Middle Keys Vacation Rentals
200 rentals with 860 photos.Most Popular
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Marathon
Enjoy our beautiful 2 bedroom waterfront home in Marathon. This rental includes free exclusive use of a private island and an out board motor boat to make the 10 minute trip between the home and the island. Relax in our...
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2 beds
1 bath
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Marathon
Very well kept four bedroom, four bath home on the Open Gulf. Magnificent unobstructed views from the main living area, dining room, two master bedrooms and screened porches. 50" plasma TV in the living room, 37" TV in ...
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per night
4 beds
4 baths
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Marathon
Sombrero Beach Seaclusion awaits with great vacation memories! Completely remodeled and updated in 2013 with new floor plans and all new granite countertops, stainless appliances, cabinets, tile flooring... the list goe...
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per night
4 beds
3 baths
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Listings
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Key Colony Beach
Enquire About Summer & Fall Specials. Side by side Stilt Duplex in Key Colony Beach near the end of the 3rd St canal, opening up to Bonefish Bay. Each half will accommodate up to 6 people very comfortably. We own these ...
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per night
2 beds
2 baths
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Marathon
Located on the Gulf of Mexico, this lovely home, with 55 feet of sliding glass doors opening onto the Gulf, offers magnificent sunsets, crystal clear water for snorkeling and lighted coconut palms. The home features vie...
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per night
3 beds
2 baths
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Duck Key
Gorgeous Waterfront Duplex located in a resort like setting in Duck Key. Unit features all the things you need to make your stay an enjoyable and memory filled vacation. The unit features a full kitchen and living room ...
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2 beds
2 baths
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Duck Key
Located on a private island in the Florida Keys, our Duck Key vacation rental home is the perfect spot for your next holiday. This tropical paradise is minutes away from many outdoor activities and offers stunning views...
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2 beds
2 baths
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Marathon
Beautifully furnished and maintained pool home located on a gulfside canal with protected dockage. Quiet residential neighborhood. Quick access to the Gulf and only a short run to Vaca Cut for Ocean access. Beautifully ...
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per night
3 beds
2 baths
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Marathon
Our 4 bedroom home has the best of all worlds, a large pool with shade for part of the day, and a deep 20 ft+ clear lagoon for swimming and snorkeling without the tidal worries of other home sites. The large tanning dec...
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per night
4 beds
3.5 baths
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Marathon
Walk to the best beach in Marathon. Private home on a well landscaped lot just moments to Siser's Creek. Large, open patio area overlooking the canal. 28X13 pool with optional heater or chiller. Large, open living area ...
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per night
4 beds
2 baths
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Marathon
Great location on a very quiet street close to the 7 mile bridge on the open Gulf. 60' of deep water dockage with a fish cleaning table and bait freezer. Magnificent pool and hot tub overlooks the Gulf. The keyzzzz iest...
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per night
4 beds
3 baths
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Marathon
The Beach House at Sombrero. Overlooking Sombrero Beach and Sister's Creek, this 2 bedroom, 2 bath home is a great vacation destination. Oceanviews, pool and dockage at the house with the addition of a great oceanfront ...
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per night
2 beds
2 baths
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Marathon
Our 3 bedroom home is in a quiet gulfside area with dock and pull-in boat slip. Enjoy 2 acres of seclusion! The home is completely furnished with everything needed to make your stay comfortable and enjoyable. It's just ...
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per night
3 beds
2 baths
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Marathon
Five Star Custom Designed Homewith lots of privacy ona quiet street. Three bedroom (with two master suites), three bath home on a quiet street close to shops, restaurants, fishing and diving. 45' of Deep Water dockage j...
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per night
3 beds
3 baths
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Marathon
Snuggle up on the wicker chaise or read a good book on the awning-covered veranda. Nestled on its own crescent beach, The Cottage on Sister's Creek looks to the ocean with panoramic views, dock, pool, jacuzzi. Beautiful...
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per night
2 beds
2 baths
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Marathon
Lovely home on a 200' wide canal in Coco Plum Beach. New city beach is just one block away. Well furnished and equipped this home features.hi speed wireless internet service, 40' wood dock with a total of 100' of deep w...
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per night
3 beds
2 baths
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Key Colony Beach
Dave's Fish n Fun in Key Colony Beach! 46' concrete dock to handle a large, deep draft boat. Fish cleaning table and bait freezer. There's a garage for all your fishing equipment as well. The living and dining area's ov...
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per night
3 beds
2 baths
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Marathon
Just one lot in from the open Gulf, with Great boating and some nice views. Single family home with 60' of Deep water dockage. There are very large proches surrounding this home with nice views of the Gulf. Kitchen has ...
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per night
3 beds
2.5 baths
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Marathon
In the heart of the Florida Keys, we have a 1 bedroom, 1 bathroom Condo in the middle of Boatman's Sombrero Reef Hotel resort. It has a full size kitchen, living room, and dining room. There is a large balcony that over...
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per night
1 bed
1 bath
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Key Colony Beach
Single Family Residence With Great Dockage & Access to Vaca Cut! 3 bedroom, 2 bath ground level home on 11th Street in Key Colony Beach. Well furnished and equipped with everything you need to make your stay delightful....
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per night
3 beds
2 baths
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Key Colony Beach
Large, two story half duplex on the shady side of the street. The main living area is upsatirs with the kitchen, living and dining area all a large open area. There are two bedrooms and two baths on this level. They eac...
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per night
4 beds
3 baths
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Marathon
Spacious two bedroom, two bath oceanfront, corner unit in a small, upscale complex. Screened patio off the master bedroom and living area with magnificent views of the Atlantic Ocean. Watch the sun rise from your patio ...
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per night
2 beds
2 baths
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Marathon
Coco Plum Beach Villas Unit 1A. Tropically decorated first floor, corner unit overlooking the pool and beach. Parking is underneath, so this unit is actually up one flight. There is an elevator in the building though. W...
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per night
2 beds
2 baths
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Blog Posts
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March 18, 2013
Marathon Florida is by far our favorite place. While Key Largo is very popular and Key West is extremely fun (if not decadent), Marathon has the best of all worlds in the Florida Keys, in our humble o...
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October 25, 2012
My mother lives in Cape Coral so I head there first for a couple days before spending the majority of my time at my father's place in Key Colony Beach in the Florida Keys. On my way back north I stop ...
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October 13, 2012
Later, Sanchez engineers his escape by arranging for the armoured truck he’s being carried in to be driven into the seas off Seven Mile Bridge, which connects Knight’s Key in the Middle Keys to Little...
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September 07, 2012
The two of us ventured out to a local marina at 10:00am for what turned out to be a private kayaking tour through the beautiful waters in Marathon....
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September 04, 2012
After a 5-hour drive from Orlando, we arrived at our new home in Key Colony Beach around 9pm on Sunday night. We unpacked our things, relaxed in the living room, and rested up for our week in the Key...
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May 23, 2012
Marathon. Well, most people grab a ball and go from there. That is what I would suggest. THere is a great beer and burger joint as you come in on the port side (I cannot remember the name) but it is t...
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March 25, 2012
Some people really know how to leave a mark. In Florida his name is Flagler. I wrote about him when we were in St. Augustine, but all along the state Henry Flagler's name keeps coming up. Pretty amazi...
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February 15, 2012
The road leads visitors from Key Largo and down to the southernmost part of the U.S., Key West. The remainder of the old bridge, south of Marathon, provides a 2.2-mile bike trail or walkway out to Pi...
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February 01, 2012
Tim and I visited the Florida Keys in February of 2011 and one highlight of the trip was our tour of the Turtle Hospital in Marathon Key. The tour begins with a presentation. Our guide, a young woman...
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February 25, 2010
You see, I purposely stopped by Duck Key on my way to Islamorada, when returning from Key West. The small 60-acre island is home to the famed Hawks Cay Resort. But, little did I know I was in for such...
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