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Key West Vacation Rentals by Owner

Large selection of Vacation Homes, book your Key West Vacation Rental here and save!

Many properties to choose from, including private Homes, Cottages or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Florida visit the perfect getaway.

We proudly partner with VRBO.com, one of the world's most trusted vacation rental platforms. As an official VRBO Affiliate, every listing on our site connects you directly to verified owners through secure booking channels. Whether you're looking for a beachfront condo, a pet-friendly cottage, or a pool home near Disney, we make it easy to find the perfect place to stay in Florida.

Condo Star 4.9 Star Review

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 2

Your Condo by the Beach with Ocean View

Private Home Star 5.0 Star Review

Key West, Florida
4 Bedrooms 4 Bath(s) Sleeps 8

BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!

Private Home Star 5.0 Star Review

Key West, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

BOTTOMS UP BUNGALOW - 2 Bedroom / 2 Bathroom With PRIVATE POOL

Condo Star 4.9 Star Review

Key west, Florida
3 Bedrooms 3 Bath(s) Sleeps 8

Panoramic 3BR/3BA Condo - Direct Beach Ocean Front

Condo Star 4.9 Star Review

Key West, Florida
2 Bedrooms 1 Bath(s) Sleeps 4

Villa Fleur at Shipyard Condominiums

Condo Star 4.9 Star Review

Key West, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West

Apartment Star 4.9 Star Review

Key West, Florida
Studio 1 Bath(s) Sleeps 2

Simonton Studio, an Old Town get-away for 2

Condo Star 4.9 Star Review

Key West, Florida
2 Bedrooms 1 Bath(s) Sleeps 4

Key West Rooster

Private Home Star 4.8 Star Review

Key West, Florida
5 Bedrooms 5 Bath(s) Sleeps 10

~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking

Condo Star 4.8 Star Review

Key West, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Peaceful Setting Amongst The Active Island Life Style

Condo Star 4.7 Star Review

Key West, Florida
2 Bedrooms 2 Bath(s) Sleeps 8

Rare Penthouse 2 bed/2bath additional King in loft

Condo Star 5.0 Star Review

Key West, Florida
2 Bedrooms 1 Bath(s) Sleeps 5

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West

Condo Star 4.8 Star Review

Key West, Florida
2 Bedrooms 2 Bath(s) Sleeps 5

Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)

Apartment Star 4.8 Star Review

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 6

Key West Suites Hotel - Adam Scott Rote Suite

Private Home

Key West, Florida
3 Bedrooms 3 Bath(s) Sleeps 6

Location, location, location in the heart of Old Town!

Condo Star 4.9 Star Review

Key West, Florida
2 Bedrooms 3 Bath(s) Sleeps 4

Old Town Key West Condo - MONTHLY RENTALS ONLY

Condo

Key West, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Lush retreat minutes away from both Mallory Square & Duval Street.

Apartment

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 2

The Maria Luz, a Key West Monthly Rental

Private Home

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 2

The Cordelia, a Key West Monthly Rental

Private Home

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 1

The Gisela, a Key West Monthly Rental

Private Home Star 5.0 Star Review

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 2

The Rex, a Key West Monthly Rental

Apart-hotel

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

Hyatt Residence Club Sunset Harbor-Old Town- Heart of Key West, Sleeps 4!

Private Home Star 4.6 Star Review

Key West, Florida
2 Bedrooms 3 Bath(s) Sleeps 8

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Private Home

Key West, Florida
7 Bedrooms 7 Bath(s) Sleeps 8

Stunning tropical home in Old Town Key West with private pool and hot tub

Private Home Star 5.0 Star Review

Key West, Florida
2 Bedrooms 3 Bath(s) Sleeps 6

Welcome to the Shady Palms - Private Pool - RealKeyWest

Apartment Star 4.8 Star Review

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 2

Superb Location, Affordably Priced

Condo Star 4.9 Star Review

Key West, Florida
2 Bedrooms 1 Bath(s) Sleeps 4

Villa Nomade at Shipyard Condominiums

Apartment Star 4.3 Star Review

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 2

Little Casita: Key West Monthly rental Close to Duval - RealKeyWest

Condo Star 4.8 Star Review

Key West, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West

Cabin Star 4.7 Star Review

Key West, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Hidden Treasure- 2 bedroom 2 bath with shared pool

Cottage Star 4.8 Star Review

Key West, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

A Touch of Bermuda at Truman Annex

Private Home Star 5.0 Star Review

Key West, Florida
2 Bedrooms 3 Bath(s) Sleeps 4

Escape to The Gumbo Limbo Cottage, a charming 2BR, 2.5BA vacation rental

Private Home Star 5.0 Star Review

Key West, Florida
3 Bedrooms 2 Bath(s) Sleeps 6

Mulligan's Place - New Listing - Beautiful 3/2 Golf Course Home

Condo

Key West, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Caroline On My Mind-New Listing-Light, Bright and Airy!

Private Home Star 5.0 Star Review

Key West, Florida
3 Bedrooms 2 Bath(s) Sleeps 8

Your own Private Resort! 50ft Dock on Canal w/ Pool and RV Hookup!

Condo Star 4.9 Star Review

Key West, Florida
2 Bedrooms 1 Bath(s) Sleeps 4

The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6



Things to Do while on Vacation In Key West Florida

Key West is just about the perfect vacation destination in Florida. As cliché as it sounds, there truly is something for everyone. Whether you are looking to party like a rock star or seeking a relaxing vacation in nature, Key West has what you are looking for. Whether you are interested in bar hopping, beach hopping, dolphin watching, bird and wildlife watching, or some of the best people watching around; Key West is a must-visit spot in Florida.

 

Duval Street

You truly can’t visit Key West without experiencing Duval Street. This 1.2-mile street is the main thoroughfare and has so much to offer. Click here to see the live feeds of Duval Street from the world-famous Sloppy Joes, coined a Key West tradition. There are more than 100 bars and dozens of shops  and boutiques along this stretch. If you love live music be sure to visit the Green Parrot Bar and The Hogs Breath Saloon, both locations are well-known for hosting phenomenal national act.

 

The Ernest Hemmingway Home and Museum

If you enjoy literature and history, you will want to plan a visit to Hemingway Home & Museum. The estate was built in 1851 and is the most popular tourist attraction in Key West. Ernest Hemingway lived there from 1931 to 1939 and wrote some of his most popular literary works on the estate.

 

Mallory Square – Sunset Celebration

One of Key West’s most popular activities is the Sunset Celebration at Mallory Square Dock. People visit from all over the world to catch these exquisite sunsets and experience this nightly arts festival. There are street performers, food vendors, art installations, and extraordinary shopping options.

 

Key West Butterfly and Nature Conservatory

If you are a nature-lover, you will want to plan a visit to The Key West Butterfly & Nature ConservatoryClick here to check out the live webcams set up at the conservatory. You can walk among hundreds of butterflies and beautiful, colorful birds inside their habitat.

 

Dry Tortugas National Park

You can also take a ferry ride on the Yankee Freedom to visit Fort Jefferson Dry Tortugas National park. Take a guided tour and learn about life at the fort in the 1860s.  The park is 100-square-miles and, aside from the fort, is known for is gorgeous blue waters, coral reefs, and wildlife watching.

Discover the Best Deals for Key West Vacation Rentals in the Florida Keys.

We have 2,3 or 4 Bedroom beachfront Vacation Rental Homes with ocean view or a Beach House for the entire family. Book Direct Here!

Key West, Florida is known for water sports, lively nightlife, beaches, historic sites and its pastel, conch-style architecture. Located at the southernmost point in the Florida Keys and the United States, visitors can enjoy the Ernest Hemingway Home and Museum, tour the Harry S. Truman Little White House, explore beautiful tropical gardens or visit Mallory Square, a waterfront plaza just west of Duval Street where its “Sunset Celebration” is one of the most popular things to see and do in Key West.

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