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Florida Keys Vacation Rentals & House Rentals - 271 Rentals Available

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271 Vacation rentals

(70)

Certificate of Excellence

1 / 25

Key West Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 58 minutes

Certificate of Excellence

“The Condo had such a beachy feel you knew you were on vacation. It was so clean and had anything you needed. Very nice pool also. The location was great only a 10-minute drive to any main attraction. Would highly recommend this unit as we will...”
- Review left on 12/10/2018

$228.00

Excellent (70 reviews)

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from $228.00 / night

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(18)

Certificate of Excellence

1 / 19

Conch Key Cottage

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly

Certificate of Excellence

$327.00

Excellent (18 reviews)

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from $327.00 / night

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(11)

1 / 24

Key Largo House

  • 3
  • 9
  • 28 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“My family and my sister's family visited this wonderful home over Spring Break and couldn't have been happier. Helen did everything she could to make sure we were comfortable and quickly settled so that we could get straight down to enjoying...”
- Review left on 07/19/2017

$176.00

Excellent (11 reviews)

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from $176.00 / night

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(17)

Certificate of Excellence

1 / 16

Key Largo Villa

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

Certificate of Excellence

“The Condo was very spacious, clean and very well presented. With a family, we appreciated the room and comfy beds! The washer and dryer were an added bonus. We liked the location and really enjoyed our stay. We wish it was longer and would love...”
- Review left on 12/06/2016

$229.00

Excellent (17 reviews)

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from $229.00 / night

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1 / 27

Pigeon Key House

  • 2
  • 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

Responds fast! Avg. 1 hour 53 minutes

$201.00

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from $201.00 / night

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1 / 17

Summerland Key House

  • 3
  • 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$201.00

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from $201.00 / night

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1 / 25

Islamorada House

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 3 hours 14 minutes

$409.00

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from $409.00 / night

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(22)

Certificate of Excellence

1 / 24

Conch Key Cottage

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly

Certificate of Excellence

$279.00

Excellent (22 reviews)

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from $279.00 / night

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1 / 28

Marathon Cottage

  • 1
  • 4
  • 3 nights min
  • Child friendly
  • Air conditioning

$157.00

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from $157.00 / night

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(145)

1 / 28

Key West Apartment

  • 2
  • 5
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 22 minutes

“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

$215.00

Excellent (145 reviews)

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from $215.00 / night

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(1)

1 / 24

Marathon Condo

  • 2
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$242.00

Excellent (1 reviews)

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from $242.00 / night

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1 / 12

Key West House

  • 2
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$465.00

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from $465.00 / night

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(52)

Certificate of Excellence

1 / 12

Key Largo Cottage

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Certificate of Excellence

“We enjoyed our Key Kargo stay. Our daughter and son in law joined us. Everything on site made for a good vacation. We were lucky to have good weather for snorkeling on the reef. Only request would be to have more plates and cutlery. We like to...”
- Review left on 01/07/2018

$229.00

Very Good (52 reviews)

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from $229.00 / night

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(1)

1 / 17

Key West Yacht

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

$229.00

Excellent (1 reviews)

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from $229.00 / night

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(3)

1 / 17

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

$270.00

Excellent (3 reviews)

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from $270.00 / night

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1 / 11

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$394.00

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from $394.00 / night

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(2)

1 / 52

Marathon House

  • 4
  • 10
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“This place is absolutely AMAZING! We stayed here with 3 families and we had plenty of room. Everything from the beautifully maintained grounds to the spacious house made this stay amazing! The views of the sunsets from the balcony were outstanding....”
- Review left on 10/01/2016

$401.00

Excellent (2 reviews)

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from $401.00 / night

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1 / 9

Key West House

  • 2
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$343.00

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from $343.00 / night

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(3)

1 / 28

Key West Villa

  • 6
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • 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

$1,432.00

Excellent (3 reviews)

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from $1,432.00 / night

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(33)

Certificate of Excellence

1 / 36

Marathon House

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Certificate of Excellence

“We were looking for a place to get away from the fast pace world. This place was a perfect fit. While the villas could use some updates, we spent most of time at the pool or the private beach. We visit the Keys every year for a quick weekend...”
- Review left on 07/02/2016

$172.00

Very Good (33 reviews)

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from $172.00 / night

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(1)

1 / 22

Marathon Shores House

  • 4
  • 10
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 14 minutes

$573.00

Excellent (1 reviews)

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from $573.00 / night

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1 / 27

Key Largo Cottage

  • 1
  • 4
  • 3 nights min
  • Child friendly
  • Air conditioning

$168.00

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from $168.00 / night

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(8)

1 / 22

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

$322.00

Excellent (8 reviews)

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from $322.00 / night

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(3)

1 / 25

Marathon House

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

$275.00

Excellent (3 reviews)

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from $275.00 / night

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(24)

1 / 32

Key Largo Condo

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We have been coming to Key Largo for the past three years and by far this was our most enjoyable stay. We are looking forward to returning next year. You could not asked for a better host than Norman. Very accommodating. The location is excellent...”
- Review left on 05/15/2017

$250.00

Very Good (24 reviews)

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from $250.00 / night

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1 / 8

Key West House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$536.00

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from $536.00 / night

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(25)

Certificate of Excellence

1 / 15

Key Largo House

  • 4
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Certificate of Excellence

“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

$401.00

Very Good (25 reviews)

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from $401.00 / night

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1 / 26

Key West House

  • 5
  • 10
  • 28 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$743.00

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from $743.00 / night

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(19)

1 / 27

Islamorada House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This house is the best!!!!! We had two familys staying and was perfect. The separate living quarters made our trip very enjoyable and very roomy. The house upstairs is remarkable and very up to date as well as downstairs. The back yard is your own...”
- Review left on 08/09/2016

$458.00

Excellent (19 reviews)

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from $458.00 / night

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(4)

1 / 11

Key West Guest house

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We rented the Conch House for our honeymoon and it was perfect! We loved the secluded feeling and the private beach. Carol was wonderful to work with and had fresh eggs and champagne waiting for us in our fridge. She picked fresh veggies for us to...”
- Review left on 04/20/2016

$393.00

Excellent (4 reviews)

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from $393.00 / night

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(43)

1 / 22

Marathon Villa

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Peninsular House ? Marathon, Florida We had a great time celebrating our 25th Wedding Anniversary at the Peninsular House ? gives you the feel of what ?old Florida? would be like - away from everyone, but actually just a hop, skip and jump from...”
- Review left on 05/25/2017

$401.00

Excellent (43 reviews)

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from $401.00 / night

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(1)

1 / 27

Key Largo House

  • 3
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$160.00

Excellent (1 reviews)

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from $160.00 / night

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(9)

1 / 14

Islamorada House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Had a great time. Beautiful house. Very convenient to everything. We highly recommend this property...”
- Review left on 08/05/2016

$533.00

Excellent (9 reviews)

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from $533.00 / night

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(18)

1 / 39

Key Largo Cottage

  • 1
  • 5
  • 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

$161.00

Excellent (18 reviews)

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from $161.00 / night

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(2)

1 / 20

Marathon House

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 2 hours 6 minutes

“My family and I went and stayed at this house for a week and had the most amazing time. The house was buitiful and very clean. The place had everything for the kids as well and for me to. I can't thank them enough for letting us stay in their...”
- Review left on 10/02/2016

$491.00

Excellent (2 reviews)

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from $491.00 / night

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(20)

1 / 22

Key West B and B

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$900.00

Excellent (20 reviews)

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from $900.00 / night

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1 / 10

Key Largo Cottage

  • 1
  • 4
  • 1 night min
  • Nearest beach 0 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 4 minutes

$310.00

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from $310.00 / night

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(2)

1 / 17

Key Largo Townhouse

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • 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

$250.00

Excellent (2 reviews)

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from $250.00 / night

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(2)

1 / 29

Cudjoe Key House

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
“The view was outstanding, the property had great amenities, and the home had all items as advertised. We were happy campers...”
- Review left on 03/13/2017

$201.00

Very Good (2 reviews)

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from $201.00 / night

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(12)

1 / 17

Marathon House

  • 3
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$422.00

Excellent (12 reviews)

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from $422.00 / 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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