Key West Rentals
From $200 per night (USD)HomeAway
Old Town Key West - Historic & Charming - 2 Blks From Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
A few words about the 'damn'pandemic… The health and safety of our guests and employees is our top priority. Our homes ...
From $200 per night (USD)HomeAway
From $327 per night (USD)VRBO
**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $327 per night (USD)VRBO
From $545 per night (USD)HomeAway
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $545 per night (USD)HomeAway
From $257 per night (USD)VRBO
Green Bamboo @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Paradise! This 2 bedroom townhouse, one bedroom is a king and the second bedroom features twin beds which can ...
From $257 per night (USD)VRBO
From $300 per night (USD)HomeAway
2 bdrm Condo w/ boat slip Pelican Landing Bermuda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $300 per night (USD)HomeAway
From $155 per night (USD)VRBO
TRANQUILITY - Meadows Monthly Vacation Rental - Private Pool - 3BDR/3BA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME TO TRANQUILITY! We are complying with the directives listed on the Monroe County website. Please be aware tha ...
From $155 per night (USD)VRBO
From $200 per night (USD)HomeAway
Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We understand that these are unprecedented times and no one knows what tomorrow will bring. Key West has mandated facial ...
From $200 per night (USD)HomeAway
From $138 per night (USD)VRBO
GOLF VILLA - Monthly Vacation Rental - 2BD/2BA -Community Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO GOLF VILLA! We are complying with the directives listed on the Monroe County website. Please be aware t ...
From $138 per night (USD)VRBO
From $291 per night (USD)HomeAway
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $291 per night (USD)HomeAway
From $531 per night (USD)VRBO
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $531 per night (USD)VRBO
From $550 per night (USD)HomeAway
**COASTAL CABANA @ LOVE LANE** Cul-de-Sac Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $550 per night (USD)HomeAway
From $45 per night (USD)VRBO
Superb Location, Affordably Priced
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key ...
From $45 per night (USD)VRBO
From $184 per night (USD)HomeAway
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $184 per night (USD)HomeAway
From $240 per night (USD)VRBO
@@ Winter Specials Enchanting garden view on the Ocean Great Rates @@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1st floor garden-view unit, King in the master bedroom, A double and a single in the guest bedroom and a queen sleeper ...
From $240 per night (USD)VRBO
From $50 per night (USD)HomeAway
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
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)HomeAway
From $207 per night (USD)VRBO
PERFECTION IN OLD TOWN!! Tropical Angler @ 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 $207 per night (USD)VRBO
From $240 per night (USD)HomeAway
Great Summer Rates! Charming home in Old Town!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise on Pine, a monthly rental, is a picture perfect home that sits high above this lovely one way street with an i ...
From $240 per night (USD)HomeAway
From $300 per night (USD)VRBO
Special Rates For Both Weekly And Monthly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Foundry are Bostonian style, 3 level townhouses that have been refurbished with tropical flair. Vaulted ceilings gre ...
From $300 per night (USD)VRBO
From $218 per night (USD)HomeAway
**SOUTHERNMOST VISTAS @ OLD TOWN** Stunning Views & Pool + LAST KEY SERVICES..
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $218 per night (USD)HomeAway
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 booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $174 per night (USD)VRBO
From $251 per night (USD)HomeAway
**VILLA MODERNA @ CASA MARINA** Sleek Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $251 per night (USD)HomeAway
From $300 per night (USD)VRBO
NEW UNIT!!! GORGEOUS!! Island Oasis @ Truman Annex
- 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 $300 per night (USD)VRBO
From $405 per night (USD)HomeAway
Tiki BeachToo! Super low rates until Jan19th.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tiki Beach Too is a Newly Renovated, 2 bedroom/2bathroom, charming town home in enchanting Truman Annex, in the heart of ...
From $405 per night (USD)HomeAway
From $150 per night (USD)VRBO
28 night minimum stay. 3 Bedroom House with a pool in Meadows
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key We ...
From $150 per night (USD)VRBO
From $104 per night (USD)HomeAway
**COCONUT** Old Town! Adorable!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $104 per night (USD)HomeAway
From $218 per night (USD)VRBO
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $218 per night (USD)VRBO
From $218 per night (USD)HomeAway
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $218 per night (USD)HomeAway
From $382 per night (USD)VRBO
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $382 per night (USD)VRBO
From $214 per night (USD)HomeAway
Shipyard 106-2 1 Bedroom newly renovated Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit ...
From $214 per night (USD)HomeAway
From $507 per night (USD)VRBO
"LADY ADMIRAL" ~ Sweet cottage & guest house with private pool off Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 8
A SWEET SURPRISE JUST OFF DUVAL... Private single family home with off street parking totaling three bedrooms, two and h ...
From $507 per night (USD)VRBO
From $763 per night (USD)HomeAway
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $763 per night (USD)HomeAway
From $273 per night (USD)VRBO
**2 COOL FISH @ THE ANNEX** Chic Villa + Pool + LAST KEY SERVICES…
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $273 per night (USD)VRBO
From $207 per night (USD)HomeAway
Manatee @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
'Manatee' is a beautiful two bedroom, one bath, 1st floor condominium located within the prestigious gated community of ...
From $207 per night (USD)HomeAway
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 $571 per night (USD)HomeAway
PRIVATE! SPACIOUS! SPECIAL MONTHLY RATES!
- Bedrooms:
- 2
- 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)HomeAway
From $171 per night (USD)VRBO
GREAT DEAL!! Blue Ocean @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $171 per night (USD)VRBO
From $170 per night (USD)HomeAway
**SUZY'S PARROT PERCH @ OLD TOWN** Cozy 2nd Floor Condo + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $170 per night (USD)HomeAway
From $300 per night (USD)VRBO
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $300 per night (USD)VRBO
From $1363 per night (USD)HomeAway
**AVALYNN HOUSE @ THE ANNEX** Lush Home by Beach & Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $1363 per night (USD)HomeAway
From $236 per night (USD)VRBO
Gracie Bay's Hideaway @ The Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Thank you for considering Gracie Bay’s Hideaway for your escape to the tropical paradise of Key West. Here you will enjo ...
From $236 per night (USD)VRBO
From $117 per night (USD)HomeAway
30 night Minimum Stay Heart of Historic downtown 214 2 bed 2 1/2 Bath
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps ...
From $117 per night (USD)HomeAway
From $281 per night (USD)VRBO
**CAYO CALYPSO @ HIGGS BEACH** Modern Home / Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $281 per night (USD)VRBO
From $279 per night (USD)HomeAway
Archipelago l @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $279 per night (USD)HomeAway
From $300 per night (USD)VRBO
Casa Colonial Island Luxury Historic Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Beautiful Casa Colonial is a luxury island residence in the heart of the historic district with a wonderful island desig ...
From $300 per night (USD)VRBO
From $395 per night (USD)HomeAway
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunday to Sunday WEEK available to book. Limited Boat Slip available onsite. Must be reserved in advance after reserva ...
From $395 per night (USD)HomeAway
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)HomeAway
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)HomeAway
From $449 per night (USD)VRBO
Down Island Digs ~ Downtown with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the m ...
From $449 per night (USD)VRBO
From $700 per night (USD)HomeAway
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)HomeAway
From $198 per night (USD)VRBO
~ BOHEMIAN HOUSE ~ Newly Renovated "Old Town" Home w/ Pvt Pool. Pets OK!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: The Bohemian House is a restored historic home full of delightful surprises! This home is placed ...
From $198 per night (USD)VRBO
From $325 per night (USD)HomeAway
200 feet from Duval Street, but quiet and secluded
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Villas is a small, historic property located 200 feet from Duval Street. This is gorgeous two bedroom, two bat ...
From $325 per night (USD)HomeAway
From $409 per night (USD)VRBO
30% OFF May 2021 28 nts PRKING FREE Ft Zach BCH PASS/ COMM POOL
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
SALE 30% OFF MAY 2021..& 25% off other months of your choice in 2021- I will deduct from price quoted. Old Town -Whitehe ...
From $409 per night (USD)VRBO
From $100 per night (USD)HomeAway
Beautifully restored 2 bed apartment in historic Old Town neighborhood.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located on one of the best streets in Old Town you are just three blocks from the Harbor….home to the freshest seafood r ...
From $100 per night (USD)HomeAway
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 $200 per night (USD)HomeAway
Beautiful Key West Townhome
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come on in, relax and enjoy our wonderful slice of paradise. Over 2,000 square feet of luxurious living space. Our two b ...
From $200 per night (USD)HomeAway
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 $209 per night (USD)HomeAway
PARADISE IN OLD TOWN!!!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to a beautiful house, hidden paradise, you never knew existed. Once you're entered into this hideaway, you'll ne ...
From $209 per night (USD)HomeAway
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)HomeAway
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)HomeAway
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 $207 per night (USD)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
From $325 per night (USD)VRBO
Classic Pet-friendly 3/2 in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming conch home is uniquely located on a corner property across the street from The Studios of Key West, in the ...
From $325 per night (USD)VRBO
From $125 per night (USD)HomeAway
"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)HomeAway
From $100 per night (USD)VRBO
Studio overlooking historic Key West waterfront.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathr ...
From $100 per night (USD)VRBO
From $284 per night (USD)HomeAway
SPECIAL PRICING MARCH 2021 "OCEAN FRONT! 90 FT BALCONY-Clean-Safe
- 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)HomeAway
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 $343 per night (USD)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
Beauty on the Green at the Key West Golf Club
- Bedrooms:
- 2
- 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)HomeAway
From $414 per night (USD)VRBO
Ocean Breeze @ the Truman Annex
- Bedrooms:
- 2
- 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 $85 per night (USD)HomeAway
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)HomeAway
From $949 per night (USD)VRBO
The Meeting Point- Key West
- Bedrooms:
- 11
- Bathrooms:
- 11
- Sleeps:
- 22
The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. ...
From $949 per night (USD)VRBO
From $80 per night (USD)HomeAway
A Palm Tree Paradise @ the Key West Golf Club
- Bedrooms:
- 2
- 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)HomeAway
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 $107 per night (USD)HomeAway
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)HomeAway
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 booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $218 per night (USD)VRBO
From $225 per night (USD)HomeAway
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)HomeAway
From $80 per night (USD)VRBO
Atlantis House's Master Suite... voted top 25 in USA - Steps from beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Atlantis House the most private and unique Guesthouse in Key West with only 2 rooms, private entrances and se ...
From $80 per night (USD)VRBO
From $400 per night (USD)HomeAway
Beautifully Restored Conch Cottage with private pool- OPEN FOR JANUARY!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Blue Sun is a charming three bedroom conch cottage that has been completely renovated by a professional interior designe ...
From $400 per night (USD)HomeAway
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)HomeAway
BEST DEAL IN THE KEYS!
- 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)HomeAway
From $163 per night (USD)VRBO
~ MARTHA TRUMAN SUITE ~ Luxury Suite w/ Spacious Sundeck & Plunge Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
About THE PROPERTY: Book your stay in the Martha Truman Suite, a lovely Key West one-bedroom vacation rental. The Mart ...
From $163 per night (USD)VRBO
From $325 per night (USD)HomeAway
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 bedrooms, living room with orginia ...
From $325 per night (USD)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
"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)HomeAway
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 $1000 per night (USD)HomeAway
Private Home with Sun-filled Pool-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Backyard pool offers lots of sunshine. This home sits in Key Lime Grove Subdivision which I was born and raised in. It ...
From $1000 per night (USD)HomeAway
From $325 per night (USD)VRBO
Caribbean Cottage- Duval St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian s ...
From $325 per night (USD)VRBO
From $140 per night (USD)HomeAway
~ COPA CABANA ~ Cute Conch Home w/ Pvt Pool In "Old Town." Live Like A Local!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Open the door to Key West’s past when you arrive at Copa Cabana, a quaint, 1923 “shotgun” house th ...
From $140 per night (USD)HomeAway
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 $1000 per night (USD)HomeAway
Luxury rental with heated private pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a Beautiful tropical oasis with a heated private pool. You will have two beach cruisers to use during your stay ...
From $1000 per night (USD)HomeAway
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)HomeAway
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)HomeAway
From $579 per night (USD)VRBO
Key West Wabi Sabi ~ Authentic Key West Cottage
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island livi ...
From $579 per night (USD)VRBO
From $315 per night (USD)HomeAway
Island Dream House one block from the Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This charming historic Conch cottage is located on a quaint lane between Eaton and Caroline Streets one block from the h ...
From $315 per night (USD)HomeAway
From $1389 per night (USD)VRBO
4Br/4.5Ba Historic Home With Pool In Old Town
- Bedrooms:
- 5.5
- Bathrooms:
- 3
- Sleeps:
- 10
This historic seasonal rental with its cypress siding was built circa 1886. Your hosts, who have spent a considerable pa ...
From $1389 per night (USD)VRBO
From $240 per night (USD)HomeAway
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)HomeAway
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 $75 per night (USD)HomeAway
All inclusive sailing charter .70 foot catamaran
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
A large sailboat capable of all types of entertainment. Large bedrooms and the largest bathrooms I have seen on this siz ...
From $75 per night (USD)HomeAway
From $148 per night (USD)VRBO
~ CASABLANCA ~ Fabulous Cottage w/ HEATED Pool, Parking & Tons of Sun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
About THE PROPERTY: Casablanca is the perfect Key West vacation rental for those seeking a good time, but who would li ...
From $148 per night (USD)VRBO
From $110 per night (USD)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
From $379 per night (USD)VRBO
PRIVATE HOME IN OLD TOWN - 3BR & 3.5 BATHS
- Bedrooms:
- 5.5
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect location just off Duval Street. A block and a half away from all the action of Duval; restaurants, shopping and ...
From $379 per night (USD)VRBO
From $140 per night (USD)HomeAway
~ LOLA'S PLACE ~ Stunning Home w/Pool, parking in the <3 of Key West. Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Lola's Place features everything you might want or need for your monthly vacation in Key West, sta ...
From $140 per night (USD)HomeAway
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
About THE PROPERTY: Chick-A-Pea is a traditional Key West cottage that has undergone a complete renovation. The charm ...
From $578 per night (USD)VRBO
From $265 per night (USD)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Pool ON DUVAL. Dogs OK!
- Bedrooms:
- 7.5
- Bathrooms:
- 6
- Sleeps:
- 12
About THE PROPERTY and BED CONFIGURATIONS: GRAND MAISON (the Main House) is located in the Gallery District right on Du ...
From $957 per night (USD)HomeAway
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 $329 per night (USD)HomeAway
"Casa Catalina" Private Home In Old Town- Pool- Steps From Duval Street-Updat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Classic Conch house with all of the historic feel and all of the modern conveniences. Larger than most cigar maker’s co ...
From $329 per night (USD)HomeAway
From $300 per night (USD)VRBO
By the Beautiful Sea
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy ...
From $300 per night (USD)VRBO
From $484 per night (USD)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
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)HomeAway
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
About THE PROPERTY: We guarantee that Tropical Dream will fulfill even the highest expectations. Amazing LUXURY Vacati ...
From $260 per night (USD)VRBO
From $1000 per night (USD)HomeAway
Stone Throw Famous Duval Street Location-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
House is located just steps from famous Dvual Street. Duval Street stretches from the Atlantic Ocean to the Gulf of Mexi ...
From $1000 per night (USD)HomeAway
From $356 per night (USD)VRBO
~POTTER'S COTTAGE~ Historic Home w/ Private Heated Pool In Prime Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Experience hotel-like 5-star luxury but with the exclusive privacy of this adorable Key West home. ...
From $356 per night (USD)VRBO
From $940 per night (USD)HomeAway
~ VILLA JOSINE ~ Luxurious "Old Town" Home w/ 18'Heated Pool & Parking!
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 8
About THE PROPERTY: Villa Josine is an amazingly beautiful home located in one of the most sought after locations in ...
From $940 per night (USD)HomeAway
From $371 per night (USD)VRBO
Hyatt Beach House- 2 Bedroom Located On The Gulf With Private White Sand Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This villa is for seven night rentals with check-in and check-out on Fridays, Saturdays and Sundays ONLY! Great destin ...
From $371 per night (USD)VRBO
From $217 per night (USD)HomeAway
~ SEAS THE DAY ~ Cute Condo w/ Pool & Private Parking! Walk to Ft Zach Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Historic Key West Vacation Rentals invites you to enjoy this vacation rental aptly named "Seas the ...
From $217 per night (USD)HomeAway
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 $85 per night (USD)HomeAway
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)HomeAway
From $59 per night (USD)VRBO
Dec 19- 26 2020 Only - Oceanfront Key West Condo - Quiet and away from crowds
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our unit at Coconut Beach Resort Note: This is available for the dates Saturday 12/19/20 to Saturday 12/26/ ...
From $59 per night (USD)VRBO
From $240 per night (USD)HomeAway
~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)HomeAway
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 $329 per night (USD)HomeAway
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 $329 per night (USD)HomeAway
From $100 per night (USD)VRBO
Lennon's Lodge-2 BR Luxury Cottage w/Private 6 person Spa, 2 Heated Pools!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Part of 4 exclusive units at Abbey Road in a private, gated compound just off Duval Street The original Cuban tile has ...
From $100 per night (USD)VRBO
From $126 per night (USD)HomeAway
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 a natural water sa ...
From $126 per night (USD)HomeAway
From $130 per night (USD)VRBO
Namaste 'the spirit within me salutes the spirit within you'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $130 per night (USD)VRBO
From $250 per night (USD)HomeAway
Bottom's Up Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfection in the Meadows awaits you in a pristine Florida Bungalow. This two bedroom, two bathroom home offers all the ...
From $250 per night (USD)HomeAway
From $350 per night (USD)VRBO
Duval Square Courtyard Condo is just steps from the action
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includ ...
From $350 per night (USD)VRBO
From $275 per night (USD)HomeAway
Beach Club #103 - Unique oceanfront living with breathtaking views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $275 per night (USD)HomeAway
From $414 per night (USD)VRBO
Key West Oasis, Seperate Cottage, Very Private Pool & Back Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $414 per night (USD)VRBO
From $178 per night (USD)HomeAway
Key West home w/shared pool and just steps from historic Old Town
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
Bright Key West Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $178 per night (USD)HomeAway
From $315 per night (USD)VRBO
~FAIR WINDS @ THE FOUNDRY~ Updated Townhome w/ Pool, Close To Ft Zach Beach!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
About THE PROPERTY: Fair Winds at the Foundry is a gorgeous coastal 3 story, 2 bedroom, 2.5 bath immaculate light and ...
From $315 per night (USD)VRBO
From $150 per night (USD)HomeAway
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)HomeAway
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 $150 per night (USD)HomeAway
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)HomeAway
From $125 per night (USD)VRBO
Historic District-Pool View-Beach Nearby-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom, fully furnished condominium is located in the Truman Annex, a gated community of private homes and condo ...
From $125 per night (USD)VRBO
From $260 per night (USD)HomeAway
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)HomeAway
From $322 per night (USD)VRBO
~ POINCIANA PARADISE ~ Historic Home w/ Hot Tub & Parking for 2 Near Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About THE PROPERTY: The Poinciana Paradise vacation rentals are located on a tiny lane in 'Old Town' Key West. This ...
From $322 per night (USD)VRBO
From $150 per night (USD)HomeAway
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)HomeAway
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 $425 per night (USD)HomeAway
Pete's Cottages: Twin Cypress cottages steps from Duval
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypre ...
From $425 per night (USD)HomeAway
From $182 per night (USD)VRBO
THOMPSON'S COURT - Mid Town Getaway with pool & jacuzzi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-styl ...
From $182 per night (USD)VRBO
From $125 per night (USD)HomeAway
Key West Coop - our tropical oasis in the Historic District close to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully remodeled Cottage in the Historic District of Key West. Walk or ride your bike to anywhere on the island. ...
From $125 per night (USD)HomeAway
From $234 per night (USD)VRBO
Key West: 3 BR, 2 BA Luxury Yacht; Special Now!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Upscale 'Keys Yacht Vacation'! 3 bedroom, 2 bath beautiful yacht. Currently located in one of the nicest marinas in all ...
From $234 per night (USD)VRBO
From $75 per night (USD)HomeAway
Harbour Place 115 in Truman Annex Key West
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Harbor Place is one of the most prestigious properties in Key West! This unit offers breath taking water views overlook ...
From $75 per night (USD)HomeAway
From $230 per night (USD)VRBO
Pete's West Cottage steps from Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypre ...
From $230 per night (USD)VRBO
From $365 per night (USD)HomeAway
Downtown Location in Historic District-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $365 per night (USD)HomeAway
From $179 per night (USD)VRBO
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 1
- 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 $179 per night (USD)VRBO
From $170 per night (USD)HomeAway
~ SEA VISTA ~ On the Gulf w/private DOCK, Pet Friendly, Pvt Pool & Parking
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 7
About THE PROPERTY: Just steps away from putting your toes in the ocean... Ever dream of waking up, walking out your ...
From $170 per night (USD)HomeAway
From $375 per night (USD)VRBO
Penthouse on Duval Street
- Bedrooms:
- 7
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly staged in the island’s city center, this spectacular downtown Key West rental received a major upscale renovat ...
From $375 per night (USD)VRBO
From $742 per night (USD)HomeAway
~ GRAND MAISON ~ Amazing Home On Duval w/ Heated Pool & Off Street Parking
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Grand Maison on Duval is located in the Gallery District right on Duval Street near the Southernmost Point ...
From $742 per night (USD)HomeAway
From $180 per night (USD)VRBO
LINGER LONGER Private Home, Steps to Pool, Family Friendly, Walk to Duval!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Just imagine stepping out of the rental and stepping right into the pool! Enjoy a carefree vacation in this beautifully ...
From $180 per night (USD)VRBO