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78 house rentals
Waterfront, dock, easy ocean access, heated pool, walk to beach! Great location!
Marathon house
2 bedrooms / 2 bathrooms / sleeps 6
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$310
Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort
Cudjoe Key cottage
2 bedrooms / 2 bathrooms / sleeps 6
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$183
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$229
Responds fast! avg. 1 hour 51 minutes
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$599
ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE
Matecumbe Key studio
Studio / 1 bathroom / sleeps 2
“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.
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$173
Responds fast! avg. 7 minutes
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$6,183
Responds fast! avg. 45 minutes
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$184
“Winter Paradise!” My wife and I stayed at this great place in January 2014 and it was wonderful. It was very clean and well maintained. The canal was great to watch the fish jump and we saw Manatees almost every day. We especially liked the kayak and did a lot of site seeing from the ocean side. Migdy was great to work with and very accommodating. We would highly recommend this place to anyone.
Responds fast! avg. 3 hours 37 minutes
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$132
“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!
Responds fast! avg. 2 hours 47 minutes
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$1,982
“AMAZING!!!!!!!” Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips when we asked. The studio was so well stocked with all the essentials and then even the ones you forgot! It was wonderful to see a manatee swim up past the dock our first morning there. A very magical spot with generous hosts. It had everything we wanted and then some. After a week there and driving around the whole Keys it was 100% the most perfect choice for us. I miss those hammocks!
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$258
House on 7th ST in KEY Colony Beach W/CABANA CLUB
Key Colony Beach house
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 19 minutes
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$212
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$58
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$194
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$369
“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!
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$270
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$420
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$582
Luxury condo overlooking harbor with ocean view
Islamorada condo
3 bedrooms / 3 bathrooms / sleeps 6
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$310
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$1,260
Comfortable Clean HouseBoat in an amazing location
Tavernier boathouse
1 bedroom / 2 bathrooms / sleeps 5
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$402
Responds fast! avg. 52 minutes
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$367
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH
Key West apartment
1 bedroom / 1 bathroom / sleeps 4
“Wonderful Experience” Beautiful decor! Perfect location - just off the beaten path but out of the hustle and bustle. Convenient to everything we wanted to do! I whole heartedly recommend this condo for a couple. Also would work nicely for three people. Might be a bit tight for four adults, but it was perfect for my husband and me.
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$230
Conch Key Villas Unit 2 Spectacular open water views!
Conch Key villa
1 bedroom / 1 bathroom / sleeps 3
Responds fast! avg. 28 minutes
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$188
Responds fast! avg. 3 hours 27 minutes
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$287
Now booking Spring/Summer 2021! Dock, Bikes, Kayak, 2 beach clubs
Key Colony Beach house
2 bedrooms / 2 bathrooms / sleeps 6
“Paradise Found” This is an adorable property. It is so "keysie"! The decor is just lovely with all the amenities you need. The kitchen is fully equipped, there was a new set of pots and pans, crockpot, blender and anything else I needed. The grill looked new, was clean and just waiting for our catch! The beds were very comfortable. The unit was immaculate. One could easily while away the day just sitting on the comfortable patio, or on the adirondack chairs at the dock and watch a variety of wildlife (birds, fish, manatee, lizards), and also watch the boats going up and down this clean canal. Don't get so busy that your forget to spend an afternoon at the Cabana Club and Inch Beach. They are not to be missed. , We rode the beach cruisers every day. Just needed a few more hours in each day. Oh! Don't forget to watch the spectacular sunset at Sunset Park! Dee, the owner is a dream to work with, full of suggestions and information, and returned our deposit in a timely manner. You will not be disappointed in this property, and believe me, you won't want to leave!
Responds fast! avg. 34 minutes
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$194
“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. 42 minutes
Travelers’ Choice award
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$112
Luxury 3BD/3B Penthouse Condo at Galleon Resort, Old Key West
Key West condo
3 bedrooms / 3 bathrooms / sleeps 8
Responds fast! avg. 3 hours 28 minutes
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$905
“Beautiful place located just across the street from the beach. The owners Capt. Steve and Kayla were wonderful hostess.” We arrived the week of Fantasy Fest, not knowing exactly what we were getting into, but had a great time. Lots of things to do or just lay around and relax. Our Master suite was perfect and the owners Steve and Kayla made us feel very welcome. Capt. Steve even went out of his way to take us fishing and then he prepared what we caught the next day for lunch. YUMMY! Perfect place to stay! Thank You, Steve and Kayla.
Responds fast! avg. 1 hour 37 minutes
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$287
Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE
Key West apartment
2 bedrooms / 3 bathrooms / sleeps 6
“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!
Responds fast! avg. 1 hour 35 minutes
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$258
KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI
Key West condo
2 bedrooms / 1 bathroom / sleeps 4
Responds fast! avg. 10 minutes
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$377
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$458
Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants
Marathon Shores house
3 bedrooms / 2 bathrooms / sleeps 8
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$342
CHARMING KEY COLONY BEACH POOL COTTAGE, PVT POOL,46 FT DCK,WIFI
Key Colony Beach cottage
2 bedrooms / 2 bathrooms / sleeps 4
“Most wonderful vacation home ever.” The pool, the hammock, the dock, the decor....it was the best place i have ever stayed. I didnt want to leave. Laying in the hammock every night listening to the palm trees swaying in the breeze. Watching the snook hit the greenies over the underwater light at the dock. Taking a refreshing swim after a long day on the boat. An evening bike ride around key colony. It was everything we wanted on our vacation. And the house was decorated exactly as my own tropical retreat would be decorated, and it is such a comfortable home. I am hoping to come back for 2 weeks next summer.
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$233
Oceanfront Anglers Reef Islamorada Florida Keys
Islamorada house
2 bedrooms / 3 bathrooms / sleeps 6
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$376
Get out of the cold Feb.5-12, 2018 in Florida Keys at Marathon,The Hammocks
Marathon Shores villa
2 bedrooms / 2 bathrooms / sleeps 6
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$556
Key Colony Beach Tropical Pool Home-Open May 2020 and week of July 18, 2020.
Key Colony Beach house
3 bedrooms / 2 bathrooms / sleeps 8
“Wow, what a Home and Location” We stayed 11 wonderful weeks at this home. The home is so enjoyable with all the amenities one needs to be comfortable--decor is so cheerful and elegant and the owners are very friendly and helpful. We enjoyed sun filled days swimming in the heated pool and relaxing around it, ending the days with the beautiful sunsets! The fishing is outstanding, we rented a boat and kept it directly at the homes private dock. The ocean and bay are only 5 minutes away, the fish even bite right off the dock. We can't wait to go back next January.
Responds fast! avg. 1 hour 26 minutes
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$437
Responds fast! avg. 1 hour 30 minutes
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$166
Sailor`s Delight 1bed/2bath Condo at The Reef with shared pool
Marathon condo
1 bedroom / 2 bathrooms / sleeps 4
Responds fast! avg. 28 minutes
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$160