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Key West Vacation Rentals by Owner

Book Your Key West Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your Florida stay enjoyable.

Vacation Rentals by Owner in Key West Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places to Rent in Key West Florida.

Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8

Pilar`s Secret - An Oasis Right Of

Private vacation home
3 Bedroom(s)
2 Bath(s) Sleeps 8


Pilar’s Secret is tucked away in the heart of Key West just half a block ....more

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

Luxurious Oceanfront 5BR Property

Private vacation home
5 Bedroom(s)
4 Bath(s) Sleeps 12


Tranquil island living just fifteen minutes from downtown Key West. Stay in an ....more

SEAPORT SKYLINE at Galleon Resort near Mallory Square—Beach, King Suite

SEAPORT SKYLINE At Galleon Resort

Condo
3 Bedroom(s)
2 Bath(s) Sleeps 6


OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & ....more

**SUMMER SOLSTICE @ OLD TOWN** Unique 9BR/9.5BA Compound + LAST KEY SERVICES…

**SUMMER SOLSTICE @ OLD TOWN** Uni

Private vacation home
9 Bedroom(s)
10 Bath(s) Sleeps 22


FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 ....more

Four Palms: Casa Marina-Monthly - Private pool-back cottage- RealKeyWest

Four Palms: Casa Marina-Monthly -

Private vacation home
3 Bedroom(s)
5 Bath(s)


WELCOME TO FOUR PALMS! <br>.<br><br>This lovely 2 story hom ....more

Sea Breeze- Walking distance & Off-Street Parking!

Sea Breeze- Walking Distance & Off

Condo
2 Bedroom(s)
1 Bath(s) Sleeps 6


Summary:<br>Sea Breeze is the perfect location for your tropical getaway ....more

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

Rose Lane Villas - Villa Vista - 2

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 4


Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is ....more

3 bedroom 3 Bathroom house with a pool downtown near seaport

3 Bedroom 3 Bathroom House With A

Private vacation home
3 Bedroom(s)
3 Bath(s) Sleeps


This traditional cottage, in the heart of Old Town, was built by a shipbuilder ....more

TROPICAL PROPERTIES VACATION RENTAL - KEY WEST

TROPICAL PROPERTIES VACATION RENTA

Private vacation home
3 Bedroom(s)
2 Bath(s) Sleeps 8


****This property requires a minimum stay of 28 nights in the same calendar mo ....more

NEW LISTING! Waterfront townhouse w/ pool, fenced backyard & deck - dogs ok

NEW LISTING! Waterfront Townhouse

Private vacation home
3 Bedroom(s)
3 Bath(s) Sleeps 6


*Please note that this home only allows minimum night stays of 28 nights or lo ....more

ISLAND PEARL - Cozy Nightly Rental  just off Duval RealKeyWest

ISLAND PEARL - Cozy Nightly Rental

Apartment
1 Bedroom(s)
1 Bath(s)


WELCOME TO ISLAND PEARL<br><br><br><br>This nightly re ....more

QUEEN CONCH ~ Stunning

QUEEN CONCH ~ Stunning "Old Town"

Private vacation home
4 Bedroom(s)
4 Bath(s)


THE PROPERTY: Queen Conch is a Key West hidden gem located in perhaps the bes ....more

Historic Old Town Waterfront 1-Bed Galleon + Beach + Sunset Tiki Bar

Historic Old Town Waterfront 1-Bed

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 2


5-Night Minimum Stay (Sat-Sat Check-In/Check-Out) - If you stay the full 7 nig ....more

Conch Republic Studio - Key West Millionaires Row

Conch Republic Studio - Key West M

Apartment
1 Bedroom(s)
1 Bath(s) Sleeps 2


In the center of Key West\'s prestigious "Millionaires Row," Co ....more

Brand New! Luxury 3 Bedroom Condo at  Bayfront Suites & Marina

Brand New! Luxury 3 Bedroom Condo

Condo
3 Bedroom(s)
3 Bath(s) Sleeps 6


Bayfront Suites offers incredibly spacious, meticulously designed homes for a ....more

Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!

Old Town Key West Compound With Po

Cottage
4 Bedroom(s)
4 Bath(s) Sleeps 12


Down a hidden lane in the heart of Old Town Key West you will find “El S ....more

Luxury Galleon Resort & Marina 2 Bed/2 Bath Marina View

Luxury Galleon Resort & Marina 2 B

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6


The Galleon Resort is located in the heart of Old Town Key West and the Marina ....more

ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool

ISLAND TIME - 5 Bed/3 Bath OldTown

Private vacation home
5 Bedroom(s)
3 Bath(s) Sleeps 12


WELCOME TO ISLAND TIME! <br>Key West Island Time is a rare find in old t ....more

Location, location, location - Walk to the Beach!

Location, Location, Location - Wal

Apartment
1 Bedroom(s)
1 Bath(s) Sleeps 2


Location, location, location!<br><br>Situated in the heart of the ....more

★Family Friendly 2BR Condo at Heart of Old Town Key West- Sleeps 6!

★Family Friendly 2BR Condo At He

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6


Located in the heart of Old Town Key West. This resort overlooks the Gulf of M ....more

Heavenly Hideaway-Monthly 2BD 2.5BA Private Pool - RealKeyWest

Heavenly Hideaway-Monthly 2BD 2.5B

Private vacation home
3 Bedroom(s)
2 Bath(s)


HEAVENLY HIDEAWAY!<br><br>This home is tucked away on a lovely qui ....more

Truman Annex Best Location in Town

Truman Annex Best Location In Town

Condo
2 Bedroom(s)
1 Bath(s) Sleeps 5


We stick to a Saturday check in during the in season months (Jan-April)<br ....more

Lifetime memories/Private pool/WiFi/Dog OK/Self check-in-out/High Cleanliness!

Lifetime Memories/Private Pool/WiF

Private vacation home
4 Bedroom(s)
5 Bath(s)


This elegant home has been constructed to the highest standards and is locate ....more

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

Rose Lane Villas - Villa Porta - 1

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 4


Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is ....more

Brand New! Waterfront 4 Bedroom Condo at Bayfront Suites & Marina

Brand New! Waterfront 4 Bedroom Co

Condo
4 Bedroom(s)
3 Bath(s) Sleeps 8


Bayfront Suites offers incredibly spacious, meticulously designed homes for a ....more

Our Key West Dream in Seaport.

Our Key West Dream In Seaport.

Private vacation home
2 Bedroom(s)
3 Bath(s) Sleeps


Family home for over 20 years, we would like to share our home to those that w ....more

Your Condo by the Beach with Ocean View

Your Condo By The Beach With Ocean

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 2


The Jungle Breeze condo at LaBrisa Condominiums.<br>*Ocean View<br> ....more

'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL!  SLEEPS 2-4,  3 BLOCKS TO SOUTH BEACH!

'LA DOLCE VITA' OLD TOWN, STEPS TO

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 4


La Dolce Vita is located in the heart of Old Town Key West and just steps to ....more

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

BOTTOMS UP BUNGALOW - 2 Bedroom /

Private vacation home
2 Bedroom(s)
2 Bath(s) Sleeps 6


Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old T ....more

Tropical Getaway! 3 Pools, On-site Restaurant, Bike Rental, Pets Allowed!

Tropical Getaway! 3 Pools, On-site

Hotel
1 Bedroom(s)
1 Bath(s) Sleeps 2


Tropical island paradise! Breathe in the ocean air from your private balcony. ....more

Welcome to the Shady Palms - Private Pool - RealKeyWest

Welcome To The Shady Palms - Priva

Private vacation home
2 Bedroom(s)
3 Bath(s) Sleeps 6


Step into this beautifully restored and redoracated 1933 Key West Home. This f ....more

The Cordelia, a Key West Monthly Rental

The Cordelia, A Key West Monthly R

Private vacation home
1 Bedroom(s)
1 Bath(s) Sleeps 2


The Cordelia is located in a Historic Conch house from the early 1900’s ....more

Tortuga Hammock

Tortuga Hammock

Private vacation home
2 Bedroom(s)
3 Bath(s) Sleeps 6


Tortuga Hammock is located on Stock Island in the Coral Hammock private gated ....more

Key West Oceanfront Condo - 'The Sea Jay'

Key West Oceanfront Condo - 'The S

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6


The condo is quite large at over 1150 square feet and looks directly at beauti ....more

Spacious Waterfront 4 Bedroom Home With Private Heated Pool

Spacious Waterfront 4 Bedroom Home

Private vacation home
4 Bedroom(s)
4 Bath(s) Sleeps 8


If you’re looking for an upscale escape by the sea, Havana Daydream is y ....more

"VILLAGE ROOSTER" ~ Quaint Cottage

Private vacation home
2 Bedroom(s)
2 Bath(s) Sleeps 4


BAHAMA VILLAGE TREASURE...<br>This Old Town Key West home is just steps ....more

SEA CONCH~ Gorgeous

SEA CONCH~ Gorgeous "Old Town" Hom

Apartment
2 Bedroom(s)
2 Bath(s)


THE PROPERTY: Sea Conch is a Key West hidden gem located in perhaps the best ....more

**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR/2BA Condo & Pool + LAST KEY SERVICE

**OLD TOWN OASIS @ THE ANNEX** Oce

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6


FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 ....more

Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer

Comfortable Home With Private Pool

Private vacation home
3 Bedroom(s)
2 Bath(s) Sleeps 8


Flagler Station<br><br>Our calendar is updated in real-time & ....more

**BANYAN ROSE @ BEACHSIDE** Modern Home & Pool + LAST KEY SERVICES…

**BANYAN ROSE @ BEACHSIDE** Modern

Private vacation home
4 Bedroom(s)
2 Bath(s) Sleeps 8


FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 ....more

TROPICAL VINEYARD in the Truman Annex

TROPICAL VINEYARD In The Truman An

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 4


Shipyard Condominiums are located in the prestigious gated community of Truman ....more

3 blocks from waterfront and 1 block off Duval in Old Town Key West

3 Blocks From Waterfront And 1 Blo

Cottage
1 Bedroom(s)
1 Bath(s) Sleeps 4


Want to “ Get Away from it all” but still in the heart of Old Town ....more

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

Rose Lane Villas - Villa Rosa - 1

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 4


Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas i ....more

Villa Nomade at Shipyard Condominiums

Villa Nomade At Shipyard Condomini

Condo
2 Bedroom(s)
1 Bath(s) Sleeps 4


Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped ki ....more

Amelia's Hideaway ~ Hidden Courtyard

Amelia's Hideaway ~ Hidden Courtya

Villa
4 Bedroom(s)
4 Bath(s) Sleeps 10


"In-the-know" travelers who return to Key West to vacation love to c ....more

Key West Charmer w/Private Swimming Pool

Key West Charmer W/Private Swimmin

Private vacation home
3 Bedroom(s)
2 Bath(s) Sleeps 6


Our "Forever Gem" is a whimsical home with modern flare in Mid-town ....more

Penthouse Level Ocean Views from every room  Tropical Excellence

Penthouse Level Ocean Views From E

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6


PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY<br> ....more

Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location

Key West Dream Townhouse * Sleeps

Private vacation home
2 Bedroom(s)
3 Bath(s) Sleeps 6


This property is a rare find! Sleeping 6 and located over 2 floors, its locate ....more

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, FL 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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