Make a Florida Upper Keys vacation rental your home away from home in the Florida Keys.

Guests of Islamadora vacation rentals will find great fishing and diving opportunities here. Highlights for guests of Islamadora vacation rentals include hiking along the nature trails at Long Key State Recreation Area and visiting the Windley Key Quarry Fossil Reef State Geologic Site. The Theater of the Sea, on Windley Key, features shows starring dolphins and other sea creatures.

The northernmost island in the Florida Keys, Key Largo is just an hour’s drive south of Miami. Guests of Key Largo vacation rentals will find a number of local operators offering snorkeling and diving trips, as well as plenty of fishing charters. Other attractions for guests of Key Largo vacation rentals include kayaking and bird watching in the nearby Everglades. Tavernier vacation rentals are also a popular choice in the Upper Keys.

You're sure to find the perfect Upper Florida Keys vacation rental for a fabulous Florida vacation. Reserve your Upper Florida Keys vacation rental today!

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Siesta Key rentals on the Gulf Coast, or Orlando vacation home rentals near Disney.

Upper Florida Keys Vacation Rentals

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Key Largo Historic Secluded Oceanfront 2 house property on 2.5 acres

— Property 174214
Upper Florida Keys estate rental - Photo of Main house from center dock
6 Bedrooms, Sleeps 16,
Estate, 3 Bathrooms, beach, waterfront, garden
Rates - per property (USD)
$575/night
$4,000/week
Calendar Updated Nov 9 2009

Property Review

This was the third time I've celebrated my birthday at Shadow Point and the fifth time I've met there with a large group of people! All 14 of us left happy and relaxed. It was the best the place...
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Elegant Bayfront Key Largo Estate

— Property 237757
Upper Florida Keys house rental - Home view from the dock
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, waterfront, balcony
Rates - per property (USD)
$6,000 - $7,000/month
Calendar Updated Nov 9 2009

Property Review

We highly recommend the stay at this house. Every little detail is included. We had a great time here. We were able to swim, fish, and hang out by the dock.
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Spectacular Oceanfront View Condo Newly Remodeled

— Property 255809
Upper Florida Keys condo rental - Lanai, Southeast
1 Bedroom, Sleeps 2,
Condo, 1 Bathroom, village, waterfront, pool
Rates - per property (USD)
$800 - $950/week
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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

— Property 231645
Upper Florida Keys condo rental - Bayside is a first floor apartment
1 Bedroom, Sleeps 4,
Condo, 2 Bathrooms, waterfront, pets considered
Rates - per property (USD)
$1,095 - $1,295/week
$4,000 - $4,500/month
Calendar Updated Nov 9 2009

Property Review

My husband and I have stayed in the Keys dozens of times and this is by far the nicest place we've been. The landscaping is beautiful, the view can't be beat. The apartment was spotless and very...
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Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

— Property 231642
Upper Florida Keys cottage rental - Our Pelican Greets you at the Front Door
2 Bedrooms, Sleeps 8,
Cottage, 2 Bathrooms, beach, near the ocean, pets considered
Rates - per property (USD)
$1,095 - $1,295/week
$4,000 - $4,500/month
Calendar Updated Nov 9 2009

Property Review

Great native surroundings, including an iguana. Squirrels ate grapes right out of our hands. House was spotless. Doors a bit tough to secure, tho. Plenty of amenities available(everything we...
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Waterfront Cottage - Beach and Dockage! Wireless Internet!

— Property 225990
Upper Florida Keys house rental - Exterior photo facing the water
2 Bedrooms, Sleeps 4,
House, 1 Bathroom, beach, waterfront, air-conditioning
Rates - per property (USD)
$125 - $150/night
$750 - $950/week
Calendar Updated Nov 9 2009

Property Review

stayed at the banana cabana in late may 06 for a fishing trip. great place to stay. put in and docked right there (16ft boat). clean and comfy. close to everything you might need or want to...
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Keys with Ease 3/3 Ocean Canal - New Open Kitchen, Dock

— Property 242664
Upper Florida Keys house rental - Keys style architecture & Lush Tropical Landscape
3 Bedrooms, Sleeps 8,
House, 3 Bathrooms, beach, waterfront, pets considered
Rates - per property (USD)
$1,000 - $1,600/week
$3,500 - $6,000/month
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Secluded waterfront home with spectacular views!!!

— Property 142418
Upper Florida Keys house rental - From seawall/dock toward house
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, beach, waterfront, garden
Rates - per property (USD)
$4,500/month
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SPECTACULAR Open Water Views & Private Dockage-Is on both the bay and beach

— Property 223571
Upper Florida Keys house rental - A lush tropical beauty with spectacular views
3 Bedrooms, Sleeps 10,
House, 2 Bathrooms, near the ocean, waterfront, balcony
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Rent this Romantic! Paradise Found in 1-of-a-Kind Key Largo Waterfront Home!

— Property 231623
Upper Florida Keys house rental - Beautiful, Cozy, Florida Keys Home!
2 Bedrooms, Sleeps 4,
House, 1 Bathroom, near the ocean, waterfront, balcony
Rates - per property (USD)
$170 - $188/night
$799/week
Calendar Updated Nov 8 2009

Property Review

My wife put me up to the impossible task of finding a rental home in the upper keys for a weekend getaway with our three children the wednesday before. No problem, I hit the various sites and...
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Key Largo Beach House! Sunsets on the Bay! Internet!

— Property 107982
Upper Florida Keys house rental - Front of house
2 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, waterfront, pets considered
Rates - per property (USD)
$175/night
$1,050 - $1,150/week
Calendar Updated Nov 7 2009

Property Review

Just got back from a wonderfull and relaxing time in Key Largo. The cottage was great, nice and quiet. Bill, John, and George are very friendly. If your looking for a quiet place you don't have to...
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Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access

— Property 201354
Upper Florida Keys townhome rental - tv area
2 Bedrooms, Sleeps 8,
Townhome, 2 Bathrooms, beach, village, pool
Rates - per property (USD)
$1,000 - $1,200/week
$3,000 - $3,200/month
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Luxurious Key Largo, Florida Keys Oceanfront Kawama Yacht Club 2+2 Condo

— Property 191399
Upper Florida Keys condo rental - Beautiful Walk-in Beach; Tiki Huts, BBQs, Shower
2 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$129 - $249/night
$900 - $1,500/week
$2,500 - $3,900/month
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Quiet Oceanfront Condo with Superb Oceanview

— Property 217210
Upper Florida Keys condo rental - Balcony view
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, beach, waterfront, tennis court
Rates - per property (USD)
$100/night
$700 - $900/week
$1,200 - $3,000/month
Calendar Updated Nov 7 2009

Property Review

We had an enjoyable week staying in key largo at this condo. It was ideal for our needs and at a reasonable price. It was a little way off the main road, so quiet, but handy location for...
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Oceanfront Beach Resort- Stunning Ocean Views - Free WIFI!

— Property 119632
Upper Florida Keys condo rental - Actual View From Private Balcony
2 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, beach, waterfront, tennis court
Rates - per property (USD)
$800 - $1,600/week
Accepts Online Payments
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Oceanfront Beach Resort - Direct Ocean Views - Free WIFI!

— Property 130386
Upper Florida Keys condo rental - Private White Sand Beach W/Tiki Huts & BBQ's
2 Bedrooms, Sleeps 7,
Condo, 2 Bathrooms, beach, near the ocean, jacuzzi
Rates - per property (USD)
$800 - $1,600/week
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Oceanfront Beach Resort - Hawaiian Island Style Setting

— Property 130780
Upper Florida Keys townhome rental - Private Beach W/BBQs, Tiki Huts & Palm Trees
2 Bedrooms, Sleeps 6,
Townhome, 1 Bathroom, 1 Half Bath, beach, resort, tennis court
Rates - per property (USD)
$800 - $1,400/week
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Oceanfront Beach Resort & Marina - Waterfront Town home

— Property 132539
Upper Florida Keys townhome rental - Private Beach
3 Bedrooms, Sleeps 8,
Townhome, 3 Bathrooms, beach, waterfront, tennis court
Rates - per property (USD)
$900 - $1,800/week
Calendar Updated Nov 7 2009

Property Review

My friends and I planned a last minute vacation to Key Largo and found this 3 bedroom condo on-line. With just days before the trip, easy payment arrangements were made along with flexibility...
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5 Star Oceanfront Resort - Key Largo's Most Upscale Destination - Free WIFI!

— Property 134355
Upper Florida Keys villa rental - Spectacular Lagoon Pool w/Zero Depth Entries
2 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, near the ocean, resort, jacuzzi
Rates - per property (USD)
$1,200 - $2,100/week
Calendar Updated Nov 7 2009

Property Review

There were two couples that stayed in the upstairs part of this unit. There were two couples on the main floor of this unit. It was a great place to stay during our vacation. We would stay here...
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Beautiful Islamorada Boater's Paradise home in the Florida Keys

— Property 192446
Upper Florida Keys house rental - Review
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, near the ocean, waterfront, balcony
Rates - per property (USD)
$2,100/week
Calendar Updated Nov 7 2009

Property Review

We just returned from a 5 night stay at this gorgeous home. The house was so clean, modern and in a great location. There was a boat ramp less then a mile away which made it very easy for my...
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$100-$400 Off Luxurious Waterfront Condo, 2 Master Bedrooms w/Private Baths

— Property 321060
Upper Florida Keys condo rental - One of the many views from your vacation home.
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, 1 Half Bath, near the ocean, waterfront, jacuzzi
Rates - per property (USD)
$1,500 - $2,000/week
Accepts Online Payments
Calendar Updated Nov 9 2009

Property Review

The property was just as it looks in the pictures. It is gorgeous! We were very impressed with the amenities it has. I (being Mom) was very pleased to have a washer & dryer in the unit so we...
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Kawama Oceanside Townhouse 2bed/2bath

— Property 218285
Upper Florida Keys townhome rental - Dining table
2 Bedrooms, Sleeps 6,
Townhome, 2 Bathrooms, beach, near the ocean, pool
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Tropical Paradise Vacation Home

— Property 182751
Upper Florida Keys house rental - Front view of home w/ privacy gate
5 Bedrooms, Sleeps 10,
House, 4 Bathrooms, waterfront, terrace
Rates - per property (USD)
$1,800/week
$3,750/month
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Quiet Open Water Hideaway Overlooking Wildlife Preserve

— Property 237766
Upper Florida Keys villa rental - sunrise on patio overlooking Nature Refuge
2 Bedrooms, Sleeps 4,
Villa, 1 Bathroom, waterfront, balcony
Rates - per property (USD)
$1,200 - $1,400/week
Calendar Updated Nov 6 2009

Property Review

My husband and I spend our time relaxing and enjoying the amenities during our visit in July of 2009. The propriety exceeded our expectation as far as the fabulous experiences swimming with the...
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Penthouse Condo on the Ocean Sunsets at Key Largo, Kawama Yacht Club Tower

— Property 233900
Upper Florida Keys condo rental - Key Largo Aerial
2 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$115 - $440/night
$795 - $1,995/week
$3,300 - $4,000/month
Calendar Updated Nov 6 2009

Property Review

My family and I just returned from a wonderful and relaxing vacation in Key Largo. Choosing the right place to stay was of utmost importance to me as I was traveling with my 7 month old baby, my...
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Key Largo Getaway

— Property 208559
Upper Florida Keys house rental - Beautiful View
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, beach, near the ocean, pets considered
Rates - per property (USD)
$150/night
$900/week
$2,250/month
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A 'Priceless' Vacation that you can Afford, this is a total eco-experience!

— Property 264101
Upper Florida Keys cottage rental - Cottage on Canal 70 ft. of Dock
1 Bedroom, Sleeps 3,
Cottage, 1 Bathroom, beach, waterfront, garden
Rates - per property (USD)
$80/night
$550/week
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NOV SAVINGS! OceanFRONT home, new 2008, panoramic ocean views, pool, beach, WIFI

— Property 186650
Upper Florida Keys house rental - View of Atlantic from deck of this oceanfront home
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, beach, waterfront, pool
Rates - per property (USD)
$2,350 - $3,050/week
Calendar Updated Nov 7 2009

Property Review

Great Accommodations! Priceless Views! We had a fabulous week of scuba diving, snorkeling with our kids, spending time with the family and some relaxing! Key Dives at Bud ‘n’ Mary’s Marina...
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Venetian Dream

— Property 7008512h
Upper Florida Keys house rental - Street view of home
3 Bedrooms, Sleeps 8,
House, 4 Bathrooms, 1 Half Bath, adventure, air-conditioning
Rates - per house (USD)
$5,200 - $6,500/month
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Beacon Reef #302

— Property 7009805h
Upper Florida Keys condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, air-conditioning, balcony
Rates - per condo (USD)
$3,700 - $4,400/month