Skip to content

Vacation rentals in Florida Keys

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Florida Keys

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

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.

$161 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 28 - Private Beach, Pool & Paradise

Unit 28 Details: First Floor Unit, Walk-in Shower, King Bed, Maximum Occupancy 2 Guests, No elevator on site and Not Handicapped Accessible. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.” Our Non-smoking Condominium is fully equipped and furnished to meet your vacation needs. You are only minutes away from the boating, fishing, snorkeling and diving North Americas only living coral reef. Our Tropical Paradise is perfect for a quiet/romantic get-away or a fun-filled vacation with family and/or friends. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Guest condos are just steps away from a refreshing swim in the heated pool or ocean. Bring your own or rent a locally delivered kayak or paddleboard that can be launched directly from our beach. Our Continental Inn Condominium units include fully equipped kitchens, secure WIFI, cable T.V., tiki huts on the beach with gas grills. Coin washers and dryers for guest use are available on the right side of the building prior to entering the breezeway from the parking lot. The City of Key Colony Beach is a tropical island paradise, located in the Heart of the Florida Keys centrally located between Key Largo and Key West. Drive 45 miles to Key West and spend the day shopping and dining, visit many famous pubs, historic sites and watch the sunset from Mallory Square. Amenities in the City of Key Colony Beach include several restaurants, clothing and gift shops, marina with fishing charters, dive and snorkel trips, boat rentals, 9-hole golf course, children's playground, pickle or bocce ball and tennis. View spectacular Florida sunsets at Sunset Park just around the corner from the Continental Inn. Something to do for everyone! Come, relax and enjoy the wonderful environment, local culture, fresh seafood, tropical island sites and weather. Love the beach! Relax on our private beach on the Atlantic Ocean or take a short drive to Sombrero Beach approximately 5 miles away or Bahia Honda Beach which is approximately 10 miles from Marathon (located just across the famous 7 Mile Bridge on the left Atlantic side) and named one of the most beautiful beaches in the United States. Florida Keys Wildlife Adventures await you, just within 7 miles from our beautiful city! The Dolphin Research Center, Florida Keys Aquarium Encounters, Crane Point Hammock and The Turtle Hospital. Come be our guest in our privately-owned condominium units and relax under a palm tree and enjoy all the Keys have to offer. Hope to Sea you soon!!!!

$189 per night
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.

$207 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Boats
  • Villas

Stay near Florida Keys's top sights

Photo of Mallory Square
Mallory Square34 locals recommend
Photo of Bahia Honda State Park
Bahia Honda State Park61 locals recommend
Photo of John Pennekamp Coral Reef State Park
John Pennekamp Coral Reef State Park111 locals recommend
Photo of Fort Zachary Taylor
Fort Zachary Taylor22 locals recommend
Photo of Sombrero Beach
Sombrero Beach41 locals recommend
Photo of Florida Keys Outlet Marketplace
Florida Keys Outlet Marketplace20 locals recommend

House rentals in Florida Keys

SUPERHOST
  1. Private room
  2. Key Colony Beach
Turtle-By-The-Sea: the Best Deal in KCB!
$138 per night
  1. Entire home
  2. Marathon
NEW LISTING! Dog-Friendly, Oceanfront Home w/Private Pool and Hot Tub!
$225 per night
SUPERHOST
  1. Entire home
  2. Key Largo
Your Keys Getaway!
$150 per night
SUPERHOST
  1. Entire home
  2. Key Largo
Waterfront Sunsets, Great Price, Relaxing Spot!!!
$157 per night
SUPERHOST
  1. Entire home
  2. Marathon
Waterfront Hideaway
$137 per night
SUPERHOST
  1. Private room
  2. Key Largo
Tropical Oasis on the water
$131 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
Paradise Found! 3/2 Beach Club included
$200 per night
  1. Entire home
  2. Key Colony Beach
Dog-friendly waterfront Home w/ private dock and pool & private beach access
$193 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
“La casa azul” step 3’ to a private pool
$248 per night
  1. Entire home
  2. Marathon
Efficient Oceanfront Condo W/ Boat Dock, Private Balcony, & Full Kitchen!
$200 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
Waterfront Villa Bring Your Boat Cabana Club Beach
$183 per night
SUPERHOST
  1. Entire home
  2. Marathon
Private waterfront sleeps 10 dock heated pool pets
$350 per night

Weekend vacation rentals in Florida Keys

SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Pulpo Cottage
$138 per night
SUPERHOST
  1. Entire condo
  2. Islamorada
Resort with Private Beach & Gorgeous Sunsets!
$212 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 39 Tiki Huts, Private Beach & Pool
$193 per night
SUPERHOST
  1. Entire guesthouse
  2. Key Largo
Cottage get away
$132 per night
  1. Entire bungalow
  2. Marathon
Cottage 02
$212 per night
SUPERHOST
  1. Entire vacation home
  2. Key Largo
Waterfront, GROUND LEVEL, Awesome Sunsets!!!
$224 per night
SUPERHOST
  1. Private room
  2. Key West
Nuns Room, A single travelers delight!
$129 per night
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Manta Cottage
$150 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 27 - The Beach is Calling You!
$173 per night
SUPERHOST
  1. Entire rental unit
  2. Key Colony Beach
Beachside Unit 22 - Private Beach on Atlantic
$193 per night
  1. Entire home
  2. Key Largo
Heart & Soul of Key Largo. 2/1 house
$150 per night
SUPERHOST
  1. Entire home
  2. Key Largo
Key Largo Gem
$106 per night

Beach house rentals in Florida Keys

SUPERHOST
  1. Entire home
  2. Key Largo
Waterfront Home, Kayaks, Fire Pit, Sunset Bay View
$249 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
P38 - 210 11th street
$229 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
Waterfront House with 37 ft Dock & Cabana Club
$201 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
Waterfront Home 37.5-ft dock, Cabana Club Included
$254 per night
  1. Entire home
  2. Marathon
Reel Paradise 2bed/2bath half duplex with brand new private pool, deck & dockage
$226 per night
  1. Entire home
  2. Key Colony Beach
Mornin’ Sunshine🌞 Waterfront 2Br/2ba in Key Colony
$161 per night
  1. Entire home
  2. Marathon
Angler`s Dream 2bed 2bath Duplex w/pool & dockage
$180 per night
  1. Entire home
  2. Key Colony Beach
KCB Sea Majestic 2Bed/2Bath Waterfront with a Pool
$313 per night
  1. Entire home
  2. Key West
Home Away from Home-Beautiful Duval Getaway
$299 per night
  1. Entire home
  2. Marathon
Reel Therapy 4 - 1bed/1bath updated half duplex with dockage
$164 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
Private Corner Lot, Wide Water Views, 30' Dock
$294 per night
SUPERHOST
  1. Entire home
  2. Marathon
Oceanside Water Access, Smart Home with SUP/kayaks
$187 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.