Reach Higher Vacation Ground and Visit the Upper Florida Keys

Visiting Florida’s Upper Keys is like finding bliss on a faraway island without traveling to the ends of the earth. Whichever isle you choose will bring a sense of escape and relief, so pick one and let the quality vacationing begin.


Key Largo is the largest of these coral-constructed Keys and is also known as the The Diving Capital of the World. Thirty three miles long and nestled just off the coast of Florida, this will be a good fit for ecotourists and adventurers alike. And, if you just want a pleasant place to frolic on the beach or relax in the shade of an umbrella this isn’t a bad choice either.


The same goes for Islamorada, a collection of a few smaller Keys. Skip back and forth from one to the next, relishing the small-town atmosphere and engaging peace and quiet. Sport fishing is popular here, as are snorkeling, windsurfing and sailing.


No matter which of the islands ends up capturing your attention, you’ll surely have the chance to sample some conch chowder, Key Lime Pie and plenty of tropical drinks as you take in a sunset from your private lanai. Choosing to stay in a condo or beach house will make the most of the Florida Keys and allow plenty of moments like this to naturally arise.


If the idea of discovering the Caribbean experience that exists just off the coast of the peninsula sounds appealing, then it sounds like you’ll soon be opening the door to a soothing and restorative vacation.

Destination: Search

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Vacation Rentals in Upper Florida Keys

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We Love Kids! Pool And Sandy Lagoon, Just A Hop, Skip & Jump From Our Door! – Property 177656

  • Upper Florida Keys rental - townhome, 2 bedrooms, sleeps 6, 1 bathroom, 1 half bath, beach, near the ocean, pool
  • $700 - $950/week
  • Calendar Last Updated On: Nov 24, 2009
Our 2 bedroom 2 story townhouse is located in the tropical resort of Kawama Yacht Club, Key Largo FL. Located at mile marker 100, an hour's drive from the Miami...

Largest Floor Plan - End Unit with Spectacular Ocean Views! – Property 145554

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, resort, jacuzzi
  • $800 - $990/week
  • Calendar Last Updated On: Nov 24, 2009
Located in a secure gated community, off the beaten path, this spacious handicap accessible apartment, on third floor, includes great room, end-unit (largest floor...

Beautiful Home by the Bay – Property 221286

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 9, 3 bathrooms, balcony, air-conditioning
  • $1,400/week
  • Calendar Last Updated On: Nov 24, 2009
Beautiful three story duplex directly on the water with open bay views. The house has two bedrooms on the second floor and the Master Bedroom is on the third floor...

Elegant, modern, private townhome – Property 237408

  • Upper Florida Keys rental - townhome, 3 bedrooms, sleeps 6, 2 bathrooms, near the ocean, waterfront, pool
  • $1,500/week
  • Calendar Last Updated On: Nov 24, 2009
Beautiful and modern townhouse, beautifully decorated, gourmet kitchen with wine chiller, plasma TV in living-room, with music equipment, and DVD player.

Bayfront Villa-Dockage, Privacy, Gorgeous Sunsets – Property 225164

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 7, 2 bathrooms, waterfront, pets considered
  • $1,800/week
  • Calendar Last Updated On: Nov 24, 2009
Breathtaking Sunsets over the Bay and Laid-back Comfort awaits you here in the heart of Key Largo. Whether your vacation dream is relaxing time soaking up rays while...

Lovely Waterfront Key Largo Getaway – Property 118645

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 6, 1 bathroom, 1 half bath, near the ocean, waterfront, sauna
  • $630 - $1,250/week
  • Calendar Last Updated On: Nov 24, 2009
Located just an hour south of Miami, you'll find your vacation getaway tucked in the private, gated community of Moon Bay. This Bay Side community boosts many...

Rent this Romantic! Paradise Found in 1-of-a-Kind Key Largo Waterfront Home! – Property 231623

  • Upper Florida Keys rental - house, 2 bedrooms, sleeps 4, 1 bathroom, near the ocean, waterfront, balcony
  • $799/week
  • Calendar Last Updated On: Nov 24, 2009
Key Largo,The most perfect location with both ocean and bay access! Walk to grocery store and church. This home is called the 'Green Dolphin' and it's located on...

Elegant Bayfront Key Largo Estate – Property 237757

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, balcony
  • Calendar Last Updated On: Nov 23, 2009
If you are ready to treat yourself, family and friends to the best vacation of your life, come down to Key Largo and stay at our luxurious bayfront estate.

Luxurious Waterfront Condo, 2 Master Bedrooms. 3 Bedroom Dec25-Jan2 Available – Property 321060

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, waterfront, jacuzzi
  • $1,500 - $2,000/week
  • Calendar Last Updated On: Nov 23, 2009
Best Location in Complex! Gorgeous Florida Keys condo rental is Licensed! Relax in this luxurious gated waterfront condominium.

Fabulous View, Split 2/2 Up, 2/1 Down, Ideal for 2 Families – Property 158012

  • Upper Florida Keys rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, near the ocean, waterfront, garden
  • Calendar Last Updated On: Nov 23, 2009
Islamorada is the fishing capital of the world! Renowned for Tarpon, Sailfish, Bone Fish, Canoeing, Wind Surfing, Lobster and reef fish, Dolphin (both edible and...

Waterfront Gem! Huge (Sleeps 19) Deep Water Ocean Access Home w/LG SPA & SAUNA – Property 232417

  • Upper Florida Keys rental - house, 6 bedrooms, sleeps 19, 3 bathrooms, 1 half bath, downtown, waterfront, pool
  • $2,800 - $3,800/week
  • Calendar Last Updated On: Nov 23, 2009
Sleeps 19 so it's great for dive groups, family reunions, and weddings. Play golf? Need a place to land your private jet or plane close by?

Meagan's Beach House - Bayfront home with spectacular sunrises and sunsets – Property 265117

  • Upper Florida Keys rental - house, 2 bedrooms, sleeps 8, 2 bathrooms, beach, waterfront, jacuzzi
  • Calendar Last Updated On: Nov 24, 2009
Beautiful bayfront home with open water view from porch and private 180 foot dock. Just 45 minutes from Miami International Airport and minutes away from John...

Oceanfront 5th Floor End Unit! Pool, Internet, Tennis, Panoramic Ocean Views – Property 151910

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, beach, waterfront, sauna
  • $850 - $1,475/week
  • Calendar Last Updated On: Nov 23, 2009
Incredible Panoramic Ocean Views from this comfy and well cared for 5th floor fully-equipped end unit directly on the ocean, just steps from the water, in highly...

Quiet, charming, unique Keys condo – Property 254896

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, near the ocean, waterfront, pool
  • Calendar Last Updated On: Nov 23, 2009
Located bayside, south of the Key Largo 'downtown', this traditional stilt construction condo offers both a respite from urban life and entry to the fabulously...

Quiet Open Water Escape Overlooking Wildlife Sanctuary – Property 210446

  • Upper Florida Keys rental - villa, 1 bedroom, sleeps 2, 1 bathroom, waterfront, terrace
  • $1,400 - $1,600/week
  • Calendar Last Updated On: Nov 22, 2009
Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your patio look-out, only 9 feet from water's edge, you...

A 'Priceless' Vacation that you can Afford, this is a total eco-experience! – Property 264101

  • Upper Florida Keys rental - cottage, 1 bedroom, sleeps 3, 1 bathroom, beach, waterfront, garden
  • $550/week
  • Calendar Last Updated On: Nov 22, 2009
'The relaxed laid back feeling of the Keys' with the trade winds blowing every night. There is lot of privacy and yet you are viewing the bay.

Condo by the ocean in Key Largo – Property 177592

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 7, 2 bathrooms, beach, near the ocean, tennis court
  • Calendar Last Updated On: Nov 22, 2009
The condo is FULLY equipped with ALL necessary kitchen and dinning items and bed and bath linens. The Master Suite has a Queen size bed, the guest bedroom has 2...

Beautiful Bayfront Two-Floor Condo in Moonbay in Key Largo – Property 242344

  • Upper Florida Keys rental - condo, 3 bedrooms, sleeps 10, 2 bathrooms, 1 half bath, waterfront, tennis court
  • $950 - $1,495/week
  • Calendar Last Updated On: Nov 22, 2009
- Bayside Condo - End Unit next to water - Boat Slip up to 30'Boat 1 minute to Hawks Channel - 2 minutes to Jewfish Creek - minutes from the Largo Cut & Pennekamp...

kEYS WITH EASE 3/3 Ocean Canal - WEEKS OPEN IN FEBRUARY!-CALL NOW – Property 242664

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, beach, waterfront, pets considered
  • $1,000 - $1,600/week
  • Calendar Last Updated On: Nov 21, 2009
Village of Islamorada License Number VR-09-62. A brand new kitchen with all wood cabinets, granite counter tops and GE profile stainless appliances greets you...

Stay Here in Beautiful Bayfront Home in Paradise – Property 254894

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, beach, waterfront, terrace
  • $1,695 - $1,995/week
  • Calendar Last Updated On: Nov 21, 2009
This home is true serenity on the bay. It has a beautiful open floor plan where each area generously works with each other. At all angles and most of the rooms you...
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