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Vacation Rentals & House Rentals in Florida Keys

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324 house rentals

Oceanfront condo w/beach access, shared tennis, pool, etc. - marina available!

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$204

75731 Overseas Highway

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. Brandi at Freewheeler Realestate was wonderful. She was prompt with answers to questions, friendly and professional. The home-owner obviously wants to see to it that the people staying in their home are well taken care of. Everything was great all the way down to the fluffy beach towels. We will definitely look at staying at this home again.

Match: Shared outdoor pool (unheated)

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Price per night from

$1,227

Bayside Home w/ Heated Pool, Rooftop Terrace & Stunning View

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$283

Brand New 3 Story Key Largo Home

Key Largo house

5 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 1 hour 27 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$407

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$90

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$430

Bay Harbour D-114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$328

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

3 bedrooms / 2 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$372

ROCK HARBOR CLUB P-8

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$103

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

Match: Shared outdoor pool (unheated)

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Price per night from

$86

TWICE THE CHARM

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Shared outdoor pool (unheated)

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Price per night from

$183

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$113

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Shared outdoor pool (unheated)

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Price per night from

$262

Comfortable condo w/ shared pool, private balcony, and beach access

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

“Relaxing and Fun” Very good location..steps away from Smathers beach. Parked car then rode bikes, scooters, and walked around the entire Key. Condo was very nice and comfortable with everything needed for a week or more stay. The only negative is that the in laid wood bedroom floors creek on every step--annoying at night. Maybe a few rugs could solve this issue. We really enjoyed the hot tub--relaxing.

Responds fast! avg. 2 hours 31 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$434

Artist Garden

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful House, sometimes loud” We stayed at the artist's Garden for one week. There were 4 adults and an 11 month old. The house is gorgeous, lots of interesting art. Some of it we had to move out of reach of our 11 month old, but that was easy enough. The only downside to this house is that it's located across the street from the post office. It wouldn't be bad except the bedroom windows face the post office. Some mornings the postal trucks banged around starting at 4:52 am! I finally had to put on a white noise app every night to drown them and the roosters out. (The roosters is a Key West issue, not this houses's ;-) ) .. It was in a great location, easy to access all the restaurants, Duval Street and Mallory square. The pool is very close and well maintained. We definitely would consider staying here again, but if a different house in Truman annex were available not close to the post office, we'd probably choose that first. We would definitely go through at Home in Key West, though! They were wonderful and helpful. They also recommended using The Hip Tourist for renting baby equipment and it was perfect!!!

Match: Shared outdoor pool (unheated)

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Price per night from

$285

Dog-friendly, tropical escape with central location, hot tub, and shared pool

Stock Island house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 31 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$227

Breezy half-duplex w/35 ft dock. Includes Cabana Club access w/ pool & beach

Key Colony Beach house

4 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 2 hours 50 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$248

Bayview Harbor

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$200

Southard Getaway

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Match: Shared outdoor pool (unheated)

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Price per night from

$215

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 32 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$6,173

Waterfront luxury Villa (34) with sunset views and boat slip

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 7 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$1,145

Waterfront in Key Largo, Terrific 1/1 Apt, 2nd Floor, Pet Friendly, Sleeps 4

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 57 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$79

BROCK HAUS ON THE GULF

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Absolutely Beautiful and convenient for boaters!” Our family stayed here for a week in late March. We had plenty of room and everything we needed was available. This is a gorgeous condo overlooking the Florida Bay. You get to see an awesome sunset every day. We also brought our boat and the dock is literally right across the condo and ocean access is not too far away by water. Manatees visited the dock about every day, you can see picture below. We looked at other condo options and by far this was the best that suited our needs. The service provided was excellent. They were a phone call away if we needed anything. We will definitely be staying here again. Thank you so much!

Match: Shared outdoor pool (unheated)

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Price per night from

$211

152 Valencia Drive

Islamorada house

4 bedrooms / 5 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$267

Key West Found

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Great rental” This is a great location. Walked to everything including snorkeling every day at Zachery beach. Stayed for a week without a car or bikes. Townhouse is extremely clean, maintained and well furnished. Need to add a few more dishes (i.e. bowls). Décor was nice but a few minor changes would make it great. Love the shaded porch. All in all a great rental. Truman annex very secure and quiet.

Match: Shared outdoor pool (unheated)

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Price per night from

$260

Dog-friendly waterfront home w/37.5-ft dock - shared pool & 2 private beaches!

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 50 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$232

75691 Overseas Highway

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$540

PALMS 314

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Wow, what a beautiful view” This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the daytime the view would take your breath. However, at night the lights from the parking lot would shine into our bedroom. Alas, with the flip of a switch an outside shutter would roll down and the room was completely dark. Talk about sleeping well! As for the complex, everyone was very friendly and we made some very good friends. The pool was heated and the hot tub was always warm and enjoyable. We have already made plans to go back next year. If you have the chance to rent a unit there, GO, you will not be sorry.

Match: Shared outdoor pool (unheated)

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Price per night from

$80

Waterfront duplex w/ shared pool & beach access, 35-ft dock!

Key Colony Beach house

7 bedrooms / 8 bathrooms / sleeps 17

Responds fast! avg. 2 hours 31 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$359

Waterfront luxury Villa (42) with sunset views and boat slip

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 7 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$1,145

Gulf View Three - 3 bedroom, 3 bathroom, Gulf Side

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

“Paradise Getaway...” My Husband and I were more than thrilled to take our vacation at the Fisherman's Haven with Dock. Right on the inlet he was able to fish and enjoy the beautiful scenery Fishing license was easy to obtain from the local Kmart just south. We were able to grill out and enjoy eating outside or dine in the beautiful and very accommodating Kitchen which was fully stocked with more than one could need. Everything was very clean.! Having a washing machine was perfect. Beds very comfortable also. We were able to drive to various Keys and enjoyed Key West so much we went twice. Thank You Rent my Island for an a+ and 5 star *** Experience!!! Ps Sharky"s just south on a! has .25 wings and shrimp from 4-6! We will definitely come back!

Match: Shared outdoor pool (unheated)

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Price per night from

$425

Newton's Nest

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Match: Shared outdoor pool (unheated)

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Price per night from

$75

Key Largo Breezy Palms Turquoise Ocean,Fishing Fun,Beach,Pools,Free WiFi

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Great place to stay” We stayed at Sally and andrew´s place for a week. When we looked for a place to stay, we wanted a place not to far of Key West and Miami, and this place was just great! There were lots of places to eat out, things to see, and Key West and Miami was not to far away. The apartment was great, Andrew was too! Everthing regarding the stay were done in a professionel way. Both before the stay and after. The way of paying could have been easier though, but that is not a big problem We had a great time, all four of us visiting from Norway. If anyone should ask me where to stay in that erea, I have absolutely no problem telling them about Sally and andrew´s place! Ps: Make shure to have the time to eat at Mrs Mac´s Kitchen...

Responds fast! avg. 3 hours 36 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$218

Moon Bay A-204

Tavernier house

2 bedrooms / 1 bathroom / sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$180

Waterfront luxury Villa (51) with sunset views and boat slip

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 6

“Relaxation” My finance and I stayed at the amazing Indigo Reef, unit 51. We choose Indigo Reef, primarily for the location. We love Marathon and desired to be close to all the fantastic restaurants and the lovely Sombrero Beach. We snorkeled for the day at the Sombrero Beach lighthouse (incredible - highly recommended)! Indigo Reef was lovely, quiet, family friendly, clean, and comfortable. The pool was a nice treat, after a long day in the sun. Unit 51 treated us very well. My fiance and I enjoyed the beautiful and very clean unit. The linens were clean and beds were very comfortable. We loved the outside balcony's and back patio view of the bay!! Our favorite space in the house was the outside patio; relaxing and watching the sun set. We captured beautiful photo's of orange/pink tints to the sky. Gorgeous! The unit was spacious enough to accommodate our friends traveling from Pgh, to spend a few nights, enjoying the keys with us! We visited Key West for the day (an hour drive). My communication with John Zito, prior to our stay, was simply fantastic. Thank you for allowing us to share this lovely place with our friends. Angela and Alex

Responds fast! avg. 2 hours 7 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$1,145

Key Colony Beach FL - Cay Condo

Key Colony Beach condo

2 bedrooms / 3 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$263

1108 Heron Road

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$249

Spacious, waterfront home w/ 33-ft dock, shared pool, & Cabana Club access!

Key Colony Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 50 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$260

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