Florida Keys, Florida Rentals

$425 avg/night

Water Front, Private Boat Dockage, Heated Private Pool, Minutes From Key West.

4 Bedrooms • 3 Bathrooms • Sleeps 8 • Cudjoe Key, Lower Keys, Florida Keys, Florida
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$215 avg/night

Shipyard Treasure by AT HOME IN KEY WEST

2 Bedrooms • 1 Bathrooms • Sleeps 4 • Old Town, Key West, Florida Keys, Florida
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$253 avg/night

Luxury Shark Key waterfront home with beach 10 minutes from downtown Key West

3 Bedrooms • 4 Bathrooms • Sleeps 8 • Key West, Florida Keys, Florida
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$113 avg/night

Beautiful Home on Canal, W/Boat Ramp & Dock, Bikes, & Kayaks

3 Bedrooms • 2 Bathrooms • Sleeps 6 • Breezeswept Beach Estates, Ramrod Key, Lower Keys, Florida Keys, Florida
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$229 avg/night

šŸ SPECIAL Luxurious, Waterview, Two King Suites, Pool, Gym,Tennis, Marina, Bikes

2 Bedrooms • 2.5 Bathrooms • Sleeps 4 • Islamorada Area, Florida Keys, Florida
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$294 avg/night

Beautiful Ocean & Sunrise Views - Sept.-Nov. SPECIAL RATES!

3 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Islamorada Area, Florida Keys, Florida
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$214 avg/night

Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

2 Bedrooms • 2 Bathrooms • Sleeps 8 • Islamorada Area, Florida Keys, Florida
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$214 avg/night

Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

1 Bedrooms • 2 Bathrooms • Sleeps 4 • Islamorada Area, Florida Keys, Florida
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$200 avg/night

Stunning Sunsets over Crystal Clear Water in a family friendly setting

2 Bedrooms • 2 Bathrooms • Sleeps 8 • Sugarloaf Shores, Sugarloaf Key, Lower Keys, Florida Keys, Florida
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$180 avg/night

Tropical Paradise for Family and Boaters

3 Bedrooms • 2 Bathrooms • Sleeps 8 • Tavernier, Key Largo Area, Florida Keys, Florida
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$238 avg/night

Book Now! Just Reduced! Private Single Family Home With Inground Heated Pool

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Marathon, Marathon Area, Florida Keys, Florida
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$179 avg/night

OCEANFRONT 5th Floor End Unit! Pool, Free WiFi, Million Dollar Ocean Views

2 Bedrooms • 2 Bathrooms • Sleeps 4 • Tavernier, Key Largo Area, Florida Keys, Florida
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$257 avg/night

Boli Townhouse - Luxury Rental in Truman Annex - Close to Everything!

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Old Town, Key West, Key West Area, Florida Keys, Florida
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$264 avg/night

Oceanfront Paradise W/ Large Screened Porch & Cable Internet::SPECIAL Aug 1000

2 Bedrooms • 2 Bathrooms • Sleeps 5 • Tavernier, Key Largo Area, Florida Keys, Florida
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$356 avg/night

Breathtaking Waterfront Home! Did not suffer Hurricane Damage. Ready to Rent!

4 Bedrooms • 3 Bathrooms • Sleeps 10 • Marathon Shores, Marathon, Florida Keys, Florida
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$315 avg/night

Beautiful Gulf Front Retreat

3 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Marathon Shores, Marathon Area, Florida Keys, Florida
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$307 avg/night

JAN & FEB Dates Open-WATERFRONT HOME, SPECTACULAR VIEWS, GREAT DOCKAGE, Wifi

3 Bedrooms • 2 Bathrooms • Sleeps 8 • Islamorada Area, Florida Keys, Florida
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$264 avg/night

WATERFRONT HOME-BOATERS DREAM- WONDERFUL DOCKAGE - WiF-CLEAN-NO STORM DAMAGE

3 Bedrooms • 3 Bathrooms • Sleeps 6 • Islamorada Area, Florida Keys, Florida
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$514 avg/night

Mickey and Lynn's House of Windows

3 Bedrooms • 3 Bathrooms • Sleeps 8 • Whispering Pines, Big Pine Key, Lower Keys, Florida Keys, Florida
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$334 avg/night

Spa Villa at Hawks Cay with dock

2 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Duck Key, Marathon Area, Florida Keys, Florida
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$358 avg/night

Truman Annex, Old Town, Key West, Private Setting with Luxury Features

2 Bedrooms • 2.5 Bathrooms • Sleeps 4 • Old Town, Key West Area, Florida Keys, Florida
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$412 avg/night

*Searenity Beach House* - Ocean Front Home with Views of the Atlantic Ocean

3 Bedrooms • 3 Bathrooms • Sleeps 10 • Islamorada Area, Florida Keys, Florida
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$1,061 avg/night

Private 100 Ft Beach front/Ocean front 1 Acre Estate With Heated Pool

5 Bedrooms • 3.5 Bathrooms • Sleeps 12 • Islamorada Area, Florida Keys, Florida
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$221 avg/night

Island Get-a-Way Beautiful Canalfront Home

3 Bedrooms • 3 Bathrooms • Sleeps 8 • Tavernier, Key Largo Area, Florida Keys, Florida
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$243 avg/night

Conch Key Bayfront Cottages With Sailboat included

1 Bedrooms • 1 Bathrooms • Sleeps 2 • Conch Key, Duck Key, Marathon Area, Florida Keys, Florida
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$100 avg/night

Florida Keys Splendor at Hammer Point

2 Bedrooms • 2 Bathrooms • Sleeps 4 • Hammer Point, Tavernier, Key Largo Area, Florida Keys, Florida
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$300 avg/night

Boat, Fish, Swim from Your Own Dock! Vr-003

3 Bedrooms • 2 Bathrooms • Sleeps 6 • Venetian Shores, Islamorada Area, Florida Keys, Florida
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$309 avg/night

Villa Marlin, renovated and remodeled, private sandy beach

3 Bedrooms • 2 Bathrooms • Sleeps 6 • White Marlin Beach, Islamorada Area, Florida Keys, Florida
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$199 avg/night

Serenity at La Brisa

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Key West, Key West Area, Florida Keys, Florida
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$186 avg/night

Deluxe two bedroom, oceanfrnt condo, reasonable rates

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Key West, Key West Area, Florida Keys, Florida
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Avg. $300 per Night

Beachfront, Deluxe 3 BR oceanfront condo, great rates

3 Bedrooms • 2 Bathrooms • Sleeps 8 • Key West, Key West Area, Florida Keys, Florida
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$333 avg/night

Key Largo waterfront home with heated pool and spa, boat dock and kaya

3 Bedrooms • 3 Bathrooms • Sleeps 8 • Anglers Park, Key Largo Area, Florida Keys, Florida
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$110 avg/night

Beautiful 2/2 Waterfront Designer Home for Your Family Getaway

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Big Pine Key, Lower Keys, Florida Keys, Florida
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$167 avg/night

***Hogfish Hideout***

3 Bedrooms • 2 Bathrooms • Sleeps 8 • Summerland Key, Lower Keys, Florida Keys, Florida
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$243 avg/night

NO H. Irma problems. Awesome Horizon Views from Every Room, Protected Boat Dock

3 Bedrooms • 2 Bathrooms • Sleeps 8 • Marathon Shores, Marathon, Florida Keys, Florida
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$250 avg/night

** Waterfront Paradise with Private Beach **

3 Bedrooms • 2 Bathrooms • Sleeps 10 • Islamorada Area, Florida Keys, Florida
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$162 avg/night

Key Largo 3 Bedroom Penthouse Condo with Boat Slip and Bay View

3 Bedrooms • 2.5 Bathrooms • Sleeps 8 • Key Largo Area, Florida Keys, Florida
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$135 avg/night

FANTASTIC FALL DEAL! (And a free Key Lime Pie :)

2 Bedrooms • 2 Bathrooms • Sleeps 6 • White Marlin Beach, Islamorada, Islamorada Area, Florida Keys, Florida
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$257 avg/night

Luxury,Elegant,Water Front Home,Heated Pool,Plantation Key,Islamorada

3 Bedrooms • 2 Bathrooms • Sleeps 8 • Sunshine Estates, Tavernier, Key Largo Area, Florida Keys, Florida
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$167 avg/night

Big Water Views, New Dock With No Neighbors To Scare Off The Key Deer

4 Bedrooms • 2.5 Bathrooms • Sleeps 8 • Sands, Big Pine Key, Lower Keys, Florida Keys, Florida
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Avg. $185 per Night

Water Front Home with Pool and Dock

4 Bedrooms • 2 Bathrooms • Sleeps 8 • Tavernier, Key Largo Area, Florida Keys, Florida
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Avg. $329 per Night

The Best House. Beautiful 3 Bedroom House. Heated Pool, Jacuzzi and Boat Dock

3 Bedrooms • 2 Bathrooms • Sleeps 8 • Marathon Shores, Marathon Area, Florida Keys, Florida
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Avg. $1500 per Night

Exclusive Private Beach, Sunsets, Boating, Water Sports, & Relaxation for 23 Ppl

6 Bedrooms • 4 Bathrooms • Sleeps 22 • Key Largo, Key Largo Area, Florida Keys, Florida
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Avg. $300 per Night

1,400/wk - Best Deal in Key West - Plus 7 Bikes Included!

2 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Stock Island,, Key West Area, Florida Keys, Florida
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Avg. $238 per Night

January Special-Key Largo Waterfront Home W Dock Frm $185 Per Night in January!!

3 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Key Largo, Key Largo Area, Florida Keys, Florida
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Avg. $218 per Night

Rates Reduced!! White Marlin Beach House, Islamorada

2 Bedrooms • 2 Bathrooms • Sleeps 5 • Islamorada Area, Florida Keys, Florida
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Avg. $103 per Night

Paradise Found Here !

4 Bedrooms • 2 Bathrooms • Sleeps 7 • Key Largo, Key Largo Area, Florida Keys, Florida
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Avg. $186 per Night

Tropical Tranquility in the Heart of Islamorada

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Tavernier, Florida, Key Largo Area, Florida Keys, Florida
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Avg. $243 per Night

Spectacular Views and Sunrises

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Tavernier, Florida, Key Largo Area, Florida Keys, Florida
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Avg. $100 per Night

Islamorada Sandy Cove - Keys Paradise!

1 Bedrooms • 1 Bathrooms • Sleeps 4 • Islamorada Area, Florida Keys, Florida
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Avg. $175 per Night

Beautiful 2 Level House on Key Largo on Deep Water Canal.

3 Bedrooms • 3 Bathrooms • Sleeps 8 • Key Largo, Key Largo Area, Florida Keys, Florida
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Avg. $303 per Night

Three Bedroom House with Pool and Dock on a Canal on Lower Matecumbe

3 Bedrooms • 3 Bathrooms • Sleeps 8 • White Marlin Beach, Islamorada Area, Florida Keys, Florida
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Avg. $100 per Night

Plantation by the Sea #215

2 Bedrooms • 1.5 Bathrooms • Sleeps 4 • Plantation by the Sea, Islamorada Area, Florida Keys, Florida
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Avg. $150 per Night

Relaxing Home in the Florida Keys

2 Bedrooms • 2 Bathrooms • Sleeps 4 • Hammer Point, Tavernier, Key Largo Area, Florida Keys, Florida
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From $71 per Night

Perfect Place, Value Priced - Dock, Private Beach, Comfort Inside

2 Bedrooms • 1 Bathrooms • Sleeps 4 • White Marlin Beach, Islamorada Area, Florida Keys, Florida
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From $312 per Night

Luxury New Home with Pool & Dock on the Atlantic Near Key West

2 Bedrooms • 3 Bathrooms • Sleeps 6 • Sunrise Beach Resort, Cudjoe Key, Lower Keys, Florida Keys, Florida
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From $288 per Night

Luxury Retreat Set in Paradise - Anglers Reefx

2 Bedrooms • 2.5 Bathrooms • Sleeps 5 • Islamorada, Islamorada Area, Florida Keys, Florida
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From $210 per Night

Hurry- Nye @ $2000 wk.! 65' Pool+2 Beaches! 30' Dk,Water Views, 6 (2 Dogs)

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Key Colony Beach, Marathon Area, Florida Keys, Florida
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From $295 per Night

2 Bedroom/2 Bath Home with 200 Ft of Deep Water Dockage! Winter Availability!

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Marathon, Marathon Area, Florida Keys, Florida
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From $141 per Night

Paradise Retreat with Special Rates!! Book Now and Save!!

2 Bedrooms • 2 Bathrooms • Sleeps 4 • Key Colony Beach, Marathon Area, Florida Keys, Florida
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From $88 per Night

A Slice of Paradise! Available December and April

2 Bedrooms • 2 Bathrooms • Sleeps 3 • Key Largo Village, Key Largo Area, Florida Keys, Florida
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From $163 per Night

Gorgeous Condo W/Boat Slip on the Bay in Key Largo-Snorkel,Swim,Fish & Relax

2 Bedrooms • 1.5 Bathrooms • Sleeps 4 • Key Largo, Key Largo Area, Florida Keys, Florida
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From $75 per Night

Very Nice 3 Bedroom Home with Large Lot! Basketball Court! Rv Hook up

3 Bedrooms • 2 Bathrooms • Sleeps 5 • Tavernier, Key Largo Area, Florida Keys, Florida
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From $259 per Night

5 Bedroom 3 Bath Beautiful Canal Front Home with Pool

5 Bedrooms • 3 Bathrooms • Sleeps 12 • Whispering Pines (Big Pine Key), Lower Keys, Florida Keys, Florida
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From $107 per Night

Spacious Home in the Florida Keys with Dock and Ocean Access

3 Bedrooms • 2 Bathrooms • Sleeps 8 • Tavernier, Key Largo Area, Florida Keys, Florida
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From $857 per Night

Ocean Front, Beach, Pool, Luxury - 'Turtle Nest Estate'

4 Bedrooms • 4 Bathrooms • Sleeps 10 • Islamorada Area, Florida Keys, Florida
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From $99 per Night

Deals! Monthly Winter Rate! in Paradise!

2 Bedrooms • 1 Bathrooms • Sleeps 4 • Cudjoe Key, Lower Keys, Florida Keys, Florida
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From $1167 per Night

Located on the Northern Tip of Key Largo in the Ocean Reef Yacht and Golf Club

3 Bedrooms • 3 Bathrooms • Sleeps 8 • Ocean Reef Club, Key Largo Area, Florida Keys, Florida
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From $220 per Night

Seaglas-20 Feet from the Gulf--Sept.Thru Oct. $994.00 Per wk . $142.00 Per Nite.

2 Bedrooms • 2.5+ Bathrooms • Sleeps 6 • Marathon Area, Florida Keys, Florida
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From $144 per Night

Deepwater Canal Gem! Boating Paradise! November & December Still Available

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Summerland Key, Lower Keys, Florida Keys, Florida
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From $141 per Night

Summer Promo** Spacious Condo in Futura Yacht Club - Free Boat & Trailer Parking

1 Bedrooms • 1 Bathrooms • Sleeps 6 • Islamorada Area, Florida Keys, Florida
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From $186 per Night

Condo in Paradise....the Best Vacation Spot Ever!

2 Bedrooms • 2 Bathrooms • Sleeps 4 • Key Colony Beach, Marathon Area, Florida Keys, Florida
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From $256 per Night

Key West 'Coral Hammock' - Poolside - 34

3 Bedrooms • 3 Bathrooms • Sleeps 6 • Stock Island, Key West Area, Florida Keys, Florida
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From $155 per Night

Rare! May 21st Just Opened! $999 Pool, Beach Access, Bikes, Dock, Wifi Included!

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Key Colony Beach, Marathon Area, Florida Keys, Florida
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From $305 per Night

Beach House with Private Pool & Dock

2 Bedrooms • 2 Bathrooms • Sleeps 4 • Marathon, Marathon Area, Florida Keys, Florida
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From $156 per Night

Waterfront Dream Great Safe Neighborhood Deep Dockage Fishing

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Marathon, Marathon Area, Florida Keys, Florida
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From $624 per Night

Private Home in Old Town - 3BR & 3.5 Baths

3 Bedrooms • 3.5 Bathrooms • Sleeps 8 • Old Town, Key West Area, Florida Keys, Florida
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From $992 per Night

Perfect for Families, Gatherings, and Weddings Historic Secluded 2 Beach Home

6 Bedrooms • 4.5 Bathrooms • Sleeps 16 • Anglers Park, Key Largo Area, Florida Keys, Florida
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From $139 per Night

Oceanview / Private Balcony/ Free Kayak Use

1 Bedrooms • 1 Bathrooms • Sleeps 5 • Islamorada Area, Florida Keys, Florida
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From $111 per Night

Key West Cottage Off the Beaten Path But Close to Everything You Want.

2 Bedrooms • 1 Bathrooms • Sleeps 4 • Midtown, Key West Area, Florida Keys, Florida
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From $150 per Night

Keys Luxury Oceanfront Paradise - Best Location

3 Bedrooms • 3.5 Bathrooms • Sleeps 8 • Long Key, Islamorada Area, Florida Keys, Florida
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From $170 per Night

Tropical Deep Water Canal with Beautiful Sunsets, Good Rates

3 Bedrooms • 2 Bathrooms • Sleeps 6 • Summerland Key, Lower Keys, Florida Keys, Florida
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From $259 per Night

Oceanfront Angler's Reef, Islamorada, Florida Keys, Slideshow Tour!

2 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Islamorada Area, Florida Keys, Florida
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From $243 per Night

Fisherman's Paradise with Boat Dock by Seven Mile Bridge

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Marathon, Marathon Area, Florida Keys, Florida
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From $254 per Night

4 Bedroom Ocean Front Villa with Heated Pool

4 Bedrooms • 2 Bathrooms • Sleeps 8 • Bay Point, Lower Keys Area, Florida Keys, Florida
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From $1803 per Night

Private Pool, Hot Tub, Parking, Roof Deck, a++ Location - Downtown Key West

6 Bedrooms • 5.5+ Bathrooms • Sleeps 16 • Downtown, Key West Area, Florida Keys, Florida
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From $214 per Night

Cudjoe Key - Water Views from Every Room

2 Bedrooms • 2 Bathrooms • Sleeps 4 • Cudjoe Key, Lower Keys, Florida Keys, Florida
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From $198 per Night

Waterfront Paradise with Private Dockage

1 Bedrooms • 1 Bathrooms • Sleeps 2 • Islamorada, Islamorada Area, Florida Keys, Florida
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From $137 per Night

The Best Location in Buttonwood Bay. Call Now!

2 Bedrooms • 1.5 Bathrooms • Sleeps 6 • Buttonwood Bay, Key Largo Area, Florida Keys, Florida
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From $184 per Night

Tropical Paradise Vacation Getaway

2 Bedrooms • 1.5 Bathrooms • Sleeps 7 • Kawama Yacht Club, Key Largo Area, Florida Keys, Florida
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Beautiful Townhouse on Blackwater Sound

2 Bedrooms • 1.5 Bathrooms • Sleeps 4 • Moon Bay, Key Largo, Key Largo Area, Florida Keys, Florida
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From $155 per Night

Private Beach-Large Pool-Walking Distance:Dining/Fishing/Golf

0 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Key Colony Beach, Marathon Area, Florida Keys, Florida
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From $330 per Night

'Oceanside Oasis' @ Kings Pointe: Direct Ocean Views & 3 BR'S

3 Bedrooms • 2 Bathrooms • Sleeps 6 • Stock Island, Key West Area, Florida Keys, Florida
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From $323 per Night

Walk to Sombrero Beach, Private Pool, Excellent Dock, Tarpon Fishing

3 Bedrooms • 2 Bathrooms • Sleeps 8 • Marathon, Marathon Area, Florida Keys, Florida
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From $348 per Night

Paradise Found*Luxury Oceanfront Key West Oceanside Marina Marina

3 Bedrooms • 2 Bathrooms • Sleeps 7 • Stock Island, Key West Area, Florida Keys, Florida
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From $216 per Night

P62-Pool, 46' Dock and Pool - New 3 BR/2 BA Half Duplex- Key Colony Beach

3 Bedrooms • 2 Bathrooms • Sleeps 6 • Key Colony Beach, Marathon Area, Florida Keys, Florida
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From $185 per Night

Penthouse Condo Sunsets at Key Largo, Kawama Yacht Club Tower

2 Bedrooms • 2 Bathrooms • Sleeps 8 • Kawama Yacht Club, Key Largo Area, Florida Keys, Florida
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From $2600 per Week

Key West 3 Bedroom Condo- Direct Beach Front

3 Bedrooms • 3 Bathrooms • Sleeps 8 • Midtown, Key West Area, Florida Keys, Florida
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From $344 per Night

Keys Home in Anglers Reef with Ocean View, Dock, Community Pool & Private Beach

2 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Islamorada, Islamorada Area, Florida Keys, Florida
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From $397 per Night

Oceanfront Luxury 'Mar Azul'

3 Bedrooms • 2.5 Bathrooms • Sleeps 8 • Marathon, Marathon Area, Florida Keys, Florida
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From $3000 per Month

Waterfront Big Pine Key Paradise

2 Bedrooms • 2 Bathrooms • Sleeps 6 • Big Pine Key, Lower Keys, Florida Keys, Florida
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From $293 per Night

Key West Vacation Townhouse Rental in the Truman Annex

2 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Truman Annex, Key West Area, Florida Keys, Florida
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From $340 per Night

Luxury Oceanfront Resort Home - Voted Best in the Keys!!!

3 Bedrooms • 2.5 Bathrooms • Sleeps 10 • Mariners Club, Key Largo Area, Florida Keys, Florida
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From $393 per Night

Lush Tropical Waterfront Oasis with Heated Pool, Dock and Wifi

4 Bedrooms • 3 Bathrooms • Sleeps 8 • Islamorada, Islamorada Area, Florida Keys, Florida
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From $340 per Night

Garden Home at Ocean Reef ... Own Pool and Dock

3 Bedrooms • 3.5 Bathrooms • Sleeps 6 • Ocean Reef Club, Key Largo Area, Florida Keys, Florida
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From $194 per Night

Island Dreams and Storybook Sunsets in Key West

2 Bedrooms • 2 Bathrooms • Sleeps 5 • Midtown, Key West Area, Florida Keys, Florida
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From $748 per Night

Lower Florida Keys: Private Open Water Executive Quality Estate

4 Bedrooms • 4 Bathrooms • Sleeps 12 • Summerland Key, Lower Keys, Florida Keys, Florida
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From $258 per Night

Villages at Hawks Cay Spa Villa

2 Bedrooms • 2.5 Bathrooms • Sleeps 6 • Duck Key, Marathon Area, Florida Keys, Florida
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