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$589
Great rentals within 20 miles that match your search
New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale
Islamorada house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
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$918
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$1,154
Oceanside waterfront 2/2 home with 55ft dock and paddle equipment
Marathon Shores house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$289
Beachfront Islamorada Villa with Dockage and Bay Views
Lower Matecumbe Key house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$351
Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool
Marathon Shores house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
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$749
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$253
New Listing! Charming Angler's Reef Home with Pool, Dockage
Islamorada house
- 2 bedrooms
- 3 bathrooms
- sleeps 6
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$462
Responds fast! avg. 1 hour 48 minutes
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$260
Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball
Islamorada house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$208
Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!
Key Colony Beach house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$345
Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!
Key Colony Beach house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$310
Oasis Canal-Front Home: Pool, 30ft Dock, BBQ, and more!
Marathon house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$518
Immaculate Waterfront ~ 2 BR ~ Private Pool, Tiki on Canal! 2 Min Walk to Beach!
Key Colony Beach house
- 2 bedrooms
- 1 bathroom
- sleeps 4
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$344
Remodeled Townhome in Waterfront Community - 20% for Spring/Summer!
Islamorada house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$604
Beautiful Waterfront Townhome in Islamorada! Perfect for Florida Keys Vacation!
Islamorada house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$604
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$378
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$414
Sunchasers Paradise - spacious lux canal front home, private pool/spa, 80' dock
Marathon house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
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$822
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$802
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$287
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$377
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$516
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$2,209
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$457
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$654
“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!
Responds fast! avg. 2 hours 56 minutes
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$327
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$458
“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!
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$573
“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.
Responds fast! avg. 2 hours 33 minutes
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$982
“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.
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$400
“Beautiful Home in Marathon” We truly loved this place, the home was clean, spacious and very comfortable! My husband still claims to this day that was the best sleep he has had in years and that's a big compliment coming from him! We loved having water access (although we didn't have a boat) it really made for some beautiful sunsets and sunrises! We found a couple of amazing restaurants that we visited on several occasions, the first and our favorite was Tarpon Creek following as a very close second was The Sunset Grill and Raw Bar, also our favorite breakfast spot became Juice Paradise Cuban Cafe (the best coffee). I'm only just now getting around to reviewing this place because we are planning another trip to the Keys in December and I was checking this place out and i didn't see our review and ask my husband about it (I thought he posted it and he thought I posted it), so finally 2 yrs later I'm giving our review!!! Unfortunately I see it's booked for our time frame and we are very disappointed about that but I know whoever booked it WILL NOT be disappointed! Thanks so much for an amazing experience, Gina & Scott PS we actually stayed Sept 2014 but it would only let me go back to Oct 2014! :-)
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$214
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$344
“Heaven On Earth!” From the moment you step foot on this beautiful island paradise, you'll feel like you've been transported to your own little private world! Every amenity has been thought of from an outstanding outdoor kitchen, complete with state of the art grill, oven and microwave along with dinnerware, glassware etc. Not to mention the kitchen inside the house comes complete with all you need also. Even spices, just not food! The house itself is amazing and has a awesome stereo system so you can have music in the house, on the decks and on then beach! You can snorkel, swim, fish, sail, canoe, kayak, go tubing walk along the perfectely maintained tropical paths. From sunrise to sunset you day will be filled with beautiful scenerey, The view from the front porch is my favorite, I could sit there all day and have! This was our 7th trip and we had a extended stay of 10 glorious days, also our first trip with friends who loved it as much as we do! We've spent my birthday and our anniversary (back to back) here many of times and there is no place else we would rather be! The island is alive with hermit and land craps and Iguanna's and birds of all sorts. It's so funny to see a hermit crap go by with some sort of object he found as a shell. At night when you turn all the outside lights on it's like a magical transformantion! I can not say enough good things about Seabird Key. The owners and care takers do such a amazing job! Thank you for sharing this tropical paradise with us and we hope to be back again soon!
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$2,004
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$500
“Wonderful stay” Post hurricane and still a spectacular place to stay. Office staff was great. Free use of tennis court, rackets, and balls. Pool and jacuzzi were very excellent. TG
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$2,290
OUTSTANDING Oceanfront House with Pool and Deep water dockage!!
Marathon house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
“Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problems. I would highly recommend this rental
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$1,145
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$1,795