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Vacation Rentals & House Rentals in Florida Keys

223 house rentals

SPECIAL FALL RATES, INCL. LABOR DAY - BOOK NOW!

Marathon house

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

Price per night from

$287

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

Amazing Ocean View Condo on the Beach!

Marathon apartment

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

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

Price per night from

$236

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

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

“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranquil. The patio faces south so you don't get blasted with the morning or evening sun making it very comfortable having your morning coffee or evening cocktail while enjoying the view. The owners have put a lot of thought into furnishing and accessorizing the unit. Tess and Mimi were wonderful to work with (Mimi met us at the condo and had great advice on where to eat, what to do...)I have stayed in several condos and this was by far my favorite, if your thinking of staying here you will not be disappointed. I will definitely be back the next time I visit the keys.

Price per night from

$330

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage

Marathon Shores house

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

Price per night from

$258

Lovely condo with stunning ocean views & entertainment - close to the beach!

Duck Key house

  • Child Friendly
  • •  Car not necessary
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$162

Relaxing retreat with full kitchen and amazing ocean views!

Duck Key house

  • Child Friendly
  • •  Car not necessary
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$130

Ocean-Front Caribbean Home.

Islamorada house

  • Swimming pool
  • •  Child Friendly
  • •  Car not necessary
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,723

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

Key Largo 2/2 Tropical Daze Oceanfront Condo

Key Largo apartment

  • Beach / lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Price per night from

$228

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

PARADISE OCEAN FRONT HOME

Marathon house

  • Nearest beach 5 mi
  • •  Child Friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$287

Escape to Paradise --2 bedroom oceanfront condo on Coco Plum

Marathon apartment

  • Beach / lakeside relaxation
  • •  Nearest beach 1 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Great condo with beautiful ocean views!!!!” We couldn't have picked a better condo and location!! Many great restaurants and bars only a few miles away. The pool was really nice overlooking the beach. The condo was nicely decorated and plenty of room for just the two us. Enjoyed sitting out on the screened in lanai having our morning coffee or in the evening having a cold drink listening to the waves and enjoying the light of the full moon reflect off the ocean. The Keys are truly a paradise and we will definitely be back and would highly recommend this condo and area to stay!!!

Price per night from

$214

Waterfront condo with rooftop patio, balcony, and dock!

Marathon Shores house

  • Car not necessary
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$212

NEW LISTING! Oceanfront home with private hot tub and amazing ocean views!

Conch Key house

  • Child Friendly
  • •  Car not necessary
  • •  Air conditioning
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$220

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

Paradise on the water

Key Largo house

  • Child Friendly
  • •  Air conditioning
  • •  Private garden
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$288

Oceanfront Condo - Pool, Beach, Tennis & Marina

Tavernier condo

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

Price per night from

$230

Key West Florida Beachfront Condo

Key West condo

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

“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks

Price per night from

$402

Waterfront Key Largo Bayside Cottage Paradise

Key Largo cottage

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

“Hidden Treasure” This cottage is one of our favorite place to stay. Clean, well equipped, private, and so relaxing. A great place to spend a relaxing vacation. We love the outdoor kitchen and sitting area.

Price per night from

$178

Gorgeous, recently-updated, waterfront home w/ beach, pool, dock, & kayaks

Duck Key house

  • Swimming pool
  • •  Car not necessary
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$771

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

Ocean Views, Heated Pool, Private Beach

Marathon condo

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

“Paradise Found” This is one of the nicest places we have ever stayed in Florida. It is clean and well supplied with everything we need. The view is fantastic, with the ocean straight out in front of us. The pool is also part of our view. Kevin is very nice and ready to help in anything we might need. Meghan is also very nice and helpful.

Price per night from

$184

KAWAMA TOWER- Beautiful Ocean view unit

Key Largo condo

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

Price per night from

$172

NEW LISTING! Waterfront condo w/ shared pool and hot tub & amazing water views

Stock Island house

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

Price per night from

$215

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Islamorada condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$229

Oceanfront Condo at Ocean Pointe Resort

Tavernier condo

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

Price per night from

$259

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

Stock Island house

  • Swimming pool
  • •  Child Friendly
  • •  Car not necessary
  • 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.

Price per night from

$305

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

NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

Islamorada condo

  • Nearest beach 2 mi
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$172

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

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

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Price per night from

$608

Paridise Found

Tavernier house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 13

Price per night from

$763

East Sister Rock Island

Marathon Shores house

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

Price per night from

$1,562

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

***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

Paradise In Marathon, FL Keys Large Oceanside Home

Marathon house

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 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

Price per night from

$401

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