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Florida Keys Vacation Rentals & House Rentals - 284 Rentals Available

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284 Vacation rentals

(11)

1 / 51

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“We have been Lucky enough to get Married at Seabird Key in 2005 & have been going back for our Anniversary ever since. It is truly amazing place away from everything . It is very well kept outside & Inside .very clean. It is beautiful & worth every...”
- Review left on 03/18/2016

$900

Excellent (11 reviews)

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from $900 / night

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(1)

1 / 23

Marathon Shores House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$425

Excellent (1 reviews)

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from $425 / night

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(7)

1 / 12

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$275

Very Good (7 reviews)

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from $275 / night

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(44)

1 / 12

Key Largo Cottage

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“we were very pleased with our stay at Alamar. We actually were the only ones on the property that weekend. It was quiet and very tranquil. I recommend this hidden little gem. We brought our two dogs and on Saturday rode down to the Islandmorada Fish...”
- Review left on 10/12/2016

$200

Very Good (44 reviews)

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from $200 / night

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(5)

1 / 13

Ramrod Key House

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We enjoyed our vacation in this spacious home. We had 5 adults and 2 small boys and never felt cramped. The wood floors and opened concept allowed us to spend a lot of time together. Great dock for the boat! Just a couple of minutes to open water....”
- Review left on 08/02/2016

$215

Very Good (5 reviews)

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from $215 / night

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(119)

1 / 28

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“we can"t say enough about the condo or Pam. She takes good care of her rental. Always clean and comfortable.The balcony overlooks the pool area which is well maintained. Pam is always available to answer any questions you might have. We stay the...”
- Review left on 12/03/2016

$200

Excellent (119 reviews)

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from $200 / night

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(39)

1 / 10

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We were very pleasantly surprised at the location of this rental. We loved the view of the sunrises over the water. The home was very adequately supplied with all kitchen utensils. Grill outside had plenty of gas. They had fresh flowers to please...”
- Review left on 02/25/2017

$157

Very Good (39 reviews)

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from $157 / night

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(3)

1 / 6

Key West Apartment

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$295

Very Good (3 reviews)

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from $295 / night

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(9)

1 / 19

Conch Key Cottage

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$175

Excellent (9 reviews)

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from $175 / night

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(8)

1 / 20

Ramrod Key House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Very clean has all the essentials. Loved being able to have the boat right there. Definately will be back”
- Review left on 09/17/2015

$110

Excellent (8 reviews)

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from $110 / night

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(3)

1 / 21

Marathon Villa

  • 3
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The house was amazing and so was Cindy! I almost hate to let the rest of the world know what a gem this property is. We booked the home with another couple and unfortunately our friend's father became terminally ill and ended up passing away during...”
- Review left on 01/26/2017

$321

Excellent (3 reviews)

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from $321 / night

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(48)

1 / 34

Cudjoe Key House

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$414

Very Good (48 reviews)

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from $414 / night

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(12)

1 / 18

Marathon House

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“It was a great place to stay. Very nice and clean. Location is great. Neighbors are friendly. For the fisherman, this place is great. Caught several fish. Would definitely refer this place to others. Look forward to coming back...”
- Review left on 11/03/2016

$257

Very Good (12 reviews)

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from $257 / night

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(9)

1 / 12

Marathon Shores House

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
“Great place to stay, owner easy to reach and help if needed. Great dock for your boat, easy to park tie up and launch. House very clean and felt like home, I plan to stay there again”
- Review left on 01/06/2016

$358

Very Good (9 reviews)

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from $358 / night

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(4)

1 / 9

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The canal front cottage was beautiful . Super clean perfectly furnished, hey 3 flat screens First class cooking utensils. Grill chairs by the dock, water, fish station & great light for night activity. Owner and manager readily available, most...”
- Review left on 08/30/2015

$156

Excellent (4 reviews)

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from $156 / night

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(2)

1 / 17

Key Largo Townhouse

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The location is amazing everything is so close, shopping, nightlife! This our second year coming back every one is so friendly. We loved it. You don't need to go nowhere Norman the owner has everything that you need , kayak,snorkeling gear fishing...”
- Review left on 03/23/2017

$250

Excellent (2 reviews)

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from $250 / night

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(2)

1 / 16

Tavernier Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My family and I had a fabulous time. Enjoyed all the perks available. Close to a local shopping center which has everything you may need. We will be back...”
- Review left on 12/02/2016

$175

Excellent (2 reviews)

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from $175 / night

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(8)

1 / 8

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“It could not have been better. The owners were excellent, and the home had everything imaginable. We will be back...”
- Review left on 12/25/2016

$243

Excellent (8 reviews)

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from $243 / night

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1 / 17

Islamorada Townhouse

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$200

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from $200 / night

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1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1000

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from $1000 / night

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(5)

1 / 15

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
“We stayed for a week and had a wonderful holiday. The booking and communication with the owner was good and the accommodation is exactly as described. It is a lovely clean well equipped apartment in a central location. Easy walk to all of the...”
- Review left on 07/13/2016

$228

Excellent (5 reviews)

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from $228 / night

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1 / 12

Summerland Key House

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning

$142

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from $142 / night

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1 / 23

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$177

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from $177 / night

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(11)

1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house and lush landscaping are beautiful! We enjoyed the pool so much. The private dock is a great touch even though we don't have a boat. We would recommend this property highly! Quaint restaurants in Marathon have some great food, too! We...”
- Review left on 11/03/2014

$393

Excellent (11 reviews)

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from $393 / night

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(19)

1 / 20

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house was just as pictured. Swimming in the gulf and canoeing was great. Waking up to that beautiful view every morning was wonderful. It's centrally located and close to everything. Definitely would stay again...”
- Review left on 01/03/2017

$343

Excellent (19 reviews)

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from $343 / night

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(1)

1 / 27

Islamorada Townhouse

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$204

Excellent (1 reviews)

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from $204 / night

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(3)

1 / 28

Key West Villa

  • 6
  • 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“This house is great for large groups. We had such a fun time having a reunion here. Close to everything, and staff was attentive and friendly...”
- Review left on 09/08/2016

$1195

Excellent (3 reviews)

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from $1195 / night

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(14)

1 / 17

Marathon House

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“From the moment we arrived we were impressed. The home was just beautiful. It was very clean, very spacious and beautifully decorated inside and out. The tropical flowers that greeted us when we arrived made us feel like we had indeed come to...”
- Review left on 07/08/2016

$414

Excellent (14 reviews)

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from $414 / night

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1 / 25

Marathon House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$300

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from $300 / night

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1 / 24

Duck Key Villa

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$340

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from $340 / night

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(10)

1 / 48

Key Largo House

  • 6
  • 16
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Shadow Point is Old Florida charm with modern comforts. The houses are brimming with history, art and personality. And yet there is everything you might want ? a great kitchen that is well stocked, good air conditioning, comfortable beds and plenty...”
- Review left on 09/18/2016

$1086

Excellent (10 reviews)

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from $1086 / night

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(17)

1 / 15

Key Largo House

  • 4
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We stayed for five days. Two families with five small children. The house was perfect! There are toddler beds tucked into 2 large walk in closets. There were two cribs and a high chair. They even had baby spoons! There is an adorable pirate ship...”
- Review left on 03/03/2016

$450

Very Good (17 reviews)

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from $450 / night

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(50)

1 / 36

Key West Condo

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed our stay at the Sunrise Suite. The place was bright with sunshine. It was clean, comfortable, nice sitting balcony and close to Duval Street. It had everything you would need for your stay. You could walk thru the complex and cross the...”
- Review left on 03/06/2017

$209

Excellent (50 reviews)

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from $209 / night

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(7)

1 / 9

Islamorada House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“We had four couples on our summer fishing vacation that we do every year in Islamorada.Couldnt have been better,we had couple days at first to go feed tarpon at Robbies and relax till seas calmed down and we got out in flat waters to fish,we caught...”
- Review left on 05/29/2015

$429

Excellent (7 reviews)

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from $429 / night

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(17)

1 / 42

Key Largo Cottage

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
“Our family of 4 stayed here over Thanksgiving week and had the best time. Penny is very organized and everything was perfect, love the ambiance. We love the old Florida feel and the tiki hut is the best. Our teenage boys had a fantastic time swimming...”
- Review left on 04/14/2016

$100

Excellent (17 reviews)

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from $100 / night

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1 / 24

Marathon Villa

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$200

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from $200 / night

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(3)

1 / 33

Islamorada House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoy coming back, weather just great. Just so relaxing. Chiki bar, pool, private dock all a plus. Est place to vacation...”
- Review left on 10/17/2016

$457

Excellent (3 reviews)

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from $457 / night

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(4)

1 / 22

Key West Townhouse

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning
“The property we rented was wonderful. It was very clean and spacious for my family to enjoy while we were attending a wedding. The grounds area was well maintained. Sitting by the pool was relaxing and to see iguanas come right down from the trees...”
- Review left on 05/29/2016

$201

Very Good (4 reviews)

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from $201 / night

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(7)

1 / 22

Key Largo House

  • 3
  • 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“By far the best spot in the Keys. Amazing views, breathtaking sunsets, and most importantly a place that feels like home. We love it so much 2016 will be our forth year. The home is imaculate from the wonderful bedding to the very well stocked...”
- Review left on 05/30/2016

$350

Very Good (7 reviews)

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from $350 / night

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(3)

1 / 16

Marathon Condo

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
“Had a fantastic time at the Gulfpointe condo in Marathon, FL. The location was great, the condo was spacious and had all the items needed to make our trip memorable for our family of three. The pool is great - spent a lot of time there. Beaches in...”
- Review left on 04/09/2015

$177

Very Good (3 reviews)

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from $177 / night

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About Florida Keys

While all the Florida Keys serve up a high dose of tropical leisure, each has its own personality and flavor. The Florida Keys are a wonderful vacation spot for families in search of a little relaxation or adventure. Enjoy Key Largo’s reputation as the dive capital of the world; Islamorada’s spectacular fishing; Marathon’s family friendly beaches; Big Pine Key and the Lower Keys' slowed pace and natural playground; and the unforgettable Key West, the Southernmost city in the continental U.S. and playground to Presidents, authors, and a number of bon vivants. And each has it's own unique offering of Florida Keys oceanfront vacation rentals to choose from. For families visiting the Florida Keys, vacation rentals by owner offer the maximum amount of space and privacy for the price.

Things to Do

Decide what sorts of fun in the sun you enjoy best and there’s a Key for that. If sports fishing and boating interests you, spend some time on Islamorada and take a dip in the Gulf Stream. If you wonder what inspired one of America’s top writers, don’t miss Key West and the historic Hemingway House. While you’re there, check out the descendants of his famous six-toed cats. No matter which Key you choose, the water is a draw around all of them. The crystalline blue surrounding these islands makes a drive up Highway 1 a spectacular way to spend some time, particularly if you’re in a convertible.

​The Keys have plenty of fun things to do for every activity level. Families who enjoy the outdoors can take advantage of the wide availability of Florida Keys condo rentals and stay right on the beach!
  • Fishing enthusiasts visiting the Florida Keys will be very excited to hear that Islamorada is known as the sport fishing capital of the world, offering a variety of game fish.
  • Water sports are also very popular in the Keys. Hang gliding, parasailing, kayaking, and paddle boarding are great choices for adventurous families.
  • Swimming with dolphins is a unique experience that every tourist of the Florida Keys should try! Through Dolphins Plus in Key Largo, visitors can go on a structured or natural swim with the dolphins or visit the sea lions through the Sea Lion Encounters program. In Islamorada, Theater of the Sea offers a wonderful opportunity to swim with dolphins, sea lions, and rays. Kids will have a blast learning about these delightful creatures.

Climate

The weather is warm for much of the year, but the balmy Caribbean breezes make it comfortable along the beaches even in summer. The highest temp ever recorded in the Keys was 97 F (36 C) back in 1880, but the summer average high is 89 F. Mosquitos like the Keys too, so keep this in mind on your visit. The highest potential for hurricanes in this part of Florida is from August 15-October 15 when waters are warmest, but it’s also a time of some of the most beautiful weather and one of the most affordable times to visit.

Shopping 

While there are shops on all the Keys, Key West provides the largest number of stores and boutiques. From literary memorabilia to craft beer, Key West offers some of the most memorable shopping of these tropical hot spots.

Events

The Keys offer a number of fishing tournaments throughout the year, not only for sport but to keep certain populations under control, especially the pervasive lion fish. Don’t miss the annual Hemingway look-alike contest in July or Key West’s annual Halloween celebration, Fantasy Fest. If you go, leave the kids at home.  

Nightlife

Nightlife or daylife, you’re on Island time here, and there’s always a party to be found, particularly in Key West. When people say “It’s 5:00 somewhere,” that somewhere is the Keys. Just ask Jimmy Buffet who is sometimes spotted in Key West, where he opened his first Margaritaville store in the mid-80s. Most of the hot bars are within walking distance on Duvall Street, making it a favorite of those looking for a party.  

Beaches and Parks

Florida Keys tourists can enjoy a leisurely day at one of the best parks in the nation. These are just a few of the Keys most popular destinations:
  • John Pennekamp Coral Reef State Park is the oldest underwater park in the world. Located in Key Largo, families can explore the 47 campsites located on 67,845 acres, split between land and underwater areas. Nature trails, beaches, kayak and canoe rentals, and glass-bottom boat tours are available.
  • Everglades National Park has many fun activities for families. Kids can become Junior Rangers or go on a wildlife hike.
  • Bahia Honda State Park is known for its beautiful beaches and crystal clear water. Visitors can book a snorkeling tour online and enjoy over an hour of snorkeling in the Looe Key National Marine Sanctuary, where swimmers will explore the gorgeous Elkhorn and Star coral.

Local History

Florida Keys visitors may want to learn a little about the history of these breathtaking islands.
  • Ernest Hemingway Home and Museum is a must for literature enthusiasts. Located in Key West, this historical landmark was Hemingway's home from 1931 to 1939, and the place in which he penned some of his most-loved work.
  • The Florida Keys Eco-Discovery Center is sure to be a hit with the kids. Housing over 6,000 square-feet of interactive exhibits, this museum is a great way to introduce kids to underwater and wildlife ecosystems. And admission is free!
Sightseeing Tours are one of the best ways to learn about the islands. Glass-bottom boat rides, sunset tours, and dinner cruises are all available. Remember to reserve your spot online ahead of time to save on ticket prices.

Fun With Kids

While vacationing in the Florida Keys, rental homes leased by owner are a great choice for families with a few kids who need a little extra space. Some of the top activities for kids are:
  • The Key West Butterfly and Nature Conservatory was voted the #1 attraction in Key West by TripAdvisor and People's Choice Awards. Take a stroll through the conservatory, which houses between 50 and 60 species of plants, waterfalls, colorful birds, and of course--butterflies.
  • The Conch Tour Train is a fun way to see Key West with the kids. In operation since 1958, the 90-minute tour will take you through all of the island's most popular attractions.
  • Tropic Cinema has been named "Best Florida Cinema" by Florida Monthly magazine for four consecutive years. This landmark theater screens Hollywood blockbusters, documentaries, and foreign films.
The Keys are a delightful mix of Old Florida and the Caribbean. They offer the recognizable feel of the U.S. with the laid back approach of the islands. Best of all, you don’t need a passport for this tropical adventure when you stay in one of the many Key West vacation rentals.
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