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From $682 per night (USD)
VRBO
Steps from the Sand! Ocean Views, 3 Pools, Nightlife, Near Southernmost Point!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $682 per night (USD)
VRBO
From $867 per night (USD)
VRBO
Authentic Florida Experience! Nightlife, Spa, Oceanfront Pool, Beach Access!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $867 per night (USD)
VRBO
From $2015 per night (USD)
VRBO
Your Florida Adventure Awaits! 2 Contemporary Units, Bike Rental, Onsite Dining!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $2015 per night (USD)
VRBO
From $960 per night (USD)
VRBO
Partial Ocean View Balcony Two Queen Room at Southernmost Beach Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $960 per night (USD)
VRBO
From $1148 per night (USD)
VRBO
Ocean View King Room at Southernmost Beach Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1148 per night (USD)
VRBO
From $855 per night (USD)
VRBO
Experience Florida Like Never Before! Oceanfront Pool, Nightlife, Beach Bar!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $855 per night (USD)
VRBO
From $865 per night (USD)
VRBO
Great for Getaways on the Lush Island of Key West! 3 Poos, Nightlife, Beach Bar!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $865 per night (USD)
VRBO
$3 Partial Ocean View Rooms w\/Balcony & 2 Queen Beds at Southernmost Beach Resort$
From $2307 per night (USD)
VRBO
3 Partial Ocean View Rooms w\/Balcony & 2 Queen Beds at Southernmost Beach Resort
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $2307 per night (USD)
VRBO
From $3013 per night (USD)
VRBO
Get Ready for Your Florida Adventure! 3 Modish Units, Bike Rentals, Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $3013 per night (USD)
VRBO
$Amazing Stay w\/ Fantastic View in Key West! 3 Convenient Rooms, Outdoor Pool$
From $1583 per night (USD)
VRBO
Amazing Stay w\/ Fantastic View in Key West! 3 Convenient 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 $1583 per night (USD)
VRBO
From $434 per night (USD)
VRBO
Your Next Getaway is Here! Deluxe Fantastic View Two Queen Beds, Outdoor Pool
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 $434 per night (USD)
VRBO
$Indoor \/ Outdoor Living in Old Key West$
Click For Pricing
Expedia
Indoor \/ Outdoor Living in Old Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our home is down a quiet lane in the heart of Key West. Walk to Duval Street, organic “fast food,” yoga, beer, fishin ...
Click For Pricing
Expedia
From $1962 per night (USD)
VRBO
4x Pool View Two Queen Beds at The Gates Hotel Key West, Onsite Swimming Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1962 per night (USD)
VRBO
From $1619 per night (USD)
VRBO
Key West Dream! 4 Serene Units, Pool, Restaurant, Parking, Gym!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1619 per night (USD)
VRBO
From $1726 per night (USD)
VRBO
Escape to the Keys! 4 Amazing Units, Pool, Restaurant, On-Site Bar, Parking!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1726 per night (USD)
VRBO
From $1050 per night (USD)
VRBO
2x Pool View Two Queen Beds Rooms at The Gates Hotel Key West!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1050 per night (USD)
VRBO
From $1841 per night (USD)
VRBO
4 Standard 2 Queens Rooms at The Gates Hotel Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1841 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Welcome to a Sun-Soaked Paradise! Discover the History and Soul of Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $462 per night (USD)
VRBO
From $920 per night (USD)
VRBO
Key West Dream! 2 Awesome Units, Pool, Restaurant, Bar, Bike Rentals, Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $920 per night (USD)
VRBO
From $405 per night (USD)
VRBO
Standard Two Queen Beds at The Gates Hotel Key West, Onsite Pool, Bike Rental!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $405 per night (USD)
VRBO
From $460 per night (USD)
VRBO
Key West Getaway! Pool, Restaurant, Bar, Gym, Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $460 per night (USD)
VRBO
From $1214 per night (USD)
VRBO
3 Standard 2 Queens Rooms at The Gates Hotel Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1214 per night (USD)
VRBO
From $1494 per night (USD)
VRBO
3 Pool View 2 Queens Rooms at The Gates Hotel Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1494 per night (USD)
VRBO
From $2191 per night (USD)
Expedia
**CASA AMARILLA @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $2191 per night (USD)
Expedia
$**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR\/2BA Cottage + LAST KEY SERVICES$
From $487 per night (USD)
VRBO
**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR\/2BA Cottage + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You have many ...
From $487 per night (USD)
VRBO
From $1972 per night (USD)
VRBO
Perfect Key West Staycation Perfect For Your Family! Four Relaxing Rooms, 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 $1972 per night (USD)
VRBO
From $294 per night (USD)
VRBO
~Reel Paradise~Beautiful private townhouse in a small gated community.
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $294 per night (USD)
VRBO
From $1421 per night (USD)
Expedia
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PROPERTY: Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will a ...
From $1421 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Looking for Relaxing Location for Your Next Getaway? Premium Ocean View Room
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 $538 per night (USD)
VRBO
From $924 per night (USD)
VRBO
Tropical Experience! 2 Gorgeous Units, Restaurant, Bar, Pool, Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $924 per night (USD)
VRBO
$Classic Key West living w\/ a full kitchen, balcony, & shared pool$
From $501 per night (USD)
VRBO
Classic Key West living w\/ a full kitchen, balcony, & shared pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Baya House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $501 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Ella Varela: Gorgeous Conch Cottage in Key West's Heart, Close to Old Town & Beaches, Dog-Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Ella Varela, a beautifully updated Conch Cottage nestled in the heart of Key West, where your furry friend is ...
From $186 per night (USD)
Expedia
$\LA DOLCE VITA\, OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!$
From $422 per night (USD)
VRBO
\"LA DOLCE VITA\", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
'La Dolce Vita' is located in Old Town, Key West!! Just 3 short blocks to Southernmost Beach and Southernmost Point ...
From $422 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Hyatt Windward Pointe 2 Bedroom
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
★Excellent Key West Location - Oceanside Property - 2-Bedroom - 2-Bathroom - Sleeps 6. ★Very Clean - Very Nice Property ...
From $613 per night (USD)
Expedia
$Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!$
From $390 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $390 per night (USD)
VRBO
$Gulf Getaway | Condo w\/Pool!$
From $284 per night (USD)
Expedia
Gulf Getaway | Condo w\/Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $284 per night (USD)
Expedia
From $892 per night (USD)
VRBO
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $892 per night (USD)
VRBO
From $831 per night (USD)
Expedia
The Mesa House | Close to Duval!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $831 per night (USD)
Expedia
Click For Pricing
VRBO
Luxurious Keywest resort condominium unit on the Atlantic.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax in style at the Hyatt Windward Pointe Resort. Located on the Atlantic Ocean. Enjoy beautiful sunrises from your ow ...
Click For Pricing
VRBO
$SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!$
From $452 per night (USD)
Expedia
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $452 per night (USD)
Expedia
Click For Pricing
VRBO
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For Pricing
VRBO
From $735 per night (USD)
Expedia
Cloud Suite on Duval | Luxury Condo, Epic Location
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Cloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located right in the heart of w ...
From $735 per night (USD)
Expedia
From $508 per night (USD)
VRBO
A PEACE OF PARADISE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with fla ...
From $508 per night (USD)
VRBO
$**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE$
From $743 per night (USD)
Expedia
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $743 per night (USD)
Expedia
From $612 per night (USD)
VRBO
**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SERENITY ON S ...
From $612 per night (USD)
VRBO
From $330 per night (USD)
Expedia
PEAK OF DUVAL | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $330 per night (USD)
Expedia
From $280 per night (USD)
VRBO
THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location, Location, LOCATION!!! Perfectly located in Old Town Key West, this beautifully remodeled 3 bedroom, 2 bathroom ...
From $280 per night (USD)
VRBO
From $693 per night (USD)
VRBO
Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
'The Plantation' is a NO SMOKING or VAPING,3 bed 3 bath townhome located within the gated community of Truman Annex in K ...
From $693 per night (USD)
VRBO
From $293 per night (USD)
VRBO
Atlantic Ocean view across from Smathers Beach - La Brisa - Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Open floor plan, 2 bedroom, 2 bath condo at La Brisa. Gated condo community. Large deep pool with saunas in the pool b ...
From $293 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Roosters Perch at Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to Roosters Perch in Truman Annex, Porter Lane. This large corner duplex is full of natural light and windows. ...
From $456 per night (USD)
Expedia
$12% Off Wk.stay Feb,March & April\n1\/2 mile 2 beach, full kitchen & front porch\n$
From $288 per night (USD)
VRBO
12% Off Wk.stay Feb,March & April\n1\/2 mile 2 beach, full kitchen & front porch\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $288 per night (USD)
VRBO
From $611 per night (USD)
Expedia
The Secret Grotto
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to The Secret Grotto! This spacious 3,220 square foot home is located on nearly a 5,000 square foot lot and fea ...
From $611 per night (USD)
Expedia
From $1030 per night (USD)
VRBO
The Gideon Lowe House - Old Town Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $1030 per night (USD)
VRBO
From $570 per night (USD)
Expedia
Keys to Paradise - Shipyard Truman Annex
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $570 per night (USD)
Expedia
From $1270 per night (USD)
VRBO
Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!
Bedrooms:
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 $1270 per night (USD)
VRBO
Click For Pricing
Expedia
Oceanfront Condo at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You won't find a better steal than a high-season stay in this beautiful and spacious second-floor condo on the Hyatt Win ...
Click For Pricing
Expedia
$One bedroom in the heart of downtown w\/ kitchen$
From $383 per night (USD)
VRBO
One bedroom in the heart of downtown w\/ kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Truman @ Duval - Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $383 per night (USD)
VRBO
From $1114 per night (USD)
Expedia
Nautical Wheeler: Waterfront Home with private Pool & lush landscaping
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1114 per night (USD)
Expedia
$3\/4 Time: Oceanfront, luxury home with private pool & lush landscaping$
From $1259 per night (USD)
VRBO
3\/4 Time: Oceanfront, luxury home with private pool & lush landscaping
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your ...
From $1259 per night (USD)
VRBO
From $1297 per night (USD)
Expedia
Southern Comfort: Luxury Waterfront Home with private pool & lush landscaping
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1297 per night (USD)
Expedia
From $1352 per night (USD)
VRBO
Paris Mango: Waterfront Luxury Home with Ocean View & Heated Private Pool!
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 $1352 per night (USD)
VRBO
From $1373 per night (USD)
Expedia
Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1373 per night (USD)
Expedia
From $1490 per night (USD)
VRBO
Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
Bedrooms:
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 $1490 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $390 per night (USD)
Expedia
$Year Rd. w.7 night stay get 10% Off!.\nFull kitchen & outside area\n1\/2 mile beach$
From $311 per night (USD)
VRBO
Year Rd. w.7 night stay get 10% Off!.\nFull kitchen & outside area\n1\/2 mile beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
GREAT LOCATION Close to beach and All! REASONABLE RATES. W. KITCHEN AND PATIO Come splash in the surf. Come soak up the ...
From $311 per night (USD)
VRBO
From $955 per night (USD)
Expedia
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $955 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Pierre's Perch | Updated Studio, Heated Pool!
Bedrooms:
1
Bathrooms:
0
Sleeps:
2
Summary: Recently renovated micro-efficiency near downtown Key West! The Galleria was once a haven for traveling artists ...
From $368 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Chagall's Studio | Newly Remodeled!
Bedrooms:
1
Bathrooms:
0
Sleeps:
2
Summary: Micro-efficiency near downtown Key West! The Galleria was once a haven for traveling artists who frequented K ...
From $292 per night (USD)
Expedia
Click For Pricing
VRBO
Two Bedroom Condo, Key West, Ocean View 3054374
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hyatt Residence Club Key West – Windward Pointe Two Bedroom Condo – Partial Ocean Views Partial ocean views and lavish ...
Click For Pricing
VRBO
$Large 2\/2 Waterfront Condo Great View Pool & Dock$
From $608 per night (USD)
VRBO
Large 2\/2 Waterfront Condo Great View Pool & Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $608 per night (USD)
VRBO
$Aruba - Downtown Waterfront 2\/2 Dock, Pool, Pet$
From $541 per night (USD)
VRBO
Aruba - Downtown Waterfront 2\/2 Dock, Pool, Pet
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $541 per night (USD)
VRBO
From $1802 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Parking, Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring your family & friends to this 2200sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $1802 per night (USD)
VRBO
$2\/2 Fully Updated Old Town Waterfront Corner Condo$
From $891 per night (USD)
VRBO
2\/2 Fully Updated Old Town Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this fully updated 1350sqft Waterfront corner condo home. Boat sl ...
From $891 per night (USD)
VRBO
From $164 per night (USD)
VRBO
Sunny Apartment with a Large Deck and Great View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming 1 bedroom second floor apartment with a large deck space for dining, sunbathing or watching sunsets. In residen ...
From $164 per night (USD)
VRBO
$Hidden Oasis | Gorgeous Home, w\/ Pvt Pool$
From $573 per night (USD)
VRBO
Hidden Oasis | Gorgeous Home, w\/ Pvt Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Hidden Oasis is a 28-night minimum rental, offering contemporary luxury in the heart of Midtown, Key West. It’s ...
From $573 per night (USD)
VRBO
$**ISLAND BLISS @ CASA MARINA** Spacious Home \/ Pool + LAST KEY SERVICES...$
From $447 per night (USD)
Expedia
**ISLAND BLISS @ CASA MARINA** Spacious Home \/ Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ISLAND BLISS ...
From $447 per night (USD)
Expedia
From $609 per night (USD)
VRBO
Charming, updated home near Duval St. with enclosed patio & walkable location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Coral Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $609 per night (USD)
VRBO
$Hyatt Residence Club Windward Pointe Key West 2br\/2ba\/6ppl$
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Expedia
Hyatt Residence Club Windward Pointe Key West 2br\/2ba\/6ppl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT Windward Pointe. Sleeps 6 people. 2 bedrooms (1King/1Quee ...
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Expedia
Click For Pricing
Expedia
Old Town Conch Cottage completely remodelled and updated
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Located in the heart of Old Town, this rare home has it all. 3 Bedrooms with 3.5 Baths in the Main House. Completed ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For Pricing
Expedia
From $233 per night (USD)
VRBO
2 Bedroom Townhome on Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Escape to paradise with this spacious 2-bedroom townhome in Key West. Ideal for families and couples alike, this propert ...
From $233 per night (USD)
VRBO
From $1614 per night (USD)
VRBO
Ideal Family Stay in Great Location, 4 Pools, Shuttle Service, Near Airport!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $1614 per night (USD)
VRBO
From $859 per night (USD)
VRBO
Beautiful Water Views! Minutes to Southernmost Point! Parking, Onsite Pools!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $859 per night (USD)
VRBO
$Experience Key West w\/ Poolside Bar, Private Terraces & Free Shuttle Service!$
From $1476 per night (USD)
VRBO
Experience Key West w\/ Poolside Bar, Private Terraces & Free Shuttle Service!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $1476 per night (USD)
VRBO
$Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W\/D$
From $303 per night (USD)
VRBO
Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W\/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Coconut Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $303 per night (USD)
VRBO
$**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR\/3.5BA Condo & Pool + LAST KEY SERVI$
From $629 per night (USD)
Expedia
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR\/3.5BA Condo & Pool + LAST KEY SERVI
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! MODERN MAJEST ...
From $629 per night (USD)
Expedia
$The Elizabeth Suite | 1 bed, 1 bath w\/shared pool$
From $466 per night (USD)
VRBO
The Elizabeth Suite | 1 bed, 1 bath w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Elizabeth Suite at The Bayview House, a nightly rental with shared pool. One of 4 units ...
From $466 per night (USD)
VRBO
$The Fleming Suite | 1 bed, 1 bath condo w\/shared pool$
From $584 per night (USD)
Expedia
The Fleming Suite | 1 bed, 1 bath condo w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Fleming Suite at The Bayview House, a 1-bedroom, 1-bathroom nightly rental with a shared ...
From $584 per night (USD)
Expedia
From $204 per night (USD)
VRBO
New Listing-Golf Course Charmer!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully ...
From $204 per night (USD)
VRBO
From $640 per night (USD)
Expedia
Southern Skies, Stylish Home in Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
About this space Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart ...
From $640 per night (USD)
Expedia
From $384 per night (USD)
VRBO
The Speakeasy Inn - Room 1A (1 Queen Bed & 1 Single Bed)
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $384 per night (USD)
VRBO
From $381 per night (USD)
Expedia
Room 2 (1 Queen Bed & Single Sleeper Sofa)
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $381 per night (USD)
Expedia
From $384 per night (USD)
VRBO
Speakeasy Inn -Room 1B-1 Queen Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $384 per night (USD)
VRBO
$Starr's Suite - 2 person K Suite w\/Private Spa!$
From $620 per night (USD)
VRBO
Starr's Suite - 2 person K Suite w\/Private Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, ...
From $620 per night (USD)
VRBO
$**KESTRAL KOVE @ THE GOLF CLUB** Townhome w\/ Community Pool + LAST KEY SERVICES…$
From $369 per night (USD)
VRBO
**KESTRAL KOVE @ THE GOLF CLUB** Townhome w\/ Community Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of va ...
From $369 per night (USD)
VRBO
$Breezy Key West First-Floor Condo w\/ Pool Access$
From $258 per night (USD)
Expedia
Breezy Key West First-Floor Condo w\/ Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $258 per night (USD)
Expedia

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