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Florida Keys Vacation Rentals <span>& House Rentals - 271 Rentals Available</span>
1 / 42

Key West Condo
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Our condo was AMAZING! So clean and had all the comforts of home! Their was a detailed binder of places to eat and what to do in the area! Our vacation was perfect because of all the extra touches and information we were provided!"
- Winnie Lucht, Wisconsin
(5) Excellent (5 reviews)
1 / 43

Marathon Home
4 BR / 5 BA / Sleeps 10 4 10 7 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"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. ..."
- Jimmy Reyes, Orlando, FL USA
(1) Excellent (1 review)
1 / 55

Key West Villa
5 BR / 5.5 BA / Sleeps 12 5 12 Min stay varies
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 5.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"I rented this house for my sister- in- law's bachelorette weekend. The house was spacious, clean, and overall one of the best houses we've stayed in."
- Raevin Poli, Lake Worth, FL
(4) Excellent (4 reviews)
1 / 26

Islamorada Condo
2 BR / 2 BA / Sleeps 4 2 4 Min stay varies
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"We had a great time at your place, very pretty decor and fantastic view of Atlantic Ocean from 5th floor! Yet not too high up. Very nice area near water to sit and enjoy sunsets and birds and boats going by, nice pool and tennis courts, too. It was..."
- Nancy, Lillington, NC
(2) Excellent (2 reviews)
1 / 24

Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"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 months..."
- Vicki Kuhns, ragersville,ohio
(56) Excellent (56 reviews)
1 / 36

Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 2 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Easy booking with the owner. Very clean, light and spacious. Great facilities: washer and dryer, iron, hair dryers, vacuum and dish washer. Very quiet at night. Lovely balcony and view. Pool and hot tub area clean and pleasant surroundings. ..."
- Rus Sprout, England
(58) Excellent (58 reviews)
1 / 9

Long Key Home
2 BR / 1 BA / Sleeps 5 2 5 Min stay varies
Home / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Microwave • Washer/Dryer
"My Husband and I have always wanted to Drive from Horseshoebay Ont Canada to the Florida Keys The owner of this property was excellent It was exactly like he said it was The ocean was all around us in a friendly gated community My 4 year old Black lab..."
- Joan Gibbs, HirseshoeBay Ontario Canada
(1) Excellent (1 review)
1 / 32

Marathon Home
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"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 getaway..."
- Mandy Harmon, St. Petersburg, FL
(15) Excellent (15 reviews)
1 / 17

Key West Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This unit was great! The location is fantastic! The condo is spacious, clean and everything we were hoping for. I like that the bedrooms are upstairs which offers more privacy!"
- Mary Shields, MIchigan
(16) Excellent (16 reviews)
1 / 29

Islamorada Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Not more I can say except we all had a great time and thanks to the hosts and location this was an amazing celebration! Definately recommend!"
- Andrew Dick, Tacoma, WA
(10) Excellent (10 reviews)
1 / 17

Islamorada Home
4 BR / 3 BA / Sleeps 12 4 12 30 night min stay
Home / 4 Bedrooms / Sleeps 12
4 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • TV (Antenna)
"Comfortable home in a super- quiet neighborhood. Easily accommodated 8 adults. Plenty of room at the dining table for dining, cards, and games. Generous kitchen allowed milling about and food prep participation. Good beds and pillows; good bathrooms...."
- Lisa Gardner, St Pete Beach, Fl and rural Wisconsin, USA
(19) Excellent (19 reviews)
1 / 15

Key West Home
3 BR / 2.5 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • TV (Antenna)
"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 outside..."
- Lynne Martino, New Jersey
(2) Excellent (2 reviews)
1 / 10

Marathon Townhouse
3 BR / 2.5 BA / Sleeps 8 3 8 7 night min stay
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 2.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Beautiful location, and terrific property. Everything was super clean and nicely organized when we arrived. Perfect location with boat slip outside the back deck. The layout was perfect for us, easy to access, quiet, cool, very friendly and helpful..."
- Jon Cammack, Washington, D.C.
(19) Excellent (19 reviews)
1 / 28

Key West Villa
6 BR / 7 BA / Sleeps 16 6 16 7 night min stay
Villa / 6 Bedrooms / Sleeps 16
6 bedrooms 7 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
"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."
- Sean Johnson, Chicago
(3) Excellent (3 reviews)
1 / 21

Key West Home
4 BR / 4 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Rooms were clean, block off duval, few block to boardwalk and front street. Fabulous location. Reasonable rates. Ask for additional keys prior to arriving if needed, only received 2 keys for 4 rooms. Minor issues with plumbing. we were able to fix..."
- Jody Vincent, LeClaire, Iowa
(8) Excellent (8 reviews)
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Top 10 Activities in Florida Keys

Top 10 Activities in Florida Keys
Whether you prefer swimming, fishing, or sunning, there’s no shortage of things to do in the Florida Keys. Read on for the top 10 activities on these tropical islands.

Seven Mile Bridge

To get to the Florida Keys, you’ll have to traverse the Seven Mile Bridge, which is an attraction in its own right. For nearly seven miles, this bridge travels over the ocean, connecting the Middle Keys to the Lower Keys and providing travelers with stunning views.

John Pennekamp Coral Reef State Park

John Pennekamp Coral Reef State Park, the first underwater park in the U.S., offers a fascinating look under the surface of the Keys. Snorkel or scuba dive to get up close and personal with the reefs, or book a glass bottom boat tour to gaze from above. The admission fee is $8 per car, and there’s an extra charge for tours.

Lignumvitae Key Botanical State Park

Though it’s only accessible by private boat, this secluded island is worth a visit, since it ...

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Three Day Itinerary: Florida Keys

Three Day Itinerary: Florida Keys
The Florida Keys are an island archipelago off of Florida's southeast coast. Though the Keys include more than 1,700 islands, most are unpopulated, and only 43 are connected by bridge. The Keys enjoy warm tropical weather year-round, but are very exposed to hurricanes and tropical cyclones. The best time to visit is between March and May, before hurricane season commences on June 1. Weather permitting, a diverse array of historic and natural highlights await you throughout the year.

Day 1: Culture and History in Key West

Begin your visit at one of Key West's most famous sites. Take a 30-minute tour of the Ernest Hemingway Home and Museum, and see where the celebrated author penned many of his great works. Around 40 to 50 six-toed cats also live on the property, exhibiting the same polydactyl trait that distinguished Hemingway's own cat.

Explore more of Key West's history at the Harry S. Truman Little White House. The building originally served as a ...

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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.


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.


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.


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 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.