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Vacation Rentals & House Rentals in Florida Keys

195 house rentals

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

  • Beach / lakeside relaxation
  • •  Nearest beach 0.5 mi
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$105

ADVENTURE AWAITS I - MARINER'S CLUB 606 - KEY LARGO RESORT STYLE VACATION HOME

Key Largo townhouse

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$460

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Beautifully appointed, waterside condo!” This property is a beautiful, two bedroom condo, very well appointed, with everything we needed for a great stay! Islamorada is a great middle point to see the other parts of the Keys, and close to great restaurants. The porch offers lovely sunrises, and peaceful enjoyment of the waterway view and harbor. The pool is heated and quiet. The owners were very helpful with our questions. We would definitely stay at this property again, and recommend it to others!

Price per night from

$215

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

Tavernier house

  • Swimming pool
  • •  Child Friendly
  • •  Car not necessary
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$82

Duck Key Paradise

Duck Key house

  • Nearest beach 19 mi
  • •  Swimming pool
  • •  Child Friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$287

Keys Cove Home #2 The Reel World

Marathon Shores house

  • Child Friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$490

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$574

Tropical Escape

Key West apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 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.

Price per night from

$247

Top floor, two bedroom,two bath condo with private balcony,close to the Ocean

Key West condo

  • Beach / lakeside relaxation
  • •  Nearest beach 2 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$230

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

Cudjoe Key cottage

  • Child Friendly
  • •  Pet Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$184

Private Beachfront Paradise

Matecumbe Key house

  • Beach / lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Swimming pool
  • 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!

Price per night from

$603

The Water's Edge

Key West house

  • Beach / lakeside relaxation
  • •  Nearest beach 0.64 mi
  • •  Swimming pool
  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“Perfect for a Memorable Key West Experience!” My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do during your Key West experience. Ocean Paradise has gorgeous views from the 3rd level balcony, a wonderful screened-in porch on the main level (perfect for al fresco dining), and an incredible pool area with a larger than expected private pool and stunning landscaping that provides both shade and privacy. The home's interior is both spacious and functional, including lovely furnishings and everything you need for a memorable vacation in beautiful Key West. Just as important to us was the ease in managing our visit to Ocean Paradise. The owner and his staff were absolutely incredible to work with throughout the entire rental process. We had originally scheduled our visit for the 2014 Thanksgiving holiday week. However, a need arose which required us to cancel that planned stay. The property owner was gracious enough to work with us in our desire to reschedule our visit for May 2015, demonstrating a focus on and respect for his guests throughout the entire process. Our Key West vacation, and specifically our week-long stay in Ocean Paradise, was undoubtedly a memorable experience for me, my husband and our two adult children (as well as the little "furry" member of our family who also joined us for our Key West adventure). We will be returning to Key West, and when we do, Ocean Paradise will be our chosen "home away from home" during our stay!

Price per night from

$843

Dream Escape in Islamorada at Anglers Reef

Islamorada villa

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$287

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

  • Beach / lakeside relaxation
  • •  Nearest beach 2 mi
  • •  Air conditioning
  • 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.

Price per night from

$230

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • Beach / lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Swimming pool
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$345

Bay and Beach Beauty

Islamorada house

  • Nearest beach 0.01 mi
  • •  Child Friendly
  • •  Air conditioning
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$402

Indigo Reef, 32' dock, Marathon FL

Marathon villa

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$345

OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

Marathon house

  • Beach / lakeside relaxation
  • •  Nearest beach 3 mi
  • •  Swimming pool
  • 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

Price per night from

$654

Ocean pointe island retreat

Tavernier condo

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$224

KeyWestStay.com

Key West apartment

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“A great spot just outside Key West” If you're at all like me, you like places that are close to where you want to be but not in the middle of a busy area. This place is exactly that. A quick 7 minute drive puts you at the entrance to Key West. For anyone fishing like we were, it's an even shorter drive to Stock Island. The apartment was very clean and quite private. We enjoyed evenings just relaxing on the rooftop deck. The only thing we were a little sad about was that the grill on the deck in the photos was not there. Otherwise, this place is exactly as it is in the pictures. We are heading back to this area again in a year and will likely try to book this place again.

Price per night from

$190

Oceanfront Condo at Ocean Pointe Resort

Tavernier condo

  • Beach / lakeside relaxation
  • •  Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$259

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$1,395

STUNNING 2 BEDROOM OCEANFRONT SUITE WITH MAGNIFICENT VIEWS

Tavernier condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$276

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

  • Beach / lakeside relaxation
  • •  Nearest beach 6 mi
  • •  Swimming pool
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$374

Bayside home with dock!

Key Largo house

  • Beach / lakeside relaxation
  • •  Nearest beach 5 mi
  • •  Child Friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Peaceful stay in Key Largo” I stayed at the Bayside home from 12/31/14-1/6/15 and it was wonderful. Joy and Doug were very accommodating and available for any and all questions. The place was perfect to sit and enjoy the beautiful sunsets or greet the fellow boaters passing through the canal. It was a perfect midpoint between Key West and Miami. Thanks, Joy and Doug for a wonderful stay!

Price per night from

$225

Villa Deja vu Key West ~ Weekly Rental

Key West house

  • Nearest beach 0.5 mi
  • •  Swimming pool
  • •  Ask about children
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great stay over the 4th of July” The Villa Deja Vu was the perfect place for our group of 10. We were on vacation in Key West for a 30th birthday celebration and had a great experience. The house was wonderful, more than we could have imagined. The pictures online truly do not give it justice. It is beautiful and brightly colored. The house was stocked, clean and comfortable for a large group. The grounds were in pristine condition and the location of the home was perfect for any activity on the island. We walked everywhere! Having a pool right in the backyard was such a great amenity. We used it every day. Most of the day we were even able to get a suntan there, even though it is hidden and private. We had one issue during our second day, the propane was empty for the grill. I called maintenance and they showed up within 15 minutes. The service was better than I could've asked for. My only suggestion for the property would be to add lighting out back for evenings at the house. We tended to eat dinner late, and used our phones for light over the grill.

Price per night from

$875

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

  • Nearest beach 0 mi
  • •  Swimming pool
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$173

Florida Keys Splendor at Hammer Point

Tavernier house

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Car not necessary
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Piece of Paradise” This home was perfect! Midgy was very accomodating. We took the kayak out several times, since it was a 2 person my husband and I could enjoy it together. The bikes that Midgy had were great for fun rides around Hammer Point. We went snorkeling at John Pennekamp Park, it was amazing! A trip to Key West is a must. We used Fury for parasailing and the dolphin adventure, they were very professional and fun tour guides. I would highly recomend this rental it surpassed all expectations!

Price per night from

$115

Please all towels most be left clean if not will be a fee. Thanks

Lower Keys house

  • Nearest beach 13 mi
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$306

***NEW 3D Tour Indigo Reef Luxury Villa Exquisite "Latitude Adjustment"! #33

Marathon villa

  • Nearest beach 7 mi
  • •  Child Friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$224

Coconut Beach

Key West apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Price per night from

$263

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

  • Beach / lakeside relaxation
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Price per night from

$149

Beautiful Private Home with Beach Access.

Key Largo house

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$58

Sunset Catch- Gulf Front Home Incredible Views Pool Dock private and spacious

Grassy Key house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$525

Licensed Manager W/10 Rentals Available - 3/3 Villa - OCEANFRONT BEACH RESORT!

Key Largo villa

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Key Largo vacation” I along with my group were very pleased with the accomodations and the location. Felt extremely safe with the gated community. Fernando was extremely friendly and helpful with prompt email replies to all questions. I have never stayed in such a rental property, but will cetainly do so in the future. It was wonderful to not have to eat out for all meals and all possible cooking utensils were available.

Price per night from

$201

Heavenly Hideout at Rainbow's End ~ Weekly Rental

Key West house

  • Ask about children
  • •  Air conditioning
  • •  Private garden
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,003

Foundry on the Waterfront ~ Weekly Rental

Key West house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$280

Good Times and Tan Lines - (New Listing) Deluxe Renovated Ocean View 2B/2B Condo

Tavernier condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$246

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