Florida Keys Vacation Rentals & House Rentals - 246 Rentals Available
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Kawama Tower Condos
1 / 3

Key Largo Condo
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • Washer/Dryer
Spacious and Lovely Condos 2 bedrooms and 2 full baths . Located at Kawama Yacht Club in Key Largo.
(6) Excellent (6 reviews)
Marathon Florida Vacation Rentals - Home
1 / 18

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
Seven Night Minimum Maximum Occupancy 6 Rare, ground level, waterfront single family home (1381 square feet), on ocean side canal with 60 feet of dockage. Easy access to the Atlantic. Two bedrooms, two full baths,...
(1) Excellent (1 review)
Marathon Florida Vacation Rentals - Home
1 / 32

Marathon Home
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
Escape to your own private tropical island! This Vacation Rental home combines the best of both worlds, a modern, fully furnished, waterfront shore home with all the amenities for your nights and your own private tro...
(1) Excellent (1 review)
Marathon Florida Vacation Rentals - Home
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
2 bedroom 2 bathroom vacation villas on Atlantic Ocean. Heated pool overlooking a natural sand beach & Tiki huts & hammocks. All homes have full kitchen, 3 TV's, and Washer & Dryer. Boat docks are available on si...
(15) Excellent (15 reviews)
Marathon Florida Vacation Rentals - Cottage
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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
Please Call/email For Availability As We Do Not Use The Calendar Shown "sunset Bay" Is A 3 Bedroom, 2 Bathroom Home Located On The Clear, Aquamarine Waters Of The Beautiful Gulf Of Mexico. This Beautiful Waterfront...
(3) Excellent (3 reviews)
Key West Florida Vacation Rentals - Condo
1 / 12

Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 30 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Discover paradise of Key West in a distinctive setting. Luxury, two- bedroom, two- bath, (sleeps 4- 6) condominium set in a tropical garden with sweeping balconies with views of the Gulf. Your vacation hideaway is dec...
(6) Excellent (6 reviews)
Ramrod Key Florida Vacation Rentals - Home
1 / 18

Ramrod Key Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
4 Bedrooms, 2 Bathrooms, Sleeps 8 Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open.. This is a spacious oceanfront 4/2 home with a heated pool/spa and breatht...
(2) Excellent (2 reviews)
Islamorada Florida Vacation Rentals - Home
1 / 29

Islamorada Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA Accommodations: House, 3 Bedrooms, 2 Baths , Sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74. 5 bay side, White Marl...
(10) Excellent (10 reviews)
Key West Florida Vacation Rentals - Townhouse
1 / 20

Key West Townhouse
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
ISLAND WIND: 2 bedroom, 2 bath Bahamian- style townhome, with tin roof and white spindled decks. Snuggle into an oh- so- comfy king bed in the Master bedroom upstairs; bathroom is ensuite. Guest bedroom downstairs...
Marathon Florida Vacation Rentals - Home
1 / 8

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 cozy, single family home in the middle of Marathon, is on a deep canal just a few houses in from the ocean. You can be on the Atlantic Ocean in minutes to go fishing, snorkeling, or diving. Sit out on the comfor...
Key West Florida Vacation Rentals - Guesthouse
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
Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from a...
(3) Excellent (3 reviews)
Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • TV (Cable/Satellite) • Private Pool
Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There...
1/4 off shore the City of Marathon, Florida Keys
1 / 13

Marathon Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
Microwave • Washer/Dryer • Air Conditioning
You own private island on the ocean side off the City of Marathon in the Florida Keys. The island is built on a coral reef. Beautiful snorkeling, diving, fishing, and all types of water sports. The island is a short 3...
1 / 16

Key Largo Home
1 BR / 1 BA / Sleeps 4 1 4 7 night min stay
Home / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
Microwave • Air Conditioning • DVD Player
If Your Desired Dates Are Booked For This Property, There Is Another Mobile House Just Near By! Send Us An Email For Availability Request! It Is Everything About Location! ! ! Lay Back And Enjoy - Our Beauti...
(10) Excellent (10 reviews)
Key Largo Florida Vacation Rentals - Villa
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
2 bedroom, 2 bathroom Ocean Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2013. It has dockage for boats up to 50 feet. This Villa is 20 feet from the Ocean and has a private beach 50 feet from...
(11) Excellent (11 reviews)
Marathon Florida Vacation Rentals - Condo
1 / 16

Marathon Condo
2 BR / 2.5 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Beautiful condominium unit at Gulfpointe in Marathon, heart of the Florida Keys. Two bedroom, two and one half bath townhouse overlooking the pool area. Limited views of the Gulf, beautifully decorated, boat dockage,...
(3) Excellent (3 reviews)
Key Largo Florida Vacation Rentals - Home
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Key Largo Home
4 BR / 3 BA / Sleeps 12 4 12 30 night min stay
Home / 4 Bedrooms / Sleeps 12
4 bedrooms 3 bathrooms Sleeps 12
Dishwasher • Microwave • Washer/Dryer
MONTHLY RENTALS ONLY! ! ! Spacious and lovely canal home w/ above ground pool and dockage for your boat. 3/2 upstairs and spacious addorable 1/1 bath bottom floor. Completely and tastefully funrished and large screene...
(2) Excellent (2 reviews)
Key West Florida Vacation Rentals - Yacht
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Key West Yacht
2 BR / 2 BA / Sleeps 4 2 4 3 night min stay
Yacht / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
Microwave • Washer/Dryer • Air Conditioning
Make your next Key West vacation on the Lion's Paw, a roomy monohull sailboat located in Key West premier marina resort - the Key West Harbour Marina. Three night to seven day vacation packages have options for half da...
Tavernier Florida Vacation Rentals - Apartment
1 / 6

Tavernier Apartment
Studio / 1 BA / Sleeps 4 0 4 1 night min stay
Apartment / Studio / Sleeps 4
Studio 1 bathroom Sleeps 4
Microwave • Air Conditioning • TV (Cable/Satellite)
Boasting a prime location on a 24- ha ocean front sanctuary, surrounded by lush tropical landscape and the iconic blue waters of the Florida Keys, this complex offers the ideal setting for any holiday experience. Fort ...
Marathon Florida Vacation Rentals - Home
1 / 24

Marathon Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • Washer/Dryer
This Brand New water front home offers amazing retreat from the hustle & bustle of daily life. It's located in the best place in Marathon, just minutes away from the Sombrero Beach, popular Bahia Honda, stores and mor...
(6) Excellent (6 reviews)
Marathon Florida Vacation Rentals - Home
1 / 42

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 • Microwave • Air Conditioning
WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own tropical island in a quiet cove of protected mangroves in the Gulf of Mexico. You stay on a 2 bedroom houseboat that is docked on the ...
(1) Excellent (1 review)
Key West Florida Vacation Rentals - Condo
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
"Tee By The Sea" Vacation Rental (we Include 7 Bikes Free For Our Guests! ! ! ) If You Love... Golf, Sport Fishing/boating, Art/theater And Fantastic Live Entertainment... Than You'll Love "tee By The Sea". We're ...
(4) Excellent (4 reviews)
Marathon Florida Vacation Rentals - Home
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
A 3 bedroom, 2 bathroom single family vacation rental home, in Marathon, Bayside at Mile Marker 58. 6 on Grassy Key. Located across the water from the Dolphin Research Center & Grassy Key Marina, the nearest boat r...
(8) Excellent (8 reviews)
Islamorada Florida Vacation Rentals - Townhouse
1 / 24

Islamorada Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This oceanfront resort is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture built in 2007. Quaint streets & walking paths wind through this village- styled retreat. Amenities incl...
SunSet Water side Tiki Hut Key Largo Cottages, A Great day of rest & relaxation
1 / 49

Key Largo Cottage
2 BR / 1 BA / Sleeps 6 2 6 5 night min stay
Cottage / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
Dishwasher • Microwave • Air Conditioning
The Owner’s Cottage is also right in front of the bay with 2 bedrooms; it can sleep 2 adults and 1 to 3 kids. The main bedroom has a queen size bed; the second bedroom has a queen size loft bed and a twin bed on the ...
(1) Excellent (1 review)
Marathon Florida Vacation Rentals - Home
1 / 16

Marathon Home
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Handicapped Accessible" ~ not ADA "official" compliance but very user friendly Seven Night Minimum Maximum Occupancy 6 A rare ground level single family home with a spacious yard located in a nice, quiet residen...
(1) Excellent (1 review)
Key Largo Florida Vacation Rentals - Home
1 / 20

Key Largo Home
6 BR / 5.5 BA / Sleeps 17 6 17 3 night min stay
Home / 6 Bedrooms / Sleeps 17
6 bedrooms 5.5 bathrooms Sleeps 17
High Speed Internet • Dishwasher • Microwave
Southern Diversion Estate Key Largo - Brand New private gated 1 acre estate on the ocean with private beach, tiki hut , tropical private pool and deepwater dockage. There are 300 feet of direct ocean access with stunn...
Key West Florida Vacation Rentals - Home
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
Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid- century Florida home with dramatic Caribbean design, has created an ideal contemporary "Floribbean" style villa in the Casa Marina di...
(2) Excellent (2 reviews)
Key Largo Florida Vacation Rentals - Cottage
1 / 42

Key Largo Cottage
1 BR / 1 BA / Sleeps 4 1 4 7 night min stay
Cottage / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Microwave • Washer/Dryer
Bright and airy PET FREE, 1 bedroom, 1 bath home with large lanai [705 sq. ft. ] at mm 101. 5 on deep water swimming canal in gated Key Largo Kampground. The MINIMUM STAY IS A WEEK, [see rates section listed above] ...
(20) Excellent (20 reviews)
Marathon Florida Vacation Rentals - Condo
1 / 24

Marathon Condo
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
A huge luxury retreat, the perfect combination of high end living and tropical comfort, you'll be comfortable here in high heels or flip flops! You'll wake up in the morning and dine al fresco on our 40 foot scree...
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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.

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.