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Vacation Rentals & House Rentals in Florida Keys

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1,253 house rentals

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$73

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

$74

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 31 minutes

Price per night from

$238

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.

Price per night from

$348

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$177

Oceanfront duplex with spectacular views, beach, and dock

Layton house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$474

Oceanfront condo w/beach access, shared tennis, pool, etc. - marina available!

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$93

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

$548

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

$575

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

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$253

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$313

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

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 49 minutes

Price per night from

$260

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

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$284

Large Townhouse in Mariner's Club Resort - 3 BR/3.5 Bath

Tavernier townhouse

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 40 minutes

Price per night from

$338

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

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 49 minutes

Price per night from

$212

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

$185

58630 Morton Street

Marathon condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

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

Studio Blue

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$220

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. 2 hours 42 minutes

Price per night from

$220

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 36 minutes

Price per night from

$257

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 57 minutes

Price per night from

$1,713

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 59 minutes

Price per night from

$262

New 3 bedroom luxury condos just 10 mins from 10 beaches!!

Dry Tortugas National Park apartment

3 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$115

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 40 minutes

Price per night from

$165

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$648

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 28 minutes

Price per night from

$404

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

Casa Havana

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,011

Paradise on the water

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 5 minutes

Price per night from

$596

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 31 minutes

Price per night from

$659

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 28 minutes

Price per night from

$200

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$207

Waterfront condo with rooftop patio, balcony, and dock!

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$229

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 49 minutes

Price per night from

$145

Waterfront Key Largo Bayside Cottage Paradise

Key Largo cottage

2 bedrooms / 4 bathrooms / sleeps 4

“Amazing” Keep your eyes opened along with your heart! You will definitely enjoy the house and the area !! Clean , new , nice home the canal is awesome we had 2 manitee hang out off back porch !!! Definitely go on kayak and look in canal in front of boat for the amazing jellyfish and other creatures!! The place is close to restaurants and attractions!! We had an awesome honeymoon can’t wait to go back !! Thanks for sharing your place worth every penny!!

Responds fast! avg. 1 hour 35 minutes

Travelers’ Choice award

Price per night from

$177

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$217

Viewing 38 of 1,253
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

Duck Key Waterfront Villa: Private Pool w/ Canal Views, Kayak & Paddleboard!
Clean and comfortable, loved the pool.

Great location, small view of the canal. All kinds of fish in the canal to see. Condo was spacious and clean. If staying more than a few days, bring supplies. Had to buy trash bags, laundry soap, toilet paper, and dishwasher soap. They provide a little, but not a weeks worth. Cannot grill on the property\grounds. Provided beach towels which was nice. Plenty of regular towels. AC worked good. Nice location, middle of the keys. Duck Key is a quiet place, very nice. Pool - just the right size, spent a lot of time lounging in the pool and back patio.see more
Real World MTV House Key West
Fun trip

We had a great time. Andrew was really great to work with. The fishing was awesome. My husband wouldn’t leave the deck the entire time we were there. There were 20 of us staying there and there was plenty of room and so much to do. We would definitely go back. … see more
500 Ocean - Tropical Florida Keys Vacation Home
2020 Mini Season

Great place to stay, extremely clean and comfortable. Updated home with spacious living room, very nice kitchen, and fantastic porch area over looking the water. My Kids loved it to! Perfect location for fishing, diving and catching lobster. Quick boat ride to the reef. Perfect place for a relaxing vacation. The owners have been great with quick responses for even the littlest questions. Thank You Chuck for a awesome trip!!!see more
Oceanfront Seclusion & Privacy with Unobstructed Atlantic Ocean Views
Great location

Location was beautiful, house was clean and owner was very helpful and responsive. Tiki hut was awesome … see more
Tropical Cottage with Sandy Beach
Amazing!

This place is the best. We will definitely return. The cottage had everything we needed, plenty of dockage for our boats, kids loved the kayaks, and spectacular views. Martha was wonderful to work with and made sure we had everything we needed. … see more
Tropical Retreat With Sandy Beach
Beautiful property

This place is way nicer then the pictures. The property itself is breathtaking and its right on the water with a beautiful deck. I love that we had access to kayaks whenever we wanted. No one else but our party was there. The house seemed pretty clean but I wish it had a quick sweep again before we got there. The barstools had lots of dead flies. Which is weird because we didn’t have any flies around even while cooking outside. I loved that we could fish right off the deck. Just wished there was a pipe outside to wash up before going in. It’s definitely heaven, I woke up at 6 one day and enjoyed the sunrise n watching Dolfins and manitees. I would definitely stay here again.see more

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