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Florida Keys Vacation Rentals & House Rentals - 195 Rentals Available

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195 Vacation rentals

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$296

Very Good (7 reviews)

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from $296 / night

(118)

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 (118 reviews)

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from $200 / night

(9)

1 / 21

Key West Condo

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
“We stayed at Touch of paradise at teh end of Oct and into Nov. Perfert location. I have stayed in Truman Annex many times and Touch of Paradise was a wounderful Unit. Location is everything in Kw because you walk alot and this unit is close to...”
- Review left on 11/13/2016

$228

Excellent (9 reviews)

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from $228 / night

(2)

1 / 15

Tavernier House

  • 5
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We have just returned from a month long celebration of retirement in the Keys. The lovely home we stayed in was perfectly located smack dab in the middle of everything there is to do in the Keys! The owner of this property was quick to respond to...”
- Review left on 02/05/2016

$168

Excellent (2 reviews)

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from $168 / night

1 / 37

Marathon Villa

  • 3
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

from $215 / night

(15)

1 / 11

Conch Key Cottage

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Air conditioning

$243

Excellent (15 reviews)

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from $243 / night

(2)

1 / 29

Key West Townhouse

  • 3
  • 6
  • 3 nights min
  • Ask about children
  • Air conditioning
“The place was very nize,cozy, clean and comfortable, felt very much at home would definitely come back again and rent the same place”
- Review left on 08/09/2016

$400

Excellent (2 reviews)

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from $400 / night

(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

(9)

1 / 16

Conch Key Cottage

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

$185

Excellent (9 reviews)

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from $185 / night

1 / 24

Marathon Villa

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

from $200 / night

(16)

1 / 21

Key West House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We rented Casa Rosa with three other couples for a week in February, 2017. Location was terrific! We could walk to many restaurants,bars, beaches and one grocery store (Fausto's). Suitable size for 8 people. Liked that each couple had their own...”
- Review left on 03/05/2017

$541

Very Good (16 reviews)

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from $541 / night

(8)

1 / 56

Key Largo House

  • 3
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“My family of five stayed in this home. We cooked on the grill while relaxing by the water watching the manatees. Plenty of space. Owners were super sweet and easy to work with during the stay”
- Review left on 01/10/2017

$229

Excellent (8 reviews)

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from $229 / night

(1)

1 / 20

Tavernier Apartment

  • 3
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Futura Yacht Club was great- our condo was 2 bedroom. The condo is older but I was pleased with how clean it was, The pool area was very new and renovated- club area - nice! People were friendly- we enjoyed dinner at picnic tables ocean side-...”
- Review left on 04/09/2015

$161

Excellent (1 reviews)

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from $161 / night

(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

(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

(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

$1196

Excellent (3 reviews)

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from $1196 / night

(2)

1 / 18

Key Largo House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The owners were wonderful to work with; their house was spacious, comfortable, and well-appointed and updated; and the location was a great spot from which to take excursions. Highly recommend...”
- Review left on 01/03/2017

$143

Excellent (2 reviews)

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from $143 / night

(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

(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

(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

$451

Very Good (17 reviews)

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from $451 / night

(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

(1)

1 / 49

Key Largo Cottage

  • 2
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“After reading other reviews, we knew we were not going into a Hilton, and that was why we chose the Key Lime Sailing Club! We are not sailors, but we do love the outdoors. Having the canoes, kayaks, stand up paddle boards, bikes, fishing and...”
- Review left on 05/02/2015

$225

Very Good (1 reviews)

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from $225 / night

1 / 12

Summerland Key House

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

from $143 / night

(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

1 / 9

Long Key House

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

from $357 / night

(7)

1 / 9

Islamorada House

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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

$300

Excellent (7 reviews)

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from $300 / night

(7)

1 / 8

Key Colony Beach Condo

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We truly enjoyed every minute of this beautiful condo in Key Colony Beach for the month of March, 2015. From the decor to the amazing views from the balcony, we were so happy with all the amenities. The kitchen was well equipped with everything we...”
- Review left on 04/05/2015

$160

Excellent (7 reviews)

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from $160 / night

(9)

1 / 14

Islamorada House

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

$391

Excellent (9 reviews)

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from $391 / night

(26)

1 / 36

Marathon House

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“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

$151

Very Good (26 reviews)

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from $151 / night

(1)

1 / 18

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“very clean nice house. the only thing the mattress in the front bedroom was not comfortable needs new one. I would stay again...”
- Review left on 06/22/2016

$144

Very Good (1 reviews)

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from $144 / night

(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

(1)

1 / 43

Marathon House

  • 4
  • 10
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
“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

$300

Excellent (1 reviews)

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from $300 / night

(3)

1 / 15

Key West House

  • 3
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“I have stayed at the Brass Palm Villa several times and I would never stay anywhere else on the island. It is decorated beautifully and exceptionally well maintained. There are many places to relax inside and outside the home. I especially enjoy the...”
- Review left on 10/10/2010

$200

Excellent (3 reviews)

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from $200 / night

1 / 22

Marathon Condo

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

from $172 / night

(9)

1 / 4

Key West Townhouse

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Traveling Buddies (3) rented this beautiful, recently renovated single-family townhouse in February, 2012 for two weeks. The house is so perfect in everyway-fully equipped...close to Duval St yet behind the gate and setback from busy Truman, its...”
- Review left on 03/27/2012

$100

Excellent (9 reviews)

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from $100 / night

(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

(7)

1 / 24

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“This was our third year in Heaven, Living the dream, House is clean as new,great location for boaters easy out to open water,fishing was great this year caught a 300 lb. grouper , weather was warmer this year , lots of calm wind days , more things...”
- Review left on 02/02/2017

$221

Very Good (7 reviews)

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from $221 / night

(38)

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 (38 reviews)

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from $157 / night

(4)

1 / 34

Marathon Villa

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“This nicely renovated unit was a great location, close to Key West, Bahia Honda, and walking distance to the 7 mile bridge. Snorkeling, jet skis and parasailing right around the corner, as well as many restaurants. The only amenities we would have...”
- Review left on 06/03/2015

$144

Excellent (4 reviews)

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from $144 / night

(18)

1 / 44

Marathon Townhouse

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We enjoyed our stay at Indigo Reef Villa 29. It was exactly what was depicted. Beautiful accommodations and the view was fantastic. Everyone we met was very nice...”
- Review left on 02/16/2016

$215

Excellent (18 reviews)

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from $215 / night

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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