Islamorada Brewery & Distillery (Islamorada)
One of the highest-rated tables near your stay.
4.9★ (3,254)
SHORT BREAKS · FLORIDA
Florida Keys,
assembled for you.
Island-hopping down the Overseas Highway to turquoise water and Key West.Premium stays1
Local picks17
Trip length1–4 nights
WHAT WE DO
We assemble the whole trip.
You just show up.
No twenty browser tabs, no spreadsheet. Tell us how long you have, your budget and how you want to feel — Retreat48 plans the entire Florida Keys trip around it: how you get there, where you stay, the spa, dinner, a proper walk and the things worth doing. One trip, decided.
Assemble my Florida Keys trip- 01TravelDoor-to-door, the low-friction way
- 02Your stayQuality-checked, real spa, right for you
- 03Spa & wellnessTreatments and time that actually exist
- 04Food & pubsWhere to eat and drink, hand-picked
- 05Walks & things to doThe good stuff, none of the research
WHY FLORIDA KEYS
Island-hopping down the Overseas Highway to turquoise water and Key West.
The Keys are a 110-mile road trip over the sea: Islamorada's fishing lodges, Marathon's reefs and Key West's sunset at the end. We choose the waterfront resorts with spas and private beaches along the chain.
Sea timeSwitching offSnorkelling
PREMIUM STAYS
1 quality-checked stay in Florida Keys.
Hand-filtered for genuine quality — 4 and 5-star hotels with strong guest reviews and real facilities, spa included where it counts. Open any stay for live prices and to plan the whole trip around it.
WHILE YOU’RE THERE
The Florida Keys shortlist.
Hand-picked and quality-checked, the same way we choose your stay — a handful of places worth your limited hours, not a directory.
Italian Food Company
One of the highest-rated tables near your stay.
4.9★ (2,906) · $$Square Grouper Islamorada
One of the highest-rated tables near your stay.
4.7★ (2,134) · $$Papa Joe's Waterfront
One of the highest-rated tables near your stay.
4.7★ (1,741) · $$Midway Cafe & Coffee Bar
One of the highest-rated tables near your stay.
4.7★ (2,289) · $$Islamorada Wine Co.
A well-loved spot for a drink near your stay.
4.9★ (87)Day Drippin Coffee
A top-rated café for a slow morning.
4.9★ (108) · $Bayside Gourmet
A top-rated café for a slow morning.
4.7★ (1,532) · $$Ciao Bella of Islamorada Salon, Day Spa, Wellness & Yoga
A highly-rated spa a short hop from your stay.
4.9★ (382)Aqua Salon and Day Spa
A highly-rated spa a short hop from your stay.
4.9★ (95)Cheeca Lodge & Spa
A highly-rated spa a short hop from your stay.
4.4★ (2,697)Clearly Unique Charters
One of the area's most-loved things to do.
4.9★ (969)History of Diving Museum
One of the area's most-loved things to do.
4.8★ (1,258)Deep Sea Scuba and Snorkeling
One of the area's most-loved things to do.
4.8★ (163)Theater of the Sea
One of the area's most-loved things to do.
4.6★ (5,208)Windley Key Fossil Reef Geological State Park
A local favourite for an unhurried hour outside.
4.5★ (739)Green Turtle Hammock Nature Preserve
A local favourite for an unhurried hour outside.
4.4★ (86)GOOD QUESTIONS
Florida Keys, answered.
When is the best time to visit Florida Keys?
Florida Keys is at its best from late spring to early autumn for the coast and the sea. May and September give you much of the warmth with far fewer crowds and better prices.
How do I get to Florida Keys?
Florida Keys is usually reached by car, or by air into the nearest regional airport and a short drive on. Retreat48 works out the sensible route and real travel time from where you're starting.
What is Florida Keys best for?
Florida Keys is best for sea time, switching off and snorkelling. Island-hopping down the Overseas Highway to turquoise water and Key West.
READY WHEN YOU ARE
Stop researching. Start leaving.
Every stay we show has passed six independent checks. Everything around it — travel, food, walks, the plan — we assemble for you around your city, your budget and the feeling you’re after.
Assemble my Florida Keys trip