Vacation Rentals & House Rentals in Florida Keys

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1,542 house rentals

20

Oceanfrontparadise: 209

Florida Keys / Islamorada

Islamorada apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$250

Price per night from

$250

(15) Excellent 

21

Islamorada Luxury Waterfront Condo with Boat Slip

Florida Keys / Islamorada

Islamorada apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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 restau
…see more

Price per night from

$214

Price per night from

$214

(19) Excellent 

26

Spectacular Atlantic Ocean View Condo (MONTHLY)

Florida Keys / Key West

Key West apartment

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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 tranqu
…see more

Price per night from

$135

Price per night from

$135

(65) Very Good 

Certificate of Excellence

11

Steps to Duval, Old Town Charm -Grand Bahama Suite

Florida Keys / Key West

Key West apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary
“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.
…see more

Certificate of Excellence

Price per night from

$329

Price per night from

$329

19

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

Florida Keys / Key West

Key West townhouse

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$299

Price per night from

$299

29

NEW LISTING! Lovely condo w/stunning ocean views & entertainment-close to beach

Florida Keys / Marathon

Marathon house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$90

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$90

35

3BR Oasis in the Keys w/ Kayaks & Bikes - Sweeping Ocean Views in Every Room!

Florida Keys / Marathon

Marathon house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$266

Price per night from

$266

(3) Very Good 

12

Conch Haven Old Town 1/1 MONTHLY Rental

Florida Keys / Key West

Key West apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$93

Price per night from

$93

(2) Excellent 

21

Ocean-Front Caribbean Home.

Florida Keys / Islamorada

Islamorada house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$1,500

Price per night from

$1,500

(16) Excellent 

37

Amazing Ocean View Condo on the Beach!

Florida Keys / Marathon

Marathon apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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 peace
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Price per night from

$206

Responds fast!
avg. 2 hours 55 minutes

Price per night from

$206

(34) Excellent 

Certificate of Excellence

17

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

Florida Keys / Key West

Key West apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
“Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent
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Certificate of Excellence

Price per night from

$279

Price per night from

$279

27

Oceanfront duplex with spectacular views, beach, and dock

Florida Keys / Long Key

Long Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$300

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$300

(2) Excellent 

26

Keys Spectacular Gulf of Mexico Views

Florida Keys / Marathon

Marathon house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$228

Price per night from

$228

38

PARADISE OCEAN FRONT HOME

Florida Keys / Marathon

Marathon house

4 11 4 nights min

  • 4 bedrooms
  • sleeps 11
  • 4 nights min
  • Nearest beach 5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$255

Price per night from

$255

(48) Very Good 

Certificate of Excellence

17

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

Florida Keys / Key West

Key West apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary
“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!
…see more

Certificate of Excellence

Price per night from

$259

Price per night from

$259

36

Keys Cove House 4

Marathon / Marathon Shores

Marathon Shores house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$428

Responds fast!
avg. 1 hour 13 minutes

Price per night from

$428

(1) Excellent 

24

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

Florida Keys / Marathon

Marathon house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$221

Price per night from

$221

(4) Excellent 

48

Key West Condo close to the Ocean

Florida Keys / Key West

Key West condo

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$260

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$260

24

NEW LISTING! Relaxing retreat w/ a full kitchen - walk to the water

Florida Keys / Duck Key

Duck Key house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$95

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$95

(5) Excellent 

36

Beautiful Condo - Moon Bay - Waterfront - Spectacular Views in Key Largo

Florida Keys / Key Largo

Key Largo apartment

2 6 6 nights min

  • 2 bedrooms
  • sleeps 6
  • 6 nights min
  • Child Friendly
“Excellent Condo” Oly was very accommodating and the place was beautiful and emaculate, the kitchen was fully stocked with everything you need. The beds were very comfortable and the ceiling fans were a nice addition. The facilities were also very clea
…see more

Price per night from

$165

Price per night from

$165

(1) Excellent 

27

WOW – waterfront, boat lift, private heated pool, walk to beach and shops!

Florida Keys / Marathon

Marathon house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$200

Price per night from

$200

30

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

Key Largo / Tavernier

Tavernier house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$132

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$132

(32) Excellent 

Certificate of Excellence

14

Center of It All - Paradise Island Suite

Florida Keys / Key West

Key West apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary
“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
…see more

Certificate of Excellence

Price per night from

$249

Price per night from

$249

(4) Excellent 

23

76004 Overseas Highway

Florida Keys / Islamorada

Islamorada house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
“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 busine
…see more

Price per night from

$321

Price per night from

$321

(13) Very Good 

32

75731 Overseas Highway

Florida Keys / Matecumbe Key

Matecumbe Key house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
“Relaxing!” The Florida Keys are so much fun and so very casual. The house was a great way to get our family together for a week and we all enjoyed ourselves, I could have stayed for a month. The guys all went fishing and the rest of us floated in the
…see more

Price per night from

$1,045

Price per night from

$1,045

40

LARGE HOME NEAR BEACH & KEY WEST

Florida Keys / Big Pine Key

Big Pine Key house

3 12 min stay varies

  • 3 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$329

Responds fast!
avg. 36 minutes

Price per night from

$329

(1) Very Good 

11

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

Florida Keys / Cudjoe Key

Cudjoe Key cottage

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$149

Price per night from

$149

(61) Excellent 

26

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

Florida Keys / Key West

Key West house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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.
…see more

Price per night from

$229

Responds fast!
avg. 1 hour 27 minutes

Price per night from

$229

24

1BR Restored Conch House w/ Pool & Deck

Florida Keys / Key West

Key West house

1 3 30 nights min

  • 1 bedroom
  • sleeps 3
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$89

Price per night from

$89

41

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

Florida Keys / Key Largo

Key Largo houseboat

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min

Price per night from

$170

Price per night from

$170

(3) Average 

24

Casa Havana

Florida Keys / Key West

Key West house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$679

Price per night from

$679

44

Keys Cove House 2

Marathon / Marathon Shores

Marathon Shores house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$428

Responds fast!
avg. 1 hour 13 minutes

Price per night from

$428

(4) Very Good 

26

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

Key Largo / Tavernier

Tavernier townhouse

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$295

Responds fast!
avg. 1 hour 56 minutes

Price per night from

$295

(1) Excellent 

16

Studio Blue

Florida Keys / Key West

Key West apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Car not necessary

Price per night from

$200

Price per night from

$200

(3) Excellent 

9

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

Florida Keys / Islamorada

Islamorada apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$175

Responds fast!
avg. 29 minutes

Price per night from

$175

(42) Excellent 

20

Waterfront Keys Home - Spectacular View, 37' Dock

Florida Keys / Marathon

Marathon house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly
“Enjoyable vacation rental and location” All is as advertised. The view is awesome. Rental unit has everything that one would need for a week or several weeks stay. Washer/dryer, comfortable beds, towels, kitchen stuff, TV, Wi-Fi, etc. All we had t
…see more

Price per night from

$136

Price per night from

$136

(3) Excellent 

44

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

Florida Keys / Key Largo

Key Largo townhouse

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$400

Price per night from

$400

(4) Excellent 

16

Newly refinished condo open water views very nice

Florida Keys / Islamorada

Islamorada condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$200

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$200

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.