Vacation Rentals & House Rentals in Florida Keys

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1,491 house rentals

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!

Price per night from

$220

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!

Price per night from

$297

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

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$303

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

Price per night from

$322

Keys Cove Home #2 The Reel World

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

Price per night from

$490

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

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

Duck Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 15 minutes

Price per night from

$134

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.

Price per night from

$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

Price per night from

$258

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 12 minutes

Price per night from

$236

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

$458

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 42 minutes

Price per night from

$338

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

$330

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$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 17 minutes

Price per night from

$257

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 24 minutes

Price per night from

$93

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

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 15 minutes

Price per night from

$89

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

$75

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$287

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,729

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.

Price per night from

$377

Key West Condo close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 38 minutes

Price per night from

$229

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

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 55 minutes

Price per night from

$201

Relaxing retreat with full kitchen and amazing ocean views!

Duck Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 15 minutes

Price per night from

$134

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

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 5 minutes

Price per night from

$287

Casa Havana

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$779

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

Canal-Front 3BR w/ Private Pool, Boat Slip, Tiki Hut & Kayaks - Near Beach

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$179

Keys Cove Home #4 Wave from it all

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

Price per night from

$573

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

Studio Blue

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$229

The Happy Crabby - Floating Tiny Home in Paradise, As Seen in Coastal Living

Key Largo houseboat

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 49 minutes

Price per night from

$196

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

$190

Bayside 3BR/3BA w/ Heated Pool, Dock Access, Rooftop Terrace & Stunning View

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$142

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

$572

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

$266

Paradise on the water

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 8 minutes

Price per night from

$287

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$458

Viewing 38 of 1,491
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

500 Ocean - Tropical Florida Keys Vacation Home
Zen Oasis with a Dock

Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!see more
Tropical Paradise at #1 Rated Resort in Marathon
Paradise

We had an amazing time in the keys! This stay just solidified our plans to move here after we retire from the military in 3 years. Coral lagoon was beautiful and perfect for our family vacation! … see more
Tropical Retreat With Sandy Beach
FANTASTIC

WE LOVED EVERY BIT OF OUR STAY !! Pretty much as described private beach deep water dock . Beautiful views !! The property is shared but the main house is owned by the same couple. There is plenty of room and lots of toys to play with. ( kayaks, fishing gear, sand toys) we will be back !!! … see more
Islamorada Luxury Waterfront Condo with Boat Slip
Great Keys Condo

Owners are very responsive. Great condo with boat slip and very good location. Very well provisioned. The condo even has a freezer chest for bait and ice. … see more
Florida Keys Sailing on Conch Key. Bayfront 2 BR cottage with 23 foot Sailboat
Great Family Vacation Getaway!

Barry And Tammy’s place was perfect! Extremely affordable, comfortable and very quaint. Loved the personality of the charming nautical decor and it was VERY clean. Be sure to bring your fishing poles and some bait... we fished off the doc almost every night and caught several. There were some huge fish lurking around. Didn’t have much wind for the sailboat but we took it out for a sunset viewing on our last night and got to see dolphins. This place was awesome and worth every penny. We will definitely look into returning one day. Thank you for the hospitality!see more
2 bedroom Condo Presented Key West Style
Great Stay!

Pam’s condo was great to stay in l, and it was easy to communicate with her—she even gave us some recommendations where to eat at. I would definitely stay here again in the near future & recommenced y’all to book her condo. … see more