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From $90 per night (USD)
VRBO
Bayview House Apt 2
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 $207 per night (USD)
VRBO
A Sunset View
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
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 $250 per night (USD)
VRBO
"MOJITO DREAMIN"~Coastal Flair!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
WELL MANICURED COMMUNITY, SHORT DISTANCE FROM KEY WEST… Enjoy this modern, coastal inspired townhome that reflects the l ...
From $250 per night (USD)
VRBO
From $288 per night (USD)
VRBO
Frost Free at 1800 Atlantic Cayo Hueso C439
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1800 Atlantic Condominiums Unit C439 Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, two bath pent ...
From $288 per night (USD)
VRBO
From $395 per night (USD)
VRBO
"MANGO MARGARITA"~ Hideaway!
Bedrooms:
3.5
Bathrooms:
2
Sleeps:
6
LOCATION... Enjoy this convenient Old Town Location. Located a block from Duval and a short walk or bike ride to everyt ...
From $395 per night (USD)
VRBO
From $480 per night (USD)
VRBO
SEAPORT SUNSETS at Galleon Resort in Old Town (Beach-Pool-BBQ)
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING VIEWS OF KEY WEST HARBOR, SUNSET KE ...
From $480 per night (USD)
VRBO
From $749 per night (USD)
VRBO
Captain's Daughter
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $749 per night (USD)
VRBO
From $321 per night (USD)
VRBO
Paris Mango
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy's "Last Mango in P ...
From $321 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Seaside Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $250 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Tropical Paradise Key West A113
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated ...
From $240 per night (USD)
VRBO
From $500 per night (USD)
VRBO
Pelican Landing St. Thomas Penthouse
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $500 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Jungle Breeze
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Jungle Breeze condo at LaBrisa Condominiums. *Ocean View *Free WiFi * Free Covered Parking * Final cleaning included ...
From $168 per night (USD)
VRBO
From $1445 per night (USD)
VRBO
"BLUE ROOSTER" ~ Paradise!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
OLD TOWN PARADISE.... Paradise awaits in a quiet Old Town location. This four bedroom home is set on a cozy lane that i ...
From $1445 per night (USD)
VRBO
From $207 per night (USD)
VRBO
Island Time @ 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 $240 per night (USD)
VRBO
Octopus's Garden
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! OCTOPUS'S GAR ...
From $240 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Nautical Wheeler
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $250 per night (USD)
VRBO
From $207 per night (USD)
VRBO
Aqua Oasis
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 $100 per night (USD)
VRBO
Splish Splash
Bedrooms:
2.5
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This jewel-li ...
From $100 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Heavenly Hideaway
Bedrooms:
2.5
Bathrooms:
3
Sleeps:
6
HEAVENLY HIDEAWAY! We are complying with the directives listed on the Monroe County website. Please be aware that info ...
From $205 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Key West Beach Luxury Rental
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all thr ...
From $319 per night (USD)
VRBO
Click For Pricing
VRBO
Key West Suites Hotel #205
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...
Click For Pricing
VRBO
From $550 per night (USD)
VRBO
"ISLAND TIME" ~ Conch Charm!
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
EASE INTO ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pas ...
From $550 per night (USD)
VRBO
From $288 per night (USD)
VRBO
Bimini Key West Penthouse C424
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic 1800 Atlantic Penthouse in the highly desirable East building of the facility Brand new living room furniture ...
From $288 per night (USD)
VRBO
From $171 per night (USD)
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Marlin Blue
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Trum ...
From $171 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Ocean Hideaway on the Atlantic A206
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Where the Ocean Meets the Windswept is nothing like . You don't have to spend a fortune to enjoy a spacious, clean and ...
From $270 per night (USD)
VRBO
From $279 per night (USD)
VRBO
A Sunrise Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool an ...
From $279 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Darling of Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Don't miss an ...
From $409 per night (USD)
VRBO
From $140 per night (USD)
VRBO
Susan's Key West Condo
Bedrooms:
1
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 $140 per night (USD)
VRBO
From $394 per night (USD)
VRBO
Swept Away
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SWEPT AWAY is ...
From $394 per night (USD)
VRBO
From $599 per night (USD)
VRBO
Seafarer's Refuge
Bedrooms:
4.5
Bathrooms:
4
Sleeps:
10
"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...
From $599 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Anchor Drop Key West A307
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the mast ...
From $300 per night (USD)
VRBO
From $195 per night (USD)
VRBO
Bohemian Rhapsody
Bedrooms:
4.5
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! You might ask ...
From $195 per night (USD)
VRBO
From $1522 per night (USD)
VRBO
Summer Solstice
Bedrooms:
10.5
Bathrooms:
9
Sleeps:
22
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! In Key West, ...
From $1522 per night (USD)
VRBO
From $683 per night (USD)
VRBO
Maison Tropicale
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Imagine a tra ...
From $683 per night (USD)
VRBO
From $495 per night (USD)
VRBO
"CAPTAIN'S QUARTERS" ~ A Gem!
Bedrooms:
3.5
Bathrooms:
4
Sleeps:
10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...
From $495 per night (USD)
VRBO
From $524 per night (USD)
VRBO
Island Chic
Bedrooms:
4.5
Bathrooms:
3
Sleeps:
8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $524 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Galleon Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $393 per night (USD)
VRBO
From $223 per night (USD)
VRBO
Sunset Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SUNSET POINT ...
From $223 per night (USD)
VRBO
From $309 per night (USD)
VRBO
STUDIO ROYALE - Welcome Pets
Bedrooms:
1
Bathrooms:
0
Sleeps:
2
Welcome to charming Studio Royale, a monthly Vacation Rental located in quirky Old Town Key West. Heated in ground pool. ...
From $309 per night (USD)
VRBO
From $125 per night (USD)
VRBO
My Florida Escape
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...
From $125 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Follow the Sun
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! FOLLOW THE SU ...
From $218 per night (USD)
VRBO
From $981 per night (USD)
VRBO
Southernmost Hospitality VII
Bedrooms:
8.5
Bathrooms:
7
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SOUTHERNMOST ...
From $981 per night (USD)
VRBO
Click For Pricing
VRBO
Villa Mer at Shipyard Condominiums
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax at Villa Mer in luxurious surroundings. Renovated in 2019 it has a fully equipped kitchen with bar seating. The li ...
Click For Pricing
VRBO
From $240 per night (USD)
VRBO
Paradise Found Cayo Hueso A111
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 Bedroom Garden-View Condo at 1800 Atlantic Key West with king in the Master bedroom, queen in the guest bedroom and a ...
From $240 per night (USD)
VRBO
From $90 per night (USD)
VRBO
Bayview House Apt 1
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 $243 per night (USD)
VRBO
Coconut Beach Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE READ CAREFULLY BEFORE YOU EMAIL OWNER This is a Timeshare and I only own 1 week. This rental is for a FULL WEEK ...
From $243 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Layover In Paradise
Bedrooms:
4.5
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! A home design ...
From $218 per night (USD)
VRBO
From $250 per night (USD)
VRBO
"THE OLD SAPODILLA HOUSE"~Peaceful!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
PERFECT GETAWAY JUST STEPS FROM DUVAL... Private family home with poolside cottage totals three bedrooms and three full ...
From $250 per night (USD)
VRBO
From $374 per night (USD)
VRBO
Key West's Crown Jewel
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We know that you will enjoy staying in this little piece of this island Paradise - Key West's Crown Jewel. This is a tw ...
From $374 per night (USD)
VRBO
From $357 per night (USD)
VRBO
Southern Comfort
Bedrooms:
4.5
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $357 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Turtle Cay Island Delight C327
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fabulous 2 bedroom island view condominium, fully equipped unit. Full kitchen and washer dryer. There is a king in the m ...
From $240 per night (USD)
VRBO
Click For Pricing
VRBO
**True Love Key West**
Bedrooms:
6
Bathrooms:
3
Sleeps:
8
**28-NIGHT MINIMUM PER CITY OF KEY WEST ORDINANCES** Fall in love with Key West while staying in our newly remodeled, g ...
Click For Pricing
VRBO
From $378 per night (USD)
VRBO
Jasmine Place
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
WELCOME TO JASMINE PLACE! We are complying with the directives listed on the Monroe County website. Please be aware th ...
From $378 per night (USD)
VRBO
From $500 per night (USD)
VRBO
"ORCHID ESCAPE"~ Historic!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
CLASSIC OLD KEY WEST HOME... This home is boasting a rare combination of location and character. A mix of historic detai ...
From $500 per night (USD)
VRBO
From $83 per night (USD)
VRBO
It's A Salt Life After All
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom 2 bath town-home is just what you are looking for. *****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONL ...
From $83 per night (USD)
VRBO
From $215 per night (USD)
VRBO
Key West Sailing Adventure
Bedrooms:
2.5
Bathrooms:
2
Sleeps:
4
Hurry book last minute summer vacation dates that just opened up now! This 37 foot boat is available Key West! This is ...
From $215 per night (USD)
VRBO
Click For Pricing
VRBO
SEAPORT PANORAMA at Galleon Resort, Key West, FL (Beach-Pool-BBQ)
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...
Click For Pricing
VRBO
From $168 per night (USD)
VRBO
Nassau Suite Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...
From $168 per night (USD)
VRBO
From $100 per night (USD)
VRBO
Sea Breeze Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the beautiful Truman Annex. Get ready ...
From $100 per night (USD)
VRBO
From $171 per night (USD)
VRBO
Annie's Hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This charming one bedroom, one bath 2nd floor property features an Olympic queen in the master bedroom and a large cover ...
From $171 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Pelican Landing Flamingo Retreat
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)
VRBO
From $240 per night (USD)
VRBO
Tranquility by the Beach C129
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 $240 per night (USD)
VRBO
From $500 per night (USD)
VRBO
Cigar Makers Tropical Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Your tropical oasis in Historic Old Town Key West awaits for your monthly rental! 1890 Cigar Maker's Tropical Cottage re ...
From $500 per night (USD)
VRBO
From $245 per night (USD)
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"THE QUARTERDECK" ~ Vibrant!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
COMFORT AND VALUE IN TRUMAN ANNEX… This newly renovated two bedroom condo is located in The Shipyard, a neighborhood of ...
From $245 per night (USD)
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From $335 per night (USD)
VRBO
@@ Sunrise on the Atlantic @@
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic 3rd floor ocean-view condominium. Unit features a full size fully equipped kitchen. Washer dryer. King in the ...
From $335 per night (USD)
VRBO
From $288 per night (USD)
VRBO
Hemingways Atlantic Retreat C339
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master b ...
From $288 per night (USD)
VRBO
From $240 per night (USD)
VRBO
High Tide at Key West 1800 Atlantic Condos
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a gr ...
From $240 per night (USD)
VRBO
From $125 per night (USD)
VRBO
Luxury Island Gem A109
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Garden View. 2 bedroom 2 full bathrooms, sleeps a max of 6. Luxurious tropical courtyard view two bedroom condo. This e ...
From $125 per night (USD)
VRBO
From $273 per night (USD)
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Puerta Coralina
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This precious ...
From $273 per night (USD)
VRBO
Click For Pricing
VRBO
Old Town Charm Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming Old Town cottage is a short walk to Duval Street nightlife, restaurants, shops and culture… and a walk or ...
Click For Pricing
VRBO
From $225 per night (USD)
VRBO
Beautiful Downtown Truman Annex Condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilt ...
From $225 per night (USD)
VRBO
From $79 per night (USD)
VRBO
Villa Fleur at Shipyard Condominiums
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and d ...
From $79 per night (USD)
VRBO
From $193 per night (USD)
VRBO
"IN GOOD SPIRITS" ~ It's a Deal!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duva ...
From $193 per night (USD)
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From $274 per night (USD)
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Magic Ocean Penthouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Ocean views from every room with floor to ceiling wind ...
From $274 per night (USD)
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From $202 per night (USD)
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Blue Heron's Cove
Bedrooms:
3.5
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! BLUE HERON'S ...
From $202 per night (USD)
VRBO
From $207 per night (USD)
VRBO
Another Three Hour Tour
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 $134 per night (USD)
VRBO
Atlantic Docks Paradise C433
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1800 Atlantic Condominiums Unit C433 2 Bedroom 2 full baths Elegant sophistication abound in this fabulous 2 bedroom 2 ...
From $134 per night (USD)
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From $599 per night (USD)
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Bayview Retreat
Bedrooms:
5.5
Bathrooms:
4
Sleeps:
10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $599 per night (USD)
VRBO
From $496 per night (USD)
VRBO
Seventh Heaven
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! As if a vacat ...
From $496 per night (USD)
VRBO
From $1195 per night (USD)
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"THE SEASHELL" ~ Spectacular!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
CLASSIC KEY WEST.... When only the best will do! The Seashell is the classic Old Town Key West home. Perfect setting for ...
From $1195 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Bird of Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Like witnessi ...
From $168 per night (USD)
VRBO
From $517 per night (USD)
VRBO
A Key West Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Fully furnished cottage home in the heart of old town key west. This place is perfect for a couple as the house is small ...
From $517 per night (USD)
VRBO
From $214 per night (USD)
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Shipyard 197
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
7 night minimum rental. Paradise is definitely found in this Non-Smoking, first floor condo only two short blocks off of ...
From $214 per night (USD)
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From $89 per night (USD)
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"STONE'S THROW" ~ Delightful!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CLOSE TO THE FUN.... This Adorable Conch Cottage is a “Stone’s Throw” from everything that Key West has to offer! Liter ...
From $89 per night (USD)
VRBO
From $293 per night (USD)
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A Mangrove Snapper
Bedrooms:
3.5
Bathrooms:
2
Sleeps:
6
This charming getaway in the prestigious Porter Court is located in the award winning Truman Annex in Old Town Key West. ...
From $293 per night (USD)
VRBO
From $414 per night (USD)
VRBO
Driftwood Buoy
Bedrooms:
3.5
Bathrooms:
2
Sleeps:
6
A luxury, ocean front, 2 bedroom, (king in master, twins or twins as king in guest bedroom, queen sleeper in living room ...
From $414 per night (USD)
VRBO
From $321 per night (USD)
VRBO
Havana Daydream
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life i ...
From $321 per night (USD)
VRBO
From $50 per night (USD)
VRBO
Villa Vista
Bedrooms:
2
Bathrooms:
2
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)
VRBO
From $245 per night (USD)
VRBO
"ATLANTIC BREEZE" ~ The Good Life!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duva ...
From $245 per night (USD)
VRBO
From $443 per night (USD)
VRBO
The Plantation
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
‘The Plantation” is a Three Bedroom Town home located within the prestigious gated community of ‘Truman Annex’ in Key We ...
From $443 per night (USD)
VRBO
From $150 per night (USD)
VRBO
Cool Breeze
Bedrooms:
3.5
Bathrooms:
3
Sleeps:
6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** | This community is ...
From $150 per night (USD)
VRBO
From $233 per night (USD)
VRBO
A Bella Capri
Bedrooms:
4.5
Bathrooms:
5
Sleeps:
10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $233 per night (USD)
VRBO
From $207 per night (USD)
VRBO
Tropical Breezes @ 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 $208 per night (USD)
VRBO
42' Catamaran "Lucy"
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
As you starting reading about my boat, I would like to tell you what we doing to protect traveling public from Covid-1 ...
From $208 per night (USD)
VRBO
From $100 per night (USD)
VRBO
Conch Retreat Condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the Beautiful Shipyard of ...
From $100 per night (USD)
VRBO
From $171 per night (USD)
VRBO
Oyster's Pearl
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...
From $171 per night (USD)
VRBO
From $125 per night (USD)
VRBO
Free Island Spirit Escape A311
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offe ...
From $125 per night (USD)
VRBO
From $378 per night (USD)
VRBO
Elizabeth's Secret
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Elizabeth's Secret! NOW A 3 Bedroom home! A tranquil and secluded flourishing tropical oasis awaits you be ...
From $378 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Pelican Landing Bonaire Retreat
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)
VRBO
From $343 per night (USD)
VRBO
Forever Young
Bedrooms:
3.5
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $343 per night (USD)
VRBO

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