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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
- 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
- 4 bedrooms
- 4 bathrooms
- sleeps 10
Price per night from
$460
Islamorada Luxury Waterfront Condo with Boat Slip
Islamorada apartment
- 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
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$82
Keys Cove Home #2 The Reel World
Marathon Shores house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Price per night from
$490
- 2 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$574
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.
Price per night from
$247
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$230
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$184
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!
Price per night from
$603
The Water's Edge
Key West house
- 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
- 2 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$287
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.
Price per night from
$230
Anglers Reef Islamorada Florida Sleeps 6
Islamorada house
- 2 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$345
Indigo Reef, 32' dock, Marathon FL
Marathon villa
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$345
- 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
- 2 bedrooms
- 2 bathrooms
- sleeps 5
Price per night from
$224
KeyWestStay.com
Key West apartment
- 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
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$259
Incredible Luxury Home with Waterfront!! Paradise
Islamorada house
- 5 bedrooms
- 6 bathrooms
- sleeps 12
Price per night from
$1,395
STUNNING 2 BEDROOM OCEANFRONT SUITE WITH MAGNIFICENT VIEWS
Tavernier condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$276
Spacious Top Floor Condo w/ Water View!!
Marathon apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Price per night from
$374
Bayside home with dock!
Key Largo house
- 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
- 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
- 1 bedroom
- 1 bathroom
- sleeps 4
Price per night from
$173
Florida Keys Splendor at Hammer Point
Tavernier house
- 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
- 2 bedrooms
- 2 bathrooms
- sleeps 8
Price per night from
$306
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$224
WELCOME TO PARADISE! In the heart of Islamorada
Islamorada condo
- 1 bedroom
- 1 bathroom
- sleeps 5
Price per night from
$149
Beautiful Private Home with Beach Access.
Key Largo house
- 2 bedrooms
- 1 bathroom
- sleeps 6
Price per night from
$58
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Price per night from
$525
- 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
- 4 bedrooms
- 4 bathrooms
- sleeps 8
Price per night from
$1,003
Foundry on the Waterfront ~ Weekly Rental
Key West house
- 2 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$280
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$246