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Vacation Rentals & House Rentals in Florida Keys

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870 house rentals

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$80

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!

Price per night from

$77

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. 2 hours 48 minutes

Price per night from

$276

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 23 minutes

Price per night from

$285

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$290

Price per night from

$309

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

$286

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$326

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

$183

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 51 minutes

Price per night from

$598

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,714

Paradise on the water

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 36 minutes

Price per night from

$590

Studio Blue

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$229

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

$571

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 37 minutes

Price per night from

$487

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

$1,225

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$199

75130 Overseas Highway

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 4

“The view and location was excellent.” The house had most of the amenities I would expect at a beach location. You can't beat the sunsets over the bay! We snorkeled at Key Largo and took a day trip into key West, so the location was perfect. The area had the best restaurants. We tried them all. Only complaints were: no outdoor grill, no wine glasses, sheets kept pulling off the bed and rusted beach chairs.

Price per night from

$246

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

Key Largo townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 59 minutes

Price per night from

$715

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

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$652

Bayside Home w/ Heated Pool, Rooftop Terrace & Stunning View

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$230

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 41 minutes

Price per night from

$427

58630 Morton Street

Marathon condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 55 minutes

Price per night from

$206

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 56 minutes

Price per night from

$400

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$555

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 45 minutes

Price per night from

$183

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

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 24 minutes

Price per night from

$204

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

$143

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 22 minutes

Price per night from

$192

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. 1 hour 26 minutes

Price per night from

$331

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

$263

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$429

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 3 hours 18 minutes

Price per night from

$686

BEBA'S REEF HOUSE

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$158

Bay Harbour D-114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$328

Catch of the Day!

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$122

Viewing 38 of 870
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

Sunrise at Seaside Condo 2 Bedroom
Convenient stay

Clean and quiet. Balcony overlooks pool. Easy parking and access to building with an elevator. Condo could use some paint updating. … see more
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Perfect!

This place is absolutely amazing! Very clean and spacious. So beautiful inside and out. I can't say 1 bad thing about this condo. I would definitely go back here and I recommend it to everybody. … see more
Bayfront Vacation Home Cottage Rental Bayside Beach *Renovated 2019*
Almar cottage

We couldn't have been more pleased with our stay in Key Largo. Everything went smoothly from arrival to departure. The owner Al was very helpful and knowledgeable. We will definitely be back again and rent from Martha and Al again. Thanks for the great week of vacation! … see more
Captains Quarters - Convenient Canal Front Home Off Boot Key Harbor, Bring The B
Perfect fishing getaway!

Two couples and our pups all enjoyed our stay at the Captains Quarters! We rented a boat for the week and had it delivered in the backyard. This home had everything we could needed for cooking and plenty of hangout space. The screened in porch was the room we used the most! The home is close to many delicious restaurants and local shopping. We cannot wait until our next vacation down in Marathon! I absolutely recommend staying here!see more
Kokomo Cove Boat House
Paradise

Could not recommend Brian’s place enough. Beautiful, clean and had everything we could possibly need. … see more
75130 Overseas Highway
Amazing views of the Gulf

Loved the split bedroom plan and the open common area. Older home and stairs difficult to navigate at times. So quiet and peaceful when construction not going on next door. Loved the private beach. Outdoor chairs could be updated. … see more

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