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Florida Keys Vacation Rentals <span>& House Rentals - 271 Rentals Available</span>
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 / 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 / 15

Marathon Cottage
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Cottage / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This was our first visit to the Florida Keys. My husband, myself, our 18 year old son and 16 year old daughter had a wonderful stay here. We were all really happy with our choice of this property. The house looked exactly as shown online. We really..."
- Karla Haire Sommers, Rogers, MN USA
(3) Excellent (3 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 / 3

Key West Guesthouse
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Guesthouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"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..."
- Kristi Koenig Martin-Smith, Fort Worth
(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)
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 / 37

Marathon Home
4 BR / 4 BA / Sleeps 10 4 10 7 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 4 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"The house was great, plenty of parking, great location, plenty of space, beds were much nicer than expected. Access to the Vaca Cut for fishing either Gulf or Atlantic was great. Main complaint was no water or electric to the dock to clean your ..."
- Shaun Lulofs, Sarasota, FL
(3) Excellent (3 reviews)
1 / 14

Marathon Home
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This is our second vacation this year at location and had a great time, snorkeling, fishing. Lots of sun at the perfect Place! !"
- Bill Batty, Turkey Point. Ontario Canada
(10) Excellent (10 reviews)
1 / 9

Marathon Home
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • TV (Antenna)
"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 helpful..."
- Lucius Moore, Georgia, USA
(7) Excellent (7 reviews)
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 / 5

Marathon Home
2 BR / 1.5 BA / Sleeps 5 2 5 7 night min stay
Home / 2 Bedrooms / Sleeps 5
2 bedrooms 1.5 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
"The 2 bedroom 1.5 bath duplex was a delight. It was very comfy, clean, inviting and accommodating for our 5 person family. We enjoyed the central location and easy access to groceries, bait, shops and Key West! We brought our small puppy and he..."
- Lisa Burchett, Lakeland, FL
(3) Excellent (3 reviews)
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 / 16

Key Largo Villa
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Villa / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This place was awesome- everything included we had paddle boards, Kayaks, golf cart and bicycles. The host Norman couldn't have been more friendly and helpful. I recommend this getaway to anyone and it is pet friendly."
- Kathryn Miller, Indiana
(14) Excellent (14 reviews)
1 / 58

Key Largo Condo
2 BR / 1.5 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 1.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"We loved your place. It is so nicely decorated, furnished with everything we could have needed and so very clean! I loved being able to walk to the water and fish from the pier. It was hard to decide whether to go in the pool, ocean or ping pong...."
- Laurie Dougherty, St Charles
(11) Excellent (11 reviews)
1 / 31

Key West Condo
3 BR / 2 BA / Sleeps 8 3 8 No min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"We loved our stay ..staff was very friendly they checked in our room when we thought someone went in our room while we were at park but it was false alarm .. Place was great but needed little extra cleanup in master bathroom jets .."
- Devinderjit Rai, Canada
(1) Excellent (1 review)
1 / 16

Marathon Home
4 BR / 3.5 BA / Sleeps 10 4 10 7 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • TV (Antenna)
"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 paradise...."
- Michael Cramer, Loveland,co
(1) Excellent (1 review)
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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.