Fleming Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Fleming Key, Florida on RentalSaver.com!

Fleming Key Rentals

From $355 per night (USD)
VRBO
613 Fleming. St. Unit 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Great location in the heart of it all. Short walk to Duval Street, bars, shops and restaurants. Quiet enough to have a p ...
From $355 per night (USD)
VRBO
From $577 per night (USD)
Expedia
The Leonella, Old Town Key West.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Leonella is an Imaginative and impeccable restoration of a Key West conch house mixing contemporary style and histor ...
From $577 per night (USD)
Expedia
From $201 per night (USD)
VRBO
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 $201 per night (USD)
VRBO
From $690 per night (USD)
Expedia
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 $690 per night (USD)
Expedia
From $4331 per night (USD)
VRBO
Old Town Caribbean Estate Key West - w Private Pool Blocks from Duval
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 $4331 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Old Town cottage - SPECIAL 20% OFF MONTHY BOOKING IN NOVEMBER AND DECEMBER!
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 $283 per night (USD)
Expedia
$Luxury 4BDR\/4BA Penthouse | 4 Bed, 4 Bath$
From $730 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 $730 per night (USD)
VRBO
From $641 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 $641 per night (USD)
VRBO
$THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Retreat Centrally Located w\/ Pool!$
From $320 per night (USD)
VRBO
THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Retreat Centrally Located w\/ Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
WHERE LIFE IS PURE… This dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West c ...
From $320 per night (USD)
VRBO
From $462 per night (USD)
Expedia
Conch Cottage Retreat in the heart of Old Town Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Experience Old Town Key West in a classic conch home! This home is only steps from shopping, restaurants, the historic s ...
From $462 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Two fully independent units in a Duplex, with independent entrances. One Rent!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to "Old Key West". Our Classic Old Town style duplex, with two independent fully renovated homes in the same pro ...
From $524 per night (USD)
VRBO
$ELIZABETH'S SECRET: 3\/2 In Old Town Key West, with a Private pool and Parking$
From $2154 per night (USD)
Expedia
ELIZABETH'S SECRET: 3\/2 In Old Town Key West, with a Private pool and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Elizabeth's Secret! You have found your secret! A very private and secluded tropical oasis awaits you behin ...
From $2154 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $304 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 $304 per night (USD)
Expedia
From $230 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 $230 per night (USD)
VRBO
$BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w\/ Pool, Spa & Exercise Room!$
From $534 per night (USD)
Expedia
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w\/ Pool, Spa & Exercise Room!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
OLD TOWN CLASSIC... This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding loc ...
From $534 per night (USD)
Expedia
From $2001 per night (USD)
VRBO
Harbor House Suite A | 4 Bed, 4 Bath
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to Luxury Harbor House Suites, an exceptional NIGHTLY vacation rental property located in the heart of Key West' ...
From $2001 per night (USD)
VRBO
From $4953 per night (USD)
Expedia
Custom House Inn | 5 BR Complex On Duval St!
Bedrooms:
6
Bathrooms:
6
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 $4953 per night (USD)
Expedia
From $368 per night (USD)
VRBO
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 $368 per night (USD)
VRBO
From $360 per night (USD)
Expedia
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 $360 per night (USD)
Expedia
From $825 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 $825 per night (USD)
VRBO
From $382 per night (USD)
Expedia
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 $382 per night (USD)
Expedia
From $1738 per night (USD)
VRBO
Key West Suites Hotel #201 on Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $1738 per night (USD)
VRBO
From $612 per night (USD)
VRBO
Old Town Bali Hideaway For 2, Just Steps From Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $612 per night (USD)
VRBO
From $1337 per night (USD)
VRBO
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 $1337 per night (USD)
VRBO
From $243 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 $243 per night (USD)
VRBO
From $215 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 $215 per night (USD)
VRBO
From $276 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 $276 per night (USD)
Expedia
From $337 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 $337 per night (USD)
VRBO
From $276 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 $276 per night (USD)
Expedia
From $258 per night (USD)
VRBO
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 $258 per night (USD)
VRBO
From $920 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
3
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 $920 per night (USD)
VRBO
From $441 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 $441 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave
Bedrooms:
2
Bathrooms:
4
Sleeps:
5
Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, ...
From $255 per night (USD)
Expedia
From $1024 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 $1024 per night (USD)
VRBO
From $497 per night (USD)
VRBO
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 $497 per night (USD)
VRBO
From $571 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 $571 per night (USD)
VRBO
$Downtown Conch House-Historic Old Town 3 bedroom, 3 bath home w\/private pool$
From $302 per night (USD)
Expedia
Downtown Conch House-Historic Old Town 3 bedroom, 3 bath home w\/private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $302 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Paradise on Pine in Key West
Bedrooms:
3
Bathrooms:
4
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 $412 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Historic Charm, Heart of Old Town, Tropical Paradise, Key West Quaint.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3-Bedroom, 1.5-Bath Historic Conch House in the Heart of Old Town Key West This charming Conch house features a queen b ...
From $290 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 Pricing
VRBO
$Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!$
From $335 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 $335 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 Pricing
Expedia
From $449 per night (USD)
Expedia
New Conch cottage, with heated pool, walking distance to downtown Key West.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Cathedral ceilings, Viking and Wolf appliances, quartz counters, wood floors, private heated pool, BBQ, waterfall and ...
From $449 per night (USD)
Expedia
From $669 per night (USD)
VRBO
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 $669 per night (USD)
VRBO
From $458 per night (USD)
Expedia
**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 $458 per night (USD)
Expedia
$Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 12 - Nov 19$
From $956 per night (USD)
VRBO
Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 12 - Nov 19
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Two story townhouse with two bedrooms, pull out couch, full kitchen, three bathrooms. Overlooking the harbor with full ...
From $956 per night (USD)
VRBO
From $542 per night (USD)
Expedia
**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 $542 per night (USD)
Expedia
From $236 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 $236 per night (USD)
VRBO
From $399 per night (USD)
Expedia
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Pool & Dog-Friendly!
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Introducing 'The Conch Chateau' – a stunning and recently updated Conch House nestled in the heart of Key West's charmin ...
From $399 per night (USD)
Expedia
$LOVE IS IN THE AIR - Charming Home-On private lane w\/pool sleeps 6$
From $723 per night (USD)
VRBO
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 $723 per night (USD)
VRBO
From $498 per night (USD)
Expedia
TROPICAL PROPERTIES VACATION RENTAL-KEY WEST
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** Tropical Properties Vacation Rent ...
From $498 per night (USD)
Expedia
From $4054 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 $4054 per night (USD)
VRBO
Click For Pricing
Expedia
Luxury Waterfront Stay @ The Galleon, Mins from Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Imagine waking up every morning in Paradise. With Balconies that overlook the marina and ocean. Private marina, private ...
Click For Pricing
Expedia
From $2937 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 $2937 per night (USD)
VRBO
From $1461 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 $1461 per night (USD)
VRBO
$Key Lime Pie by AvantStay | Ideal Location w\/ Splash Pool & Out Door Dining$
From $263 per night (USD)
VRBO
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 $263 per night (USD)
VRBO
From $989 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 $989 per night (USD)
Expedia
From $482 per night (USD)
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 ...
From $482 per night (USD)
VRBO
$Tranquility by AvantStay | Close to Duval St w\/ BBQ & Shared Pool$
From $651 per night (USD)
Expedia
Tranquility by AvantStay | Close to Duval St w\/ BBQ & Shared Pool
Bedrooms:
2
Bathrooms:
2
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 $651 per night (USD)
Expedia
$Paradise Place by AvantStay | Key West Old Town Condo w\/ Shared Pool$
From $511 per night (USD)
VRBO
Paradise Place by AvantStay | Key West Old Town Condo w\/ Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's, and eve ...
From $511 per night (USD)
VRBO
From $507 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 $507 per night (USD)
VRBO
$The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars$
From $666 per night (USD)
VRBO
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 $666 per night (USD)
VRBO
From $249 per night (USD)
Expedia
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 $249 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Single home with pool, center of Old Town
Bedrooms:
1
Bathrooms:
3
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 $452 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Conch Republic Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This historic conch home, circa 1890, is your dream vacation spot. The welcoming property has been completely renovated ...
From $205 per night (USD)
Expedia
From $409 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 $409 per night (USD)
VRBO
$\A Bird's Eye View\ at The Truman Annex in Key West$
From $558 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 $558 per night (USD)
Expedia
From $756 per night (USD)
VRBO
4-bedroom vacation home in Key West - steps to Duval St & Florida Keys Beaches
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Escape to the heart of Key West's historic district and immerse yourself in the vibrant island lifestyle. This 4-bedroom ...
From $756 per night (USD)
VRBO
$Downtown 4\/4 Waterfront Penthouse Pool, Dock, Pet$
From $1605 per night (USD)
VRBO
Downtown 4\/4 Waterfront Penthouse Pool, Dock, Pet
Bedrooms:
4
Bathrooms:
4
Sleeps:
15
Summary: Bring your family & friends to this 2400sqft waterfront Penthouse condo. Boat slips available on site with com ...
From $1605 per night (USD)
VRBO
From $1526 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 $1526 per night (USD)
VRBO
From $647 per night (USD)
Expedia
**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 $647 per night (USD)
Expedia
From $707 per night (USD)
VRBO
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 $707 per night (USD)
VRBO
From $301 per night (USD)
Expedia
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 $301 per night (USD)
Expedia
From $157 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 $157 per night (USD)
VRBO
From $383 per night (USD)
Expedia
The Courtyard in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can ...
From $383 per night (USD)
Expedia
From $615 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 $615 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Anchor's Away in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom ...
From $237 per night (USD)
Expedia
From $500 per night (USD)
VRBO
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 $500 per night (USD)
VRBO
From $274 per night (USD)
Expedia
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 $274 per night (USD)
Expedia
From $502 per night (USD)
VRBO
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 $502 per night (USD)
VRBO
From $123 per night (USD)
Expedia
Bay's Hideaway in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just the mere idea of planning a vacation puts a smile on most faces. If your vacation includes a stay in the Conch Repu ...
From $123 per night (USD)
Expedia
From $1074 per night (USD)
VRBO
Quilted Giraffe in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes yo ...
From $1074 per night (USD)
VRBO
From $235 per night (USD)
Expedia
MONTHLY - 1 block from the Seaport and 2 blocks from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This beautifully decorated property has soaring ceilings with a lovely outdoor dining & bbq area and is walking distance ...
From $235 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Land Of Love by AvantStay | Pets Allowed! Shared Pool! Great Location!
Bedrooms:
2
Bathrooms:
3
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 $203 per night (USD)
VRBO
From $238 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 $238 per night (USD)
Expedia
$Ibis by AvantStay | Close to Duval Street w\/ Shared Pool | Month Long Stays Only$
From $182 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 $182 per night (USD)
VRBO
$Easy Livin' by AvantStay | Key West Home w\/ Pool & BBQ | Week Long Stays Only$
From $1521 per night (USD)
Expedia
Easy Livin' by AvantStay | Key West Home w\/ Pool & BBQ | Week Long Stays Only
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for 7+ night stays only.* Cozy, but upscale, this charming vacation rental wit ...
From $1521 per night (USD)
Expedia
$Artist Garden by AvantStay | Great Location w\/ Balcony, Shared Pool & BBQ!$
From $588 per night (USD)
VRBO
Artist Garden by AvantStay | Great Location w\/ Balcony, Shared Pool & BBQ!
Bedrooms:
3
Bathrooms:
3
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 $588 per night (USD)
VRBO
$Paradise Palms by AvantStay | Great Location w\/ Outdoor Dining, BBQ$
From $213 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 $213 per night (USD)
Expedia
$First Breath by AvantStay | Close to Old Town w\/ Pool | Month Long Stays Only$
From $396 per night (USD)
VRBO
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 $396 per night (USD)
VRBO
$Casa de Rosalie by AvantStay | Great Location w\/ Pool, BBQ & Outdoor Dining$
From $475 per night (USD)
Expedia
Casa de Rosalie by AvantStay | Great Location w\/ Pool, BBQ & Outdoor Dining
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for 28+ night stays only.* Built-in 1889 with original Dade County Pine, histo ...
From $475 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Lazy Gecko by AvantStay | Walk to Duval St in Key West! | Month Long Stays Only
Bedrooms:
2
Bathrooms:
3
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 $254 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Priced to book! Sleeps 4- Walking Distance to Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
From $338 per night (USD)
Expedia
$Three Condos w\/ Entertainment, Private Parking & Beach Nearby - Great for Groups$
From $3181 per night (USD)
VRBO
Three Condos w\/ Entertainment, Private Parking & Beach Nearby - Great for Groups
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Three Flowers Guesthouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $3181 per night (USD)
VRBO
$Large waterfront 2\/2 end unit with boat slip$
From $886 per night (USD)
VRBO
Large waterfront 2\/2 end unit with boat slip
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 $886 per night (USD)
VRBO
From $202 per night (USD)
VRBO
The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared Pool & Pet-Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Introducing 'The Oasis' – a beautifully updated 1BR home ideally situated near the intersection of Old Town and the Whit ...
From $202 per night (USD)
VRBO
$Open and spacious home near Key West activities with WiFi, AC, & private W\/D$
From $331 per night (USD)
Expedia
Open and spacious home near Key West activities with WiFi, AC, & private W\/D
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Key West Holidays Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $331 per night (USD)
Expedia
$Ashe St Serenade: 3BD\/3.5BA Luxury Retreat, Private Pool in an Island Oasis.$
From $621 per night (USD)
VRBO
Ashe St Serenade: 3BD\/3.5BA Luxury Retreat, Private Pool in an Island Oasis.
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excite ...
From $621 per night (USD)
VRBO
Click For Pricing
Expedia
Dog-friendly downtown studio near beach with WiFi, AC, fridge, oven, microwave
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Sunshine Casita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
Expedia

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Results: 805 Rentals