Florida - Florida Keys Vacation Rental Getaways

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  • Property Options
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  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
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  • Ski in/out
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  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

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

2 Br, 2 Ba Margaritavilla Beach Cottage In Old Town

Key West
IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you ...
Cottage 2 / 2 / 6

$350 - $660
Per Night

La Dolce Vita, Steps to Duval! 3 blks to South Beach!

Key West
La Dolce Vita is a one bedroom, one bath condo located in Heart of the Historic District of Old Tow...
Condo 1 / 1 / 4

$188 - $288
Per Night

$1200 - $1800
Per Week

2 Br, 1 Ba Margaritavilla Beach Cottage In Old Town

Key West
IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you ...
Cottage 2 / 1 / 6

$290 - $516
Per Week

535 Ocean Way Home

Key Largo
This is a very spacious 2,352 sf canal front house accommodating up to 12 guess. It is fully furnish...
Home 3 / 2 / 12

*
Online booking available

Contact
Owner
Directly
For Rates

Sunset Villas Conch Key Open Water 2-Bed Dockage Ramp

Conch Key - Marathon
Sunset Villas on Conch Key offers 1 and 2 bedroom OPEN WATER FRONT accommodations with dockage and u...
Villa 2 / 1 / 4

$159 - $199
Per Night

$995 - $1295
Per Week

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

1 Br Margaritavilla Beach Cottage In Old Town Key West

Key West
IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you...
Cottage 1 / 1 / 2

$240 - $468
Per Night

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

Pete's Cottages: Twin Cypress cottages steps from Duval

Key West
This property has it all! The styling of the original shot gun homes of Key West restored with a bea...
Home 4 / 2 / 8

*
Online booking available

$451 - $626
Per Night

$3218 - $6300
Per Week

Osprey

Key West
OSPREY - This bright and colorful studio Key West rental cottage is located in the same small commun...
Cottage 0 / 1 / 2

$125 - $385
Per Night

$875 - $2695
Per Week

A Little Slice Of Paradise

Key West
A LITLE SLICE OF PARADISE: Imagine yourself in a secluded, gated community steps from the golf cours...
Home 2 / 1.5 / 6

$157 - $157
Per Night

$1099 - $1099
Per Week

Lovely Key Colony Beach 3/2 Sfh, pool, 80" deep water doc...

Key Colony Beach
Lovely Key Colony Beach 3/2 Sfh, pool, 80" deep water dockage Absolutely charming, warm and invitin...
Home 3 / 2 / 8

*
Online booking available

$2100 - $3300
Per Week

Duval Breeze

Key West
DUVAL BREEZE: 2 bedroom 2.5 bath townhome in Duval Square. 1st floor offers an open floor plan w...
Home 2 / 2.5 / 6

$210 - $550
Per Night

$1470 - $3850
Per Week

The Hemingway

Key West
THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Tr...
Condo 2 / 2 / 4

$210 - $550
Per Night

$1470 - $3850
Per Week

Key West Ginger House

Key West
KEY WEST GINGER HOUSE: 2 bedrooms, 2 full baths ensuite. Historic home built in 1933 takes adv...
Home 2 / 2 / 6

$200 - $550
Per Night

$1400 - $3850
Per Week

Duval Square Retreat: A beautiful condo steps from the ac...

Key West
Duval Square Retreat: A beautiful condo steps from the action Duval Square - The Retreat. In the he...
Condo 2 / 2.5 / 4

*
Online booking available

$307 - $550
Per Night

$2022 - $3850
Per Week

Crowner's Jewel

Key West
CROWNER'S JEWEL: Delightful 2 bedroom 2.5 bath Conch-style townhome in the quiet gated community o...
Condo 2 / 2.5 / 6

$225 - $605
Per Night

$1575 - $4235
Per Week

Sip your coffee looking out to a tropical sunrise

Marathon
Picture yourself on a tropical island, half-asleep in a poolside lounge chair of your own private ho...
Home 4 / 3 / 10

*
Online booking available

$4200 - $5800
Per Week

Ann Street Cottage: A bright and airy home near Duval Street

Key West
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a ch...
Cottage 1 / 1.5 / 2

*
Online booking available

$271 - $431
Per Night

$1811 - $2800
Per Week

Key West Found

Key West
KEY WEST FOUND: 2 bedroom, 2.5 bath townhome in the historic brick Foundry building within the Trum...
Home 2 / 2.5 / 6

$250 - $660
Per Night

$1750 - $4620
Per Week

Finn Key

Key West
FINN KEY: 2 bedroom 1 bath downstairs condo in The Shipyard section of Truman Annex, one of the most...
Condo 2 / 1 / 4

$180 - $462
Per Night

$1260 - $3234
Per Week

Newly Renovated Condo, Canal Front. Walk To Shopping, Res...

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

*
Online booking available

$125 - $150
Per Night

$800 - $1000
Per Week

Conch Corner

Key West
CONCH CORNER: Here's a little gem in a long-established local residential neighborhood just across f...
Home 3 / 3 / 6

$214 - $214
Per Night

$1500 - $1500
Per Week

Southard Street Queen Conch - A Historic compound with la...

Key West
Southard Street Queen Conch - A Historic compound with large sunny pool On a lovely tree-lined resi...
Home 4 / 4 / 8

*
Online booking available

$713 - $960
Per Night

$5094 - $9800
Per Week

 

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