Key West vacation rentals sit at the southern end of the Overseas Highway — 90 miles north of Cuba and the most-visited destination in the Florida Keys. Key West is the only walkable region in the chain, with a dense Old Town, active nightlife, historic homes, and the Keys’ only true urban energy.
If your priority is a walkable downtown, restaurants and bars within walking distance, and historic charm, Key West delivers. If you want a private waterfront home with a pool and dock, the Middle Keys (Marathon) consistently delivers better value for the money.
For broader context, see our Florida Keys vacation rentals overview, ” Where to Stay in the Florida Keys guide, and the Florida Keys travel guide.
Why Key West for a Florida Keys Vacation Rental
- Walkable Old Town. The only Keys destination where a 4-night stay works without a car. Bars, restaurants, museums, and beaches are all within walking distance.
- Historic and cultural depth. Hemingway Home, Truman Little White House, and 19th-century architecture throughout Old Town.
- Active nightlife. Duval Street is the only legitimate nightlife district in the Keys.
- Dry Tortugas access. Day trips to the most remote U.S. national park depart only from Key West.
Top Things to Do in Key West
- Mallory Square sunset celebration — nightly street fair with performers and vendors
- Hemingway Home and Museum — period-furnished home of Ernest Hemingway, six-toed cats
- Duval Street — bars, restaurants, shops, history; the spine of Old Town
- Southernmost Point Buoy — iconic photo spot
- Dry Tortugas National Park — full-day ferry trip to Fort Jefferson and isolated reef snorkeling
- Conch Train or Old Town Trolley — narrated city tours, hop-on/hop-off
- Truman Little White House — presidential vacation residence, guided tours
- Smathers Beach — the longest beach in Key West, popular with locals
- Higgs Beach — pier, dog beach, AIDS Memorial
- Fort Zachary Taylor — state park beach with the clearest water in Key West
What to Look for in a Key West Vacation Rental
- Old Town location. The closer to Duval Street, the higher the price — but walkability is Key West’s entire value proposition
- Off-street parking — rare and valuable; on-street parking in Old Town is scarce
- Pool — common at mid-range and luxury rentals; smaller than Marathon pools
- Sleeping capacity — Key West rentals trend smaller than Marathon; most homes are 2- to 3-bedroom historic conch houses
- Quiet block — rentals on Duval or its closest streets get noise late into the night; check before booking
How to Get to Key West
- From Miami International (MIA): 3.5 to 4 hours south on US-1, 160 miles
- From Marathon: 1 hour south on US-1, 50 miles
- By air: Key West International (EYW) has limited connections from Atlanta, Charlotte, Miami, Newark
- By ferry: Key West Express runs from Fort Myers and Marco Island
- By cruise: Major cruise lines call at Key West for day visits
Where to Eat in Key West
- Blue Heaven — Iconic backyard restaurant with chickens, famous breakfast, and dinner
- Pepe’s Cafe — The oldest restaurant in Key West, a breakfast institution
- El Siboney — Old-school Cuban; ropa vieja and roast pork
- Latitudes — Boat-only access on Sunset Key, romantic dinner
- Garbo’s Grill — Food truck classic, fresh fish tacos
- Kermit’s Key Lime Pie — The benchmark for the Keys’ most-famous dessert
Best Time to Visit Key West
December through April delivers the best weather, but the highest prices and densest crowds. Spring break (March) is especially busy. May and November are the value sweet spots. Avoid Fantasy Fest (late October) if you want a calmer Key West — the city packs out. View the best time to visit the Florida Keys.
Frequently Asked Questions
Is a Key West vacation rental better than a hotel?
Depends on the trip. Hotels work better for short stays (2–3 nights), couples-only trips, and travelers who want walkable resort amenities. Vacation rentals work better for groups of 4 or more, stays of 4+ nights, and travelers who want a kitchen and outdoor space. Per-person costs favor rentals at 4+ guests.
Where should I stay in Key West for the first time?
Old Town between Duval Street and the Atlantic side — close to attractions and dining without sitting on top of Duval Street’s late-night noise. Bahama Village and the area near Truman Avenue both work well. Avoid New Town if walkability is the priority — you’ll need a car or rideshare.
How many days should you spend in Key West?
2 to 4 nights is the sweet spot for most travelers. Less than 2 nights, and you spend most of the trip driving or flying. More than 4 nights, and many travelers find Key West repetitive without day trips to the Lower Keys, Bahia Honda, or Marathon.
Are Key West vacation rentals expensive?
Yes — Key West rentals are among the priciest in the Keys, especially in Old Town. Peak-season nightly rates often exceed $500 for a 2-bedroom, $1,000+ for a 4-bedroom historic home. Marathon delivers comparable property quality at meaningfully lower rates with a 1-hour drive each way.
Can you have a private dock at a Key West vacation rental?
Rare — most Old Town rentals are inland, and Key West’s waterfront is dominated by hotels, marinas, and public spaces. Stock Island (just north of Key West) has dock-equipped rentals. Marathon offers the highest concentration of private deep-water slips. At Keys Cove, our 4-bedroom homes include assigned slips with 30A/50A power, a feature nearly impossible to find in Key West Old Town.
Is Key West family-friendly?
Mixed. Daytime is great for families — Smathers Beach, Fort Zachary Taylor, the Mel Fisher Maritime Museum, and the Key West Aquarium are all kid-friendly. Evenings on Duval Street are not family-oriented. Marathon is the more family-forward Keys region overall.
Where to Find Luxury Florida Keys Vacation Rentals Near Key West
For travelers who want a 4-bedroom waterfront home with a private pool, deep-water dock with 30/50A, and direct open-water access at a fraction of Old Town’s rates, our Keys Cove collection in Marathon is 1 hour north on US-1. The drive is direct, and many travelers split a Keys trip: 2 nights in Old Town for the walkability, 4 nights at Keys Cove for the central base. Discover why Marathon is the ultimate family vacation destination.
Keys Cove address: 2264 Overseas Highway, Marathon, FL 33050
Get Directions →
Helpful resources:
- Browse Keys Cove waterfront homes
- Things to do in the Florida Keys
- Where to stay in the Florida Keys
- Florida Keys travel guide
- Explore more in our Directory
Plan Your Key West Vacation
Old Town rentals book heavily — popular dates sell out 90+ days in advance. If Fantasy Fest, Hemingway Days, or Christmas–New Year’s are on your itinerary, reserve 6 months ahead.
Browse Florida Keys vacation rentals → | See Marathon homes →
External resource: Florida Keys & Key West tourism — Key West for official visitor information.