Vacation Rentals by Keys Holiday Rentals - Representing Vacation Rental Properties along the 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
  Fishing
  Deep Sea Fishing
  For Sale
  Golfing
  Group and Reunion
  Honeymoon
  Horseback Riding
  Hunting
  Lake
  Mountain Biking
  State National Parks
  Nightclub and Disco
  Over 55 Community
  Sailing
  Scuba Diving
  Skiing
  Cross Country Skiing
  Snowmobiling
  Spa
  Surfing
  Theatre
  Wedding
  White Water Rafting
  Wineries and Vineyards
  Fly Fishing
  Wind Surfing
  Hang Gliding
  Disney
  LegoLand
  Hiking
  Rental Exchange
  Specials
  Ultra Luxury
  Family Vacations
  Kayaking

Vacation Rental Travel Guide

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

Back of Home
$8,750/month
Home in Islamorada Florida
4 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals

Front of Home
$6,500/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
$11,000/month
Home in Plantation Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals

Community Beach Access with this rental
$7,900/month
Home in Islamorada Florida
4 Beds • 3 Full Baths • Sleeps 8
Keys Holiday Rentals

Aerial of Home
$11,750/month
Home in Tavernier Florida
4 Beds • 3 Full Baths • Sleeps 8
Keys Holiday Rentals

Back of Home
$11,000/month
Home in Plantation Key Florida
4 Beds • 3 Full Baths • Sleeps 6
Keys Holiday Rentals

Canal Aerial View
Home in Key Largo Florida
3 Beds • 3 Full Baths • Sleeps 8
Keys Holiday Rentals

Pool
$6,450/month
Home in Tavernier Florida
3 Beds • 2 Full Baths • Sleeps 8
Keys Holiday Rentals

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

Rooftop Views
$3,500/month
Home in Islamorada Florida
3 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Neighborhood Private Beach
$6,200/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

Palms Aerial
$2,800/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Dockage
$4,300/month
Home in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Endless Water Views
$3,000/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
$1,595/week
Townhouse in Plantation Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Balcony Views
$2,900/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 6
Keys Holiday Rentals

Pool and Wade Pool
$1,325/week
Condo in Key Largo Florida
2 Beds • 1 Full Bath • Sleeps 6
Keys Holiday Rentals

Views from Balcony
$3,000/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 5
Keys Holiday Rentals

Balcony View
$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

Picnic & BBQ Area
$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
$3,700/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Beacon Reef Aerial View
$3,300/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

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

Views from Balcony
$3,375/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

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

Beacon Reef from Dock
$3,700/month
Condo in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

Hot Tub and Pool Views
$4,800/month
Home in Islamorada Florida
2 Beds • 2 Full Baths • Sleeps 4
Keys Holiday Rentals

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

Views from Property
$1,450/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