Key West Vacation Rentals & Beach Homes

Island Stays Near Duval Street, Beaches, Sunsets & Old Town Adventures

7 stays availableCitywide

About Key West

Guest reviews for Key West: 4.9 average from 49 reviews across 7 stays
Key West is the southernmost city in the continental United States and the county seat of Monroe County, sitting at the end of U.S. Highway 1. Its tropical setting, historic architecture, surrounding waters, and distinctive island culture have made it one of Florida’s best-known vacation destinations. The heart of the destination is Old Town, where colorful historic homes, Duval Street, the Historic Seaport, and Mallory Square create a walkable mix of sightseeing, dining, shopping, and nightlife. Mallory Square itself has deep roots in Key West’s maritime history and remains an important waterfront gathering place. Beyond Old Town, visitors can enjoy beaches, snorkeling, fishing, boating, cycling, and waterfront activities, as well as landmarks such as Fort Zachary Taylor Historic State Park. Choosing a Key West vacation rental gives travelers a comfortable base for experiencing historic neighborhoods, famous sunsets, tropical waters, and the unique character of the Lower Florida Keys.

Overview

Discover Key West vacation rentals by owner in Florida, featuring beach homes, condos, cottages, and tropical island stays close to the action. Wander through historic Old Town, explore Duval Street, watch the sunset at Mallory Square, or spend the day boating, snorkeling, and fishing. With distinctive neighborhoods and a one-of-a-kind island atmosphere, Key West offers an unforgettable Florida Keys vacation.

Things to do in Key West

Top experiences and activities around Key West.

  • Explore Old Town & Duval Street

    Walk through historic Old Town, admiring colorful architecture, local shops, galleries, restaurants, and famous Duval Street. Exploring on foot or by bicycle is one of the best ways to experience Key West’s distinctive island character.

  • Watch the Sunset at Mallory Square

    Experience Key West’s famous Sunset Celebration at Mallory Square, where visitors gather along the waterfront for Gulf views, street performers, local artists, and one of the island’s signature sunset experiences.

  • Snorkel, Sail & Explore the Water

    Head beyond the shoreline for snorkeling, sailing, kayaking, fishing, or a sunset cruise. Key West’s surrounding tropical waters and coral reef ecosystem make getting out on the water an essential part of a Florida Keys vacation.

Nearby attractions in Key West

Landmarks and day trips close to Key West.

Show nearby attractions
  • The Hemingway Home and Museum

    Explore the historic home where Ernest Hemingway lived and wrote during the 1930s. Visitors can tour the house and gardens and meet the property’s famous six-toed cats. It’s one of Key West’s signature cultural attractions.

  • Fort Zachary Taylor Historic State Park Beach

    Combine history and a beach day at this distinctive Key West attraction. Explore the historic 19th-century fort, then enjoy swimming, snorkeling, fishing, picnicking, and waterfront scenery.

  • The Key West Butterfly and Nature Conservatory

    Walk through a lush, glass-enclosed tropical habitat filled with butterflies, colorful birds, plants, and waterfalls. Located on Duval Street, it’s an excellent family-friendly attraction and a change of pace from Key West’s outdoor adventures.

  • Truman Little White House

    Discover Key West’s presidential history at Harry S. Truman’s former winter residence. Truman spent significant time here during his presidency, and today visitors can tour the historic property and learn about its role in American history.

Popular neighbourhoods in Key West

Popular areas to base yourself in Key West.

Best time to visit Key West

When to plan your stay in Key West.

Visit Key West from December through May for drier weather, comfortable evenings, and excellent conditions for snorkeling, boating, fishing, and exploring Old Town. April and May can be especially appealing for warm water and fewer peak-winter crowds.
Local travel tips for Key West

Practical advice for your trip to Key West.

  • Skip the Car When Exploring Old Town

    Old Town Key West is best explored on foot, by bike, or using local transit. Parking can be limited, and the historic streets are compact. Use Key West Transit when traveling farther across the island.

  • Plan Around Peak Traffic

    Traffic can become heavier during peak season and busy arrival periods, so allow extra time when driving into or out of Key West. Once settled, group nearby attractions together and explore one area at a time to avoid unnecessary driving.

Frequently asked questions

Common questions about Key West.

What types of vacation rentals are available in Key West?

Key West vacation rentals include historic cottages, vacation homes, condos, townhomes, and waterfront stays. Options range from properties near lively Old Town to quieter residential areas suited to couples, families, and groups.

What is the best area to stay in Key West?

Old Town is ideal for travelers wanting easy access to Duval Street, Mallory Square, restaurants, and historic attractions. Truman Annex is popular for its convenient yet quieter setting, while New Town offers additional residential-style accommodations.

Can you walk to attractions from Key West vacation rentals?

Many Old Town Key West vacation rentals are within walking or biking distance of Duval Street, Mallory Square, the Historic Seaport, restaurants, and museums. A car may be more useful when staying farther from the historic district.

What are the best things to do during a Key West vacation?

Popular experiences include watching the Mallory Square sunset, exploring Duval Street and Old Town, snorkeling, boating, fishing, visiting Fort Zachary Taylor, touring historic homes, and enjoying Key West’s waterfront dining.

Why book a Key West vacation rental by owner?

Booking a Key West vacation rental by owner can provide more privacy, kitchens, multiple bedrooms, and distinctive local accommodations. Direct booking may also reduce certain third-party fees, helping travelers save up to 30% on their stay.

Explore the Lower Florida Keys with Key West vacation rentals by owner, from charming cottages to condos near Old Town, Duval Street, beaches, and Mallory Square. Spend your days on the water and evenings chasing famous island sunsets. Book directly with property owners and save up to 30%!