Key West Rentals
From $704 per night (USD)VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $704 per night (USD)VRBO
From $490 per night (USD)Expedia
High Tide awaits your next visit upgraded condo close to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 Bedroom Garden-View Condo at 1800 Atlantic – Key West, FL Your Tropical Getaway Awaits! Experience the ultimate in c ...
From $490 per night (USD)Expedia
From $1554 per night (USD)VRBO
**CASA VICTORIA @ OLD TOWN** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $1554 per night (USD)VRBO
From $460 per night (USD)Expedia
**FOLLOW THE SUN** Ocean Condo / Pool & Tennis + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! FOLLOW THE SU ...
From $460 per night (USD)Expedia
From $2211 per night (USD)VRBO
**NOONA'S MANSION @ THE ANNEX** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located in Tr ...
From $2211 per night (USD)VRBO
From $408 per night (USD)Expedia
Tranquility by Smathers and 10 minute bike downtown Key West value savings
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 Bedroom 2 bath Island View King in the master bedroom, king in the the guest bedroom and a queen sleeper sofa in the ...
From $408 per night (USD)Expedia
From $676 per night (USD)VRBO
Somewhere on the Beach a dream property all amenities included simply amazing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Somewhere on the Beach – Oceanfront 2-Bedroom Condo in Key West Location, Location, Location... Welcome to Somewhere on ...
From $676 per night (USD)VRBO
From $565 per night (USD)Expedia
**THE ARTISTS' MUSE @ LOVE LANE** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For many, the ...
From $565 per night (USD)Expedia
From $681 per night (USD)VRBO
**DIAMOND GIRL @ THE ANNEX** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Seals & Croft ...
From $681 per night (USD)VRBO
From $782 per night (USD)Expedia
**THE SMILING IBIS @ OLD TOWN** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $782 per night (USD)Expedia
From $471 per night (USD)VRBO
**NATURES EDGE** Ocean Condo / Pool & Tennis + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! NATURE'S EDGE ...
From $471 per night (USD)VRBO
From $515 per night (USD)Expedia
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1800 Atlantic 4th floor condominiums unit C439. Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, tw ...
From $515 per night (USD)Expedia
From $314 per night (USD)VRBO
**SUNDRENCHED REFLECTIONS** Bayfront Condo + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNDRENCHED R ...
From $314 per night (USD)VRBO
From $1115 per night (USD)Expedia
**SWEET HOME ANGELITA @ OLD TOWN** Home + Last Key White Glove Service...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This renovate ...
From $1115 per night (USD)Expedia
From $961 per night (USD)VRBO
Rooftop Penthouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Rooftop Penthouse- Luxury Penthouse in prime Downtown location The Space: The high-end sophisticated Rooft ...
From $961 per night (USD)VRBO
From $302 per night (USD)Expedia
Truman Annex, two blocks from Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Available for monthly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful ...
From $302 per night (USD)Expedia
From $325 per night (USD)VRBO
**SOUTHERNMOST PALMS @ THE ANNEX** Villa + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! When you thin ...
From $325 per night (USD)VRBO
From $697 per night (USD)Expedia
**VILLA ANGELITA @ OLD TOWN** Condo Off Duval + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This modern O ...
From $697 per night (USD)Expedia
From $460 per night (USD)VRBO
**SUZY'S PARROT PERCH @ OLD TOWN** Condo + Last Key White Glove Service...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SUZY'S PARROT ...
From $460 per night (USD)VRBO
From $780 per night (USD)Expedia
Mar Y Sol –Luxurious oceanfront Key West Breathtaking Atlantic Sunrise Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Mar Y Sol – Luxury Oceanfront Condo in Key West Breathtaking Views. Unbeatable Comfort. Perfect Location. Welcome to Ma ...
From $780 per night (USD)Expedia
From $607 per night (USD)VRBO
Little Paradise, Historic Harbor Old Town Key West 2/1.5
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $607 per night (USD)VRBO
From $527 per night (USD)Expedia
**HAVANA HOUSE @ OLD TOWN** Cottage Near Duval + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located on So ...
From $527 per night (USD)Expedia
From $794 per night (USD)VRBO
**WINDSWEPT PALMS** Seaside / Pool & Jacuzzi + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Imagine a hom ...
From $794 per night (USD)VRBO
From $499 per night (USD)Expedia
Great Family Vacation Rental.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Family friendly vacation rental just outside of Key West with everything you need to enjoy a great getaway just 10 minut ...
From $499 per night (USD)Expedia
From $318 per night (USD)VRBO
Queen’s Lair Rockhouse 28 day minimum rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
(((Third bedroom is an awesome open loft with a queen size bed- it is upstairs above the living room and master suite an ...
From $318 per night (USD)VRBO
From $269 per night (USD)Expedia
Southernmost View - Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps fr ...
From $269 per night (USD)Expedia
From $361 per night (USD)VRBO
Conch Get Enough at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $361 per night (USD)VRBO
From $1723 per night (USD)Expedia
Key West Oasis - Truman Annex Estate
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Key West Oasis Luxury | Privacy | Iconic Location in Truman Annex Tucked away on one of the most exclusive ...
From $1723 per night (USD)Expedia
From $794 per night (USD)VRBO
Sky Suite with Balcony Overlooking Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $794 per night (USD)VRBO
From $1248 per night (USD)Expedia
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + Last Key White Glove Service...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! All year long ...
From $1248 per night (USD)Expedia
From $859 per night (USD)VRBO
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $859 per night (USD)VRBO
From $676 per night (USD)Expedia
Duval Dream Loft - On Duval street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located in the heart of world-famous Duval Street, this unique property offers an authentic downtown Key West ...
From $676 per night (USD)Expedia
From $677 per night (USD)VRBO
The Collins - On Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Co ...
From $677 per night (USD)VRBO
From $238 per night (USD)VRBO
Modern 2BR Condo Old Town/Balcony & Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $238 per night (USD)VRBO
From $465 per night (USD)VRBO
Green Goddess - Sunsets Included - 4BD/3Bath - 360° Rooftop - Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This ...
From $465 per night (USD)VRBO
From $859 per night (USD)Expedia
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $859 per night (USD)Expedia
From $393 per night (USD)VRBO
Fairway Villa w/ Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Fairway Villa — a stunning, spacious 3-bedroom, 3-bathroom townhouse nestled on the beautiful Key West Golf C ...
From $393 per night (USD)VRBO
From $288 per night (USD)Expedia
**CARIBBEAN CHARM** Villa Near Duval & Beach + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! The sound of ...
From $288 per night (USD)Expedia
From $3780 per night (USD)VRBO
**ALL TOGETHER NOW @ OLD TOWN** 3 Home Compound + Last Key White Glove Service…
- Bedrooms:
- 14
- Bathrooms:
- 13
- Sleeps:
- 32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $3780 per night (USD)VRBO
From $1081 per night (USD)Expedia
**MAYA’S SECRET TREASURE** Pool & Balcony + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1081 per night (USD)Expedia
From $1371 per night (USD)VRBO
Duval's Duet - Double Balconies Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval' ...
From $1371 per night (USD)VRBO
From $360 per night (USD)Expedia
5 STAR HOME 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental.
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $360 per night (USD)Expedia
From $427 per night (USD)VRBO
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $427 per night (USD)VRBO
From $389 per night (USD)Expedia
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $389 per night (USD)Expedia
From $390 per night (USD)VRBO
Charming 'Boho Breeze' Retreat w/ Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $390 per night (USD)VRBO
From $389 per night (USD)Expedia
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $389 per night (USD)Expedia
From $432 per night (USD)VRBO
Island Oasis at the Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $432 per night (USD)VRBO
From $195 per night (USD)Expedia
NEW MONTHLY RENTAL, Old Town Duplex, private backyard, pets welcome, 2BR/2BA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $195 per night (USD)Expedia
From $707 per night (USD)VRBO
Enjoy Old Town Key West in this Beautifully furnished house
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $707 per night (USD)VRBO
From $296 per night (USD)Expedia
Yellow Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red b ...
From $296 per night (USD)Expedia
From $317 per night (USD)VRBO
Blue Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red b ...
From $317 per night (USD)VRBO
From $326 per night (USD)Expedia
Green Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red b ...
From $326 per night (USD)Expedia
From $417 per night (USD)VRBO
Poolside King Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $417 per night (USD)VRBO
From $412 per night (USD)Expedia
Poolside Queen Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $412 per night (USD)Expedia
From $498 per night (USD)VRBO
One Bedroom Deck Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $498 per night (USD)VRBO
From $244 per night (USD)Expedia
Duval Street Suites on Duval Free Parking and heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duva ...
From $244 per night (USD)Expedia
From $296 per night (USD)VRBO
Duval Street Suites full kitchen, free parking, & heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic ...
From $296 per night (USD)VRBO
From $269 per night (USD)Expedia
Duval Street Suites full kitchen, free parking, heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Paradise Suite is a one bedroom (king bed) 1 bath suite with a murphy bed (queen) and kitchen. In historic Ol ...
From $269 per night (USD)Expedia
From $257 per night (USD)VRBO
Duval Street Suites full kitchen and pool view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (king) and kitchen. Overlookin ...
From $257 per night (USD)VRBO
From $271 per night (USD)Expedia
Duval Street Suites with full kitchen heated pool, free parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Mile Zero Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (king) and full kitchen. Overlooking ...
From $271 per night (USD)Expedia
From $1935 per night (USD)VRBO
6 BR 6 BA Duval Street Suites free parking & pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with six individual suites each ...
From $1935 per night (USD)VRBO
From $490 per night (USD)Expedia
Poolside Suite - Pool & Close to Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hea ...
From $490 per night (USD)Expedia
From $209 per night (USD)VRBO
Away From It All @ The Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $209 per night (USD)VRBO
From $596 per night (USD)Expedia
Galleon Resort beach hotel luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $596 per night (USD)Expedia
From $1636 per night (USD)VRBO
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1636 per night (USD)VRBO
From $195 per night (USD)Expedia
MONTHLY Rental, JAN, FEB, MAR 2027 just opened, Old Town, pets ok
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $195 per night (USD)Expedia
From $940 per night (USD)VRBO
**THE ZESTY LIME @ OLD TOWN** Restored Home + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $940 per night (USD)VRBO
From $492 per night (USD)Expedia
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront Oasis in Key West – Steps from Smathers Beach Escape to paradise in this spacious 2-bedroom, 2-bath condo wi ...
From $492 per night (USD)Expedia
From $405 per night (USD)VRBO
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Caribbean Conch – Your Island Retreat Awaits Escape to the serene beauty of Caribbean Conch, a spacious and ...
From $405 per night (USD)VRBO
From $395 per night (USD)Expedia
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $395 per night (USD)Expedia
From $256 per night (USD)VRBO
Duval Street Suites full kitchen Old Town with heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete ...
From $256 per night (USD)VRBO
From $379 per night (USD)Expedia
The Palms...A beautiful space in the perfect place.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $379 per night (USD)Expedia
From $395 per night (USD)VRBO
**DANCE OF THE BUTTERFLIES** New Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For a month i ...
From $395 per night (USD)VRBO
From $892 per night (USD)Expedia
**THE TOASTED COCONUT @ OLD TOWN** Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $892 per night (USD)Expedia
From $203 per night (USD)VRBO
2 Bdrm Ocean Breezes Tropical Island Key West Sunrises Resort amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Elegant Ocean-View Condo at 1800 Atlantic – Fully Renovated 2BR/2BA Experience refined coastal living in this beautiful ...
From $203 per night (USD)VRBO
From $172 per night (USD)Expedia
Florida Escape 2 bdrm monthly spacious resort amenities Key West Mid Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our piece of paradise in Key West! Our beautifully maintained, fully tiled 2-bedroom condo is your perfect ho ...
From $172 per night (USD)Expedia
From $1453 per night (USD)VRBO
Contra House - Private Pool & Steps to Duval St.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home ...
From $1453 per night (USD)VRBO
From $567 per night (USD)Expedia
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming Historic Bungalow with Private Pool & Detached Cottage – Steps from Duval Street! Experience the best of Key W ...
From $567 per night (USD)Expedia
From $625 per night (USD)VRBO
Happy’s Houseboat Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $625 per night (USD)VRBO
From $281 per night (USD)Expedia
Private Paradise with Heated Waterfall Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $281 per night (USD)Expedia
From $1460 per night (USD)VRBO
Sublime Sunsets at the Truman Annex in Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $1460 per night (USD)VRBO
From $626 per night (USD)Expedia
Afternoon Delight at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $626 per night (USD)Expedia
From $2349 per night (USD)VRBO
**SWEET AMERICANA** 8BR/8BA Compound & 2 Pools + Last Key White Glove Service...
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $2349 per night (USD)VRBO
From $1123 per night (USD)Expedia
**GOOD VIBRATIONS @ OLD TOWN** Villa & Pool + Last Key White Glove Service...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1123 per night (USD)Expedia
From $3099 per night (USD)VRBO
1 Block to Duval St | Banana's Foster Guesthouse
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histor ...
From $3099 per night (USD)VRBO
From $345 per night (USD)Expedia
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $345 per night (USD)Expedia
From $256 per night (USD)VRBO
Upscale end unit home @ Truman Annex close to Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $256 per night (USD)VRBO
From $231 per night (USD)Expedia
**DRIFTWOOD DREAMS** Beachside Condo & Pool + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This freshly ...
From $231 per night (USD)Expedia
From $946 per night (USD)VRBO
Poolside Paradise - Heated Pool & Steps to Duval St
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home ...
From $946 per night (USD)VRBO
From $385 per night (USD)Expedia
Shared Heated Pool, Near Duval - Poolside Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled ...
From $385 per night (USD)Expedia
From $520 per night (USD)VRBO
STEPS TO DUVAL, OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLKS TO STH BCH
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
STEPS TO DUVAL! WALK EVERYWHERE...TO ALL THE SHOPS, RESTAURANTS AND BARS OF OLD TOWN! You don’t need a car with ...
From $520 per night (USD)VRBO
From $442 per night (USD)Expedia
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s ...
From $442 per night (USD)Expedia
From $1058 per night (USD)VRBO
Old Town Retreat near Upper Duval St
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1058 per night (USD)VRBO
From $333 per night (USD)Expedia
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $333 per night (USD)Expedia
From $332 per night (USD)VRBO
Galleon Resort efficiency
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
From $332 per night (USD)VRBO
From $955 per night (USD)Expedia
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $955 per night (USD)Expedia
From $260 per night (USD)VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $260 per night (USD)VRBO
From $903 per night (USD)Expedia
Coconut Palm - Steps from Duval with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Step into the heart of Key West at Coconut Palm! Just one block from Duval Street, this tropical gem features ...
From $903 per night (USD)Expedia
From $910 per night (USD)VRBO
Parking & Shared Pool - Casa Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: - Please note the pool will be closed for renovations 9/8-9/9. - Located on the south end of Duval Street st ...
From $910 per night (USD)VRBO
From $539 per night (USD)Expedia
Sea Breeze - One Block from Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Sea Breeze is the perfect location for your tropical getaway. This two bedroom condo is located in the heart o ...
From $539 per night (USD)Expedia