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Vacation Rentals & House Rentals in Florida Keys

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842 house rentals

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$80

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.

Price per night from

$1,227

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 11 minutes

Price per night from

$312

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$287

Pools, Jacuzzis, Rec Room, Gym, 24/7 security! Stay at Mariner's Club 606!!

Key Largo townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$719

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

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$574

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$328

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$288

Price per night from

$311

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 16 minutes

Price per night from

$200

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

Cudjoe Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$184

58630 Morton Street

Marathon condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

Studio Blue

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$331

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. 32 minutes

Price per night from

$346

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 47 minutes

Price per night from

$460

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,719

Duck Key 50% off October

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 51 minutes

Price per night from

$340

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 57 minutes

Price per night from

$207

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 14 minutes

Price per night from

$658

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. 2 hours 23 minutes

Price per night from

$516

76004 Overseas Highway

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

“Wonderful accommodations” Aside from being rainy for the majority of our stay, the accommodations were amazing. We will certainly be going back to this house. This house sleeps 8-10 adults comfortably. Freewheeler Realty was a pleasure to do business with and was the only company that was responsive to my inquiries. The house has an amazing view, full laundry, kitchen upstairs and downstairs. My favorite part were the stairs that go directly into crystal clear water to snorkel!

Price per night from

$328

Paradise on the water

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 56 minutes

Price per night from

$570

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 11 minutes

Price per night from

$822

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

Conch Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 21 minutes

Price per night from

$188

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$195

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.

Price per night from

$144

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. 2 hours 1 minutes

Price per night from

$252

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 46 minutes

Price per night from

$266

75130 Overseas Highway

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful Sunsets in Islamorada” There is a great view from the roof top deck for sunsets. The screen porch was great at night to keep the bugs away. The beach was very nice too. The setup is good for two couples or a small family. Also the staff from Freewheeler was great in getting us moved from our original rental.

Price per night from

$247

Bay Harbour D-114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$328

132 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

“Fantastic getaway” This is a great vacation rental property for a couple or small groups of 4 or less people. First of all, you can't beat the panoramic view of the water and what's more, the water is just 10 ft away. The front yard is one of the best if not the best with a lot of gardening and the antiques placed in the garden easily beats the boring gnomes. The interior of the house has a very wood cabin like feel to it and if you're looking for modern furniture, you'll be disappointed but if you're into a quaint little cottage like atmosphere, this will not disappoint. The 2 bedrooms are well kept and there are tons of pictures on the wall from the owners' travels all over the world and they're very interesting. There is no flat screen TV but the old color TV is more than sufficient - it has cable with most big channels you'll need (no premium ones except maybe Encore). They also have a ton of Dvds and Music CDs for your entertainment if you ever get bored of the views from the wrap around deck :-) The sunrises from this deck are awesome if you can wake up early - no sunsets cuz that's on the other side but you can always walk/drive over to the Overseas highway within minutes to catch the sunsets from there. The other amenities worth mentioning are the inground hot tub/spa they have which was awesome - you can view the ocean from the spa. If that wasn't close enough a view, you can pick up the huge Kayak they have and walk right into the water and row away. If there was any drawback, it was these bugs called no-see-ums that come out in full force in the evenings and if you aren't taking necessary protection, they will wreak havoc on your skins, but the owners/realtors can't do much about this. Just get some Off spray or something and you'll be fine. Overall this was a memorable trip for us and we hope it will be for you too. Thanks!

Price per night from

$328

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 55 minutes

Price per night from

$438

Key Largo 2/2 Tropical Daze Oceanfront Condo

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

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

Responds fast! avg. 10 minutes

Price per night from

$333

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

$171

Oceanfront Condo: Ocean Views, Pool, WIFI - Discounted Rate August

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 58 minutes

Price per night from

$195

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$345

8c, Efficiency located 50 yards from Ocean

Marathon studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 39 minutes

Price per night from

$230

Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals)

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$167

Viewing 38 of 842
rentals in Florida Keys

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About Florida Keys

Florida Keys, FL, including the islands of Key West, Key Largo, Islamorada, Marathon Key and Big Pine Key offers the perfect mix of family beach fun and peaceful vacation relaxation. Spend your days strolling one of the many boardwalks, or swim, snorkel, and kayak in the pristine Gulf. After a long day, retreat back to your vacation rental home at night, escape the crowds, and watch the sunset across the Gulf from your personal porch or deck. With your own private tennis court and pool, luxuries that many rentals offer, you can have a great time without even leaving your vacation home.

Wake up to the sound of waves rolling in and the scent of the salty ocean air, then walk just minutes to the beach for great boardwalk shopping, dining, and entertainment. Truly escape the winter chill by heading to the southernmost point in the United States, Key West, Florida. Take U.S. Highway 1, known to locals as "The Overseas Highway" to get there, and enjoy the breath-taking natural beauty of the ocean scenery and wilderness that borders the road.

Here are a few additional suggestions for your trip to the Florida Keys:

  • Visit the Key West Butterfly & Nature Conservatory: Key West is home to a magnificent array of butterflies from South America, Africa, and Southeast Asia. This Conservatory emphasizes the importance of wildlife preservation, offering group tours, unique films, and resident rainforest birds guaranteed to ignite your love for wildlife.
  • Swim with the dolphins: Key West is known for its dolphin friendly environment and facilities that offer guests the opportunity to swim and play with these amazing animals.
  • Explore The Harry S. Truman Little White House: Established in 1890 as a command center during the Spanish American War, this house was later used as a means of escape during the Cold War. For years, presidents relaxed and restored body and mind here while dealing with war threats. The site is now a living history museum.
  • Sleep under the stars: Spend a night under the legendary stars of Key West. Florida Keys campgrounds are plentiful, and Florida Keys camping can also happen at sea. Charter a boat and drift off with the night sky above and the ocean below.
  • Take a sunset dinner cruise: Gourmet dinner cruises to Florida Keys' destinations are widely available. Nothing is more romantic than raising a glass on a luxury sailboat as the sun sets over the Atlantic.
  • Take a charter fishing trip: An experienced outfitter can provide the boat and equipment you need to pursue deep water species like marlin and swordfish.

Whether you're here for a Florida Keys honeymoon, a family reunion, or a vacation getaway with friends, you'll easily find a perfect vacation rental with all the amenities you need to relax in style. Stay in a charming beach condo close to the restaurants and nightlife or rent an elegant villa with a balcony and stunning views of the ocean. You may also want to make some time during your vacation to visit nearby destinations like Naples or Marco Island.

Top Destination reviews

Island Hideaway
Key West

It was perfect for us. Only thing was the washer and dryer were persnickety. We each had our own space which was nice. … see more
Bayfront Vacation Home Villa Rental Bayside Beach View
Great Rental Property

My family and I had a great time at this rental property, and would recommend it. House was nice and roomy for a family of four. Great fishing off of the dock. Beautiful sunsets. Kayaks on site to use at no additional cost. Owner is very nice. This location will help you relax. We hope to come back soonsee more
Bayfront Vacation Home Cottage Rental Bayside Beach *Renovated 2019*
Perfect

Great house. Very clean and simple. You share the beach and dock with the two other houses in the property but was never an issue. Location is great in Largo. Martha was a great host and very friendly. Will definetly be going back. … see more
Sunshine suit (2/2 apartment)
Nice

It was a great place wit your family .my daughter loved it cause the pool was right on front our building … see more
Paraidise with or witout boat
Fun I. The Keys

The owner was very accommodating. And very willing to work with us in adjusting our reservation as tropical storm Elsa inspired us to adjust our stay date. Living area is nicely decorated. Location is excellent. Marathon's Sombrero Beach is a bike ride away. Recreation trail runs right in front of the house. We brought our boat and enjoyed snorkling at Sombrero reef. Fished at several locations on the Atlantic side. Did lots of tubing on the gulf side. Only down side was the back deck and steps need a bit of attention. We would definitely stay there again.see more
Dolphin Oasis 4bdr/4bth Pool/hot tub 115' dockage
Excellent

Location is great. Especially if you bring your boat. Home is wonderful. Pool was great after long day on the water. Owners have done a great job of making their home accommodating. My family had a wonderful time. Will be back. … see more

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