Vacation Rentals & House Rentals in Florida Keys

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612 house rentals

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 56 minutes

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$105

Amazing Ocean View Condo on the Beach!

Marathon apartment

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!

Responds fast! avg. 3 hours 13 minutes

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$236

Best Location, 1/2 Block to Duval, Bimini Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Perfect!” This was the perfect size suite for 4 adults, with a little pool oasis right off our doorstep, in the center of it all without the noise of Duval. Loved every second of my stay!

Responds fast! avg. 3 hours 59 minutes

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$297

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

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 53 minutes

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$287

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 1 hour 14 minutes

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$230

Private Home, with Beach Access, Best Value in the Keys

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect house for casual getaway” We wanted a clean and comfy place to stay for a long weekend that would be close to everything. This house had everything we wanted and more. We brought our 2 year old with us and felt like it was exactly the cozy and safe place we needed. If we weren't relaxing on the front or back deck, there were a number of board games that entertained us while our child napped. The owner was pretty quick to respond to any questions we had. We hope to stay here again for future getaways!

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$75

3BR Oasis in the Keys w/ Kayaks & Paddle Boards - Sweeping Ocean Views!

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

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$303

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

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

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$574

Center of It All - Paradise Island Suite

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Great location in the heart of Old Town Key West, just a block off Duval..” We stayed in the Paradise Suite. Great front porch to hang out on, pool in back with pergola for lounging. Place was set up perfect, pool towels hanging by the door, bathroom had necessary items, kitchen well set up with needed items as well. Very well maintained and cleaned, bedding all set. Wi-Fi and other amenities available. Perfect for two couples, with room for even an extra guest. Driveway accommodates three cars, unmetered parking around the corner. Local market just 1/2 block away, and the highly recommended Thirsty Mermaid restaurant on the corner. Owner and managers very available and responsive. Will certainly stay again.

Responds fast! avg. 3 hours 59 minutes

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$286

Steps to Duval, Old Town Charm -Grand Bahama Suite

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Can't wait to return” We loved staying at the Grand Bahama suite. It was spacious, clean and centrally located just a street from all the action. We loved the courtyard and pool. I was a little concerned about parking but it worked out fine for us. We just coordinated with the other tenants. We will definitely be staying here again.

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$378

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!

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$215

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 12

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$287

1/2 Block to Duval, World of its own -Nassau Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent

Responds fast! avg. 3 hours 59 minutes

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$321

Keys Cove Home #2 The Reel World

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 41 minutes

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$490

Waterfront Keys Home - Spectacular View, 37' Dock

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful location” My husband, son, and I had a fantastic vacation here. The private boat dock and Bay Area was perfect for our needs. We were out in the gulf in a few minutes and could reach the Atlantic via Vaca Pass or 7 Mile bridge in just a short boat ride. The house itself was the perfect size for the 3 of us(& 2 shelties), giving each of us our own space. The view from the house is great. We watched tarpon, turtles, and dolphin!! The airport right behind us was not an issue!! In fact, we thought it was kind of cool to watch some of planes/helicopters!! The storage area with the bait fridge/freezer was a great plus!! There were 2 things that I noticed could improve (but by no means a reason to not stay here!!). First there was not any pantry storage. We just used the island top. No big deal. And the lint screen for the dryer was falling apart. Again no big deal. I would not hesitate to stay here again!!

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$200

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

Key Largo townhouse

4 bedrooms / 4 bathrooms / sleeps 10

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$460

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

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 45 minutes

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$230

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

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.

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Price per night from

$330

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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$1,723

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 12 minutes

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$287

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

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 13 minutes

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$258

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

Responds fast! avg. 3 hours 15 minutes

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$402

Key Largo Kampground Vacation

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

“Great location and pleasantly surprised!” Romberto's Camprground vacation was definitely more than i expected. There was ample room for my husband and I, the folks were nice and the area was quiet and clean. The marina was convenient (small boats only). There was a small leak in the bathroom in the overhead skylight but it was almost negligible unless it was pouring. we will definitely be back.

Responds fast! avg. 2 hours 56 minutes

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$144

Ocean pointe island retreat

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 28 minutes

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$224

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.

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$247

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

Cudjoe Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$184

Family Retreat ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 18

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$573

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

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$206

Seas the Day in this Waterfront Home on Oceanside MM90

Tavernier house

5 bedrooms / 3 bathrooms / sleeps 14

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$201

Blue Bungalow

Key Largo bungalow

1 bedroom / 1 bathroom / sleeps 2

“The Cozy Blue Bungalow” We stayed for a week on January 2019. It was perfect. Laura and Janet are thoughtful hosts and seem to have considered every need of their guests. They graciously allowed us to bring our 35 and 55 lb rescue dogs with us. The small deck in the fenced in back of the house has a nice shade, a really nice grill and is a lovely place to just sit and relax. Inside, a king size day bed and a small table and chairs. While no stove/ oven, you do not need one as their is a microwave and the grill has a gas burner for cooking. The bathroom has a beautiful, large shower that I cover. Convenient location and they provide many suggestions for restaurants, fishing, etc. There is a fenced in private park on the water at the end of the street where our dogs could run freely. Can’t recommend this highly enough! We really enjoyed our stay.

Responds fast! avg. 1 hour 2 minutes

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$87

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!

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$843

OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

Marathon house

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

Responds fast! avg. 3 hours 13 minutes

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$654

Brand New 3 Story Key Largo Home

Key Largo house

5 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 1 hour 24 minutes

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$408

Oceanfront Condo - Pool, Beach, Tennis & Marina

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 2 minutes

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$230

Waterfront Key Largo Bayside Cottage Paradise

Key Largo cottage

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.

Responds fast! avg. 1 hour 3 minutes

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$178

Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise

Conch Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 23 minutes

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$189

KAWAMA TOWER- Beautiful Ocean view unit

Key Largo condo

2 bedrooms / 2 bathrooms / sleeps 6

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$172

2 Great Waterfront FL Keys Homes - 1 Low Price

Marathon house

4 bedrooms / 4 bathrooms / sleeps 12

“Excellent Stay!” We rented out both sides for the week and we couldn't have asked for a better location! Great fishing, lobstering, and diving. We took the boat out almost everyday right from the house. Just enough room for our 9 people plus 1 baby. I loved how the kitchen was fully stocked with any possible cooking thing we needed. Everything worked perfect and was up to date.

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$372

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