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

Beach Club #201

Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes coo...
Condo 2 / 2 / 4

$270 - $400
Per Night

$1820 - $2730
Per Week

La Brisa #206E - Brisa Del Mar

Key West
Let "the breeze" of La Brisa cool you as you relax on your ocean view balcony. This residential con...
Condo 2 / 2 / 4

$200 - $290
Per Night

$1330 - $1960
Per Week

Bali Hideaway

Key West
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an A...
Cottage 1 / 1 / 2

$190 - $250
Per Night

$1260 - $1680
Per Week

A Place in Paradise

Key West
A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 ...
Condo 2 / 3 / 6

$1550 - $3444
Per Week

Southard Sophistication

Key West
30 DAY MINIMUM RENTAL This amazing restoration of a majestic Key West bungalow is incredible. Mo...
Home 2 / 2 / 4

Contact
Owner
Directly
For Rates

Shipyard 106-2

Key West
Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom an...
Condo 1 / 1 / 4

*
Online booking available

$1500 - $2100
Per Week

Atlantic Blues

Key West
ATLANTIC BLUES - A stylish example of a Conch cottage, renovated with gorgeous hardwood floors, be...
Home 2 / 1 / 4

Contact
Owner
Directly
For Rates

Southard Street - Queen Conch

Key West
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet...
Home 4 / 4 / 8

$730 - $930
Per Night

$4900 - $6300
Per Week

Villa Soleil

Key West
VILLA SOLEIL -- Located in the historic Foundry building of Truman Annex, a beautiful gated communit...
Condo 2 / 3 / 6

$1650 - $3553
Per Week

Pete's East Cottage

Key West
This property has it all! This award winning renovation has been completed recently and offers the ...
Home 2 / 1 / 4

$280 - $330
Per Night

$1820 - $2170
Per Week

La Brisa #304W Egrets Landing

Key West
30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy a...
Condo 2 / 2 / 4

Contact
Owner
Directly
For Rates

Bahama Dreaming

Key West
BAHAMA DREAMING: When you're dreaming of the ideal place to stay in Key West, imagine this sweet 3-...
Home 3 / 2 / 8

$465 - $906
Per Night

$2925 - $6018
Per Week

Apr 8 - Apr 30   *** SOUTHARD CHARM FOR A GREAT RATE! *** April spr ...

Southard Charm

Key West
SOUTHARD CHARM (formerly Garden House): A lovely jewel, Southard Charm is a quaint Conch house nest...
Home 3 / 2 / 8

$400 - $856
Per Night

$2650 - $5873
Per Week

Pete's Cottages

Key West
This property has it all! This award winning renovation offers the styling of the original shot g...
Home 4 / 2 / 8

$450 - $620
Per Night

$3010 - $4340
Per Week

Beach Club #204

Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes coo...
Condo 2 / 2 / 4

$270 - $400
Per Night

$1820 - $2730
Per Week

Villa Tropicale

Key West
Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this...
Home 4 / 4 / 8

$710 - $990
Per Night

$4830 - $6790
Per Week

Casa Atlantica One Bedroom

Key West
Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding pro...
Condo 1 / 1 / 2

$170 - $220
Per Night

$1120 - $1470
Per Week

Tranquility

Key West
TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity...
Home 1 / 2 / 3

$210 - $413
Per Night

$1175 - $2465
Per Week

La Brisa #403E Ocean Vista

Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for ...
Condo 2 / 2 / 4

$180 - $280
Per Night

$1190 - $1820
Per Week

La Brisa #303W

Key West
30 DAY MINIMUM RENTAL Let "the breeze" of La Brisa cool you as you relax on your ocean view or natur...
Condo 2 / 2 / 4

Contact
Owner
Directly
For Rates

A Suite Paradise

Key West
A SUITE PARADISE - This lovely home is truly a tropical hideaway tucked away in a secluded Key West ...
Home 2 / 2 / 6

Contact
Owner
Directly
For Rates

Parrot Perch

Key West
PARROT PERCH -- Located in the gated Shipyard Community in prestigious Truman Annex, this home is in...
Condo 2 / 2 / 5

$1175 - $2719
Per Week

Townhomes on Windsor #4

Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete tow...
Home 3 / 3.5 / 6

$558 - $658
Per Night

$3906 - $4606
Per Week

Villa Paradiso

Key West
This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Medit...
Home 3 / 3 / 6

$380 - $540
Per Night

$2450 - $3570
Per Week

Duval Roost

Key West
This sanctuary is located one half block from Duval Street in the heart of Old Town tucked away on a...
Home 3 / 3.5 / 6

$410 - $570
Per Night

$2730 - $3780
Per Week

 

More Getaway Locations and Properties