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Vacation Rentals by Keys Holiday Rentals - Representing vacation rental properties in the captivating Islands of the Upper Florida Keys!

Showing 1-48 of 51 Rentals

Sunrise on Sunset
Home in Islamorada Florida
Islamorada Oceanfront vacation home rental
$9,000/month

PARADISE
Home in Plantation Key Florida
Aerial View 1
$30,000/month

TROPICAL OASIS
Home in Key Largo Florida
Back of Home
$8,750/month

LYONS LANDING
Home in Islamorada Florida
Front of Home
$7,850/month

TWICE THE CHARM
Home in Key Largo Florida
Front of Home
$5,500/month

PLANTATION ADVENTURE
Home in Plantation Key Florida
Outdoor Area
$6,500/month

CONCH BAR SOUTH
Home in Plantation Key Florida
View of Bay
$9,500/month

PALM HARBOR
Home in Plantation Key Florida
Back of Home
$9,975/month

CRYSTAL CLEAR BAY HOME
Home in Plantation Key Florida
Balcony Views
$7,500/month

GULFVIEW GETAWAY
Home in Islamorada Florida
Dock
$9,500/month

BLUE WATER RETREAT
Home in Islamorada Florida
View of Ocean From Home
$5,500/month

CASA DORADO
Home in Islamorada Florida
Private Fishing Pier
$18,500/month

MANATEE MANOR
Home in Tavernier Florida
Pool
$5,950/month

Bay Therapy
Home in Key Largo Florida
Canal Aerial View
$4,800/month

MOSAIC HOUSE
Villa in Islamorada Florida
Street-side Entry
$6,000/month

MY PARADISE
Home in Islamorada Florida
Beach View
$7,850/month

KEY LARGO YACHT CLUB 8
Townhouse in Key Largo Florida
Views from Balcony
$3,500/month

Bayside Breeze
Home in Plantation Key Florida
Street View of Home
$3,750/month

KEY LARGO YACHT CLUB 20
Townhouse in Key Largo Florida
Community Marina
$3,800/month

Antigua Place
Home in Islamorada Florida
Private Neighborhood Beach
$5,200/month

PALMS 301
Condo in Islamorada Florida
Pool
$2,300/month

PALMS 405
Condo in Islamorada Florida
Palms from the Water
$3,100/month

VILLA RIOLO
Home in Islamorada Florida
Dockage
$3,675/month

LITTLE BAY - Cottage
Cottage in Islamorada Florida
Endless Water Views
$2,500/week

LITTLE BAY - Lower Duplex
Apartment in Islamorada Florida
Endless Views of the Water
$2,500/week

LITTLE BAY - Upper Duplex
Apartment in Islamorada Florida
Endless Water Views
$2,500/week

ROCK HARBOR CLUB P-8
Townhouse in Key Largo Florida
Aerial
$2,875/month

BROCK HAUS ON THE GULF
Townhouse in Plantation Key Florida
Balcony
$1,575/week

FLAMINGO COTTAGE
Home in Islamorada Florida
Rooftop Views
$3,000/month

PALMS 404
Condo in Islamorada Florida
Balcony Views
$2,300/month

MOON BAY A206
Condo in Key Largo Florida
Living Area 1
$3,150/month

PALMS 309
Condo in Islamorada Florida
Views from Balcony
$2,575/month

PALMS 314
Condo in Islamorada Florida
Pool
$2,400/month

WEST PLAZA DEL LAGO
Home in Islamorada Florida
Canal
$4,000/month

MOON BAY A410
Condo in Key Largo Florida
Pool
$3,360/month

Beacon Reef 222
Condo in Islamorada Florida
View from Balcony
$4,400/month

BEACON REEF 310
Condo in Islamorada Florida
View from Balcony
$3,300/month

BEACON REEF 501
Condo in Islamorada Florida
Pool & Hot Tub
$3,300/month

PALMS 214
Condo in Islamorada Florida
Balcony Views
$2,300/month

PALMS 402
Condo in Islamorada Florida
Grounds at The Palms
$2,400/month

PALMS 407
Condo in Islamorada Florida
Balcony View
$2,400/month

BEBA'S REEF HOUSE
Home in Plantation Key Florida
Street View
$4,500/month

SUNSET HAMMOCK 4B
Condo in Tavernier Florida
Marina
$4,250/month

BEACON REEF 406
Condo in Islamorada Florida
Aerial of Beacon Reef
$3,000/month

BEACON REEF 522
Condo in Islamorada Florida
Views from Balcony
$4,400/month

BEACON REEF 503
Condo in Islamorada Florida
View from Balcony
$4,300/month

Palms 313
Condo in Islamorada Florida
Kitchen
$2,200/month

PALMS 417
Condo in Islamorada Florida
Ocean Views at The Palms
$2,100/month