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Vacation Rentals & House Rentals in Florida Keys

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78 house rentals

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Price per night from

$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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Price per night from

$183

Studio Blue

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$229

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$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

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 7 minutes

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Price per night from

$6,183

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 45 minutes

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Price per night from

$184

Florida Keys Splendor at Hammer Point

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

“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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Price per night from

$132

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“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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Price per night from

$1,982

Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom / 1 bathroom / sleeps 2

“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

Beautiful Private Home with Beach Access.

Key Largo house

2 bedrooms / 1 bathroom / sleeps 6

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$58

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

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$194

Key Colony Beach Griffins' Getaway

Key Colony Beach house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$369

Reef Resort - Peaceful Getaway 204

Marathon condo

1 bedroom / 2 bathrooms / sleeps 4

“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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Price per night from

$270

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$420

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$582

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

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$310

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$1,260

Comfortable Clean HouseBoat in an amazing location

Tavernier boathouse

1 bedroom / 2 bathrooms / sleeps 5

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Price per night from

$402

New Listing Family Friendly

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 52 minutes

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Price per night from

$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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Price per night from

$188

Key Largo Beautiful House

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 27 minutes

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Price per night from

$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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Price per night from

$194

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“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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Price per night from

$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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Price per night from

$905

Atlantis House Master Suite

Key West cottage

1 bedroom / 1 bathroom / sleeps 2

“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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Price per night from

$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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Price per night from

$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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Price per night from

$377

Gorgeous waterfront home

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$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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Price per night from

$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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Price per night from

$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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Price per night from

$437

Private Key Largo Bayside Canalfront home

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 4

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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Price per night from

$160

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