Key West Vacation Rentals by Owner
We offer Vacation Homes by Owner: Book your Key West Vacation Rentals direct here and save!
Key West Vacation Rentals: Whether you're looking for a beachfront condo, a pet-friendly cottage, beach houses, or a private pool home, we have many properties to choose from. Many of our properties come with Wi-Fi, Private Pool and Other Amenities thus making your stay in Florida the perfect getaway.
We make it easy to find the perfect place to stay in Key West Florida!
We proudly partner with VRBO.com, one of the world's most trusted vacation rental platforms. As an official affiliate, every listing on our site connects you directly to verified owners through secure booking channels.
To view more details, find out about availability and book a rental, select one of the vacation rentals below.
Condo
4.9 Star Review
Key West, Florida
1 Bedrooms
1 Bath(s) Sleeps 2
Your Condo by the Beach with Ocean View
Private Vacation Home
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 Vacation Home
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
4.9 Star Review
Key west, Florida
3 Bedrooms
3 Bath(s) Sleeps 8
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
Condo
4.9 Star Review
Key West, Florida
2 Bedrooms
1 Bath(s) Sleeps 4
Villa Fleur at Shipyard Condominiums
Condo
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
4.9 Star Review
Key West, Florida
Studio
1 Bath(s) Sleeps 2
Simonton Studio, an Old Town get-away for 2
Condo
4.9 Star Review
Key West, Florida
2 Bedrooms
1 Bath(s) Sleeps 4
Key West Rooster
Private Vacation Home
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
4.8 Star Review
Key West, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Peaceful Setting Amongst The Active Island Life Style
Condo
4.7 Star Review
Key West, Florida
2 Bedrooms
2 Bath(s) Sleeps 8
Rare Penthouse 2 bed/2bath additional King in loft
Condo
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
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
4.8 Star Review
Key West, Florida
1 Bedrooms
1 Bath(s) Sleeps 6
Key West Suites Hotel - Adam Scott Rote Suite
Private Vacation Home
Key West, Florida
3 Bedrooms
3 Bath(s) Sleeps 6
Location, location, location in the heart of Old Town!
Condo
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 Vacation Home
Key West, Florida
1 Bedrooms
1 Bath(s) Sleeps 2
The Cordelia, a Key West Monthly Rental
Private Vacation Home
Key West, Florida
1 Bedrooms
1 Bath(s) Sleeps 1
The Gisela, a Key West Monthly Rental
Private Vacation Home
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 Vacation Home
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 Vacation 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 Vacation Home
5.0 Star Review
Key West, Florida
2 Bedrooms
3 Bath(s) Sleeps 6
Welcome to the Shady Palms - Private Pool - RealKeyWest
Apartment
4.8 Star Review
Key West, Florida
1 Bedrooms
1 Bath(s) Sleeps 2
Superb Location, Affordably Priced
Condo
4.9 Star Review
Key West, Florida
2 Bedrooms
1 Bath(s) Sleeps 4
Villa Nomade at Shipyard Condominiums
Apartment
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
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
4.7 Star Review
Key West, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Hidden Treasure- 2 bedroom 2 bath with shared pool
Cottage
4.8 Star Review
Key West, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
A Touch of Bermuda at Truman Annex
Private Vacation Home
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 Vacation Home
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 Vacation Home
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
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 Conservatory. Click 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.