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

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Vacation Rental Travel Guide

Gorgeous Bay Views
$3,800/week
Cottage in Islamorada Florida
4 Beds • 3 Full Baths • Sleeps 12
Keys Holiday Rentals

Front of Home
$7,850/month
Home in Islamorada Florida
4 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals

Front of Home
$5,500/month
Home in Key Largo Florida
4 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals

Outdoor Area
$6,500/month
Home in Plantation Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals

View of Bay
$9,500/month
Home in Plantation Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals

Private Fishing Pier
$18,500/month
Home in Islamorada Florida
4 Beds • 3 Full Baths • Sleeps 8
Keys Holiday Rentals

Back of Home
$9,975/month
Home in Plantation Key Florida
4 Beds • 3 Full Baths • Sleeps 8
Keys Holiday Rentals

Balcony Views
$7,900/month
Home in Islamorada Florida
4 Beds • 3 Full Baths • Sleeps 8
Keys Holiday Rentals

View of Ocean From Home
$5,500/month
Home in Islamorada Florida
3 Beds • 3 Full Baths • Sleeps 8
Keys Holiday Rentals

Canal Aerial View
$4,800/month
Home in Key Largo Florida
3 Beds • 3 Full Baths • Sleeps 8
Keys Holiday Rentals

Pool
$5,950/month
Home in Tavernier Florida
3 Beds • 2 Full Baths • Sleeps 8
Keys Holiday Rentals

Beach View
$8,250/month
Home in Islamorada Florida
3 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Rooftop Views
$3,000/month
Home in Islamorada Florida
3 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Antigua Place Islamorada Florida Keys Holiday Rentals
$5,600/month
Home in Islamorada Florida
3 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Oceanfront Covered Seating
$7,000/month
Condo in Islamorada Florida
3 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Pool
$2,300/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Palms from the Water
$3,100/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Dockage
$3,675/month
Home in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Endless Water Views
$2,750/week
Cottage in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Endless Views of the Water
$3,000/week
Apartment in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Endless Water Views
$3,000/week
Apartment in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Aerial
$3,100/month
Townhouse in Key Largo Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Balcony
$1,475/week
Townhouse in Plantation Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Balcony Views
$2,300/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

MOON BAY A206 Key Largo Florida Keys Holiday Rentals
$1,325/week
Condo in Key Largo Florida
2 Beds • 1 Full Bath • Sleeps 6
Keys Holiday Rentals

Views from Balcony
$2,575/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 5
Keys Holiday Rentals

Pool
$2,400/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 5
Keys Holiday Rentals

Canal
$4,000/month
Home in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 5
Keys Holiday Rentals

Pool
$1,175/week
Condo in Key Largo Florida
2 Beds • 1 Full Bath • Sleeps 5
Keys Holiday Rentals

View from Balcony
$4,000/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

View from Balcony
$3,400/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Pool & Hot Tub
$3,300/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Grounds at The Palms
$2,400/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Balcony View
$3,000/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Street View
$5,000/month
Home in Plantation Key Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Marina
$4,250/month
Condo in Tavernier Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Aerial of Beacon Reef
$3,000/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Views from Balcony
$4,650/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

View from Balcony
$4,300/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Kitchen
$2,600/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Aerial of Beacon Reef
$3,500/month
Home in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Beacon Reef from Dock
$3,000/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

The Palms from the Water
$1,900/month
Condo in Islamorada Florida
1 Bed • 1 Full Bath • Sleeps 4
Keys Holiday Rentals

Views from Property
$1,350/week
Apartment in Islamorada Florida
1 Bed • 1 Full Bath • Sleeps 3
Keys Holiday Rentals

Ocean Views at The Palms
$2,100/month
Condo in Islamorada Florida
1 Bed • 2 Full Baths • Sleeps 2
Keys Holiday Rentals