Florida - Florida Keys Vacation Rental Getaways

Select a vacation destination from the list below.
You can narrow your search by selecting specific travel dates, a price range or other search options.

Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Sunset Dream Bayside Islamorada sleeps 4-6

Islamorada
Located on the bayside in Beautiful Islamorada this 2Br 1 and half bath condo is on the 4th floor wi...
Condo 2 / 1.5 / 6

Contact
Owner
Directly
For Rates

535 Ocean Way Home

Key Largo
This is a very spacious house accommodating up to 14 guess. It's located on a 7,200 sf corner lot at...
Home 3 / 2 / 14

*
Online booking available

Contact
Owner
Directly
For Rates

2/2 corner unit condo just a mile from Sombrero Beach

Marathon
2/2 second floor corner condo completely renovated with canal view! This cute condo has a serene be...
Condo 2 / 2 / 4

*
Online booking available

$1500 - $2000
Per Week

Tarpon, dolphin, cobia--name your fishing season

Marathon
Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. Thi...
Home 3 / 4.5 / 8

*
Online booking available

$3000 - $4000
Per Week

Leeward Isle Key West Retreat

Key West
LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome communi...
Condo 2 / 2 / 4

$275 - $573
Per Night

$1725 - $3516
Per Week

2Br w/ Canal Dock & Backyard Oasis ? Outdoor Tiki Hut, Ba...

Key Largo
2Br w/ Canal Dock & Backyard Oasis ? Outdoor Tiki Hut, Bar & Hot Tub Make the most of the Key Largo...
Home 2 / 2 / 8

*
Online booking available

$907 - $1386
Per Week

4Br/4Ba Home w/ Waterfront Balconies, Docks, Bikes - Near...

Marathon
4Br/4Ba Home w/ Waterfront Balconies, Docks, Bikes - Near Restaurants & Bars A fisherman?s dream, t...
Home 4 / 3 / 12

*
Online booking available

$1100 - $3596
Per Week

Tropical condo with spectacular ocean view

Key Colony Beach
14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area,...
Condo 2 / 2 / 4

*
Online booking available

$1200 - $1479
Per Week

Parrot Perch

Key West
PARROT PERCH: Great location and great value for a great vacation. Parrot Perch is an upstairs 2...
Condo 2 / 2 / 5

$235 - $486
Per Night

$1365 - $3009
Per Week

Panoramic view, deep water dockage

Marathon
Beautiful 3 bedroom home on Flamingo Island. Panoramic view of the harbor from this porch. Downstai...
Home 3 / 3 / 8

*
Online booking available

$3000 - $4000
Per Week

Casa de Rosalie

Key West
CASA DE ROSALIE: This classic 3-bedroom Conch home is located across the street from Bayview Park, ...
Home 3 / 2 / 8

$393 - $393
Per Night

$2750 - $2750
Per Week

Secluded Luxury 4Br Casa Marina East w/ 50' Pool in reope...

Key West
Secluded Luxury 4Br Casa Marina East w/ 50' Pool in reopened Florida Keys Designed by noted histori...
Home 4 / 4.5 / 8

*
Online booking available

$2986 - $2993
Per Week

Sunny View

Key West
SUNNY VIEW - Adorable, affordable, and a great location! You bet! Sunny View is the monthly rental K...
Cottage 1 / 2 / 2

$179 - $179
Per Night

$1250 - $1250
Per Week

Tranquility

Key West
TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity...
Cottage 1 / 1.5 / 4

$215 - $418
Per Night

$1230 - $2603
Per Week

Fall Special !! $1200 per week+tax,hsp on Key Colony Beac...

Key Colony Beach
Fall Special !! $1200 per week+tax,hsp on Key Colony Beach 3/2 Sfh, pool Absolutely charming, warm ...
Home 3 / 2 / 8

*
Online booking available

$1500 - $3200
Per Week

Beach Club #103 - Unique oceanfront living with breathtak...

Key West
Beach Club #103 - Unique oceanfront living with breathtaking views Unique oceanfront living only 65...
Condo 2 / 2 / 6

*
Online booking available

$334 - $503
Per Night

$2212 - $4168
Per Week

3Br w/ Stunning Bay Views from Rooftop Terrace

Marathon
Mariners will find this 3BR/3BA home the perfect retreat after a day on the water. You?ll feel on t...
Villa 3 / 3 / 8

*
Online booking available

$1027 - $2346
Per Week

Artist Garden

Key West
ARTIST GARDEN : 2 bedroom 2.5 bath located in the prestigious Admirals Lane neighborhood of Truman...
Home 2 / 2.5 / 4

$315 - $616
Per Night

$1910 - $4118
Per Week

Sundown Refuge

Key West
SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refug...
Condo 2 / 2 / 5

$330 - $711
Per Night

$2025 - $4060
Per Week

Contemporary 4Br Tropical Oasis on Fleming w/ Private Poo...

Key West
Contemporary 4Br Tropical Oasis on Fleming w/ Private Pool & Hot Tub A fabulous Key West vacation a...
Condo 4 / 3.5 / 10

*
Online booking available

$3785 - $10044
Per Week

Havana Lane: A classic conch cottage with rustic charm

Key West
Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch ...
Home 2 / 2 / 4

*
Online booking available

$361 - $514
Per Night

$2148 - $4408
Per Week

Coral Casita

Key West
Coral Casita - Weekly Vacation Rental Completely re-designed, re-decorated and ready for your isla...
Home 3 / 3 / 8

$245 - $450
Per Night

$1380 - $2781
Per Week

1 bedroom condo at resort, near Sombrero Beach

Marathon
Newly Renovated Condo, Canal Front. Walk To Shopping, Restaurants & Golf. 1 Bedroom, 1 Bath, Sleeps...
Condo 1 / 1 / 4

*
Online booking available

$125 - $129
Per Night

$800 - $900
Per Week

True Paradise

Key West
TRUE PARADISE: Nestled in the ever popular local residential neighborhood known as The Meadows, thi...
Condo 2 / 2 / 4

$214 - $214
Per Night

$1500 - $1500
Per Week

Beach Club #112 - Unique Oceanfront living

Key West
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peacef...
Condo 2 / 2 / 5

*
Online booking available

$334 - $503
Per Night

$2212 - $4168
Per Week

 

More Getaway Locations and Properties