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Vacation rentals in Florida Keys

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Top-rated vacation rentals in Florida Keys

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

SUPERHOST
  1. Entire condo
  2. Marathon
Tropical Paradise ~ The Reef Marathon, 2BR Villa!

The Reef at Marathon is situated right in the center of the Florida Keys within an exciting, family-oriented island community. Whether visiting to experience the world-class fishing opportunities or simply to lounge under the radiant Florida sunshine, you are sure to love your time at The Reef at Marathon! Each unit at The Reef at Marathon is a standalone villa that includes 2 BR/2 BA, private balcony, a full kitchen, and a washer & dryer. Free Wi-Fi, and parking.

G$35,447 per night
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Tiburon Cottage

Our one bedroom suite features separate bedroom and living areas, giving you the space and comfort to relax, sleep and eat. Set yourself up in a large in-suite space with private entrance. The suite provides all the comforts of home. Unpack and stretch out in a stylish suite with a sofa, flat screen TV, complimentary Wi-Fi and premium cable programming or explore all the Keys have to offer. Here, you’ll have everything you need, because to us it’s not a temporary accommodation, it’s your home.

G$33,496 per night
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Pulpo Cottage

Our one bedroom studio features a queen size bed and living areas, giving you the space and comfort to relax, sleep and eat. Set yourself up in a large studio with private entrance. The suite provides all the comforts of home. Unpack and stretch out in a stylish suite with a sofa, flat screen TV, complimentary Wi-Fi and premium cable programming or explore all the Keys have to offer. Here, you’ll have everything you need, because to us it’s not a temporary accommodation, it’s your home.

G$34,214 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Boats
  • Villas

House rentals in Florida Keys

  1. Private room
  2. Florida City
Coral Cottage
G$10,258 per night
  1. Entire home
  2. Key Largo
Ocean view house freekayaks and paddle board
G$37,474 per night
SUPERHOST
  1. Entire home
  2. Key Largo
Key Largo Gem
G$20,517 per night
  1. Entire home
  2. Key Largo
Casa Marina - heated pool, ramp & 70 ft of dock!
G$37,265 per night
  1. Entire home
  2. Key Largo
Beautiful NEW Home in Key Largo Resort
G$31,403 per night
  1. Entire home
  2. Key Largo
Heart & Soul of Key Largo. 2/1 house
G$18,842 per night
SUPERHOST
  1. Private room
  2. Key Largo
Tropical Oasis on the water
G$29,458 per night
  1. Entire home
  2. Marathon
NEW LISTING! Dog-Friendly, Oceanfront Home w/Private Pool and Hot Tub!
G$52,547 per night
  1. Entire home
  2. Key Largo
Ocean-Inspired Key Largo Coconut Cottage
G$25,122 per night
SUPERHOST
  1. Entire home
  2. Marathon
Waterfront Hideaway
G$32,389 per night
  1. Entire home
  2. Key Largo
New listing - Newly Renovated Private Single House
G$23,029 per night
  1. Entire home
  2. Marathon
Angler`s Dream 2bed 2bath Duplex w/pool & dockage
G$37,683 per night

Weekend vacation rentals in Florida Keys

SUPERHOST
  1. Entire condo
  2. Islamorada
Resort with Private Beach & Gorgeous Sunsets!
G$44,309 per night
SUPERHOST
  1. Entire guesthouse
  2. Key Largo
Bayside Cottage, beach, fishing pier & sunsets 😎
G$37,175 per night
SUPERHOST
  1. Private room
  2. Key Largo
Keys Great Weekend Get Away
G$25,811 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 39 Tiki Huts, Private Beach & Pool
G$40,359 per night
SUPERHOST
  1. Private room
  2. Key West
Nuns Room, A single travelers delight!
G$30,207 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 14 -Tiki Huts, Beach, Pool...Oh My!
G$40,359 per night
  1. Entire serviced apartment
  2. Marathon
Sunset Villas, 1-bedroom suite w/ Full Kitchen
G$27,006 per night
SUPERHOST
  1. Entire guesthouse
  2. Key Largo
Cottage get away
G$27,216 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 28 - Private Beach, Pool & Paradise
G$39,475 per night
SUPERHOST
  1. Entire condo
  2. Key West
Key West Studio a short walk from Higgs & Duval
G$24,823 per night
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Manta Cottage
G$31,731 per night
  1. Private room
  2. Key Largo
Sleeping Rm Private Ent w use of RV Park Bathroom
G$20,935 per night

Florida Keys beach vacation rentals

SUPERHOST
  1. Entire condo
  2. Tavernier
Best View Ocean Pointe Beach Pool Marina Key Largo
G$51,530 per night
  1. Entire guest suite
  2. Islamorada
Efficiency - Snorkel, Swim, Kayak
G$28,891 per night
SUPERHOST
  1. Tiny home
  2. Key Largo
The Oasis in key largo with your own private beach
G$52,338 per night
  1. Entire cottage
  2. Key Largo
Tip’Sea 🐢Turtle Beach House
G$31,403 per night
  1. Tiny home
  2. Key Largo
Cozy Home- Beach, Pool, Boat Ramp, Dock for Rent
G$20,636 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
Paradise Found! 3/2 Beach Club included
G$50,244 per night
SUPERHOST
  1. Entire home
  2. Marathon
Waterfront Bungalow- Take your Boat on Vacation!
G$31,551 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
Waterfront Villa Bring Your Boat Cabana Club Beach
G$45,758 per night
SUPERHOST
  1. Entire home
  2. Marathon
Private waterfront sleeps 10 dock heated pool pets
G$73,273 per night
  1. Entire home
  2. Key West
Home Away from Home-Beautiful Duval Getaway
G$52,009 per night
  1. Hotel room
  2. Marathon
Unit 11 The Mutton Snapper One Bedroom Apartment
G$47,134 per night
SUPERHOST
  1. Entire condo
  2. Marathon
Tropical Paradise
G$37,893 per night

Your guide to Florida Keys

All About The Florida Keys

From vibrant Key West to the mysteriously named No Name Key, the Florida Keys offer historical intrigue and geographical wonder in a graceful archipelago, stretching out from the Everglades towards Havana. Postcard-worthy turquoise waters make the Keys a popular destination for sports fishing, scuba diving, and boating. If you fancy a more leisurely set of activities during your visit, boat rides in the tropical sun and snorkeling let you set your own pace for exploring the dazzling coral islands.

The strong culinary culture of the Keys is centered around fresh seafood, from mahi-mahi to snapper to blackfin tuna, alongside other edible delights, like Key lime pie on a stick. For those wanting to explore both land and sea, consider venturing into the Mel Fisher Maritime Heritage Museum or the Key West Shipwreck Treasure Museum, both of which are excellent forays into the impact the ocean has had on the history of these islands.


How do I get around Florida Keys?

There are multiple ways to get to the Florida Keys, the simplest being by plane. Several major airlines offer flights to Key West International Airport (EYW) on a daily basis. Alternative means of accessing the area include taking bus or shuttle services, driving to the Keys via the All-American Road, or even sailing your own boat. Once you’re there, the best way to get around is by biking. The region has many oceanside roads, and cycling along the cerulean waters is an experience in itself. Another means of transit is the local bus services. The area is served by five bus routes that traverse the majority of Key West, including its Old Town. There is also a shuttle service that connects the different islands.


When is the best time to stay in a vacation rental in Florida Keys?

The best time to look for Florida Keys vacation rentals is between March and May. There are typically fewer crowds during this time and the weather is still warm without being humid, unlike in the muggier summer months.. The islands also host a variety of events in the spring. The 7 Mile Bridge Run in April is an annual marathon spanning the entirety of one of the island’s bridges. The Taste of Key West, also in April, is an annual celebration of the various cuisines that call the archipelago home, and feature everything from fine dining to seafood shacks and food trucks. The Key West Songwriters’ Festival in May has been going strong for 25 years and features dozens of performers across genres such as country, reggae, and rock.


What are the top things to do in Florida Keys?

Duval Street

Duval Street, running from Mallory Square to the Southernmost Point marker, is one of Key West’s most lively streets. Host to museums, shops, galleries, and cafes, Duval Street is great not only for people-watching, with its many annual parades and events, but also for learning about the history of the Florida Keys, with attractions such as the Ernest Hemingway Home and Museum, and the former Strand Theater.

Dry Tortugas National Park

Dry Tortugas National Park, 70 miles from Key West, is only accessible by boat or plane, but is a worthwhile stop on any trip to the Florida Keys. An archipelago of seven beach-ringed islands, one is taken up entirely by the preserved ruins of Fort Jefferson, which stands guard over the coral, seagrass, and shipwrecks that welcome snorkelers from around the world. Popular snorkeling spots are the Historic Coaling Pier, Fort Jefferson's moat wall, and Garden Key. Boaters can explore around Loggerhead Key's Little Africa Reef and the Windjammer Wreck.

Marathon

Not to be confused with the activity, or the location of the same name in Greece, Marathon is the sportfishing center of the Florida Keys. Charters are easily arranged here for deep-sea, reef, and flats fishing. A variety of beaches and beachfront restaurants line the strip, while the former Seven Mile Bridge on the island makes a scenic path for walkers, joggers, and cyclists.