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Vacation Rentals & House Rentals in Florida Keys

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Vacation Rentals & House Rentals in Florida Keys

About Florida Keys

1,503 house rentals

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$94

1 / 12

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$215

1 / 21

Steps to Duval, Old Town Charm -Grand Bahama Suite

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Family Holiday” This was perfect for my family of four! My husband snores, so we put him in the master bedroom on the other side and didn't hear a sound. I think the nice high bed helped him sleep better. My son had and room and my daughter and I shared the other room and claimed the larger bathroom:). The suite was even better than I expected and the pictures don't do it justice. Everything worked out just fine for our first experience with a vacation rental. It was nice not having to waste time checking in or having to ask for extra towels. The location made it really easy to go to Duval and back to rest. I wish we could have planned a longer stay, but was glad we booked it last minute and hope to go again!

Responds fast! avg. 2 hours 39 minutes

Price per night from

$329

1 / 11

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$251

1 / 20

Sunrise Drive

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 4 minutes

Price per night from

$174

1 / 24

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

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$166

1 / 36

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

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“Casa Del Sol .....Fabulous!” Recently spent one week at Casa del Sol. This rental was in a perfect location, wonderful amenities, tastefully decorated and as neat as a pin. The Truman Annex location was very quiet and only a few blocks from Duval and restaurants. We loved it and didn't want to leave

Responds fast! avg. 1 hour 34 minutes

Price per night from

$215

1 / 26

Vaca Cove - Open Water, Protected Dockage and Great Pool, Jan, Feb Specials!!!

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“The Perfect Vacation!” The house was perfect for three families. The nice having a toast, coffee pot, blener and every thing we needed. The dock was perfect for our 25' boat. The kids loved the pool. The owners were there and were some of the kindest people we have ever met. Everything was clean and fresh. Convenient to restaurants, inlet, and boat ramp.

Price per night from

$451

1 / 22

Private Beachfront Paradise

Matecumbe Key house

4 bedrooms / 3 bathrooms / sleeps 8

“Pictures do not do this amazing rental house justice” We recently stayed at this beautiful house in July 2014 with two families total. It was paradise! The house truly met our needs and wants, from the private pool, hot tub, beautiful views, beach volleyball court, hammock, enormous amount of outdoor living space, up to date furniture and appliances, grill upstairs off kitchen/family room and grill on patio on lower level, tables to eat outside on upper deck and patio, comfortable beds, flat screen TVs in every room, just to start the list. The kitchen is well stocked for what you need to cook just about anything and plenty of extras (spices, oils, condiments, paper towels, etc) We also encountered the seaweed and foul smell, but it did not change our time here in the least. Lisa, the owner is quick to respond to you before and during your vacation, has thought of everything and really wants her guests to have a great experience. We would definitely come back and rent this house again!

Price per night from

$501

1 / 47

Tropical Keys Home - Gulf View, 40' Dock, Kayak

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Great Location” The house is wonderful, clean and airy with everything for a comfortable vacation. The area was nice and quiet and everyone we met was friendly. Joe was great to deal with, he was helpful and answered any queries we had promptly . We have already booked for next year.

Price per night from

$164

1 / 19

Private Home, with Beach Access, Best Value in the Keys

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful Home” This was a wonderful family home and we loved staying here. Central for everything we wanted to do Pennekamp and even a trip up to Miami for the Dolphins game lots of facilities bars nearby and loads to do. The home is well maintained and had everything and more for a family. Only one tiny issue the shower window in the main bedroom needs the privacy glass replacing as it faces the neighbours property but just a small issue. We really enjoyed our stay.

Price per night from

$56

1 / 68

Waterfront Keys Home - Spectacular View, 37' Dock

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Great Location and Property!” Wonderful location and property! We all enjoyed our stay and our rental property. The location is beautiful and centrally located. The rental was clean and well equipped. Our close friends rented the other side of the duplex and that worked well, because you share the area. We will definitely be back next summer!

Price per night from

$137

1 / 20

Center of It All - Paradise Island Suite

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Perfect spot to entertain and vacation in Key West” We stayed here for a week, for our destination wedding. We were able to entertain all of our wedding guests from out of town. Perfect size for our needs; great front porch, charming back yard, we loved the pool. The location was perfect, off of busy Duval, but right in the middle of things. I would recommend this place to anyone, and will stay here again in the future.

Responds fast! avg. 2 hours 39 minutes

Price per night from

$249

1 / 14

Sunrise At Seaside Condo 2 bedroom 2 bath

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“A wonderful place to stay.” My family and I traveled to Key West for the sunset wedding of my Grandson and Bride. What a wonderful stay we had over 5 days! The condo had everything except groceries and we shopped at the nearby Publix. I am telling everyone that couldn't attend about our place and of course I took lots of photo's to share. My family will be talking about this trip for a long time.

Responds fast! avg. 3 hours 41 minutes

Price per night from

$160

1 / 12

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

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$201

1 / 27

Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 2 Kayaks and padl board

Cudjoe Key caravan/mobile home

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$136

1 / 12

Key Largo 2/2 Tropical Daze Oceanfront Condo

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

“A great peaceful and tranquil break from the rest of the world” My wife has ms and we needed a place that would allow her reasonable access to the facilities. The condo was accessible, the beach area was a nice place to take her to enjoy being close to the atlantic and hear the surf. I prepared some of our meals at the condo and we frequented several of the restaurants in the Keys. The central location of the condo made going to Key West and John Pennekamp State Park great outings.

Responds fast! avg. 54 minutes

Price per night from

$200

1 / 38

Sunset Bay (weekly rental)

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$255

1 / 19

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 36 minutes

Price per night from

$166

1 / 19

Keys Spectacular Gulf of Mexico Views

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$229

1 / 26

Fisherman's Paradise with a 30 Ft Boat Slip

Long Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Our Honeymoon!” Our Honey Moon was very special at Fisherman's Paradise. Everything was top shelf and facilities are the best. The care that Bob Hubert paid to our every need was very special to us and the memories will last forever! Sincerely, Paget and Bennie McGee

Responds fast! avg. 2 hours 35 minutes

Price per night from

$180

1 / 22

FALL SPECIAL STAY 4 NIGHTS GET 5TH NIGHT FREE

Duck Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 27 minutes

Price per night from

$201

1 / 12

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

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Comfortable and close to everything” The Bimini Suite in Bahama house is either a 2 Bed room or a 3 bedroom suite and we six were comfortably housed as a 3BR just one block from Duval St, in the heart of Key West. Every thing is within walking distance including a grocery store. Bahama House is an older typical Key West house which is newly renovated. The Bimini is nicely decorated with comfortable beds, fresh bedding and a well equipped kitchen. Flat screens in every bed room and the Living Room and the WiFi worked well. The shady yard has a BBQ and seating. Customer service was always available and quickly sorted out any issues. There is some sound transfer from some of the other 3 suites of Bahama House to be aware of. We thought it great value for a great location.

Responds fast! avg. 2 hours 39 minutes

Price per night from

$260

1 / 17

Moon Bay B407

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$143

1 / 14

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“March Paradise” This condo was one of the most incredible find we found we discovered while searching the internet. After staying there it was even more then we expected. Rating it between 1 and 10...10 doesn't tell it all. The owners, the realtor and the property was a dream come true. We are looking forward to next year. The place to be!

Price per night from

$126

1 / 26

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

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic Location!” First time in the Keys, and we could not have asked for a better location in Key West. We were within walking distance of everything! Our unit (2BD/2BA) was roomy and met all of our needs. The support staff were quick and thorough when a minor plumbing issue developed in the first day. Other than that single bump in the road, the unit was a perfect fit for our group of four. In fact, we easily could have accommodated two more. Full kitchen came in handy, as did the pool and its associated lounge area. (Did not read closely. So I was very pleasantly surprised to find the pool available on site.) All communications before the trip were thorough and helpful. I will certainly be back!

Responds fast! avg. 2 hours 39 minutes

Price per night from

$280

1 / 17

New 4 bedroom,4bath in Beautiful Key Colony Beach

Key Colony Beach house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$258

1 / 21

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$130

1 / 19

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. 3 hours 33 minutes

Price per night from

$200

1 / 26

BAY THERAPY

Tavernier house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$160

1 / 25

Luxury Open Water Vacation Home

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$269

1 / 19

Gorgeous, dog-friendly, waterfront home with beach, pool, dock, & kayaks

Marathon house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 52 minutes

Price per night from

$501

1 / 37

Indigo Reef, 32' dock, Marathon FL

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$401

1 / 23

Please all towels most be left clean if not will be a fee. Thanks

Lower Keys house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$201

1 / 33

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 2 hours 12 minutes

Price per night from

$999

1 / 291

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 3 minutes

Price per night from

$380

1 / 31

Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Fabulous luxury home in Fabulous Key West” Beautiful, private, historic 2 BR/2 bath home, lovely heated pool, outdoor dining & living areas in addition to most attractive indoor spaces. Wonderful Old Town neighborhood. Can walk, cycle, & Lyft everywhere (including great restaurants)--no car needed. 2nd BR is in the guest house beyond the pool--fabulous outdoor shower completes the "only-in-Key West" ambiance. The owner, Kim, is super responsive.

Price per night from

$472

1 / 23

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 20 minutes

Price per night from

$201

1 / 16
Viewing 38 of 1,503

About Florida Keys

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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.

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