Key West Rentals
- From $478 per night (USD)
VRBO
POCKETFUL OF SUNSHINE ~ Renovated 5 BR\/5.5 Ba Midtown Home w\/ Pool!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
EXQUISITE MODERN FAMILY COMPOUND... If a large home with all the modern luxuries is a must for your next island getaway, ...
From $478 per night (USD)VRBO
- From $218 per night (USD)
VRBO
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $218 per night (USD)VRBO
- From $233 per night (USD)
VRBO
SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CLASSIC UPDATED CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in the heart of Bah ...
From $233 per night (USD)VRBO
- From $888 per night (USD)
VRBO
Waterfront Sunset Harbor Resort Near Old Town+Amenities: 2BR FindingMeili
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to FindingMeili🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! An Additional Savings from $500 ...
From $888 per night (USD)VRBO
- From $657 per night (USD)
VRBO
NEW Spacious 2\/2 Waterfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip a ...
From $657 per night (USD)VRBO
- From $607 per night (USD)
VRBO
OASIS SOUTH~Opening Rates in this Stunning 5 BR\/3 Ba w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
BRING THE WHOLE GANG... If you and your large band of loved ones are looking for the perfect gathering in southernmost ...
From $607 per night (USD)VRBO
- From $443 per night (USD)
VRBO
McCartney's Manor - Deluxe K Suite W\/Pvt. Spa!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cool pastel, Caribbean inspired decor with original art throughout by Robin Hix. Bose speaker, Alexa Echo, full kitche ...
From $443 per night (USD)VRBO
- From $6158 per night (USD)
VRBO
CHANGES IN LATITUDES ~ Renovated 3 BR\/2.5 Ba Home w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
MODERN MERGES WITH HISTORIC CHARM... Discover a blend of sleek contemporary elegance that interweaves with the rich tape ...
From $6158 per night (USD)VRBO
- From $179 per night (USD)
VRBO
Charming + Circa 1889 Historic Eyebrow Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 Night Minimum. Welcome to "The Saltbox"! Featured in design magazines. 710 Ashe Street is a charming house circa 18 ...
From $179 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront Resort, New Year’s Eve, Hyatt, 2 Nights, Sleeps 6, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary amongst the lush landscape of Key W ...
Click For PricingVRBO
- Click For Pricing
VRBO
Ocean view apartment on coconut resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Coconut Beach Resort once belonged to the late Senator John Spottswood. He originally purchased the property because of ...
Click For PricingVRBO
- From $182 per night (USD)
VRBO
CASA DE CANAL ~ 3 BR, 2 Ba. Canal Front Home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
KEY WEST BOATER'S BONANZA... This waterfront gem is a dream for boating and fishing enthusiasts. Indulge in all your nau ...
From $182 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront Retreat, Offshore Boat Races, Near RWO Mole, 3 Night, Hyatt, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imbibe in the relaxed Key West lifestyle from a coveted location nestled in the heart of Key West’s famed Old Town at th ...
Click For PricingVRBO
- Click For Pricing
VRBO
Waterfront Retreat, Offshore Boat Races, Near RWO Mole, 7 Nights Hyatt Sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Imbibe in the relaxed Key West lifestyle from a coveted location nestled in the heart of Key West’s famed Old Town at th ...
Click For PricingVRBO
- From $352 per night (USD)
VRBO
THE GOOD LIFE ~ Charming 1 Bedroom, 1 Bath Truman Annex Condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
COZY VALUE IN TRUMAN ANNEX… This one bedroom, one bath condo is located in The Shipyard, a neighborhood of the coveted T ...
From $352 per night (USD)VRBO
- From $677 per night (USD)
VRBO
SALTWATER SOPHISTICATION ~ Renovated 4 BR, 4.5 Ba Downtown Home w\/ Pool!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
PREMIER HISTORICAL RETREAT... Just steps from the Seaport District hosting the best waterfront restaurants and world fam ...
From $677 per night (USD)VRBO
- From $110 per night (USD)
VRBO
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $110 per night (USD)VRBO
- From $325 per night (USD)
Expedia
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Our Home Away from home. Our condo is located in the LaBrisa complex which is a GATED COMMUNITY across from ...
From $325 per night (USD)Expedia
- Click For Pricing
Expedia
La Casa De Luces- 2 bedroom 2 bath steps off Duval street.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come to relax or to play while enjoying the spectacular sunsets and blue waters of Key West! This ample-sized, ground le ...
Click For PricingExpedia
- From $744 per night (USD)
Expedia
Craig & Cindy's 4 Bedroom Key West Truman Annex Porter House with private pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The two story Truman Annex Porter House is the largest of our Key West properties and features 4 bedrooms and a private ...
From $744 per night (USD)Expedia
- From $122 per night (USD)
VRBO
Mango Tree Key West Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
True Key West flavor! 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with h ...
From $122 per night (USD)VRBO
- Click For Pricing
Expedia
Deckside Suite | 1 bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get ...
Click For PricingExpedia
- Click For Pricing
Expedia
Secret Courtyard-2 bedroom 2 bath just steps off Duval street.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Secret Courtyard Cottage is truly the best kept secret in Key West. Recently renovated, this small historic cigar maker ...
Click For PricingExpedia
- Click For Pricing
Expedia
The Hollinsed House | Harvey`s Haven
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Harvey's Haven—a beautiful studio in the heart of Old Town Key West! Ideally located at the Hollinsed House o ...
Click For PricingExpedia
- Click For Pricing
Expedia
Porchside Paradise - 1 bedroom 1 bath just steps away from Duval street.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Porchside Paradise is located in the front section of the Conch Republic Cottages. This beautiful home-away-from-home fe ...
Click For PricingExpedia
- From $643 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sunday ...
From $643 per night (USD)VRBO
- From $305 per night (USD)
VRBO
GARDEN HIDEAWAY ~ Beautiful lush landscaped oasis located in the Casa Marina!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
PARADISE AWAITS... This charming home is located in one of the most desirable locations in Key West, Casa Marina. Garden ...
From $305 per night (USD)VRBO
- From $215 per night (USD)
VRBO
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
SIMPLISTIC ELEGANCE... Enjoy easy island living in this quaint and cozy Key West gem located in the attractive community ...
From $215 per night (USD)VRBO
- From $507 per night (USD)
VRBO
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $507 per night (USD)VRBO
- From $899 per night (USD)
VRBO
Hyatt Residence Club - Key West, FL - 2 Bedroom Unit - Beach House Location!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a tropical getaway designed in classic Key West style, o ering manicured gardens and panoramic views of the G ...
From $899 per night (USD)VRBO
- From $347 per night (USD)
VRBO
💲 HUGE DISCOUNT for 28 day OCEAN FRONT! 90 FT BALCONY💰
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please contact the owner for stays less than 28 days before you try to book. Military Vouchers are Welcome! In Key We ...
From $347 per night (USD)VRBO
- From $719 per night (USD)
VRBO
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
- 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 $719 per night (USD)VRBO
- From $307 per night (USD)
VRBO
Enjoy More Privacy in a Truman Annex End Unit Townhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $307 per night (USD)VRBO
- Click For Pricing
Expedia
Thalia`s Retreat at Duval Square- 2 bedroom 2.5 bath with shared rooftop pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parkin ...
Click For PricingExpedia
- From $399 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 $399 per night (USD)VRBO
- From $371 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 $371 per night (USD)VRBO
- Click For Pricing
Expedia
Orchid Suite- 1 bedroom 1.5 bath with shared pool one half block off Duval
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
The Orchid Suite is a bi-level suite decorated in a rich contemporary Danish style. The bedroom is located upstairs with ...
Click For PricingExpedia
- From $600 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 $600 per night (USD)VRBO
- From $565 per night (USD)
VRBO
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
- Bedrooms:
- 3
- 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 $565 per night (USD)VRBO
- Click For Pricing
Expedia
Windsor Townhome #3 - Green Gecko
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently ...
Click For PricingExpedia
- From $198 per night (USD)
VRBO
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mojitoville is perfect for the discriminating guest who wants to enjoy close proximity to Key West's Historic Seaport wi ...
From $198 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Quintessential Key West Resort! Hyatt Windward Pointe two bedroom. Best rates!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sunday ...
From $625 per night (USD)VRBO
- From $243 per night (USD)
VRBO
SMATHER'S BEACH, Deluxe 2 BR oceanview unit, GREAT RATES ,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront at Smathers Beach in beautiful Key West, Florida. Why pay for a hotel, when you can enjoy your own private o ...
From $243 per night (USD)VRBO
- From $1450 per night (USD)
Expedia
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $1450 per night (USD)Expedia
- From $248 per night (USD)
VRBO
Key Lime Cottage (Monthly)
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Located on the edge of Old Town near the art district on White Street the Key Lime Cottage offers great accommodations f ...
From $248 per night (USD)VRBO
- From $237 per night (USD)
VRBO
Esperanza Suite- Monthly Rental
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Esperanza Suite is a bi-level suite with a very spacious upstairs King bedroom with a writing desk and chair and a color ...
From $237 per night (USD)VRBO
- From $393 per night (USD)
VRBO
TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ADORING RETREAT ONE BLOCK FROM DUVAL… One bedroom gem on Simonton Street one block from Duval. Totaling one bedroom, on ...
From $393 per night (USD)VRBO
- From $191 per night (USD)
VRBO
BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w\/ Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $191 per night (USD)VRBO
- From $214 per night (USD)
VRBO
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $214 per night (USD)VRBO
- From $271 per night (USD)
VRBO
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
PICTURE PERFECT PARADISE... This newly renovated 3 bedroom, 2 bathroom retreat is nestled in the highly sought-after, hi ...
From $271 per night (USD)VRBO
- From $350 per night (USD)
VRBO
A Bit of Heaven- Monthly Rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Bit of Heaven This quintessential Key West eyebrow home is located in Old Town's prime Historic District sitting just ...
From $350 per night (USD)VRBO
- From $509 per night (USD)
VRBO
Bahama Breeze- Monthly Rental
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This newer 3 bedroom 3.5 bath home in Old Town is a rare find. There is off street parking and a beautiful private pool ...
From $509 per night (USD)VRBO
- From $107 per night (USD)
VRBO
SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town. A great place for a coup ...
From $107 per night (USD)VRBO
- From $606 per night (USD)
VRBO
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $606 per night (USD)VRBO
- From $915 per night (USD)
VRBO
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w\/ Pool and Ocean Views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
YOUR OCEANFRONT OASIS AWAITS... This remarkable and magical retreat is sure to provide all the R & R you need to refresh ...
From $915 per night (USD)VRBO
- From $358 per night (USD)
VRBO
THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $358 per night (USD)VRBO
- From $645 per night (USD)
VRBO
The Most Perfect Old Town Key West Location for a Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroo ...
From $645 per night (USD)VRBO
- From $193 per night (USD)
VRBO
HEMINGWAY'S HIDEOUT ~ Sophisticated, Historic Old Town Cottage with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
ISLAND SOPHISTICATION AWAITS… Step up to this serene, tropical cottage inviting you in with a multitude of swaying palms ...
From $193 per night (USD)VRBO
- From $869 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Home in Desirable Downtown Location!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $869 per night (USD)VRBO
- From $878 per night (USD)
VRBO
STRIPES ~ Delightful Condo w\/Shared Pool in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key W ...
From $878 per night (USD)VRBO
- From $1952 per night (USD)
VRBO
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $1952 per night (USD)VRBO
- From $418 per night (USD)
VRBO
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
- 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 $418 per night (USD)VRBO
- From $186 per night (USD)
VRBO
SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
IMMACULATE RETREAT JUST STEPS FROM IT ALL... Beautifully designed and decorated townhouse located in the Southernmost Ca ...
From $186 per night (USD)VRBO
- From $929 per night (USD)
VRBO
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $929 per night (USD)VRBO
- From $593 per night (USD)
VRBO
ATLANTIC BREEZE ~ 2B\/2BA Renovated Retreat w\/ Pool, Fitness Area & Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BEACHES ON BOTH SIDES... This newly renovated two bedroom condo is close to the airport, beaches, restaurants and minute ...
From $593 per night (USD)VRBO
- From $331 per night (USD)
VRBO
Perfect Staycation! Close to Local Attractions! Deluxe Room w\/ Pool View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $331 per night (USD)VRBO
- From $582 per night (USD)
VRBO
GARDEN OASIS ~ Great Casa Marina Location with True Island Elegance!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
WHEN ONLY THE BEST WILL DO... Located in the Casa Marina Area of Key West known for spacious and elegant fine homes; the ...
From $582 per night (USD)VRBO
- From $702 per night (USD)
VRBO
JASMINE PLACE:1 block to Duval - Private Pool - Parking! - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO JASMINE PLACE! Jasmine Place is a beautiful and enchanting home conveniently located next door to the Ernes ...
From $702 per night (USD)VRBO
- From $238 per night (USD)
VRBO
ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pass by from ...
From $238 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Stone's Throw ~ Beautiful home in a great location with shared pool!
- 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 $175 per night (USD)VRBO
- From $1056 per night (USD)
VRBO
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
- Bedrooms:
- 3
- 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 $1056 per night (USD)VRBO
- From $1102 per night (USD)
VRBO
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
- Bedrooms:
- 3
- 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 $1102 per night (USD)VRBO
- From $329 per night (USD)
VRBO
BOOMERANG BOATHOUSE ~ Relax in This Beautiful 4 Bedroom\/2.5 Bath Location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
RETURN TO EQUANIMITY... “Boomerang Boathouse” is nestled in the peaceful neighborhood locals refer to as The Meadows. T ...
From $329 per night (USD)VRBO
- From $517 per night (USD)
Expedia
LATITUDE 24 ~ 3 B\/3 Ba Two-Story Home in Old Town with Lush Outdoor Oasis!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
ARRIVE IN PARADISE... Step into island time with this incredibly bright and inviting Key West home in a beautiful and qu ...
From $517 per night (USD)Expedia
- From $852 per night (USD)
VRBO
MANGO MARGARITA~ 2 bedroom\/2.5 bath, heated pool, and close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
LOCATION LOCATION LOCATION... Enjoy this convenient Old Town Location. Located a block from Duval and a short walk or b ...
From $852 per night (USD)VRBO
- From $978 per night (USD)
VRBO
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West. Located on Southard Street just steps from Du ...
From $978 per night (USD)VRBO
- From $805 per night (USD)
VRBO
CONCH HEAVEN ~ Stylish 2B\/2Ba, Sleeps 6 in Old Town w\/ Heated Cocktail Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OLD TOWN LOCATION... A beautifully furnished and comfortable home, located just 5 short blocks to Duval Street. Have bi ...
From $805 per night (USD)VRBO
- From $945 per night (USD)
VRBO
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
JUST OFF DUVAL... Private single family home with three bedrooms and three bathrooms. Open the rear French doors to a p ...
From $945 per night (USD)VRBO
- From $289 per night (USD)
VRBO
SEA LA VIE ~ Living in Complete Luxury in This Elegant Three Story Home!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
THREE STORY GRANDEUR… Located in the Casa Marina District in Old Town. This home is elegant, yet quite the tropical del ...
From $289 per night (USD)VRBO
- From $476 per night (USD)
VRBO
FOUNDRY 7- Weekly Vacation Rental - Shared Pool - 2BD\/2.5BA RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
WELCOME TO FOUNDRY 7! Escape to the historic and luxurious neighborhood of Truman Annex in Key West, where you'll find ...
From $476 per night (USD)VRBO
- From $342 per night (USD)
VRBO
THE QUARTERDECK ~ Colorful & Comfortable 2Ba\/ 1Ba Unit in The Shipyard!
- 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 $342 per night (USD)VRBO
- From $1215 per night (USD)
VRBO
Perfect Beach Getaway! Four Convenient Rooms, Driving Distance to the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1215 per night (USD)VRBO
- From $824 per night (USD)
VRBO
Perfect staycation! 3 Convenient Spaces, Close to Amazing Beach, Outdoor Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $824 per night (USD)VRBO
- From $1090 per night (USD)
VRBO
Ideal Location! Three Spacious Spaces, Close to Beach, Outdoor Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1090 per night (USD)VRBO
- From $911 per night (USD)
VRBO
Beach Getaway For Family and Friends! 3 Spacious Ocean View Rooms, Outdoor Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $911 per night (USD)VRBO
- From $1453 per night (USD)
VRBO
Amazing Land and Sea Getaway! Four Convenient Rooms, Close to Nearest Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1453 per night (USD)VRBO
- From $1278 per night (USD)
VRBO
Ideal Location for Family and Friends! Four Spacious Rooms, Outdoor Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1278 per night (USD)VRBO
- From $825 per night (USD)
VRBO
Fantastic Land and Sea Vacation! 3 Relaxing Spaces, Outdoor Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $825 per night (USD)VRBO
- From $639 per night (USD)
VRBO
Fantastic Land and Sea Vacation! 2 Spacious Rooms, Close to Nearest Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $639 per night (USD)VRBO
- From $1166 per night (USD)
VRBO
Fantastic Land and Sea Vacation! Four Convenient Spaces, Close to Nearest Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1166 per night (USD)VRBO
- From $958 per night (USD)
VRBO
Beautiful Key West! Close to the Beach! Amazing Ocean View, Outdoor Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $958 per night (USD)VRBO
- From $1250 per night (USD)
VRBO
Fantastic Land and Sea Vacation! 4 Relaxing Rooms, Minutes to the Closest Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1250 per night (USD)VRBO
- From $1109 per night (USD)
VRBO
Perfect For Family and Friends! Four Spacious Rooms (w\/ 2 Queen Beds Each)
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1109 per night (USD)VRBO
- From $727 per night (USD)
VRBO
Perfect Staycation! Two Convenient Rooms, Onsite Pool, Minutes to Closest Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $727 per night (USD)VRBO
- From $992 per night (USD)
VRBO
Perfect Staycation! Four Spacious Rooms, Outdoor Swimming Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $992 per night (USD)VRBO
- From $1045 per night (USD)
VRBO
Perfect staycation! Four Gorgeous Spaces (w\/ 2 Queen Beds Each), Outdoor Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1045 per night (USD)VRBO
- From $125 per night (USD)
VRBO
GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
AN ESCAPE LIKE NO OTHER… Disconnect from the real world and reconnect with each other in this picture perfect, quaint co ...
From $125 per night (USD)VRBO
- From $745 per night (USD)
VRBO
Ideal Location! 3 Great Units, Near Beach, Pool and Attractions
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $745 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Excellent Choice! Family-friendly Room, Fantastic View, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $275 per night (USD)VRBO
- From $497 per night (USD)
VRBO
Fantastic Land & Sea Vacation! 2 Convenient Rooms, Close from the Nearest Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $497 per night (USD)VRBO