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From $1206 per night (USD)
VRBO
Sailor's Son: Waterfront 4 Bedroom 4 bath Luxury Home in Key Cove Landings
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1206 per night (USD)
VRBO
$GOLF VILLA - Monthly Rental - 2BD\/2BA -Community Pool - RealKeyWest$
From $281 per night (USD)
Expedia
GOLF VILLA - Monthly Rental - 2BD\/2BA -Community Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Golf Villa, your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse ...
From $281 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $399 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Sea Breeze at 1800 Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
New Listing January 2022! Sea Breeze at 1800 Atlantic is a two bedroom / two bathroom fully furnished condo located in ...
From $304 per night (USD)
Expedia
From $534 per night (USD)
VRBO
St. Martin Suite | Beautifully Updated, Pool View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: - Welcome to the tropical & relaxing Sunrise Suites Resort, located on the quiet side of Key West! - Just 1 mil ...
From $534 per night (USD)
VRBO
From $555 per night (USD)
Expedia
The Exuma Cay by Brightwild | Pool View & Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $555 per night (USD)
Expedia
$Sunny, Dog-Friendly Historical Home w\/ Private Hot Tub, Central AC, WiFi, & W\/D$
Click For Pricing
VRBO
Sunny, Dog-Friendly Historical Home w\/ Private Hot Tub, Central AC, WiFi, & W\/D
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Casa Eloise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
VRBO
Click For Pricing
Expedia
BEACHFRONT-Coconut Beach Resort, 7 nights only, May 11-18, on Atlantic, beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Private tropical Paradise on the Atlantic Ocean in Key West, Florida. This condo unit is a 1 bedroom, with 2 full bathro ...
Click For Pricing
Expedia
From $338 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $338 per night (USD)
VRBO
$Ocean Front & Ocean View. Across from Smathers beach. Sleeps 6, 2\/2 baths.$
From $423 per night (USD)
VRBO
Ocean Front & Ocean View. Across from Smathers beach. Sleeps 6, 2\/2 baths.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
"Kokomo" is what we have named our unit. It is a 2 bedroom 2 baths with queen sleeper sofa in living room . We sleep 6 g ...
From $423 per night (USD)
VRBO
From $760 per night (USD)
VRBO
Get Ready for Your Florida Adventure! Nightlife, Bike Rentals, 3 Pools, Spa!
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 $760 per night (USD)
VRBO
From $571 per night (USD)
Expedia
1 BLOCK OFF DUVAL! PRIVATE POOL AND HOT TUB
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy one of Old Town's wonderful historic homes with private pool and hot tub. Casa Rosa one of only seventy five remai ...
From $571 per night (USD)
Expedia
From $638 per night (USD)
VRBO
Your Exciting Florida Vacay Starts Here! Nightlife, Island View, Restaurant!
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 $638 per night (USD)
VRBO
From $646 per night (USD)
VRBO
Beachside Dream! Steps to Sand, Pool, Beach Bar, Nightlife! Near Duval Street!
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 $646 per night (USD)
VRBO
From $364 per night (USD)
VRBO
La Mer Dewey Island View Accommodation 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 $364 per night (USD)
VRBO
From $323 per night (USD)
VRBO
Tropical Key West Getaway! Enjoy Island View from your Room, Swimming Pools!
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 $323 per night (USD)
VRBO
From $1293 per night (USD)
VRBO
2 x Partial Ocean View Balcony 2 Queen Beds Rooms at Southernmost Beach Resort
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 $1293 per night (USD)
VRBO
From $332 per night (USD)
VRBO
Your Key West Adventure Awaits! Ocean View, Pool, Outdoor Dining, Nightlife!
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 $332 per night (USD)
VRBO
From $684 per night (USD)
VRBO
Steps From The Sand! Ocean Views, 3 Pools, Onsite Dining, Bike Rental, Nightlife
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 $684 per night (USD)
VRBO
From $574 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 $574 per night (USD)
VRBO
From $452 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 $452 per night (USD)
VRBO
From $664 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 $664 per night (USD)
VRBO
From $718 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 $718 per night (USD)
VRBO
From $375 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 $375 per night (USD)
VRBO
From $641 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 $641 per night (USD)
VRBO
From $563 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 $563 per night (USD)
VRBO
$3 Partial Ocean View Rooms w\/Balcony & 2 Queen Beds at Southernmost Beach Resort$
From $1932 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 $1932 per night (USD)
VRBO
From $995 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 $995 per night (USD)
VRBO
$Amazing Stay w\/ Fantastic View in Key West! 3 Convenient Rooms, Outdoor Pool$
From $1024 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 $1024 per night (USD)
VRBO
From $272 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 $272 per night (USD)
VRBO
$Indoor \/ Outdoor Living in Old Key West$
Click For Pricing
VRBO
Indoor \/ Outdoor Living in Old Key West
Bedrooms:
3
Bathrooms:
2
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
VRBO
From $1326 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 $1326 per night (USD)
VRBO
From $273 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 $273 per night (USD)
VRBO
From $1113 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 $1113 per night (USD)
VRBO
From $693 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 $693 per night (USD)
VRBO
From $646 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 $646 per night (USD)
VRBO
From $665 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 $665 per night (USD)
VRBO
From $1308 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 $1308 per night (USD)
VRBO
From $282 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 $282 per night (USD)
VRBO
From $322 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 $322 per night (USD)
VRBO
From $830 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 $830 per night (USD)
VRBO
From $565 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 $565 per night (USD)
VRBO
From $1152 per night (USD)
VRBO
**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 $1152 per night (USD)
VRBO
$**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR\/2BA Cottage + LAST KEY SERVICES$
From $246 per night (USD)
Expedia
**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 $246 per night (USD)
Expedia
From $331 per night (USD)
VRBO
Dream Vacation! Near Famous Duval Street!
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 $331 per night (USD)
VRBO
From $1318 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 $1318 per night (USD)
VRBO
From $998 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 $998 per night (USD)
VRBO
$Classic Key West living w\/ a full kitchen, balcony, & shared pool$
From $489 per night (USD)
Expedia
Classic Key West living w\/ a full kitchen, balcony, & shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Baya House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $489 per night (USD)
Expedia
From $301 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 $301 per night (USD)
VRBO
From $743 per night (USD)
Expedia
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
Bedrooms:
3
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 $743 per night (USD)
Expedia
From $312 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 $312 per night (USD)
VRBO
From $176 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 $176 per night (USD)
Expedia
$\LA DOLCE VITA\, OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!$
From $456 per night (USD)
VRBO
\"LA DOLCE VITA\", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
'La Dolce Vita' is located in Old Town, Key West!! Just 3 short blocks to Southernmost Beach and Southernmost Point ...
From $456 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Hyatt Windward Pointe 2 Bedroom
Bedrooms:
2
Bathrooms:
2
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 $344 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 $344 per night (USD)
VRBO
$Gulf Getaway by Brightwild | Condo w\/Pool!$
From $290 per night (USD)
Expedia
Gulf Getaway by Brightwild | Condo w\/Pool!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $290 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
From $1090 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $1090 per night (USD)
Expedia
From $1347 per night (USD)
VRBO
The Mesa House by Brightwild | Close to Duval!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $1347 per night (USD)
VRBO
$SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!$
From $774 per night (USD)
Expedia
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $774 per night (USD)
Expedia
Click For Pricing
VRBO
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For Pricing
VRBO
From $810 per night (USD)
Expedia
Cloud Suite on Duval | Luxury Condo, Epic Location
Bedrooms:
3
Bathrooms:
2
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 $810 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 $1092 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 $1092 per night (USD)
Expedia
From $639 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 $639 per night (USD)
VRBO
From $426 per night (USD)
Expedia
PEAK OF DUVAL | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $426 per night (USD)
Expedia
From $275 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 $275 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 $529 per night (USD)
Expedia
Roosters Perch at Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Roosters Perch in Truman Annex, Porter Lane. This large corner duplex is full of natural light and windows. ...
From $529 per night (USD)
Expedia
$Key West Retreat $99.Spec.+extras some dates in Aug & Sept.\n$
From $194 per night (USD)
VRBO
Key West Retreat $99.Spec.+extras some dates in Aug & Sept.\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $194 per night (USD)
VRBO
$One bedroom in the heart of downtown w\/ kitchen$
From $319 per night (USD)
Expedia
One bedroom in the heart of downtown w\/ kitchen
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Truman @ Duval - Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $319 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Varela Street Retreat. $99 spec.+ extras. some dates in Aug. +Sept.
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 $208 per night (USD)
VRBO
From $627 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 $627 per night (USD)
Expedia
From $610 per night (USD)
VRBO
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 $610 per night (USD)
VRBO
From $833 per night (USD)
Expedia
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 $833 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Keys to Paradise - Shipyard Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $495 per night (USD)
VRBO
From $1497 per night (USD)
Expedia
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 $1497 per night (USD)
Expedia
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VRBO
Oceanfront Condo at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
2
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
VRBO
From $1206 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 $1206 per night (USD)
Expedia
$3\/4 Time: Oceanfront, luxury home with private pool & lush landscaping$
From $1397 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 $1397 per night (USD)
VRBO
From $1309 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 $1309 per night (USD)
Expedia
From $1394 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 $1394 per night (USD)
VRBO
From $1778 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 $1778 per night (USD)
Expedia
From $2024 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 $2024 per night (USD)
VRBO
From $242 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 $242 per night (USD)
Expedia
From $283 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 $283 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Chagall's Studio by Brightwild | 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 $369 per night (USD)
Expedia
From $1166 per night (USD)
VRBO
Authentic Key West Adventure! 3 Comfortable Units, 3 Pools, Pets Allowed!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1166 per night (USD)
VRBO
From $1588 per night (USD)
VRBO
Family and Friends Getaway! 4 Comfortable Units, 3 Pools, Onsite Dining!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1588 per night (USD)
VRBO
From $456 per night (USD)
VRBO
Two Bedroom Condo, Key West, Ocean View 3054374
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hyatt Residence Club Key West – Windward Pointe Two Bedroom Condo – Partial Ocean Views Partial ocean views and lavish ...
From $456 per night (USD)
VRBO
$Large 2\/2 Waterfront Condo Great View Pool & Dock$
From $690 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 $690 per night (USD)
VRBO
$Aruba - Downtown Waterfront 2\/2 Dock, Pool, Pet$
From $703 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 $703 per night (USD)
VRBO
From $700 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 $700 per night (USD)
VRBO
$2\/2 Fully Updated Old Town Waterfront Corner Condo$
From $437 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 $437 per night (USD)
VRBO
From $153 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 $153 per night (USD)
VRBO
$Hyatt Residence Club Windward Pointe Key West 2br\/2ba\/6ppl$
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
$Hidden Oasis | Gorgeous Home, w\/ Pvt Pool$
From $390 per night (USD)
Expedia
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 $390 per night (USD)
Expedia
$**ISLAND BLISS @ CASA MARINA** Spacious Home \/ Pool + LAST KEY SERVICES...$
From $336 per night (USD)
VRBO
**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 $336 per night (USD)
VRBO
From $390 per night (USD)
Expedia
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 $390 per night (USD)
Expedia

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