Key West Rentals
From $80 per night (USD)VRBO
A Palm Tree Paradise @ the Key West Golf Club
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...
From $80 per night (USD)VRBO
From $500 per night (USD)VRBO
4 bd w/loft Condo w/ boat slip Pelican Landing St Croix
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
St. Croix Penthouse (for 12 people) features four bedrooms and four private baths. The master bedroom has a king bed, on ...
From $500 per night (USD)VRBO
From $279 per night (USD)VRBO
Pelican's Perch @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $279 per night (USD)VRBO
From $90 per night (USD)VRBO
Luxurious Historic House With Pool in Old Town INTRODUCTORY RATES!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Monthly rental STUDIO with POOL just AVAILABLE. Same amenities. Save money if planing to come for over 14 days! Find it ...
From $90 per night (USD)VRBO
From $202 per night (USD)VRBO
Galleon Resort Efficiency Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You w ...
From $202 per night (USD)VRBO
From $80 per night (USD)VRBO
Beauty on the Green at the Key West Golf Club
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
Beauty on the Green --2 BDRM/1.5 BA townhome with easy access to the front pool.*****PLEASE NOTE THIS IS A MONTHLY RENTA ...
From $80 per night (USD)VRBO
From $174 per night (USD)VRBO
**HERE COMES THE SUN @ CASA MARINA** Home / Large Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Imagine being ...
From $174 per night (USD)VRBO
From $284 per night (USD)VRBO
SPECIAL PRICING May 2021 "OCEAN FRONT! 90 FT BALCONY-Spectacular View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Notice: Due to Corona Virus We suggest you purchase "Cancel For Any Reason Insurance". (CFAR) CSA Insurance In the even ...
From $284 per night (USD)VRBO
From $50 per night (USD)VRBO
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $50 per night (USD)VRBO
From $491 per night (USD)VRBO
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Hidden amongs ...
From $491 per night (USD)VRBO
From $343 per night (USD)VRBO
Above it All in Mills Place @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
IMMACULATE RETREAT STEPS FROM IT updated and redecorated, this beautifully designed and appointed Truman Annex multi-le ...
From $343 per night (USD)VRBO
From $171 per night (USD)VRBO
A Pleasant Stay @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $171 per night (USD)VRBO
From $274 per night (USD)VRBO
Top Floor Ocean Views from every window Newly Renovated for 2020
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Key West Paradise Found hes been renovated for 2020 an ...
From $274 per night (USD)VRBO
From $571 per night (USD)VRBO
Beautiful Large home!
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $571 per night (USD)VRBO
From $207 per night (USD)VRBO
Green Spot @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastef ...
From $207 per night (USD)VRBO
From $188 per night (USD)VRBO
CORAZON Old Town MONTHLY vacation rental - Private Pool - LARGE 2BD/2.5BA
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO CORAZON! We are complying with the directives listed on the Monroe County website. Please be aware that inf ...
From $188 per night (USD)VRBO
From $207 per night (USD)VRBO
Havana Views @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $207 per night (USD)VRBO
From $175 per night (USD)VRBO
Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
'The Plantation' is a 3 bed 3 bath townhome located within the gated community of Truman Annex in Key West's Old Town ar ...
From $175 per night (USD)VRBO
From $203 per night (USD)VRBO
Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perche ...
From $203 per night (USD)VRBO
From $125 per night (USD)VRBO
"LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
'La Dolce Vita' is located in Old Town, Key West!! Just 3 short blocks to Southernmost Beach and Southernmost Point ...
From $125 per night (USD)VRBO
From $160 per night (USD)VRBO
LAVENDER JUNGLE Whimsical Vibe, Large Outdoor Space, Shared Pool, Walk to All
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West' ...
From $160 per night (USD)VRBO
From $240 per night (USD)VRBO
~ STEAMPLANT #211 ~ World Class Luxury Condo w/ Amazing Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 211! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)VRBO
From $180 per night (USD)VRBO
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is ...
From $180 per night (USD)VRBO
From $700 per night (USD)VRBO
CASA GRANDE - Entertainers Dream, Great for Families and Events, Private Pool
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 12
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and clo ...
From $700 per night (USD)VRBO
From $198 per night (USD)VRBO
~ BOHEMIAN HOUSE ~ Newly Renovated "Old Town" Home w/ Pvt Pool. Pets OK!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: The Bohemian House is a restored historic home full of delightful surprises! This home is placed on the N ...
From $198 per night (USD)VRBO
From $409 per night (USD)VRBO
Off street PRKING- FREE Ft Zach BCH PASS/ COMM POOL
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
Old Town -Whitehead St- BEST LOCATION -On Whitehead St. -Steps to Duval -Walk a few blocks to new Truman Annex water par ...
From $409 per night (USD)VRBO
From $275 per night (USD)VRBO
VILLA SERENA@DUVAL SQUARE - A peaceful retreat in the heart of Old Town.
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Recently renovated in February 201 ...
From $275 per night (USD)VRBO
From $240 per night (USD)VRBO
~ THE STEAMPLANT 210 ~ Luxurious Condo w/ Breathtaking Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 210! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)VRBO
From $185 per night (USD)VRBO
Orange Blossom Suite - Nightly rental one half block off World Famous Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to sweet paradise! Located at 510 Petronia, the 'Orange Blossom Suite' is in close proximity to all the fun-fill ...
From $185 per night (USD)VRBO
From $414 per night (USD)VRBO
Ocean Breeze @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! ...
From $414 per night (USD)VRBO
From $107 per night (USD)VRBO
Parrots Perch B415: 2 BR, 2 BA Condominium in Key West, Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fabulous top floor ocean-view penthouse condo. Available during the Spring/Summer Season. Enjoy the Ocean-breeze's from ...
From $107 per night (USD)VRBO
From $218 per night (USD)VRBO
**THE MELLOW MACAW** Cozy Condo Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This colorful ...
From $218 per night (USD)VRBO
From $425 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 $425 per night (USD)VRBO
From $103 per night (USD)VRBO
Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We want to let you know that your safety and comfort is our priority. Past reviews have always praised how clean our con ...
From $103 per night (USD)VRBO
From $140 per night (USD)VRBO
PARADISE PLACE - Cozy & Romantic, Pet Friendly Condo, Dipping Pool + Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even ...
From $140 per night (USD)VRBO
From $225 per night (USD)VRBO
Hidden Oasis- Private Cottage 2 Blocks from Duval Street- Shared pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tucked among a colony of free standing Conch style cottages, amidst lush tropical landscaping, sits newly renovated Hidd ...
From $225 per night (USD)VRBO
From $132 per night (USD)VRBO
Old Town Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly redecorated by a one of Key West top interior designers!! Elegant and adorable cottage on one of the nicest lanes ...
From $132 per night (USD)VRBO
From $65 per night (USD)VRBO
The Hollinsed House "Victorian Delights" - Large 1 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $65 per night (USD)VRBO
From $200 per night (USD)VRBO
Architect's Personal Residence, Private Pool, 1 Blk. to Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Completed in 1992, this two bedroom two bath home was designed by a local architect for the relaxed Key West tropical li ...
From $200 per night (USD)VRBO
From $174 per night (USD)VRBO
HANDS DOWN THE BEST DEAL IN KEY WEST
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $174 per night (USD)VRBO
From $163 per night (USD)VRBO
~ MARTHA TRUMAN SUITE ~ Luxury Suite w/ Spacious Sundeck & Plunge Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Book your stay in the Martha Truman Suite, a lovely 1 bed, 1 bath luxury suite located on the 2nd floor of ...
From $163 per night (USD)VRBO
From $230 per night (USD)VRBO
DUVAL SEA TURTLE Desired Rooftop Location, Shared Pool, Overlooks Duval St.
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea ...
From $230 per night (USD)VRBO
From $325 per night (USD)VRBO
Downtown Cottage in Historic District-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the Conch Republic Consul General's Cottage. Historic Cottage Atocha offers 2 private bedrooms, living room with ...
From $325 per night (USD)VRBO
From $310 per night (USD)VRBO
Salacia- Luxury 2/2 Ocean-front condo- Gated Key West Beach Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Imagine enjoying morning coffee, an afternoon cocktail or an evening meal of stone crabs on a spacious and comfy third-f ...
From $310 per night (USD)VRBO
From $225 per night (USD)VRBO
Orchid Suite - Idyllic courtyard and location- Shared pool- Gated compound
- Bedrooms:
- 2.5
- Bathrooms:
- 1
- Sleeps:
- 6
Orchid Suite – Old Town Our fantastic getaway is perfect for the family or couple looking for a quiet location but loc ...
From $225 per night (USD)VRBO
From $110 per night (USD)VRBO
PRICES HAVE NEVER BEEN LOWER!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
SO WHY NOT TURN LEMONS INTO LEMONADE STERILIZED WITH 4 QUAD CLEAN ...
From $110 per night (USD)VRBO
From $150 per night (USD)VRBO
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...
From $150 per night (USD)VRBO
From $130 per night (USD)VRBO
"Tranquility " at Ann Street Gardens Steps from Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $130 per night (USD)VRBO
From $207 per night (USD)VRBO
Craig & Cindy Truman Annex Foundry Townhouses (2 bedrooms 2 1/2 baths)
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $207 per night (USD)VRBO
From $225 per night (USD)VRBO
Sunrise Suite 203-Fun and Relaxation of Resort Living,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suite 203 vacation rental in Key West is a quiet alternative to the bustling noise of downtown Key West. Locate ...
From $225 per night (USD)VRBO
From $140 per night (USD)VRBO
~ COPA CABANA ~ Cute Conch Home w/ Pvt Pool In "Old Town." Live Like A Local!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: Open the door to Key West’s past when you arrive at Copa Cabana, a quaint, 1923 “shotgun” house that was o ...
From $140 per night (USD)VRBO
From $200 per night (USD)VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 2.5
- 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 $200 per night (USD)VRBO
From $225 per night (USD)VRBO
~VISTA FRESCO~ Oceanside condominiums with resort-style amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors ...
From $225 per night (USD)VRBO
From $225 per night (USD)VRBO
Luxurious monthly rental in mid-town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 Day minimum Rental: Tucked away behind a contemporary privacy fence and an attractive cobblestoned driveway is this h ...
From $225 per night (USD)VRBO
From $329 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 $329 per night (USD)VRBO
From $578 per night (USD)VRBO
~ Chick-A-Pea Cottage ~ Breathtaking Home w/ Pool & Parking, 1 Block to Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Chick-A-Pea is a traditional Key West cottage that has undergone a complete renovation. The charm and hist ...
From $578 per night (USD)VRBO
From $265 per night (USD)VRBO
Bonaire Suite- A beautiful Island Retreat- Shared Pool- Gated compound
- Bedrooms:
- 2.5
- Bathrooms:
- 1
- Sleeps:
- 6
Bonaire Suite is bi-level suite with 2 queen beds upstairs separated by a privacy curtain and a queen sofa bed in the li ...
From $265 per night (USD)VRBO
From $275 per night (USD)VRBO
OCEANFRONT ECSTASY - KW Beach Club #304
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy endless views just feet away from the tranquil waters of the Atlantic Ocean. “Beach Club #304” is a serene waterfr ...
From $275 per night (USD)VRBO
From $214 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 $214 per night (USD)VRBO
From $275 per night (USD)VRBO
Positively Poolside - 2 Bedroom 2 1/2 Bath Townhome in Key West Golf Club
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This fantastic 2 bedroom 2 1/2 bath townhome is in a gated community nestled among the fairways and greens of the covete ...
From $275 per night (USD)VRBO
From $85 per night (USD)VRBO
Key Lime Pie Suite at Top Of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)VRBO
From $325 per night (USD)VRBO
Island Hideway Minutes From Higgs Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Higgs Beach Hideaway offers all the amenities for a long term stay in Key West. This tropical home features 3 bedrooms w ...
From $325 per night (USD)VRBO
From $957 per night (USD)VRBO
~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Pool ON DUVAL. Dogs OK!
- Bedrooms:
- 7.5
- Bathrooms:
- 6
- Sleeps:
- 12
THE PROPERTY and BED CONFIGURATIONS: GRAND MAISON (the Main House) is located in the Gallery District right on Duval Str ...
From $957 per night (USD)VRBO
From $325 per night (USD)VRBO
Downtown Cottage just off famous Duval Street-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $325 per night (USD)VRBO
From $520 per night (USD)VRBO
Amelia's Hideaway ~ Hidden Courtyard
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
"In-the-know" travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as th ...
From $520 per night (USD)VRBO
From $484 per night (USD)VRBO
Key West Dreamin' ~ Private Pool Near Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities ...
From $484 per night (USD)VRBO
From $215 per night (USD)VRBO
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Key West Condo, the Key West Cabana. This spacious well appointed 2 bedroom, 2 full bath condo that’s ri ...
From $215 per night (USD)VRBO
From $186 per night (USD)VRBO
Beachfront, Deluxe 3 BR oceanfront condo, great rates
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Oceanfront at Smathers Beach in Beautiful Key West, Florida. Why pay for a hotel, when you can enjoy your own private oa ...
From $186 per night (USD)VRBO
From $165 per night (USD)VRBO
RENOVATED - Conch Get Enough! - Old Town's Truman Annex
- Bedrooms:
- 3.5
- 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 $165 per night (USD)VRBO
From $45 per night (USD)VRBO
Truman Annex unit202-3
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Truman Annex unit202-3 This upstairs unit has beautiful views and offers a private front and back porch. There is a quee ...
From $45 per night (USD)VRBO
From $85 per night (USD)VRBO
Mile Zero Suite at Top Of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)VRBO
From $50 per night (USD)VRBO
Condo 2 br, Ocean view from Balcony, Pets Welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is privately owned and managed. No condo fees. Condo's features one and two bedrooms, with a king bed in the ...
From $50 per night (USD)VRBO
From $250 per night (USD)VRBO
Ole Olivia! 4 bedroom- MONTHLY RENTAL ONLY- Open for Feb and March 2019
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
You will be delighted with this wonderful home with recent renovations, perfectly placed pool, and plenty of outdoor liv ...
From $250 per night (USD)VRBO
From $150 per night (USD)VRBO
South Street Cottage: Bright & sunny in the Casa Marina district
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. ...
From $150 per night (USD)VRBO
From $649 per night (USD)VRBO
Key West Golf Club - Completely Renovated - Tree House Too.
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
You may rely on the accuracy of the calendar that appears on VRBO. Please note we are flexible with dates. It is not re ...
From $649 per night (USD)VRBO
From $260 per night (USD)VRBO
~TROPICAL DREAM~ World Class Luxury Home w/Pool, Roma Spa & Parking. Dogs OK!
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: We guarantee that Tropical Dream will fulfill even the highest expectations. Amazing LUXURY Vacation Home ...
From $260 per night (USD)VRBO
From $356 per night (USD)VRBO
~POTTER'S COTTAGE~ Historic Home w/ Private Heated Pool In Prime Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: Experience hotel-like 5-star luxury but with the exclusive privacy of this adorable Key West home. Potte ...
From $356 per night (USD)VRBO
From $940 per night (USD)VRBO
~ VILLA JOSINE ~ Luxurious "Old Town" Home w/ 18' Heated Pool & Parking!
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Villa Josine is an amazingly beautiful home located in one of the most sought after locations in Key West ...
From $940 per night (USD)VRBO
From $217 per night (USD)VRBO
~ SEAS THE DAY ~ Cute Condo w/ Pool & Private Parking! Walk to Ft Zach Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: Historic Key West Vacation Rentals invites you to enjoy this vacation rental aptly named "Seas the Day!" ...
From $217 per night (USD)VRBO
From $450 per night (USD)VRBO
Three bedroom, two bath with private pool 2 blocks from Duval street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This historic Conch House has been completely redesigned and custom crafted by 2 architects as their home away from home ...
From $450 per night (USD)VRBO
From $425 per night (USD)VRBO
Villa Paradiso: A unique mid-town paradise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This mid-town Key West home is recently refreshed with light colors and beautiful British Colonial furnishings. It featu ...
From $425 per night (USD)VRBO
From $240 per night (USD)VRBO
DUVAL BREEZE Great Location, Walk Everywhere, Overlooks Duval, Rooftop Pool!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and g ...
From $240 per night (USD)VRBO
From $400 per night (USD)VRBO
Top Of Duval - Your Own Private 6 Bedroom Hotel
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $400 per night (USD)VRBO
From $148 per night (USD)VRBO
~ CASABLANCA ~ Fabulous Cottage w/ HEATED Pool, Parking & Tons of Sun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Casablanca is the perfect Key West vacation rental for those seeking a good time, but who would like to st ...
From $148 per night (USD)VRBO
From $110 per night (USD)VRBO
Turn lemons into lemonade Jan. Feb. & March. Prices lowest ever!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
STERILIZED WITH 4 QUAD CLEANING SYSTEM ...
From $110 per night (USD)VRBO
From $240 per night (USD)VRBO
~STEAMPLANT 207~ Luxury 3-Story Condo w/ Pvt Rooftop Pool & Amazing Views!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Steamplant 207! Two Level, 5 Star Luxury Residence Breathtaking panoramic views of Key West. * Private Ro ...
From $240 per night (USD)VRBO
From $200 per night (USD)VRBO
One bedroom, two bath, sleeps 2 - Monthly Rental- AVAILABLE FOR JANUARY
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This cozy and comfortable home will transition you from the hustle and bustle of your everyday life to the relaxing hist ...
From $200 per night (USD)VRBO
From $450 per night (USD)VRBO
The Caroline House Estate
- Bedrooms:
- 4.5
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $450 per night (USD)VRBO
From $150 per night (USD)VRBO
Majestic Escape near Duval! Pool, wifi, renovated 2/2 1/2, private courtyard.
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This prope ...
From $150 per night (USD)VRBO
From $55 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 $55 per night (USD)VRBO
From $500 per night (USD)VRBO
Casa Loca- One of a kind estate 1/2 block from Duval in Old Town Key West
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Loca ---Experience the uniqueness of Key West by staying at one of Key West Hideaways one of a kind vacation rent ...
From $500 per night (USD)VRBO
From $150 per night (USD)VRBO
Luxurious Key West Pool Home block from Duval & completely remodeled in 2017!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Old Town refuge barely a block from world famous Duval Street with glimpse of Key West Light House! Located in the Histo ...
From $150 per night (USD)VRBO
From $450 per night (USD)VRBO
Conch Republlic Cottage - Nightly Group Rental Unit - Sleeps up to 10 off Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This nightly group rental consists of 3 separate units, Porchside Paradise, Orange Blossom Suite and Deckside Suite. Co ...
From $450 per night (USD)VRBO
From $260 per night (USD)VRBO
La Casa del Luces- Steps from the Beach and Duval - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
La Casa de Luces - Come to relax or to play while enjoying the spectacular sunsets and the blue waters of Key West! This ...
From $260 per night (USD)VRBO
From $322 per night (USD)VRBO
~ POINCIANA PARADISE ~ Historic Home w/ Hot Tub & Parking for 2 Near Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: The Poinciana Paradise vacation rentals are located on a tiny lane in 'Old Town' Key West. This two stor ...
From $322 per night (USD)VRBO
From $150 per night (USD)VRBO
KEY WEST CHARMING Lounge on the Patio or Shared Pool, Walk to Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home ...
From $150 per night (USD)VRBO
From $85 per night (USD)VRBO
Club Cuba Suite at Top of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)VRBO
From $450 per night (USD)VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 4.5
- 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 $450 per night (USD)VRBO
From $159 per night (USD)VRBO
~ MY HAPPY PLACE ~ Tropical Home w/ Private Pool In Heart of 'Old Town' KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: My Happy Place is an exemplary renovation of an historic, Key West house. It retains its original charact ...
From $159 per night (USD)VRBO
From $380 per night (USD)VRBO
Havana Lane: An updated classic conch cottage with still a rustic edge!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming conch cottage has gone through some wonderful changes in 2019! Enter the private courtyard of the home, t ...
From $380 per night (USD)VRBO