Key West Vacation Rentals

Plan your Key West getaway

Key West works best on foot and by water, with Old Town landmarks, sunset gathering spots, historic sites, and reef access shaping the trip. Key West, FL vacation rentals fit couples, families, friend groups, and repeat visitors who want to stay near the Ernest Hemingway Home and Museum, Mallory Square, the Historic Seaport, and Lower Keys day trips without making every plan revolve around Duval Street.

As you compare homes, think about whether you want to stay near Old Town, close to the waterfront, within walking distance of dining and nightlife, or in a quieter cottage-style setting. Each home is unique, so review listing details for parking, kitchens, pet policies, WiFi, laundry, outdoor space, pools, and seasonal access notes before you book.

Things to do in Key West

Looking for things to do in Key West, FL? Start with Old Town’s historic landmarks and sunset culture, then add harborfront time, beach-meets-history stops, and boat-based outings that show how the island connects to the wider Florida Keys.

The Ernest Hemingway Home and Museum

The Ernest Hemingway Home and Museum preserves the author’s Key West years through historic rooms, gardens, writing history, and the famous six-toed cats. It’s one of the island’s most recognizable indoor stops, making it useful for culture-minded first-timers, literary travelers, and rainy-day planning.

Best for:

• First-time visitors
• Literary history
• Rainy-day plans
• Old Town sightseeing

Mallory Square

Mallory Square is the classic Key West first-evening stop, with harbor views, street performers, food vendors, shops, and the nightly sunset gathering. It works well when your group wants the island’s social energy without committing the whole night to Duval Street.

Best for:

• First evenings
• Sunset plans
• Families and groups
• Harborfront wandering

Fort Zachary Taylor Historic State Park

Fort Zachary Taylor Historic State Park combines a historic fort with beach time, swimming, snorkeling, and coastal views at the southern edge of Key West. It’s a strong choice when your group wants one stop that balances history and water without leaving the island.

Best for:

• Beach time with history
• Swimming and snorkeling
• Families and couples
• A slower afternoon outdoors

Southernmost Point Buoy

The Southernmost Point Buoy is Key West’s most recognizable photo landmark, marking the island’s southernmost-point identity and close-to-Cuba setting. Treat it as a quick Old Town stop to pair with nearby sights rather than a standalone half-day activity.

Key West Historic Seaport

Key West Historic Seaport is a harborfront district with dining, shopping, live music, museums, marinas, and water excursions along the waterfront. Use it as the bridge between daytime wandering and boat-based plans, especially if your trip includes reef, fishing, or sunset cruises.

Where to eat in Key West

Key West dining is easiest to plan by area. Duval Street is the island’s main strip for bars, cafes, late-night energy, and people-watching, while the Historic Seaport is better for waterfront seafood, harborfront meals, breweries, and food stops tied to boating and marina activity.

Around Mallory Square, sunset-adjacent drinks, Cuban and conch flavors, sweets, and quick bites fit naturally before or after the evening crowd gathers. If you prefer relaxed meals at your rental, check each listing for kitchen setup, dining space, outdoor seating, and parking, since features vary by home.

Sloppy Joe’s Bar

Sloppy Joe’s Bar is an iconic Duval Street nightlife anchor with live music, a long-running Key West identity, and a come-as-you-are atmosphere. Use it as a classic bar stop connected to Duval Street, not as a general restaurant recommendation.

Kermit’s Key Lime Shop

Kermit’s Key Lime Shop is built around Key lime pies, sweets, and the island’s signature tart flavor. It works best as a dessert, snack, or take-home stop rather than a full meal.

Key West local tips

• Build one sightseeing loop around Old Town instead of treating every landmark as a separate outing. Hemingway Home, Southernmost Point, Mallory Square, Duval Street, and the Historic Seaport work best when grouped by location and time of day.
• Treat Dry Tortugas National Park as a separate boat or seaplane excursion from Key West, not a casual in-town attraction.
• Start reef-focused plans with the Florida Keys Eco-Discovery Center or NOAA sanctuary information if you want context before a snorkel, dive, fishing, or boating trip.
• Choose Fort Zachary Taylor when you want beach time with a historic site attached, rather than a beach stop that is only about sand and water.
• Keep Lower Keys wildlife outings, such as National Key Deer Refuge or Bahia Honda State Park, in a separate day-trip bucket so the core Key West section stays geographically accurate.
• As you browse Key West vacation rentals, check each listing for parking, pet policies, WiFi, kitchens, laundry, pools, outdoor space, and walking distance to Old Town or the waterfront. Amenities vary by home.

Day trips from Key West

Key West makes a compact island base, but some of the region’s most memorable nature experiences require a boat, seaplane, or drive into the Lower Keys. Plan these as separate outings, and check current ferry, tour, park, weather, and access details before you go.

Dry Tortugas National Park

Dry Tortugas National Park is a remote offshore national park west of Key West, with Fort Jefferson, blue water, coral reefs, marine life, and birdlife. It’s the iconic Key West excursion for travelers willing to devote a separate planning block to getting there by boat or seaplane.

National Key Deer Refuge

National Key Deer Refuge on Big Pine Key protects endangered Key deer and rare Lower Keys habitats, including pine rockland, hardwood hammock, wetlands, and mangroves. It’s a Lower Keys wildlife outing for travelers who want a nature day beyond Old Town and the beach.

Bahia Honda State Park

Bahia Honda State Park is a Lower Keys park known for clear water, beaches, snorkeling, paddling, wildlife viewing, and views tied to the old railroad bridge. Use it as the regional beach-and-nature alternative when your group wants a different Keys landscape than Key West offers.

Key West National Wildlife Refuge

Key West National Wildlife Refuge is a boat-accessible refuge west of Key West, with mangrove islands, shallow saltwater habitat, wildlife viewing, snorkeling, diving, and fishing. Treat it as a guided or boat-based backcountry outing, not a walkable Key West attraction.

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