Fleming Key Rentals
- From $559 per night (USD)
VRBO
Deluxe Key West Ocean Front Condo Week - April 22 - 29, 2025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Deluxe Ocean Front Condo in Key West Florida with a spectacular 3rd Floor balcony view of the Marina and Ocean. One Full ...
From $559 per night (USD)VRBO
- From $220 per night (USD)
VRBO
Luxury 4BDR\/4BA Penthouse | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Luxury Harbor House Suites! We proudly offer you a newly renovated 2,400SF, 4BDR/4BA Penthouse in the Cit ...
From $220 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Old Town cottage - SPECIAL 25% OFF MONTHY BOOKING IN MAY OR JUNE!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
The newly remodeled home is located in the middle of Old Town down a private lane just a block from Duval Street. One of ...
From $250 per night (USD)VRBO
- From $2800 per night (USD)
VRBO
3 BEDROOM SUITE-THE GALLEON-RARE FIND-KEY WEST, POOL!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to ...
From $2800 per night (USD)VRBO
- From $1682 per night (USD)
VRBO
Custom House Inn | 5 BR Complex On Duval St!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 20
Summary: Stay right on Duval Street at this one-of-a-kind modern condo complex known as Custom House Inn! Each one of ou ...
From $1682 per night (USD)VRBO
- From $286 per night (USD)
Expedia
Birds of a Feather at Custom House Inn | On Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to 'Birds of a Feather' at the Custom House Inn! Each apartment in our five unit complex is uniquely de ...
From $286 per night (USD)Expedia
- From $160 per night (USD)
VRBO
UPTOWN FUNK ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
IMMACULATE UPSCALE DELIGHT… Embrace the island vibes and immerse yourself in the Key West spirit in this enchanting 3 st ...
From $160 per night (USD)VRBO
- From $495 per night (USD)
VRBO
2 bedroom home with private fenced courtyard
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Brand new 2 bedroom one bath located on North side of the Island in Key West. Full kitchen, fully equipped. Large bathro ...
From $495 per night (USD)VRBO
- From $515 per night (USD)
VRBO
Ann Street Tranquility: A cozy and peaceful cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Stre ...
From $515 per night (USD)VRBO
- Click For Pricing
Expedia
HISTORIC OLD TOWN, KEY WEST, MONTLY RENTAL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Designed in the Key West style, this cozy island retreat is located in the heart of Old Town and only a few blocks from ...
Click For PricingExpedia
- From $227 per night (USD)
VRBO
**ELECTRIC SUNSHINE @ MIDTOWN** Groovy Private Home + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If the weathe ...
From $227 per night (USD)VRBO
- From $150 per night (USD)
Expedia
Quaint Pool Cottage in Old Town Key West Great value
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perfectly situated in Old Town Key West. This quaint pool cottage is perfect for a couple with occasional visitors. beau ...
From $150 per night (USD)Expedia
- From $572 per night (USD)
VRBO
FERNWOOD ~ Dreamy, Lush Estate with Incredible Outdoor Space with Pool & Spa!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
THERE'S NO PLACE LIKE YOUR ISLAND HOME... Located in the highly sought-after area of The Meadows and beneath peaceful sw ...
From $572 per night (USD)VRBO
- From $2010 per night (USD)
VRBO
Old Town Caribbean Estate
- Bedrooms:
- 8
- Bathrooms:
- 10
- Sleeps:
- 21
The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-s ...
From $2010 per night (USD)VRBO
- From $150 per night (USD)
VRBO
The Sandy Beach House in Historic Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Spend time in Key West and live like a local in a true Conch Home! The Sandy Beach Cottage, a fully-renovated first floo ...
From $150 per night (USD)VRBO
- From $259 per night (USD)
Expedia
Tropical Cottage with Shared Pool, Private Hot Tub, WiFi, AC, & Street Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Palm Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $259 per night (USD)Expedia
- From $128 per night (USD)
VRBO
Garden of Eden Cottage | 1 Bed, 1.5 Bath
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Experience paradise at our Key West Cottage vacation rental - a hidden gem tucked away in a lush Garden of Eden. This ch ...
From $128 per night (USD)VRBO
- From $969 per night (USD)
Expedia
Harbor House Suite A | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Luxury Harbor House Suites, an exceptional NIGHTLY vacation rental property located in the heart of Key West' ...
From $969 per night (USD)Expedia
- From $256 per night (USD)
VRBO
Classic King with Private Balcony - Curry Mansion
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $256 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Key West Suites Hotel #201 on Duval
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $399 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Old Town Bali Hideaway For 2, Just Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $400 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Paradise on Pine in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise on Pine, is a picture perfect home that sits high above this lovely one way street with an inviting front porc ...
From $350 per night (USD)Expedia
- From $306 per night (USD)
VRBO
Historic Charm, Heart of Old Town, Tropical Paradise, Key West Quaint.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedroom 1 & half bath Historic Conch House in the Heart of Old Town Key West Queen in the Master, 1 Queen in 1st guest ...
From $306 per night (USD)VRBO
- From $326 per night (USD)
VRBO
WINDSONG DELIGHT - Cute house on Windsor Ln
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This two story townhome has both location and amenities for a wonderful month long visit to Key West. Secluded at the r ...
From $326 per night (USD)VRBO
- From $500 per night (USD)
VRBO
HONU WAVE - 2 Bedroom \/ 2 Bathroom - Old Town Key West W\/ Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come relax in Key West at Honu Wave, located in Old Town Key West just 4 blocks from Duval Street and 6 blocks to the be ...
From $500 per night (USD)VRBO
- From $287 per night (USD)
Expedia
Downtown Conch House-Historic Old Town 3 bedroom, 3 bath home w\/private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $287 per night (USD)Expedia
- From $336 per night (USD)
VRBO
TROPICAL PROPERTIES VACATION RENTAL-KEY WEST
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** Tropical Properties Vacation Rent ...
From $336 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Solimar Key West - private pool and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Solimar" - Spanish for sun and ocean! Located in the heart of historic Old Town Key West, just blocks from D ...
From $300 per night (USD)Expedia
- Click For Pricing
VRBO
Luxury Waterfront Stay @ The Galleon, Mins from Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine waking up every morning in Paradise. With Balconies that overlook the marina and ocean. Private marina, private ...
Click For PricingVRBO
- From $2328 per night (USD)
VRBO
CLASSIC KEY WEST - Grand home in Old Town location
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
The Mansion, circa 1840’s is a lovingly restored and renovated three story Classic Folk Victorian home with seven bedroo ...
From $2328 per night (USD)VRBO
- From $944 per night (USD)
VRBO
PERFECTION...STEPS FROM DUVAL ~
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The Villa is a newer built poolside home, situated steps away from famous Duval Street, the historic seaport and everyth ...
From $944 per night (USD)VRBO
- From $336 per night (USD)
Expedia
little bodega in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Very nice 1 br/bath house on Solaris Hill centered 2 blks off Duvall St. in Old Town Key West. Enjoy bustling Duvall wi ...
From $336 per night (USD)Expedia
- From $512 per night (USD)
VRBO
**MODERN IN THE MEADOWS @ THE MEADOWS** Chic Private Home & Pool + LAST KEY SERV
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! MODERN IN THE ...
From $512 per night (USD)VRBO
- From $474 per night (USD)
VRBO
Great Location & Amenities! Pool & Garden View, Pets Allowed, Onsite Dining!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $474 per night (USD)VRBO
- From $565 per night (USD)
VRBO
Adventure Awaits! Partial Harbor View, Onsite Dining, 2 Blocks Away From Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $565 per night (USD)VRBO
- From $980 per night (USD)
Expedia
Three-Condo Getaway in Old Town with WiFi, Shared Pool, and Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Palm Gardens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $980 per night (USD)Expedia
- From $194 per night (USD)
VRBO
Private Home in Heart of Old Town (Shared Pool!)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come escape to paradise in this newly updated and available home steps from Duval! Equipped with all the amenities for a ...
From $194 per night (USD)VRBO
- From $231 per night (USD)
Expedia
The Rex, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located apartment. Just a short walk from some of Key West best restaurants ...
From $231 per night (USD)Expedia
- From $287 per night (USD)
VRBO
The Maria Luz, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Maria Luz a is located in a Historic Conch house from the early 1900’s updated and decorated by its owner. Feature ...
From $287 per night (USD)VRBO
- From $168 per night (USD)
Expedia
The Gisela, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
The Gisela is located in the rear of an adorable Conch Cottage. Finished with a soft and neutral color scheme that will ...
From $168 per night (USD)Expedia
- From $855 per night (USD)
VRBO
SEAPORT SKYLINE at Galleon Resort near Mallory Square—King Suite-Beach-Pool-BBQ
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
OCEANFRONT CASUAL LUXURY CONDO RENTAL WITH BREATHTAKING VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO. PENTHOUSE COND ...
From $855 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Caroline On My Mind-New Listing-Light, Bright and Airy!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting exp ...
From $254 per night (USD)Expedia
- From $504 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
From $504 per night (USD)VRBO
- Click For Pricing
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
Click For PricingVRBO
- From $211 per night (USD)
VRBO
Cozy 3 Bedroom Home in Old Town with Pool
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, ...
From $211 per night (USD)VRBO
- From $361 per night (USD)
VRBO
CONCH CASA @ The Colony ~ the perfect monthly escape
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The property features a beautiful, heated community pool and one reserved off-street parking space (a coveted old town r ...
From $361 per night (USD)VRBO
- Click For Pricing
Expedia
Home with pool, outdoor shower, grill, firepit, central AC, W\/D, & office
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Gecko Lane Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
Click For PricingExpedia
- From $337 per night (USD)
Expedia
**ANGELA’S ECLECTIC GALLERY @ SOLARIS HILL** Exceptional Home & Pool + LAST KEY
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! On an island ...
From $337 per night (USD)Expedia
- Click For Pricing
VRBO
Beautiful Two-Bed, Two-Bath Suite at Galleon Resort - pool - harbor views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Feel free to message me with any questions. Our space is a lovely two-bedroom, two-bathroom serviced apartment with harb ...
Click For PricingVRBO
- From $317 per night (USD)
Expedia
Tranquility by AvantStay | Close to Duval St w\/ BBQ & Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Settled in a small community in Old Town, only a short walk to Duval Street, this lovely cottage offers everything you c ...
From $317 per night (USD)Expedia
- From $274 per night (USD)
VRBO
Paradise Place by AvantStay | Key West Old Town Condo w\/ Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's, and eve ...
From $274 per night (USD)VRBO
- From $256 per night (USD)
Expedia
Old Town Key West Home w\/ Pool! Walkable to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Key West Home! This beautiful condo is in the heart of Old Town, walkable to everything in Key West. What ...
From $256 per night (USD)Expedia
- From $125 per night (USD)
VRBO
Land Of Love by AvantStay | Pets Allowed! Shared Pool! Great Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Your perfect escape to Key West awaits you in the L ...
From $125 per night (USD)VRBO
- From $128 per night (USD)
Expedia
Boat House by AvantStay | Character Cottage | Central Location Month Long Stays
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
*Please note that this home is available for 28+ night stays only.* Step into a tranquil community on a quiet lane and ...
From $128 per night (USD)Expedia
- From $101 per night (USD)
VRBO
Ibis by AvantStay | Close to Duval Street w\/ Shared Pool | Month Long Stays Only
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*Please note that this home is available for 28+ night stays only.* Enjoy your private front porch in this quiet neighb ...
From $101 per night (USD)VRBO
- From $631 per night (USD)
Expedia
Easy Livin' by AvantStay | Key West Home w\/ Pool & BBQ | Week Long Stays Only
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
*Please note that this home is available for 7+ night stays only.* Cozy, but upscale, this charming vacation rental wit ...
From $631 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Artist Garden by AvantStay | Great Location w\/ Balcony, Shared Pool & BBQ!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 7+ night stays only.* This spacious home with a large outside deck is tuck ...
From $350 per night (USD)VRBO
- From $135 per night (USD)
Expedia
Paradise Palms by AvantStay | Great Location w\/ Outdoor Dining, BBQ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Make your next Florida vacation something special w ...
From $135 per night (USD)Expedia
- From $98 per night (USD)
VRBO
Windchime by AvantStay | Walk to Duval Street | Month Long Stays Only
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Please note that this home is available for 28+ night stays only.* Searching for an affordable monthly vacation rental ...
From $98 per night (USD)VRBO
- From $436 per night (USD)
Expedia
First Breath by AvantStay | Close to Old Town w\/ Pool | Month Long Stays Only
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*Please note that this home is available for 28+ night stays only.* Bring the family to this 3 bed, 2 bath private conc ...
From $436 per night (USD)Expedia
- From $226 per night (USD)
VRBO
Casa de Rosalie by AvantStay | Great Location w\/ Pool, BBQ & Outdoor Dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*Please note that this home is available for 28+ night stays only.* Built-in 1889 with original Dade County Pine, histo ...
From $226 per night (USD)VRBO
- From $159 per night (USD)
Expedia
Lazy Gecko by AvantStay | Walk to Duval St in Key West! | Month Long Stays Only
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Grab your bike and head for some fresh seafood at t ...
From $159 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Priced to book! Sleeps 4- Walking Distance to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
From $350 per night (USD)VRBO
- From $146 per night (USD)
Expedia
Key Lime Pie by AvantStay | Ideal Location w\/ Splash Pool & Out Door Dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Key Lime Pie is a private cottage that perfectly en ...
From $146 per night (USD)Expedia
- Click For Pricing
VRBO
The Queens Villa
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 4
Former Fantasy Fest Queens private residence. I also own the number one hotel in Key West. Best location at the END of ...
Click For PricingVRBO
- From $250 per night (USD)
Expedia
Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages.The compound is located one block ...
From $250 per night (USD)Expedia
- Click For Pricing
Expedia
Historic Old Town Conch House newly furnished Condo-walk 5min beach, 7min Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
A true Key West classic, wonderfully renovated, 2nd floor apartment, with large outdoor back deck and relaxing front por ...
Click For PricingExpedia
- From $382 per night (USD)
Expedia
Beautiful renovated 3 Bed 2.5 Bath Private home in Old Town. Walk to everything.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated Old Town home with high amenities throughout. Once you check in, you will not want to leave, but i ...
From $382 per night (USD)Expedia
- From $248 per night (USD)
VRBO
**SOUL OF THE SOUTH @ OLD TOWN** Adorable Historic Home & Pool + LAST KEY SERVIC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUL OF THE S ...
From $248 per night (USD)VRBO
- From $850 per night (USD)
Expedia
Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 12 - Nov 19
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Two story townhouse with two bedrooms, pull out couch, full kitchen, three bathrooms. Overlooking the harbor with full ...
From $850 per night (USD)Expedia
- From $3298 per night (USD)
VRBO
WATSON HOUSE GRAND ESTATE on Simonton St
- Bedrooms:
- 11
- Bathrooms:
- 11
- Sleeps:
- 22
The Grand Estate is comprised of the Mansion and the Villa offering 11 bedrooms and baths. It is ideal for family gather ...
From $3298 per night (USD)VRBO
- From $315 per night (USD)
Expedia
LOVE IS IN THE AIR - Charming Home-On private lane w\/pool sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy a month-long stay or longer in this beautiful Three-bedroom Key West Home. Hidden in the heart of Old-Town Key W ...
From $315 per night (USD)Expedia
- From $361 per night (USD)
VRBO
New Conch cottage, with heated pool, walking distance to downtown Key West.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cathedral ceilings, Viking and Wolf appliances, quartz counters, wood floors, private heated pool, BBQ, waterfall and ...
From $361 per night (USD)VRBO
- From $374 per night (USD)
Expedia
Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 story Townhouse is in "Old Town Villas". A Caribbean inspired community in the heart of Key West. Built in 2017. ...
From $374 per night (USD)Expedia
- From $481 per night (USD)
VRBO
**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $481 per night (USD)VRBO
- From $161 per night (USD)
VRBO
ESCAPE ON FLEMING - A charming 2 bedroom home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL ... This property is not allowed to accept pets. Break away from it all at Escape on Fleming. Thi ...
From $161 per night (USD)VRBO
- From $276 per night (USD)
VRBO
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Pool & Dog-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Introducing 'The Conch Chateau' – a stunning and recently updated Conch House nestled in the heart of Key West's charmin ...
From $276 per night (USD)VRBO
- From $425 per night (USD)
Expedia
The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your tropical vacation, whether work-free or not, in this Old Town home only a couple of minutes from Duval and Wh ...
From $425 per night (USD)Expedia
- From $144 per night (USD)
VRBO
Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Keys Please Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $144 per night (USD)VRBO
- From $389 per night (USD)
Expedia
Single home with pool, center of Old Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful, newly renovated single home of corner lot in the center of old town. 4 blocks from Duval and 4 blocks from se ...
From $389 per night (USD)Expedia
- Click For Pricing
Expedia
Rose Treehouse in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in i ...
Click For PricingExpedia
- From $150 per night (USD)
Expedia
Conch Republic Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
SPRING Specials! Rates Discounted.This historic conch home, circa 1890, is your dream vacation spot. The welcoming prope ...
From $150 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Old Town Classic with plenty of charm, porch swing and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful home with covered porch and swing! Full kitchen, washer/dryer, TV, Internet, A/C, separate patio area with twi ...
From $313 per night (USD)VRBO
- From $336 per night (USD)
Expedia
\"A Bird's Eye View\" at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stunning, Modern 2 bedroom, 1 bathroom second floor condo in the Truman Annex Shipyard Complex completely renovated. Ful ...
From $336 per night (USD)Expedia
- Click For Pricing
Expedia
Rose Haven in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
If you want to engage with Key West's past and be perfectly positioned to take advantage of its present, Rose Haven is t ...
Click For PricingExpedia
- From $1418 per night (USD)
VRBO
Downtown 4\/4 Waterfront Penthouse Pool, Dock, Pet
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Bring your family & friends to this 2400sqft waterfront Penthouse condo. Boat slips available on site with com ...
From $1418 per night (USD)VRBO
- From $1343 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Dock, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Bring your family & friends to this 2000sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $1343 per night (USD)VRBO
- Click For Pricing
Expedia
Sunshine Siesta Cottage~Great Old Town Location, Pool, Private Hot Tub!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
BOOK NOW! Walk down the secluded brick path of the 4-unit compound, past the tropical foliage to Unit B, adjacent to the ...
Click For PricingExpedia
- From $528 per night (USD)
VRBO
**MARGARET’S MAGIC COMPOUND @ SOLARIS HILL** Old Town Compound & Pool + LAST KEY
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Travelers fro ...
From $528 per night (USD)VRBO
- From $615 per night (USD)
Expedia
Eliza's Secret - Elegant Tropical Oasis with Private Pool & Guest House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy all of Key West's exciting activities from the privacy and comfort of your own two-story, historic home in Old Tow ...
From $615 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Campbell Eyebrow House
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
The uniqueness of Campbell Eyebrow House starts with its Classical Revival "eyebrow" styling, an iconic gable roof creat ...
From $225 per night (USD)VRBO
- Click For Pricing
Expedia
Truman House in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home w ...
Click For PricingExpedia
- From $117 per night (USD)
VRBO
Campbell Cottage in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location...Location...Location! Campbell Cottage is perfectly located to walk to almost everything Key West has to offer ...
From $117 per night (USD)VRBO
- From $429 per night (USD)
Expedia
The Courtyard in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spring Special - Price Discounted!Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyar ...
From $429 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Paradise Grand in Key West
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Experience paradise in sumptuous style. That's what Paradise Grand, a breath-taking yet comfortable five-bedroom, four-b ...
From $400 per night (USD)VRBO
- From $167 per night (USD)
Expedia
Anchor's Away in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SPRING SPECIALS!Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of th ...
From $167 per night (USD)Expedia
- From $395 per night (USD)
VRBO
Ann Street Gardens in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key ...
From $395 per night (USD)VRBO
- From $324 per night (USD)
Expedia
Coral Condo in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom ...
From $324 per night (USD)Expedia
- From $167 per night (USD)
VRBO
La Hacienda in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most dis ...
From $167 per night (USD)VRBO
- From $408 per night (USD)
Expedia
Campbell Suite in Key West
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell S ...
From $408 per night (USD)Expedia