Key West Rentals
From $605 per night (USD)VRBO
Beach Club #103 - Unique oceanfront living with breathtaking views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $605 per night (USD)VRBO
From $583 per night (USD)VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $583 per night (USD)VRBO
From $562 per night (USD)VRBO
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes th ...
From $562 per night (USD)VRBO
From $433 per night (USD)VRBO
Reduced Pricing!!! A Slice of Paradise! @ the Shipyard Palms!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Old Town, with the beautiful community of private homes and condominiums of Truman Annex, this Shipyard ...
From $433 per night (USD)VRBO
From $328 per night (USD)VRBO
SEA-NIC VIEW ~ 2 BR/2Ba Water-front views, Heated Pool Access and Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
IT'S A SWELL LIFE… Endless island treasures engulf this oceanfront haven which is your one stop destination for a comple ...
From $328 per night (USD)VRBO
From $347 per night (USD)VRBO
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Description: Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. ...
From $347 per night (USD)VRBO
From $1267 per night (USD)VRBO
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $1267 per night (USD)VRBO
From $248 per night (USD)Expedia
ALMOST HEAVEN ~ Stunning 2 Bedroom, 2 Bathroom Condo with Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $248 per night (USD)Expedia
From $318 per night (USD)VRBO
Ashe Splashe: A beautiful restoration of a historic Key West property
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
28 DAY MINIMUM RENTAL From the owners of South of Frances, here is another beautiful, historic restoration project. Th ...
From $318 per night (USD)VRBO
From $437 per night (USD)VRBO
Elizabeth Retreat: A three bedroom historic home in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just ...
From $437 per night (USD)VRBO
From $378 per night (USD)VRBO
Key West Private Home/Pool/on the Water\n\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LOCATION LOCATION! Located on the only canal in Key West, with a protected bird sanctuary across the canal. A short Ub ...
From $378 per night (USD)VRBO
From $174 per night (USD)Expedia
Home away from home!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the gated community of the Key West Golf Club, enjoy your morning coffee in the enclosed back porch overlooki ...
From $174 per night (USD)Expedia
From $613 per night (USD)VRBO
Charming 3 bedroom blocks from Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming Conch Style home on Southard street is just a few blocks from Duval St and across from the old Harris Scho ...
From $613 per night (USD)VRBO
From $633 per night (USD)Expedia
SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FAR FROM ORDINARY... Extraordinary moments and blissful surroundings lie ahead for your Key West adventure as you soak i ...
From $633 per night (USD)Expedia
From $593 per night (USD)VRBO
PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Open the door to Paradise Place and find yourself transported to a peaceful sanctuary. The downstairs living area is ...
From $593 per night (USD)VRBO
From $870 per night (USD)VRBO
VILLA SERENA@DUVAL SQUARE - A peaceful retreat in the heart of Old Town.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Villa Serena is the perfect space ...
From $870 per night (USD)VRBO
From $549 per night (USD)VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $549 per night (USD)VRBO
From $512 per night (USD)Expedia
QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
YOUR PIECE OF PARADISE… Residing in an attractive neighborhood at the highest point of Key West referred to as “Solares ...
From $512 per night (USD)Expedia
From $233 per night (USD)VRBO
**LARGE PRIVATE HEATED POOL and PATIO**1/3 Mile from Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on a quiet residential street in the beautiful key west neighborhood of casa marina just blocks from Higgs Beach ...
From $233 per night (USD)VRBO
From $265 per night (USD)VRBO
Perfect 2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sophisticated 2 bedroom, 1 bathroom Key West Home just steps from the white sand and salty hues of Smathers Beach, short ...
From $265 per night (USD)VRBO
From $525 per night (USD)VRBO
LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
UNMATCHED ISLAND RETREAT… Tucked away within one of the island’s most impressive lanes in the Casa Marina district, this ...
From $525 per night (USD)VRBO
From $178 per night (USD)Expedia
PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. One of ...
From $178 per night (USD)Expedia
From $406 per night (USD)VRBO
Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg/bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the Key West Shire! A sublime sanctuary where all your worldly troubles melt away and relaxation is paramoun ...
From $406 per night (USD)VRBO
From $1812 per night (USD)Expedia
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $1812 per night (USD)Expedia
From $1304 per night (USD)VRBO
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
YOUR SOUTHERN SANCTUARY... Find your serenity in this stylish and cheery townhome, just a short distance away from the s ...
From $1304 per night (USD)VRBO
From $255 per night (USD)Expedia
INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w/ Community Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
YOUR PEACEFUL PARADISE AWAITS… Find this unmatched island escape tucked away in the lust and intimate Southernmost Caban ...
From $255 per night (USD)Expedia
From $465 per night (USD)VRBO
CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w/ Pool & Compact Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
LET THE REAL WORLD SLIP AWAY... Experience quintessential island serenity within this charming and newly renovated home ...
From $465 per night (USD)VRBO
From $395 per night (USD)Expedia
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
SALT AIR & SUNSHINE... This 1 bedroom, 1 bathroom private single family home is a sweet surprise just off Duval St. It's ...
From $395 per night (USD)Expedia
From $1233 per night (USD)VRBO
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
SPOIL YOURSELF IN PARADISE... Indulge yourself in the rustic charm of historic Key West enveloped in lush, vibrant surro ...
From $1233 per night (USD)VRBO
From $1283 per night (USD)Expedia
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
KEY WEST IN STYLE... Imagine carefree days in the tropics, spent in the comfort of this exceptionally located retreat wi ...
From $1283 per night (USD)Expedia
From $450 per night (USD)VRBO
Sunrise 103-2BR/2BA condo near beaches with pool, parking, balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $450 per night (USD)VRBO
From $1429 per night (USD)Expedia
Villa Déjà vu Key West - 4BR Private Villa in Old Town Key West with Heated Pool sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get ...
From $1429 per night (USD)Expedia
From $1755 per night (USD)VRBO
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $1755 per night (USD)VRBO
From $429 per night (USD)VRBO
Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Dade County pine house has a strong connection to the sea. It was built in 1910 by ship's carpenters and owned for ...
From $429 per night (USD)VRBO
From $565 per night (USD)VRBO
La Brisa - Ocean Views Across from Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy beautiful views of the Atlantic Ocean while sitting on your private porch. Located in the scenic La Brisa complex, ...
From $565 per night (USD)VRBO
From $2481 per night (USD)VRBO
~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Villa Josine not only has curb appeal but also is a stunning example of a Key West eyebrow house. This arc ...
From $2481 per night (USD)VRBO
From $781 per night (USD)VRBO
2BR Condo - Hyatt Beach House Resort - Private Beach - Resort Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located 2.7 miles from Smathers Beach and 3.8 miles from the Ernest Hemingway Home & Museum, this quiet piece of Key Wes ...
From $781 per night (USD)VRBO
From $465 per night (USD)VRBO
Charming Old Town Bungalow
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Charming two story, 3 Bedroom 3 Bathroom. Renovated home built in 1908, on a corner lot in Historical Old Town Key West. ...
From $465 per night (USD)VRBO
From $1731 per night (USD)VRBO
Secret Villa I @ Old Town with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...
From $1731 per night (USD)VRBO
From $180 per night (USD)VRBO
Nan-sea's Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This inviting 2-bedroom, 2-bathroom ground-floor condo is the perfect retreat for one or two couples. The first bedroom ...
From $180 per night (USD)VRBO
From $208 per night (USD)VRBO
Elegant Key West Tree House - Walking Distance to Beach and Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Elegant Key West Tree House is a unique monthly rental to stay anytime of the year. Discretely built back off the st ...
From $208 per night (USD)VRBO
From $1107 per night (USD)Expedia
SERENDIPITY ~ Grand 4 Bedroom/4.5 Bathroom Home in Heart of Key West!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
TIME TO CREATE LIFELONG MEMORIES… Your long-awaited island retreat is sure to have all expectations exceeded within this ...
From $1107 per night (USD)Expedia
From $783 per night (USD)VRBO
Newly Renovated Luxury Coastal Home in the Heart of Old Town Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to La Margarita, a newly renovated home with coastal charm only blocks away from Duval Street, the Historic Seap ...
From $783 per night (USD)VRBO
From $432 per night (USD)VRBO
Luxurious monthly rental in mid-town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 Day minimum Rental: Secured behind a contemporary privacy fence and an attractive cobblestone driveway is this hidden ...
From $432 per night (USD)VRBO
From $212 per night (USD)VRBO
Conch Republic House - Key West Millionaires Row
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
In the center of Key West's prestigious "Millionaires Row," Conch Republic House is a tranquil getaway for up to six in ...
From $212 per night (USD)VRBO
From $773 per night (USD)Expedia
🏝️3 Bdrm - Ocean View Every Room-Secluded -Quiet-OCEAN FRONT- 90 FT BALCONY
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🏝️Thank you for your interest in our stunning Oceanfront 3-bedroom property in Key West! Before proceeding , we kindly ...
From $773 per night (USD)Expedia
From $535 per night (USD)VRBO
Colony Sunset- Bright and airy cottage in the heart of old town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in The Colony, a secluded, gated enclave just steps from Duval Street, Colony Sunset is a colorful and relaxing ...
From $535 per night (USD)VRBO
From $221 per night (USD)VRBO
Shipyard end unit - NOW AVAILABLE SEPT 2025
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A Change In Latitudes is a non-smoking, 1st floor end unit in the serene section of Shipyard, Truman Annex. All the ame ...
From $221 per night (USD)VRBO
From $226 per night (USD)VRBO
Monthly Availability beginning May 2025
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
To provide our guests with a clean and sanitized home, our cleaning service cleans AND disinfects all high-touch surface ...
From $226 per night (USD)VRBO
From $399 per night (USD)VRBO
Ohana Paradise At The Historic Seaport , Old Town. Private Home.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amaz ...
From $399 per night (USD)VRBO
Click For PricingVRBO
QUIET KEY WEST RESORT NEXT TO AIRPORT - FANTASY FEST - 2/2 WATERFRONT BALCONY
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West, FL. Available Sat. Oct.19 - Sat. 26, 2024. Located in the Southeast end of Key West at the Hyatt Windward Poin ...
Click For PricingVRBO
From $392 per night (USD)VRBO
Paradise on Eaton- 3 bedroom 3 bath home w/private pool near Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $392 per night (USD)VRBO
From $266 per night (USD)VRBO
Our Key West Dream in Seaport.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Family home for over 20 years, we would like to share our home to those that want to relax, see an amazing sunset, and e ...
From $266 per night (USD)VRBO
From $557 per night (USD)Expedia
BLUE ROOSTER ~ Spectacular 4 Bed/4 Bath with Pool and Solarium in Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
OLD TOWN PARADISE.... Paradise awaits in a quiet Old Town location. This four bedroom home is set on a cozy lane that i ...
From $557 per night (USD)Expedia
From $378 per night (USD)VRBO
Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
BIlly's Blue Heaven is fresh, clean and Pristine. We have updated the condo with all new paint, a new Smart Tv in the ...
From $378 per night (USD)VRBO
From $496 per night (USD)Expedia
BELLA VITA ~ 2/1.5 located in the Truman Annex with a community pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
IDEAL LOCATION IN GREAT COMMUNITY... Enjoy your stay at the President's Walk at Truman Annex. This well manicured commu ...
From $496 per night (USD)Expedia
From $459 per night (USD)VRBO
Key West Oceanfront Condo - 'The Sea Jay'
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The condo is quite large at over 1150 square feet and looks directly at beautiful Smathers Beach. The 'Sea Jay' is loca ...
From $459 per night (USD)VRBO
From $710 per night (USD)VRBO
Discover the lure of Casa Catalina, a blend of Key West charm and modern comfort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Casa Catalina – Your Key West Oasis! Step into the enchanting world of Key West with a stay at the newly ren ...
From $710 per night (USD)VRBO
From $916 per night (USD)VRBO
★2BR Resort Villa at Heart of Old Town Key West- Sleeps 6!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $916 per night (USD)VRBO
From $804 per night (USD)VRBO
Near Duval - Tiki Bar - Private Beach - 2BR Condo - Old Town Key West - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $804 per night (USD)VRBO
From $625 per night (USD)VRBO
Stunning Historic Estate – 20% Off Summer Bookings, Heated Pool & Bikes Included
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Discover a delightful four-bedroom getaway nestled within the historic district of Key West. Nestled just a 13-minute wa ...
From $625 per night (USD)VRBO
From $267 per night (USD)Expedia
GOOD FEELIN ~ Charming 2 BR/2 Ba Home Conveniently Located w/ Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
SPOIL YOURSELF… Come unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of sw ...
From $267 per night (USD)Expedia
From $223 per night (USD)VRBO
POSITIVE VIBES ~ Charming 2 BR, 1 Ba Cottage in Peaceful Area w/ Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LOST ON ISLAND TIME… Treasure your time together within this charming Key West cottage tucked away on this peaceful and ...
From $223 per night (USD)VRBO
From $385 per night (USD)Expedia
GOOD VIBES ~ 2 Cottages w/ 4 BR/3 Ba, Outdoor Oasis and Parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
MEMORIES TO LAST A LIFETIME… This unique set of 2 charming, Conch style homes provide the perfect compound setting for y ...
From $385 per night (USD)Expedia
From $163 per night (USD)VRBO
Cozy cottage apartment with front porch & upgraded finishes - close to beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Borrowed Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $163 per night (USD)VRBO
From $145 per night (USD)Expedia
A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Caroline's Cottage KW Welcome to Caroline’s Cottage steps away from the world’s famous Duval Street in Key West Fla. Yo ...
From $145 per night (USD)Expedia
From $242 per night (USD)VRBO
OUR HAPPY PLACE ~ Adorable 2 Bedroom, 2 Bath Condo Steps from the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $242 per night (USD)VRBO
From $998 per night (USD)Expedia
ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $998 per night (USD)Expedia
From $1441 per night (USD)VRBO
NEW LISTING Old Town Private Pool in Garden Of Eden tropical spa-like Oasis
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 4
( NEW LISTING SEE VRBO LISTING 1223004 for reviews on my other property ) Newly renovated, invitingly spacious, serenely ...
From $1441 per night (USD)VRBO
From $809 per night (USD)VRBO
Oceanfront Property - 2BR/2BA - Near Smather's Beach - Poolside Bar and Grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
★Excellent Key West Location - Oceanside Resort - Two Bedroom - Two Bath - Sleeps 6 ★Very Clean - Very Nice Property. T ...
From $809 per night (USD)VRBO
From $1932 per night (USD)VRBO
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 20
ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring eve ...
From $1932 per night (USD)VRBO
From $1832 per night (USD)Expedia
Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Octopus’s Garden — Top-Rated Key West Rental with 150+ 5-Star Reviews! Location: Steps from Duval Street & Ernest Hemin ...
From $1832 per night (USD)Expedia
From $286 per night (USD)VRBO
Eleanor's Place Key West - Historic Old Town Cottage Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Eleanor's Place is a charming Key West Cottage in the heart of Key West! Featured on HGTV's Island Life, our renovated c ...
From $286 per night (USD)VRBO
From $327 per night (USD)VRBO
~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $327 per night (USD)VRBO
From $205 per night (USD)VRBO
Dreamworks Conch Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
PEACEFUL RETREAT... A quintessential Key West cottage in the heart of Old Town and only a few blocks away from Higgs Bea ...
From $205 per night (USD)VRBO
From $162 per night (USD)VRBO
Seaside Condo, 2 pools, close to Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Upon waking in the morning we hear the murmuring of tropical birds , feel the gentle sea breezes and the fragrance of j ...
From $162 per night (USD)VRBO
From $432 per night (USD)VRBO
Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion ...
From $432 per night (USD)VRBO
From $546 per night (USD)Expedia
EBB AND FLO ~ Newly Renovated Retreat in Old Town with Incredible Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
OLD TOWN KEY WEST… Surround yourself in this newly renovated gem located in the desirable Casa Marina neighborhood neari ...
From $546 per night (USD)Expedia
From $353 per night (USD)VRBO
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CATCH YOUR SECOND WIND… Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambianc ...
From $353 per night (USD)VRBO
From $731 per night (USD)VRBO
Penthouse Suite @ KW, Galleon Resort, Not Available in 2024-2025
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
From $731 per night (USD)VRBO
From $428 per night (USD)VRBO
Ocean views and beach breezes at La Brisa's #303 West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL Let "the breeze" of La Brisa cool you as you relax on your balcony overlooking the salt ponds, a ...
From $428 per night (USD)VRBO
From $411 per night (USD)Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $411 per night (USD)Expedia
From $451 per night (USD)VRBO
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $451 per night (USD)VRBO
From $448 per night (USD)Expedia
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $448 per night (USD)Expedia
From $885 per night (USD)VRBO
Duval Street, Condo, Luxury,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
We know that you will enjoy staying in this oasis of comfort in the paradise of Key West. Our Cuban Club Condo is a 1500 ...
From $885 per night (USD)VRBO
From $472 per night (USD)Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo w/ balcony at Mile Marker 0!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 2 full bath {queen ...
From $472 per night (USD)Expedia
Click For PricingVRBO
Pet friendly Monthly Rental with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lush tropical grounds greet you upon entrance of this enhanced 3/2 monthly rental home. This adorable retreat is located ...
Click For PricingVRBO
From $419 per night (USD)Expedia
SOUTHERN CROSS ~ Conveniently Located 3 Bedroom, 2.5 Bathroom Gem w/ Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
SOUTHERN HOSPITALITY... Find your luxurious, island retreat nestled in the heart of Old Town, just blocks from the beaut ...
From $419 per night (USD)Expedia
From $755 per night (USD)VRBO
2-Bedroom Villa at Hyatt Beach House! Quiet Beachfront Location! Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $755 per night (USD)VRBO
From $675 per night (USD)VRBO
Key West On THE BEACH New Years! Dec 27th - Jan 3rd 2026
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE READ CAREFULLY BEFORE YOU EMAIL OWNER This rental is for a 7 NIGHT HOLIDAY 1 week RENTAL ONLY! This is for 7 n ...
From $675 per night (USD)VRBO
From $225 per night (USD)VRBO
Key West-Coconut Beach Resort - Avail 11/14/26 to 11/21/26
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Book it before it's gone - 7 day rental - available from Saturday 11/14/26 to Saturday 11/21/26 only. Cozy and comforta ...
From $225 per night (USD)VRBO
From $325 per night (USD)VRBO
ShangriLa Suite / Queen Studio / Sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $325 per night (USD)VRBO
From $326 per night (USD)VRBO
Tropical Paradise In Key West-Coconut Beach Resort - Avail 4/25/25 to 5/2/26
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Book it before it's gone! 7 Day rental - available from Saturday 4/25/26 to Saturday 5/2/26 only. Cozy and comfortable ...
From $326 per night (USD)VRBO
From $338 per night (USD)Expedia
LA PUERTA ROSA~Charming 3 bed/2 bath Conch Home in Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $338 per night (USD)Expedia
From $220 per night (USD)VRBO
Single Family Home, 3 Bedroom, 2 Baths, Pool. Great Value!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private b ...
From $220 per night (USD)VRBO
From $816 per night (USD)VRBO
Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE Lane This home is a perfect example of WHY people c ...
From $816 per night (USD)VRBO
From $791 per night (USD)VRBO
Classic Key West cottage with pool & courtyard - walk to beach & Duval St dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Papa's Hideaway - Garden of Eden Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $791 per night (USD)VRBO
From $594 per night (USD)VRBO
Truman Annex unit 254
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 ...
From $594 per night (USD)VRBO
From $952 per night (USD)VRBO
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please choose a Saturday check-in, all rentals will be in seven night increments. Bedding configuration may vary, depend ...
From $952 per night (USD)VRBO
From $481 per night (USD)VRBO
Key West GULF FRONT Home with Private Dock and Heated Pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
On the entire island of Key West there are fewer than 50 private homes on open water and only a few with their own priva ...
From $481 per night (USD)VRBO