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Vacation Rentals & House Rentals in Florida Keys

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107 house rentals

Tropical Escape

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Very comfortable and all around great place to stay.” It was very clean, comfortable and homey. The pool was great and it's very close to Key West and a beach. We really enjoyed our stay. Provided plenty of towels, pool accessories, kitchenware, etc.... No complaints.

Match: Private outdoor pool (unheated)

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Price per night from

$246

Private Beachfront Paradise

Matecumbe Key house

4 bedrooms / 3 bathrooms / sleeps 8

“Nicest rental property we have ever stayed in!!” Beautiful home on spotless white beach! Property has been updated with upscale furnishings throughout. Granite, leather furniture, redone bathrooms. Well stocked for all your vacation needs -- towels, beach chairs, beach toys, kitchen full of everything you need, 2 grills. Outside patio was amazing for our meals, sunrises and after dinner activities. The backyard was the beach filled with palm trees for natural shade. Hammock and volleyball court, beautiful pool with waterfall, tables and chairs everywhere for meals or for just relaxing. We traveled as two families and there was more than enough room for all of us. We felt right at home right away. Highly recommend this paradise!

Match: Private outdoor pool (unheated)

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Price per night from

$746

Canal-Side Home w/ Large Private Dock, Covered Patio & Waterfront Pool

Key Colony Beach house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$329

TWICE THE CHARM

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$183

Waterfront house w/ covered patio, private pool, & 75 ft. dock - dogs welcome!

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$294

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$262

East Sister Rock Island

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$1,559

Big house

Key West house

5 bedrooms / 5 bathrooms / sleeps 12

“Bachelorette in Key West” I rented this house for my sister-in-law's bachelorette weekend in Key West. The house was spacious, clean, and overall the best place I've ever stayed! It was worth every penny!

Match: Private outdoor pool (unheated)

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Price per night from

$700

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 32 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$6,173

Paradise In Marathon, FL Keys Large Oceanside Home

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

“Wonderful property. We had a great stay!” Super close to publix and boat ramp ($30 fee in and out) so convenient. Very nice accommodations. Wonderful to have the boat right out back

Responds fast! avg. 43 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$412

Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!

Stock Island house

3 bedrooms / 2 bathrooms / sleeps 10

“What a fun time !!!” I brought my daughter & her boyfriend, my middle daughter and her boyfriend, my son who is a freshman at psu, my girlfriend suzie & myself. We golfed( great golf course ) !!! We jet skiied around key west... you guys have to do this!!! great and wonderful guides, we chartered a boat for a three- four hour tour. we all caught fish. & one was for dinner:) black fin tuna, and a trophy fish 5' 6" barracuda;) !!! The people were friendly, the atmosphere was warm and cozy. The Pool was great, The rooms were more than enough. Easy access to Duval street. Many clubs and eateries on duvalt street. The books left on the counter tops for things to do were very very very helpful. The night life is fun. and everybody was very friendly and helpful...I will be back with my family

Responds fast! avg. 2 hours 1 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$512

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$100

Clean Keys 3/3 w/Davits Clear Canal Bay Side/Views Fenced 2Level Tavernier Home

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 51 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$172

Waterfront Resort Villa w/ Private Plunge Pool!

Duck Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$245

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$100

Lighthouse Villa

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$193

Coconut Cottage

Key West house

1 bedroom / 2 bathrooms / sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$77

HOUSE DORADO

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$617

tropical Casita

Key West house

1 bedroom / 2 bathrooms / sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$107

Marlin Bay Resort & Marina - Luxury Residence in Resort-Style Setting

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$748

Gulf View Place w/ Dock, Pool, Kayaks, Sandy Shore

Marathon house

4 bedrooms / 4 bathrooms / sleeps 10

“Awsomely relaxing yet centrally located for easy day trips.” Very clean and nicely equipped with everything needed for a relaxing and comfortable at home feel vacation. Lots of room for family reunions. Centrally located in the Keys so day trips either north or south are easy. Don't miss Savannah Sweets Bakery and Cafe for the best key lime pie. Property manager a phone call away but never needed as everything was in good working order. Owners very nice and have thought of everything. Pool more of an oversized hot tub but does the trick on hot days. Can't wait to return!!

Match: Private outdoor pool (unheated)

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Price per night from

$490

Gulf View Suites w/Docks, Pools, Kayaks -Sleeps 20

Marathon house

8 bedrooms / 6 bathrooms / sleeps 20

“Awesome location, close to many popular destinations.” My husband and I really enjoyed our vacation to Marathon Fl. Our vacation home was very clean and close to many great restaurants and beaches. We used the kayaks, swam in our own pool and sat out on the deck to just watch the world go by. We would highly recommend Rent My Island.

Match: Private outdoor pool (unheated)

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Price per night from

$948

Key Lime Pie

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Loved Off Season Key West” Spent a month in this very secluded house within walking distance of everything, including the marina, Duval Street and my favorite Watering Hole, Finnegan's Irish Wake pub. Renting in October, the off season, meant I got to experience an uncrowded Key West. And best of all, at the end of the month, to experience Fantasy Fest in its entirety. What a rush. House was wonderful. Had it all including a hot tub. Private parking, a real plus in Key West. Plan to do it again.

Match: Private outdoor pool (unheated)

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Price per night from

$87

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$198

CONCH BAR SOUTH

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$317

Conch Republic Retreat

Key West cottage

2 bedrooms / 2 bathrooms / sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$107

Perfect Pineapple

Key West house

2 bedrooms / 1 bathroom / sleeps 4

“Kudos to Owner” The owners updated many things such as new bathroom tile, area rugs, washer and dryer area as well as painting. Still needed are more dinner and salad plates as it is necessary to run the dishwasher almost every day. The timer system for the garden lights needs to be repaired. Guests came to visit and it was very crowded with 4 people even with two bedrooms. This is a perfect place for a couple. The big negative is the Iguana's who wander from the cemetery area . A 3 1/2 foot Iguana can scare the heck out of you.

Match: Private outdoor pool (unheated)

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Price per night from

$100

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

Match: Private outdoor pool (unheated)

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Price per night from

$441

Amelia Home

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect” We loved this house! It was the perfect little getaway. It was in a great location, very convenient to everything. The house was beautiful with very nice decorating inside to the beautiful lush garden outside. If we visit Key West again, I’d stay here without hesitation. I highly recommend!.

Match: Private outdoor pool (unheated)

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Price per night from

$325

Flagler Station

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

“Little gem is right!” Can't say enough good about this place! Newly renovated 1800 square foot home;3 be king in master, queen and double Beds in third room. Loved the small private pool and gourmet kitchen, much thought, love and detail went into making this a home away from home. 5 blocks from the public beach and a couple of miles from duval street. So close to so much but still have some privacy and parking.. Would love to bring bikes next time. Y'all save a place for me next summer we hope to come back! And the home away folks get an A plus for the process of renting, it was so easy...

Match: Private outdoor pool (unheated)

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Price per night from

$107

DEC & APRIL DEAL MONTH MINIMUM ENJOY! 9545791140

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$174

PLANTATION ADVENTURE

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$217

Rosalie's House

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$100

Fabulous 6bedroom /4bathroom Waterfront Pool Home in Islamorada - 3/2 Each Level

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 33 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$386

Tropical Dreaming

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Oasis in busy Key West” We have stayed at Tropical Dreaming several years in a row. It is a lovely setting a couple of blocks off Duval so it is its own oasis.

Match: Private outdoor pool (unheated)

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Price per night from

$325

Easy Livin'

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Great Experience” This house was beautiful. The pictures don't do it justice. It's the perfect house for families. The location couldn't be better - walking distance to everything.

Match: Private outdoor pool (unheated)

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Price per night from

$550

The Dolphin House

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

“Perfect” Perfect house. Perfect pool. Perfect location. I want to live there. Secluded but so close to everything!

Match: Private outdoor pool (unheated)

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Price per night from

$550

PALM HARBOR

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$333

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