is hurricane season and should I worry?
Hurricane season runs June through November, with peak risk in September and October. Most Keys properties are built to strict storm codes, but mandatory evacuations do happen. Travel insurance is worth it during peak hurricane months.
Continue Planning
Related Travel Collections
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