Skip to Main Content.
Download the app button
Download the app button with download icon
Get the app
United States
Trip Boards
List your property
Help
My trips
Sign in
Vrbo just got better
Earn rewards across our family of brands with One Keyâ„¢
Sign in
Sign in as an owner
Learn about One Key
Feedback
Opens in a new window
Beginning of main content
Going to
Going to
Dates
Dates
Travelers
Adults
Adults
Decrease the number of adults
Increase the number of adults
Children
Ages 0 to 17
Decrease the number of children
Increase the number of children
I am traveling with pets
If checked, only properties that allow pets will be shown
Done
Search
Filters
Popular
Price
Rooms & spaces
Sort by recommended
300+ properties
How our sort order works
Opens in a new window
Search results showing properties in South Beach, Key West, Florida, United States of America
Google map showing 500 properties
Photo gallery for Unique Home with loft @ Truman Annex
Sunset... - Now you know why we named the home "Sunset on Southard"
Show previous image for Unique Home with loft @ Truman Annex
Show next image for Unique Home with loft @ Truman Annex
Premier Host
Condo · 0.74 mi from South Beach
Unique Home with loft @ Truman Annex
Sleeps 4 · 1 bedroom · 1 bathroom
9.8/10
Exceptional
(103 reviews)
9.8 out of 10 Exceptional (103 reviews)
The price is $260
$260
avg per night
avg per night
More information about Unique Home with loft @ Truman Annex, opens in a new tab
Photo gallery for Poolside Cottage #411
Pool
Show previous image for Poolside Cottage #411
Show next image for Poolside Cottage #411
Premier Host
House · 3.14 mi from South Beach
Poolside Cottage #411
Sleeps 6 · 1 bedroom · 1 bathroom
10/10
Exceptional
(13 reviews)
10 out of 10 Exceptional (13 reviews)
The price is $216
$216
avg per night
avg per night
More information about Poolside Cottage #411, opens in a new tab
Photo gallery for Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Living Room - Living room with a lot of natural light
Show previous image for Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Show next image for Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Apartment · 0.7 mi from South Beach
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Sleeps 2 · 1 bedroom · 1 bathroom
9.0/10
Wonderful
(4 reviews)
9.0 out of 10 Wonderful (4 reviews)
The price is $123
$123
avg per night
avg per night
More information about Little Casita: Key West Monthly rental Close to Duval - RealKeyWest, opens in a new tab
Apartment · 0.4 mi from South Beach
Steps from Duval, Pool & Bikes $129-$299 Night!
Sleeps 2 · 1 bathroom
9.6/10
Exceptional
(327 reviews)
9.6 out of 10 Exceptional (327 reviews)
The price is $194
$194
avg per night
avg per night
More information about Steps from Duval, Pool & Bikes $129-$299 Night!, opens in a new tab
Condo · 1.28 mi from South Beach
Your Condo by the Beach with Ocean View
Sleeps 2 · 1 bedroom · 1 bathroom
10/10
Exceptional
(143 reviews)
10 out of 10 Exceptional (143 reviews)
The price is $327
$327
avg per night
avg per night
More information about Your Condo by the Beach with Ocean View, opens in a new tab
Condo · 0.69 mi from South Beach
THE GOOD LIFE ~ Charming 1 Bedroom, 1 Bath Truman Annex Condo!
Sleeps 2 · 1 bedroom · 1 bathroom
10/10
Exceptional
(14 reviews)
10 out of 10 Exceptional (14 reviews)
The price is $286
$286
avg per night
avg per night
More information about THE GOOD LIFE ~ Charming 1 Bedroom, 1 Bath Truman Annex Condo!, opens in a new tab
House · 0.25 mi from South Beach
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
Sleeps 4 · 1 bedroom · 1 bathroom
9.8/10
Exceptional
(58 reviews)
9.8 out of 10 Exceptional (58 reviews)
The price is $388
$388
avg per night
avg per night
More information about KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!, opens in a new tab
Condo · 1.13 mi from South Beach
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Sleeps 4 · 1 bedroom · 1 bathroom
9.8/10
Exceptional
(257 reviews)
9.8 out of 10 Exceptional (257 reviews)
The price is $367
$367
avg per night
avg per night
More information about Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym, opens in a new tab
Condo · 1.25 mi from South Beach
Beach House with Ocean View-No Contact Check-In
Sleeps 4 · 1 bedroom · 1 bathroom
9.8/10
Exceptional
(132 reviews)
9.8 out of 10 Exceptional (132 reviews)
The price is $238
$238
avg per night
avg per night
More information about Beach House with Ocean View-No Contact Check-In, opens in a new tab
Apartment · 0.35 mi from South Beach
Charming 2nd-story apartment with balcony & lighthouse view - walk everywhere
Sleeps 2 · 1 bedroom · 1 bathroom
9.6/10
Exceptional
(4 reviews)
9.6 out of 10 Exceptional (4 reviews)
The price is $296
$296
avg per night
avg per night
More information about Charming 2nd-story apartment with balcony & lighthouse view - walk everywhere, opens in a new tab
Cottage · 0.92 mi from South Beach
Heart of Downtown Key West Cottage With Off-Street Parking
Sleeps 3 · 2 bedrooms · 1 bathroom
10/10
Exceptional
(97 reviews)
10 out of 10 Exceptional (97 reviews)
The price is $333
$333
avg per night
avg per night
More information about Heart of Downtown Key West Cottage With Off-Street Parking, opens in a new tab
Apartment · 0.42 mi from South Beach
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Sleeps 2 · 1 bedroom · 1 bathroom
9.0/10
Wonderful
(182 reviews)
9.0 out of 10 Wonderful (182 reviews)
The price is $199
$199
avg per night
avg per night
More information about Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC, opens in a new tab
House · 0.39 mi from South Beach
**SWEPT AWAY @ OLD TOWN** Dreamy Private Home & Pool + LAST KEY SERVICES...
Sleeps 4 · 2 bedrooms · 2 bathrooms
10/10
Exceptional
(8 reviews)
10 out of 10 Exceptional (8 reviews)
The price is $200
$200
avg per night
avg per night
More information about **SWEPT AWAY @ OLD TOWN** Dreamy Private Home & Pool + LAST KEY SERVICES..., opens in a new tab
Condo · 0.71 mi from South Beach
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Sleeps 5 · 2 bedrooms · 1 bathroom
10/10
Exceptional
(151 reviews)
10 out of 10 Exceptional (151 reviews)
The price is $310
$310
avg per night
avg per night
More information about MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West, opens in a new tab
House · 3.86 mi from South Beach
Paradise found at the Key West Golf Club!
Sleeps 4 · 2 bedrooms · 1+ bathroom
9.8/10
Exceptional
(19 reviews)
9.8 out of 10 Exceptional (19 reviews)
The price is $163
$163
avg per night
avg per night
More information about Paradise found at the Key West Golf Club!, opens in a new tab
House · 0.55 mi from South Beach
~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.
Sleeps 2 · 1 bedroom · 1 bathroom
9.6/10
Exceptional
(146 reviews)
9.6 out of 10 Exceptional (146 reviews)
The price is $235
$235
avg per night
avg per night
More information about ~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat., opens in a new tab
Condo · 0.71 mi from South Beach
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Sleeps 2 · 1 bedroom · 1 bathroom
10/10
Exceptional
(267 reviews)
10 out of 10 Exceptional (267 reviews)
The price is $245
$245
avg per night
avg per night
More information about Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi, opens in a new tab
House · 0.89 mi from South Beach
GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!
Sleeps 2 · 1 bedroom · 1 bathroom
10/10
Exceptional
(6 reviews)
10 out of 10 Exceptional (6 reviews)
The price is $127
$127
avg per night
avg per night
More information about GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!, opens in a new tab
Tell us how we can improve our site
Share feedback