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Florida Keys Vacation Rentals <span>& House Rentals - 353 Rentals Available</span>
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 / 23

Summerland Key Home
4 BR / 3 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Nice quant house on the canal, with a short distance to either the Atlantic Ocean or The Gulf. Had a great time with Family. Did some site seeing, fishing, diving- snorkeling and enjoyed hanging with Parents, Kids and Grandkids. Had only one mishap,..."
- Debra Thomas, Ft Pierce, FL
(1) Excellent (1 review)
1 / 28

Key West Villa
6 BR / 7 BA / Sleeps 16 6 16 Min stay varies
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)
1 / 20

Ramrod Key Home
4 BR / 2 BA / Sleeps 8 4 8 30 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"This house was great. Had everything you could ask for. The owner even called to make sure we made it ok and if we needed anything. Best view, plenty of space absolutely gorgeous couldn't of asked for better."
- Gina Ashton-Jones, Magnolia TX
(2) Excellent (2 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 / 16

Marathon Home
3 BR / 2.5 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"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! ..."
- Rhonda Wilburn, Olive Hill, KY USA
(12) Excellent (12 reviews)
1 / 25

Tavernier Home
3 BR / 2 BA / Sleeps 9 3 9 30 night min stay
Home / 3 Bedrooms / Sleeps 9
3 bedrooms 2 bathrooms Sleeps 9
High Speed Internet • Dishwasher • Microwave
"We had a wonderful time in this home. The owner was so helpful and friendly. There was plenty of room for all of us to spread out and enjoy ourselves. Being on the water was a huge plus especially since one of our group brought his motor boat. We also..."
- Jody Carrier Hetchka, Amelia Island FL
(2) Excellent (2 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 • Microwave
"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 / 17

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 / 29

Key Largo Condo
3 BR / 1.5 BA / Sleeps 6 3 6 7 night min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 1.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"If you are looking for a great fishing place. This is the place for you. You have your own boat slip and it is seconds from where you wake up in the morning. You are on the gulf with the ocean a stone throw away on the other side. Own is a great guy and..."
- Sandra Hartman, Cincinnati,Ohio
(3) Excellent (3 reviews)
1 / 15

Marathon Home
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"We had an awesome trip! The location is very private. The views are amazing! Kayaking and fishing on site was super fun! Plenty of wildlife. We were able to see dolphin swim by a couple mornings and there are tons of iguanas around. The house is clean..."
- Jennifer Benn, Lake worth, FL
(8) Excellent (8 reviews)
1 / 21

Key West Cottage
1 BR / 1.5 BA / Sleeps 4 1 4 Min stay varies
Cottage / 1 Bedroom / Sleeps 4
1 bedrooms 1.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"The home was clean and in a great location. Bars are close by and there is a cute grocery store down the street. Parking is limited to only one space so make sure you only have one car when you visit."
- Idania Reyes, Miami Beach, FLUSA
(3) Excellent (3 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.