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

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Number of Guests

Bedrooms

Bathrooms
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Price Range

Amenities
  Air Conditioning
  Dishwasher
  Fireplace
  Grill
  Hot Tub (Private)
  Luxury
  Pets Allowed
  Pool (Private)
  Ski-in/Ski-out
  Washer/Dryer
  Wheelchair Accessible

Activities and Interests
  Beach
  Biking
  Boating
  Canoeing
  Casino
  Corporate and Executive
  Disney
  Family Vacations
  Fishing
  Deep Sea Fishing
  Fly Fishing
  For Sale
  Golfing
  Group and Reunion
  Hang Gliding
  Hiking
  Honeymoon
  Horseback Riding
  Hunting
  Kayaking
  Lake
  LegoLand
  Mountain Biking
  Nightclub and Disco
  Over 55 Community
  Rental Exchange
  Sailing
  Scuba Diving
  Skiing
  State National Parks
  Cross Country Skiing
  Snowmobiling
  Spa
  Specials
  Surfing
  Theatre
  Ultra Luxury
  Wedding
  White Water Rafting
  Wind Surfing
  Wineries and Vineyards

Vacation Rental Travel Guide

Front of Home
$7,500/month
Home in Islamorada Florida
5 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals

Aerial View 1
$30,000/month
Home in Plantation Key Florida
4 Beds • 4 Full Baths • Sleeps 10
Keys Holiday Rentals

Back of Home
$8,750/month
Home in Key Largo Florida
4 Beds • 4 Full Baths • Sleeps 10
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

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

Islamorada Oceanfront vacation home rental
$8,800/month
Home in Islamorada Florida
3 Beds • 3 Full Baths • Sleeps 9
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

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

Canal Aerial View
$4,800/month
Home in Key Largo Florida
3 Beds • 2 Full Baths • Sleeps 8
Keys Holiday Rentals

Street-side Entry
$6,000/month
Villa in Islamorada Florida
3 Beds • 3 Full Baths • Sleeps 6
Keys Holiday Rentals

Beach View
$7,850/month
Home in Islamorada Florida
3 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Views from Balcony
$3,500/month
Townhouse in Key Largo Florida
3 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Street View of Home
$3,750/month
Home in Plantation Key Florida
3 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Community Marina
$3,800/month
Townhouse in Key Largo Florida
3 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Private Neighborhood Beach
$5,200/month
Home 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
$2,500/week
Cottage in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

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

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

Aerial
$2,875/month
Townhouse in Key Largo Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Balcony
$1,575/week
Townhouse in Plantation Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Rooftop Views
$3,000/month
Home in Islamorada 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

Living Area 1
$3,150/month
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
$3,360/month
Condo in Key Largo Florida
2 Beds • 1 Full Bath • Sleeps 5
Keys Holiday Rentals

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

Street View
$4,500/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
$4,400/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
$2,200/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

Ocean Views at The Palms
$2,100/month
Condo in Islamorada Florida
1 Bed • 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